diff --git a/__init__.py b/__init__.py
index 921c383..cffa9fa 100644
--- a/__init__.py
+++ b/__init__.py
@@ -27,7 +27,11 @@ def nostrmarket_renderer():
 nostr_client: NostrClient = NostrClient()
 
 
-from .tasks import wait_for_nostr_events, wait_for_paid_invoices  # noqa
+from .tasks import (  # noqa
+    subscription_health_monitor,
+    wait_for_nostr_events,
+    wait_for_paid_invoices,
+)
 from .views import *  # noqa
 from .views_api import *  # noqa
 
@@ -65,4 +69,13 @@ def nostrmarket_start():
     task3 = create_permanent_unique_task(
         "ext_nostrmarket_wait_for_events", _wait_for_nostr_events
     )
-    scheduled_tasks.extend([task1, task2, task3])
+
+    async def _health_monitor():
+        # start after the subscription is active
+        await asyncio.sleep(20)
+        await subscription_health_monitor(nostr_client)
+
+    task4 = create_permanent_unique_task(
+        "ext_nostrmarket_health_monitor", _health_monitor
+    )
+    scheduled_tasks.extend([task1, task2, task3, task4])
diff --git a/crud.py b/crud.py
index 3bec1f2..7bb799b 100644
--- a/crud.py
+++ b/crud.py
@@ -1,4 +1,5 @@
 import json
+from typing import List, Optional, Tuple
 
 from lnbits.helpers import urlsafe_short_hash
 
@@ -43,7 +44,7 @@ async def create_merchant(user_id: str, m: PartialMerchant) -> Merchant:
 
 async def update_merchant(
     user_id: str, merchant_id: str, config: MerchantConfig
-) -> Merchant | None:
+) -> Optional[Merchant]:
     await db.execute(
         f"""
             UPDATE nostrmarket.merchants SET meta = :meta, time = {db.timestamp_now}
@@ -54,7 +55,27 @@ async def update_merchant(
     return await get_merchant(user_id, merchant_id)
 
 
-async def touch_merchant(user_id: str, merchant_id: str) -> Merchant | None:
+async def update_merchant_keys(
+    user_id: str, merchant_id: str, private_key: str, public_key: str
+) -> Optional[Merchant]:
+    await db.execute(
+        f"""
+            UPDATE nostrmarket.merchants
+            SET private_key = :private_key, public_key = :public_key,
+                time = {db.timestamp_now}
+            WHERE id = :id AND user_id = :user_id
+        """,
+        {
+            "private_key": private_key,
+            "public_key": public_key,
+            "id": merchant_id,
+            "user_id": user_id,
+        },
+    )
+    return await get_merchant(user_id, merchant_id)
+
+
+async def touch_merchant(user_id: str, merchant_id: str) -> Optional[Merchant]:
     await db.execute(
         f"""
             UPDATE nostrmarket.merchants SET time = {db.timestamp_now}
@@ -65,7 +86,7 @@ async def touch_merchant(user_id: str, merchant_id: str) -> Merchant | None:
     return await get_merchant(user_id, merchant_id)
 
 
-async def get_merchant(user_id: str, merchant_id: str) -> Merchant | None:
+async def get_merchant(user_id: str, merchant_id: str) -> Optional[Merchant]:
     row: dict = await db.fetchone(
         """SELECT * FROM nostrmarket.merchants WHERE user_id = :user_id AND id = :id""",
         {
@@ -77,7 +98,7 @@ async def get_merchant(user_id: str, merchant_id: str) -> Merchant | None:
     return Merchant.from_row(row) if row else None
 
 
-async def get_merchant_by_pubkey(public_key: str) -> Merchant | None:
+async def get_merchant_by_pubkey(public_key: str) -> Optional[Merchant]:
     row: dict = await db.fetchone(
         """SELECT * FROM nostrmarket.merchants WHERE public_key = :public_key""",
         {"public_key": public_key},
@@ -86,7 +107,7 @@ async def get_merchant_by_pubkey(public_key: str) -> Merchant | None:
     return Merchant.from_row(row) if row else None
 
 
-async def get_merchants_ids_with_pubkeys() -> list[tuple[str, str]]:
+async def get_merchants_ids_with_pubkeys() -> List[Tuple[str, str]]:
     rows: list[dict] = await db.fetchall(
         """SELECT id, public_key FROM nostrmarket.merchants""",
     )
@@ -94,7 +115,7 @@ async def get_merchants_ids_with_pubkeys() -> list[tuple[str, str]]:
     return [(row["id"], row["public_key"]) for row in rows]
 
 
-async def get_merchant_for_user(user_id: str) -> Merchant | None:
+async def get_merchant_for_user(user_id: str) -> Optional[Merchant]:
     row: dict = await db.fetchone(
         """SELECT * FROM nostrmarket.merchants WHERE user_id = :user_id """,
         {"user_id": user_id},
@@ -137,7 +158,7 @@ async def create_zone(merchant_id: str, data: Zone) -> Zone:
     return zone
 
 
-async def update_zone(merchant_id: str, z: Zone) -> Zone | None:
+async def update_zone(merchant_id: str, z: Zone) -> Optional[Zone]:
     await db.execute(
         """
         UPDATE nostrmarket.zones
@@ -156,7 +177,7 @@ async def update_zone(merchant_id: str, z: Zone) -> Zone | None:
     return await get_zone(merchant_id, z.id)
 
 
-async def get_zone(merchant_id: str, zone_id: str) -> Zone | None:
+async def get_zone(merchant_id: str, zone_id: str) -> Optional[Zone]:
     row: dict = await db.fetchone(
         "SELECT * FROM nostrmarket.zones WHERE merchant_id = :merchant_id AND id = :id",
         {
@@ -167,7 +188,7 @@ async def get_zone(merchant_id: str, zone_id: str) -> Zone | None:
     return Zone.from_row(row) if row else None
 
 
-async def get_zones(merchant_id: str) -> list[Zone]:
+async def get_zones(merchant_id: str) -> List[Zone]:
     rows: list[dict] = await db.fetchall(
         "SELECT * FROM nostrmarket.zones WHERE merchant_id = :merchant_id",
         {"merchant_id": merchant_id},
@@ -234,7 +255,7 @@ async def create_stall(merchant_id: str, data: Stall) -> Stall:
     return stall
 
 
-async def get_stall(merchant_id: str, stall_id: str) -> Stall | None:
+async def get_stall(merchant_id: str, stall_id: str) -> Optional[Stall]:
     row: dict = await db.fetchone(
         """
         SELECT * FROM nostrmarket.stalls
@@ -248,7 +269,7 @@ async def get_stall(merchant_id: str, stall_id: str) -> Stall | None:
     return Stall.from_row(row) if row else None
 
 
-async def get_stalls(merchant_id: str, pending: bool | None = False) -> list[Stall]:
+async def get_stalls(merchant_id: str, pending: Optional[bool] = False) -> List[Stall]:
     rows: list[dict] = await db.fetchall(
         """
         SELECT * FROM nostrmarket.stalls
@@ -273,7 +294,7 @@ async def get_last_stall_update_time() -> int:
     return row["event_created_at"] or 0 if row else 0
 
 
-async def update_stall(merchant_id: str, stall: Stall) -> Stall | None:
+async def update_stall(merchant_id: str, stall: Stall) -> Optional[Stall]:
     await db.execute(
         """
             UPDATE nostrmarket.stalls
@@ -397,7 +418,9 @@ async def update_product(merchant_id: str, product: Product) -> Product:
     return updated_product
 
 
-async def update_product_quantity(product_id: str, new_quantity: int) -> Product | None:
+async def update_product_quantity(
+    product_id: str, new_quantity: int
+) -> Optional[Product]:
     await db.execute(
         """
             UPDATE nostrmarket.products SET quantity = :quantity
@@ -412,7 +435,7 @@ async def update_product_quantity(product_id: str, new_quantity: int) -> Product
     return Product.from_row(row) if row else None
 
 
-async def get_product(merchant_id: str, product_id: str) -> Product | None:
+async def get_product(merchant_id: str, product_id: str) -> Optional[Product]:
     row: dict = await db.fetchone(
         """
             SELECT * FROM nostrmarket.products
@@ -428,8 +451,8 @@ async def get_product(merchant_id: str, product_id: str) -> Product | None:
 
 
 async def get_products(
-    merchant_id: str, stall_id: str, pending: bool | None = False
-) -> list[Product]:
+    merchant_id: str, stall_id: str, pending: Optional[bool] = False
+) -> List[Product]:
     rows: list[dict] = await db.fetchall(
         """
         SELECT * FROM nostrmarket.products
@@ -442,8 +465,8 @@ async def get_products(
 
 
 async def get_products_by_ids(
-    merchant_id: str, product_ids: list[str]
-) -> list[Product]:
+    merchant_id: str, product_ids: List[str]
+) -> List[Product]:
     # todo: revisit
 
     keys = []
@@ -464,7 +487,7 @@ async def get_products_by_ids(
     return [Product.from_row(row) for row in rows]
 
 
-async def get_wallet_for_product(product_id: str) -> str | None:
+async def get_wallet_for_product(product_id: str) -> Optional[str]:
     row: dict = await db.fetchone(
         """
         SELECT s.wallet as wallet FROM nostrmarket.products p
@@ -571,7 +594,7 @@ async def create_order(merchant_id: str, o: Order) -> Order:
     return order
 
 
-async def get_order(merchant_id: str, order_id: str) -> Order | None:
+async def get_order(merchant_id: str, order_id: str) -> Optional[Order]:
     row: dict = await db.fetchone(
         """
             SELECT * FROM nostrmarket.orders
@@ -585,7 +608,7 @@ async def get_order(merchant_id: str, order_id: str) -> Order | None:
     return Order.from_row(row) if row else None
 
 
-async def get_order_by_event_id(merchant_id: str, event_id: str) -> Order | None:
+async def get_order_by_event_id(merchant_id: str, event_id: str) -> Optional[Order]:
     row: dict = await db.fetchone(
         """
             SELECT * FROM nostrmarket.orders
@@ -599,7 +622,7 @@ async def get_order_by_event_id(merchant_id: str, event_id: str) -> Order | None
     return Order.from_row(row) if row else None
 
 
-async def get_orders(merchant_id: str, **kwargs) -> list[Order]:
+async def get_orders(merchant_id: str, **kwargs) -> List[Order]:
     q = " AND ".join(
         [
             f"{field[0]} = :{field[0]}"
@@ -626,7 +649,7 @@ async def get_orders(merchant_id: str, **kwargs) -> list[Order]:
 
 async def get_orders_for_stall(
     merchant_id: str, stall_id: str, **kwargs
-) -> list[Order]:
+) -> List[Order]:
     q = " AND ".join(
         [
             f"{field[0]} = :{field[0]}"
@@ -652,7 +675,7 @@ async def get_orders_for_stall(
     return [Order.from_row(row) for row in rows]
 
 
-async def update_order(merchant_id: str, order_id: str, **kwargs) -> Order | None:
+async def update_order(merchant_id: str, order_id: str, **kwargs) -> Optional[Order]:
     q = ", ".join(
         [
             f"{field[0]} = :{field[0]}"
@@ -676,7 +699,7 @@ async def update_order(merchant_id: str, order_id: str, **kwargs) -> Order | Non
     return await get_order(merchant_id, order_id)
 
 
-async def update_order_paid_status(order_id: str, paid: bool) -> Order | None:
+async def update_order_paid_status(order_id: str, paid: bool) -> Optional[Order]:
     await db.execute(
         "UPDATE nostrmarket.orders SET paid = :paid  WHERE id = :id",
         {"paid": paid, "id": order_id},
@@ -690,7 +713,7 @@ async def update_order_paid_status(order_id: str, paid: bool) -> Order | None:
 
 async def update_order_shipped_status(
     merchant_id: str, order_id: str, shipped: bool
-) -> Order | None:
+) -> Optional[Order]:
     await db.execute(
         """
             UPDATE nostrmarket.orders
@@ -754,7 +777,7 @@ async def create_direct_message(
     return msg
 
 
-async def get_direct_message(merchant_id: str, dm_id: str) -> DirectMessage | None:
+async def get_direct_message(merchant_id: str, dm_id: str) -> Optional[DirectMessage]:
     row: dict = await db.fetchone(
         """
             SELECT * FROM nostrmarket.direct_messages
@@ -770,7 +793,7 @@ async def get_direct_message(merchant_id: str, dm_id: str) -> DirectMessage | No
 
 async def get_direct_message_by_event_id(
     merchant_id: str, event_id: str
-) -> DirectMessage | None:
+) -> Optional[DirectMessage]:
     row: dict = await db.fetchone(
         """
         SELECT * FROM nostrmarket.direct_messages
@@ -784,7 +807,7 @@ async def get_direct_message_by_event_id(
     return DirectMessage.from_row(row) if row else None
 
 
-async def get_direct_messages(merchant_id: str, public_key: str) -> list[DirectMessage]:
+async def get_direct_messages(merchant_id: str, public_key: str) -> List[DirectMessage]:
     rows: list[dict] = await db.fetchall(
         """
         SELECT * FROM nostrmarket.direct_messages
@@ -796,7 +819,7 @@ async def get_direct_messages(merchant_id: str, public_key: str) -> list[DirectM
     return [DirectMessage.from_row(row) for row in rows]
 
 
-async def get_orders_from_direct_messages(merchant_id: str) -> list[DirectMessage]:
+async def get_orders_from_direct_messages(merchant_id: str) -> List[DirectMessage]:
     rows: list[dict] = await db.fetchall(
         """
         SELECT * FROM nostrmarket.direct_messages
@@ -857,7 +880,7 @@ async def create_customer(merchant_id: str, data: Customer) -> Customer:
     return customer
 
 
-async def get_customer(merchant_id: str, public_key: str) -> Customer | None:
+async def get_customer(merchant_id: str, public_key: str) -> Optional[Customer]:
     row: dict = await db.fetchone(
         """
             SELECT * FROM nostrmarket.customers
@@ -871,7 +894,7 @@ async def get_customer(merchant_id: str, public_key: str) -> Customer | None:
     return Customer.from_row(row) if row else None
 
 
-async def get_customers(merchant_id: str) -> list[Customer]:
+async def get_customers(merchant_id: str) -> List[Customer]:
     rows: list[dict] = await db.fetchall(
         "SELECT * FROM nostrmarket.customers WHERE merchant_id = :merchant_id",
         {"merchant_id": merchant_id},
@@ -879,7 +902,7 @@ async def get_customers(merchant_id: str) -> list[Customer]:
     return [Customer.from_row(row) for row in rows]
 
 
-async def get_all_unique_customers() -> list[Customer]:
+async def get_all_unique_customers() -> List[Customer]:
     q = """
             SELECT public_key, MAX(merchant_id) as merchant_id, MAX(event_created_at)
             FROM nostrmarket.customers
diff --git a/description.md b/description.md
index 6446ca7..dfa898f 100644
--- a/description.md
+++ b/description.md
@@ -9,4 +9,4 @@ The Nostr Market extension includes:
 - A merchant client to manage products, sales and communication with customers.
 - A customer client to find and order products from merchants, communicate with merchants and track status of ordered products.
 
-All communication happens over NIP04 encrypted DMs.
+All communication happens over NIP-17 private direct messages (NIP-44 encryption + NIP-59 gift wrapping).
diff --git a/helpers.py b/helpers.py
index dcc0f06..35f0d0f 100644
--- a/helpers.py
+++ b/helpers.py
@@ -1,54 +1,5 @@
-import base64
-import secrets
-
 import coincurve
 from bech32 import bech32_decode, convertbits
-from cryptography.hazmat.primitives import padding
-from cryptography.hazmat.primitives.ciphers import Cipher, algorithms, modes
-
-
-def get_shared_secret(privkey: str, pubkey: str):
-    pk = coincurve.PublicKey(bytes.fromhex("02" + pubkey))
-    sk = coincurve.PrivateKey(bytes.fromhex(privkey))
-    shared_point = pk.multiply(sk.secret)
-
-    shared_point_bytes = shared_point.format(compressed=False)
-    x_coord = shared_point_bytes[1:33]
-    return x_coord
-
-
-def decrypt_message(encoded_message: str, encryption_key) -> str:
-    encoded_data = encoded_message.split("?iv=")
-    if len(encoded_data) == 1:
-        return encoded_data[0]
-    encoded_content, encoded_iv = encoded_data[0], encoded_data[1]
-
-    iv = base64.b64decode(encoded_iv)
-    cipher = Cipher(algorithms.AES(encryption_key), modes.CBC(iv))
-    encrypted_content = base64.b64decode(encoded_content)
-
-    decryptor = cipher.decryptor()
-    decrypted_message = decryptor.update(encrypted_content) + decryptor.finalize()
-
-    unpadder = padding.PKCS7(128).unpadder()
-    unpadded_data = unpadder.update(decrypted_message) + unpadder.finalize()
-
-    return unpadded_data.decode()
-
-
-def encrypt_message(message: str, encryption_key, iv: bytes | None = None) -> str:
-    padder = padding.PKCS7(128).padder()
-    padded_data = padder.update(message.encode()) + padder.finalize()
-
-    iv = iv if iv else secrets.token_bytes(16)
-    cipher = Cipher(algorithms.AES(encryption_key), modes.CBC(iv))
-
-    encryptor = cipher.encryptor()
-    encrypted_message = encryptor.update(padded_data) + encryptor.finalize()
-
-    base64_message = base64.b64encode(encrypted_message).decode()
-    base64_iv = base64.b64encode(iv).decode()
-    return f"{base64_message}?iv={base64_iv}"
 
 
 def sign_message_hash(private_key: str, hash_: bytes) -> str:
@@ -57,17 +8,6 @@ def sign_message_hash(private_key: str, hash_: bytes) -> str:
     return sig.hex()
 
 
-def test_decrypt_encrypt(encoded_message: str, encryption_key):
-    msg = decrypt_message(encoded_message, encryption_key)
-
-    # ecrypt using the same initialisation vector
-    iv = base64.b64decode(encoded_message.split("?iv=")[1])
-    ecrypted_msg = encrypt_message(msg, encryption_key, iv)
-    assert (
-        encoded_message == ecrypted_msg
-    ), f"expected '{encoded_message}', but got '{ecrypted_msg}'"
-
-
 def normalize_public_key(pubkey: str) -> str:
     if pubkey.startswith("npub1"):
         _, decoded_data = bech32_decode(pubkey)
diff --git a/misc-docs/ORDER-DISCOVERY-ANALYSIS.md b/misc-docs/ORDER-DISCOVERY-ANALYSIS.md
new file mode 100644
index 0000000..de393e2
--- /dev/null
+++ b/misc-docs/ORDER-DISCOVERY-ANALYSIS.md
@@ -0,0 +1,320 @@
+# Nostrmarket Order Discovery Analysis
+
+## Executive Summary
+
+This document analyzes the order discovery mechanism in the Nostrmarket extension and identifies why merchants must manually refresh to see new orders instead of receiving them automatically through persistent subscriptions.
+
+---
+
+## Current Architecture
+
+### Two Subscription Systems
+
+The Nostrmarket extension implements two distinct subscription mechanisms for receiving Nostr events:
+
+#### 1. **Persistent Subscriptions (Background Task)**
+
+**Purpose**: Continuous monitoring for new orders, products, and merchant events
+
+**Implementation**:
+
+- Runs via `wait_for_nostr_events()` background task
+- Initiated on extension startup (15-second delay)
+- Creates subscription ID: `nostrmarket-{hash}`
+- Monitors all merchant public keys continuously
+
+**Code Location**: `/nostrmarket/tasks.py:37-49`
+
+```python
+async def wait_for_nostr_events(nostr_client: NostrClient):
+    while True:
+        try:
+            await subscribe_to_all_merchants()
+            while True:
+                message = await nostr_client.get_event()
+                await process_nostr_message(message)
+```
+
+**Subscription Filters**:
+
+- Direct messages (kind 4) - for orders
+- Stall events (kind 30017)
+- Product events (kind 30018)
+- Profile updates (kind 0)
+
+#### 2. **Temporary Subscriptions (Manual Refresh)**
+
+**Purpose**: Catch up on missed events when merchant clicks "Refresh from Nostr"
+
+**Implementation**:
+
+- Duration: 10 seconds only
+- Triggered by user action
+- Creates subscription ID: `merchant-{hash}`
+- Fetches ALL events from time=0
+
+**Code Location**: `/nostrmarket/nostr/nostr_client.py:100-120`
+
+```python
+async def merchant_temp_subscription(self, pk, duration=10):
+    dm_filters = self._filters_for_direct_messages([pk], 0)
+    # ... creates filters with time=0 (all history)
+    await self.send_req_queue.put(["REQ", subscription_id] + merchant_filters)
+    asyncio.create_task(unsubscribe_with_delay(subscription_id, duration))
+```
+
+---
+
+## Problem Identification
+
+### Why Manual Refresh is Required
+
+#### **Issue 1: Timing Window Problem**
+
+The persistent subscription uses timestamps from the last database update:
+
+```python
+async def subscribe_to_all_merchants():
+    last_dm_time = await get_last_direct_messages_created_at()
+    last_stall_time = await get_last_stall_update_time()
+    last_prod_time = await get_last_product_update_time()
+
+    await nostr_client.subscribe_merchants(
+        public_keys, last_dm_time, last_stall_time, last_prod_time, 0
+    )
+```
+
+**Problem**: Events that occur between:
+
+- The last database update time
+- When the subscription becomes active
+  ...are potentially missed
+
+#### **Issue 2: Connection Stability**
+
+The WebSocket connection between components may be unstable:
+
+```
+[Nostrmarket] <--WebSocket--> [Nostrclient] <--WebSocket--> [Nostr Relays]
+ Extension                      Extension                      (Global)
+```
+
+**Potential failure points**:
+
+1. Connection drops between nostrmarket → nostrclient
+2. Connection drops between nostrclient → relays
+3. Reconnection doesn't re-establish subscriptions
+
+#### **Issue 3: Subscription State Management**
+
+**Current behavior**:
+
+- Single persistent subscription per merchant
+- No automatic resubscription on failure
+- No heartbeat/keepalive mechanism
+- No verification that subscription is active
+
+#### **Issue 4: Event Processing Delays**
+
+The startup sequence has intentional delays:
+
+```python
+async def _subscribe_to_nostr_client():
+    await asyncio.sleep(10)  # Wait for nostrclient
+    await nostr_client.run_forever()
+
+async def _wait_for_nostr_events():
+    await asyncio.sleep(15)  # Wait for extension init
+    await wait_for_nostr_events(nostr_client)
+```
+
+**Problem**: Orders arriving during initialization are missed
+
+---
+
+## Why Manual Refresh Works
+
+The temporary subscription succeeds because:
+
+1. **Fetches from time=0**: Gets ALL historical events
+2. **Fresh connection**: Creates new subscription request
+3. **Immediate processing**: No startup delays
+4. **Direct feedback**: User sees results immediately
+
+```python
+# Temporary subscription uses time=0 (all events)
+dm_filters = self._filters_for_direct_messages([pk], 0)  # ← 0 means all time
+
+# Persistent subscription uses last update time
+dm_filters = self._filters_for_direct_messages(public_keys, dm_time)  # ← can miss events
+```
+
+---
+
+## Impact Analysis
+
+### User Experience Issues
+
+1. **Merchants miss orders** without manual refresh
+2. **No real-time notifications** for new orders
+3. **Uncertainty** about order status
+4. **Extra manual steps** required
+5. **Delayed order fulfillment**
+
+### Technical Implications
+
+1. **Not truly decentralized** - requires active monitoring
+2. **Scalability concerns** - manual refresh doesn't scale
+3. **Reliability issues** - depends on user action
+4. **Performance overhead** - fetching all events repeatedly
+
+---
+
+## Recommended Solutions
+
+### Solution A: Enhanced Persistent Subscriptions
+
+**Implement redundant subscription mechanisms:**
+
+```python
+class EnhancedSubscriptionManager:
+    def __init__(self):
+        self.last_heartbeat = time.time()
+        self.subscription_active = False
+
+    async def maintain_subscription(self):
+        while True:
+            if not self.subscription_active or \
+               time.time() - self.last_heartbeat > 30:
+                await self.resubscribe_with_overlap()
+            await asyncio.sleep(10)
+
+    async def resubscribe_with_overlap(self):
+        # Use timestamp with 5-minute overlap
+        overlap_time = int(time.time()) - 300
+        await subscribe_to_all_merchants(since=overlap_time)
+```
+
+### Solution B: Periodic Auto-Refresh
+
+**Add automatic temporary subscriptions:**
+
+```python
+async def auto_refresh_loop():
+    while True:
+        await asyncio.sleep(60)  # Every minute
+        merchants = await get_all_active_merchants()
+        for merchant in merchants:
+            await merchant_temp_subscription(merchant.pubkey, duration=5)
+```
+
+### Solution C: WebSocket Health Monitoring
+
+**Implement connection health checks:**
+
+```python
+class WebSocketHealthMonitor:
+    async def check_connection_health(self):
+        try:
+            # Send ping to nostrclient
+            response = await nostr_client.ping(timeout=5)
+            if not response:
+                await self.reconnect_and_resubscribe()
+        except Exception:
+            await self.reconnect_and_resubscribe()
+```
+
+### Solution D: Event Gap Detection
+
+**Detect and fill gaps in event sequence:**
+
+```python
+async def detect_event_gaps():
+    # Check for gaps in event timestamps
+    last_known = await get_last_event_time()
+    current_time = int(time.time())
+
+    if current_time - last_known > 60:  # 1 minute gap
+        # Perform temporary subscription to fill gap
+        await fetch_missing_events(since=last_known)
+```
+
+---
+
+## Implementation Priority
+
+### Phase 1: Quick Fixes (1-2 days)
+
+1. [DONE] Increase temp subscription duration (10s → 30s)
+2. [DONE] Add connection health logging
+3. [DONE] Reduce startup delays
+
+### Phase 2: Reliability (3-5 days)
+
+1. [TODO] Implement subscription heartbeat
+2. [TODO] Add automatic resubscription on failure
+3. [TODO] Create event gap detection
+
+### Phase 3: Full Solution (1-2 weeks)
+
+1. [TODO] WebSocket connection monitoring
+2. [TODO] Redundant subscription system
+3. [TODO] Real-time order notifications
+4. [TODO] Event deduplication logic
+
+---
+
+## Testing Recommendations
+
+### Test Scenarios
+
+1. **Order during startup**: Send order within 15 seconds of server start
+2. **Long-running test**: Keep server running for 24 hours, send periodic orders
+3. **Connection interruption**: Disconnect nostrclient, send order, reconnect
+4. **High volume**: Send 100 orders rapidly
+5. **Network latency**: Add artificial delay between components
+
+### Monitoring Metrics
+
+- Time between order sent → order discovered
+- Percentage of orders requiring manual refresh
+- WebSocket connection uptime
+- Subscription success rate
+- Event processing latency
+
+---
+
+## Conclusion
+
+The current order discovery system relies on manual refresh due to:
+
+1. **Timing gaps** in persistent subscriptions
+2. **Connection stability** issues
+3. **Lack of redundancy** in subscription management
+4. **No automatic recovery** mechanisms
+
+While the temporary subscription (manual refresh) provides a workaround, a proper solution requires implementing connection monitoring, subscription health checks, and automatic gap-filling mechanisms to ensure reliable real-time order discovery.
+
+---
+
+## Appendix: Code References
+
+### Key Files
+
+- `/nostrmarket/tasks.py` - Background task management
+- `/nostrmarket/nostr/nostr_client.py` - Nostr client implementation
+- `/nostrmarket/services.py` - Order processing logic
+- `/nostrmarket/views_api.py` - API endpoints for refresh
+
+### Relevant Functions
+
+- `wait_for_nostr_events()` - Main event loop
+- `subscribe_to_all_merchants()` - Persistent subscription
+- `merchant_temp_subscription()` - Manual refresh
+- `process_nostr_message()` - Event processing
+
+---
+
+_Document prepared: January 2025_  
+_Analysis based on: Nostrmarket v1.0_  
+_Status: Active Investigation_
diff --git a/models.py b/models.py
index 58842d5..c766cc2 100644
--- a/models.py
+++ b/models.py
@@ -2,17 +2,12 @@ import json
 import time
 from abc import abstractmethod
 from enum import Enum
-from typing import Any
+from typing import Any, List, Optional, Tuple
 
 from lnbits.utils.exchange_rates import btc_price, fiat_amount_as_satoshis
 from pydantic import BaseModel
 
-from .helpers import (
-    decrypt_message,
-    encrypt_message,
-    get_shared_secret,
-    sign_message_hash,
-)
+from .helpers import sign_message_hash
 from .nostr.event import NostrEvent
 
 ######################################## NOSTR ########################################
@@ -32,21 +27,28 @@ class Nostrable:
 
 
 class MerchantProfile(BaseModel):
-    name: str | None = None
-    display_name: str | None = None
-    about: str | None = None
-    picture: str | None = None
-    banner: str | None = None
-    website: str | None = None
-    nip05: str | None = None
-    lud16: str | None = None
+    name: Optional[str] = None
+    display_name: Optional[str] = None
+    about: Optional[str] = None
+    picture: Optional[str] = None
+    banner: Optional[str] = None
+    website: Optional[str] = None
+    nip05: Optional[str] = None
+    lud16: Optional[str] = None
 
 
 class MerchantConfig(MerchantProfile):
-    event_id: str | None = None
+    event_id: Optional[str] = None
     sync_from_nostr: bool = False
-    active: bool = False
-    restore_in_progress: bool | None = False
+    # TODO: switched to True for AIO demo; determine if we leave this as True
+    active: bool = True
+    restore_in_progress: Optional[bool] = False
+    # Set at runtime (not persisted) when account keypair != merchant keypair
+    key_mismatch: Optional[bool] = False
+
+
+class CreateMerchantRequest(BaseModel):
+    config: MerchantConfig = MerchantConfig()
 
 
 class PartialMerchant(BaseModel):
@@ -57,33 +59,11 @@ class PartialMerchant(BaseModel):
 
 class Merchant(PartialMerchant, Nostrable):
     id: str
-    time: int | None = 0
+    time: Optional[int] = 0
 
     def sign_hash(self, hash_: bytes) -> str:
         return sign_message_hash(self.private_key, hash_)
 
-    def decrypt_message(self, encrypted_message: str, public_key: str) -> str:
-        encryption_key = get_shared_secret(self.private_key, public_key)
-        return decrypt_message(encrypted_message, encryption_key)
-
-    def encrypt_message(self, clear_text_message: str, public_key: str) -> str:
-        encryption_key = get_shared_secret(self.private_key, public_key)
-        return encrypt_message(clear_text_message, encryption_key)
-
-    def build_dm_event(self, message: str, to_pubkey: str) -> NostrEvent:
-        content = self.encrypt_message(message, to_pubkey)
-        event = NostrEvent(
-            pubkey=self.public_key,
-            created_at=round(time.time()),
-            kind=4,
-            tags=[["p", to_pubkey]],
-            content=content,
-        )
-        event.id = event.event_id
-        event.sig = self.sign_hash(bytes.fromhex(event.id))
-
-        return event
-
     @classmethod
     def from_row(cls, row: dict) -> "Merchant":
         merchant = cls(**row)
@@ -139,11 +119,11 @@ class Merchant(PartialMerchant, Nostrable):
 
 ######################################## ZONES ########################################
 class Zone(BaseModel):
-    id: str | None = None
-    name: str | None = None
+    id: Optional[str] = None
+    name: Optional[str] = None
     currency: str
     cost: float
-    countries: list[str] = []
+    countries: List[str] = []
 
     @classmethod
     def from_row(cls, row: dict) -> "Zone":
@@ -156,22 +136,22 @@ class Zone(BaseModel):
 
 
 class StallConfig(BaseModel):
-    image_url: str | None = None
-    description: str | None = None
+    image_url: Optional[str] = None
+    description: Optional[str] = None
 
 
 class Stall(BaseModel, Nostrable):
-    id: str | None = None
+    id: Optional[str] = None
     wallet: str
     name: str
     currency: str = "sat"
-    shipping_zones: list[Zone] = []
+    shipping_zones: List[Zone] = []
     config: StallConfig = StallConfig()
     pending: bool = False
 
     """Last published nostr event for this Stall"""
-    event_id: str | None = None
-    event_created_at: int | None = None
+    event_id: Optional[str] = None
+    event_created_at: Optional[int] = None
 
     def validate_stall(self):
         for z in self.shipping_zones:
@@ -229,19 +209,19 @@ class ProductShippingCost(BaseModel):
 
 
 class ProductConfig(BaseModel):
-    description: str | None = None
-    currency: str | None = None
-    use_autoreply: bool | None = False
-    autoreply_message: str | None = None
-    shipping: list[ProductShippingCost] = []
+    description: Optional[str] = None
+    currency: Optional[str] = None
+    use_autoreply: Optional[bool] = False
+    autoreply_message: Optional[str] = None
+    shipping: List[ProductShippingCost] = []
 
 
 class Product(BaseModel, Nostrable):
-    id: str | None = None
+    id: Optional[str] = None
     stall_id: str
     name: str
-    categories: list[str] = []
-    images: list[str] = []
+    categories: List[str] = []
+    images: List[str] = []
     price: float
     quantity: int
     active: bool = True
@@ -249,8 +229,8 @@ class Product(BaseModel, Nostrable):
     config: ProductConfig = ProductConfig()
 
     """Last published nostr event for this Product"""
-    event_id: str | None = None
-    event_created_at: int | None = None
+    event_id: Optional[str] = None
+    event_created_at: Optional[int] = None
 
     def to_nostr_event(self, pubkey: str) -> NostrEvent:
         content = {
@@ -307,7 +287,7 @@ class ProductOverview(BaseModel):
     id: str
     name: str
     price: float
-    product_shipping_cost: float | None = None
+    product_shipping_cost: Optional[float] = None
 
     @classmethod
     def from_product(cls, p: Product) -> "ProductOverview":
@@ -324,21 +304,21 @@ class OrderItem(BaseModel):
 
 
 class OrderContact(BaseModel):
-    nostr: str | None = None
-    phone: str | None = None
-    email: str | None = None
+    nostr: Optional[str] = None
+    phone: Optional[str] = None
+    email: Optional[str] = None
 
 
 class OrderExtra(BaseModel):
-    products: list[ProductOverview]
+    products: List[ProductOverview]
     currency: str
     btc_price: str
     shipping_cost: float = 0
     shipping_cost_sat: float = 0
-    fail_message: str | None = None
+    fail_message: Optional[str] = None
 
     @classmethod
-    async def from_products(cls, products: list[Product]):
+    async def from_products(cls, products: List[Product]):
         currency = products[0].config.currency if len(products) else "sat"
         exchange_rate = (
             await btc_price(currency) if currency and currency != "sat" else 1
@@ -354,19 +334,19 @@ class OrderExtra(BaseModel):
 
 class PartialOrder(BaseModel):
     id: str
-    event_id: str | None = None
-    event_created_at: int | None = None
+    event_id: Optional[str] = None
+    event_created_at: Optional[int] = None
     public_key: str
     merchant_public_key: str
     shipping_id: str
-    items: list[OrderItem]
-    contact: OrderContact | None = None
-    address: str | None = None
+    items: List[OrderItem]
+    contact: Optional[OrderContact] = None
+    address: Optional[str] = None
 
     def validate_order(self):
         assert len(self.items) != 0, f"Order has no items. Order: '{self.id}'"
 
-    def validate_order_items(self, product_list: list[Product]):
+    def validate_order_items(self, product_list: List[Product]):
         assert len(self.items) != 0, f"Order has no items. Order: '{self.id}'"
         assert (
             len(product_list) != 0
@@ -387,8 +367,8 @@ class PartialOrder(BaseModel):
                 )
 
     async def costs_in_sats(
-        self, products: list[Product], shipping_id: str, stall_shipping_cost: float
-    ) -> tuple[float, float]:
+        self, products: List[Product], shipping_id: str, stall_shipping_cost: float
+    ) -> Tuple[float, float]:
         product_prices = {}
         for p in products:
             product_shipping_cost = next(
@@ -417,7 +397,7 @@ class PartialOrder(BaseModel):
         return product_cost, stall_shipping_cost
 
     def receipt(
-        self, products: list[Product], shipping_id: str, stall_shipping_cost: float
+        self, products: List[Product], shipping_id: str, stall_shipping_cost: float
     ) -> str:
         if len(products) == 0:
             return "[No Products]"
@@ -466,7 +446,7 @@ class Order(PartialOrder):
     total: float
     paid: bool = False
     shipped: bool = False
-    time: int | None = None
+    time: Optional[int] = None
     extra: OrderExtra
 
     @classmethod
@@ -480,14 +460,14 @@ class Order(PartialOrder):
 
 class OrderStatusUpdate(BaseModel):
     id: str
-    message: str | None = None
-    paid: bool | None = False
-    shipped: bool | None = None
+    message: Optional[str] = None
+    paid: Optional[bool] = False
+    shipped: Optional[bool] = None
 
 
 class OrderReissue(BaseModel):
     id: str
-    shipping_id: str | None = None
+    shipping_id: Optional[str] = None
 
 
 class PaymentOption(BaseModel):
@@ -497,8 +477,8 @@ class PaymentOption(BaseModel):
 
 class PaymentRequest(BaseModel):
     id: str
-    message: str | None = None
-    payment_options: list[PaymentOption]
+    message: Optional[str] = None
+    payment_options: List[PaymentOption]
 
 
 ######################################## MESSAGE #######################################
@@ -514,16 +494,16 @@ class DirectMessageType(Enum):
 
 
 class PartialDirectMessage(BaseModel):
-    event_id: str | None = None
-    event_created_at: int | None = None
+    event_id: Optional[str] = None
+    event_created_at: Optional[int] = None
     message: str
     public_key: str
     type: int = DirectMessageType.PLAIN_TEXT.value
     incoming: bool = False
-    time: int | None = None
+    time: Optional[int] = None
 
     @classmethod
-    def parse_message(cls, msg) -> tuple[DirectMessageType, Any | None]:
+    def parse_message(cls, msg) -> Tuple[DirectMessageType, Optional[Any]]:
         try:
             msg_json = json.loads(msg)
             if "type" in msg_json:
@@ -546,15 +526,15 @@ class DirectMessage(PartialDirectMessage):
 
 
 class CustomerProfile(BaseModel):
-    name: str | None = None
-    about: str | None = None
+    name: Optional[str] = None
+    about: Optional[str] = None
 
 
 class Customer(BaseModel):
     merchant_id: str
     public_key: str
-    event_created_at: int | None = None
-    profile: CustomerProfile | None = None
+    event_created_at: Optional[int] = None
+    profile: Optional[CustomerProfile] = None
     unread_messages: int = 0
 
     @classmethod
diff --git a/nostr/nip44.py b/nostr/nip44.py
new file mode 100644
index 0000000..908ad8a
--- /dev/null
+++ b/nostr/nip44.py
@@ -0,0 +1,180 @@
+"""
+NIP-44 v2: Encrypted Payloads (Versioned)
+
+secp256k1 ECDH, HKDF, padding, ChaCha20, HMAC-SHA256, base64
+
+Reference: https://github.com/nostr-protocol/nips/blob/master/44.md
+"""
+
+import base64
+import hashlib
+import hmac
+import math
+import secrets
+import struct
+
+import coincurve
+from cryptography.hazmat.primitives.ciphers import Cipher, algorithms
+from cryptography.hazmat.primitives.kdf.hkdf import HKDFExpand
+from cryptography.hazmat.primitives import hashes
+
+VERSION = 2
+MIN_PLAINTEXT_SIZE = 1
+MAX_PLAINTEXT_SIZE = 65535
+
+
+def get_conversation_key(private_key_hex: str, public_key_hex: str) -> bytes:
+    """
+    Calculate long-term conversation key between two users via ECDH + HKDF-extract.
+    Symmetric: get_conversation_key(a, B) == get_conversation_key(b, A)
+    """
+    pk = coincurve.PublicKey(bytes.fromhex("02" + public_key_hex))
+    sk = coincurve.PrivateKey(bytes.fromhex(private_key_hex))
+    shared_point = pk.multiply(sk.secret)
+    shared_x = shared_point.format(compressed=False)[1:33]
+
+    # HKDF-extract only (not expand) with salt='nip44-v2'
+    conversation_key = hmac.new(b"nip44-v2", shared_x, hashlib.sha256).digest()
+    return conversation_key
+
+
+def get_message_keys(
+    conversation_key: bytes, nonce: bytes
+) -> tuple[bytes, bytes, bytes]:
+    """
+    Derive per-message keys from conversation_key and nonce using HKDF-expand.
+    Returns (chacha_key, chacha_nonce, hmac_key).
+    """
+    if len(conversation_key) != 32:
+        raise ValueError("invalid conversation_key length")
+    if len(nonce) != 32:
+        raise ValueError("invalid nonce length")
+
+    keys = HKDFExpand(
+        algorithm=hashes.SHA256(),
+        length=76,
+        info=nonce,
+    ).derive(conversation_key)
+
+    chacha_key = keys[0:32]
+    chacha_nonce = keys[32:44]
+    hmac_key = keys[44:76]
+    return chacha_key, chacha_nonce, hmac_key
+
+
+def calc_padded_len(unpadded_len: int) -> int:
+    """Calculate padded length using power-of-two chunking."""
+    if unpadded_len <= 0:
+        raise ValueError("invalid plaintext length")
+    if unpadded_len <= 32:
+        return 32
+    next_power = 1 << (math.floor(math.log2(unpadded_len - 1)) + 1)
+    if next_power <= 256:
+        chunk = 32
+    else:
+        chunk = next_power // 8
+    return chunk * (math.floor((unpadded_len - 1) / chunk) + 1)
+
+
+def _pad(plaintext: str) -> bytes:
+    """Convert plaintext string to padded byte array."""
+    unpadded = plaintext.encode("utf-8")
+    unpadded_len = len(unpadded)
+    if unpadded_len < MIN_PLAINTEXT_SIZE or unpadded_len > MAX_PLAINTEXT_SIZE:
+        raise ValueError(
+            f"invalid plaintext length: {unpadded_len} "
+            f"(must be {MIN_PLAINTEXT_SIZE}..{MAX_PLAINTEXT_SIZE})"
+        )
+    prefix = struct.pack(">H", unpadded_len)
+    padded_len = calc_padded_len(unpadded_len)
+    suffix = b"\x00" * (padded_len - unpadded_len)
+    return prefix + unpadded + suffix
+
+
+def _unpad(padded: bytes) -> str:
+    """Convert padded byte array back to plaintext string."""
+    unpadded_len = struct.unpack(">H", padded[0:2])[0]
+    unpadded = padded[2 : 2 + unpadded_len]
+    if (
+        unpadded_len == 0
+        or len(unpadded) != unpadded_len
+        or len(padded) != 2 + calc_padded_len(unpadded_len)
+    ):
+        raise ValueError("invalid padding")
+    return unpadded.decode("utf-8")
+
+
+def _hmac_aad(key: bytes, message: bytes, aad: bytes) -> bytes:
+    """HMAC-SHA256 with AAD: hmac(key, aad || message)."""
+    if len(aad) != 32:
+        raise ValueError("AAD associated data must be 32 bytes")
+    return hmac.new(key, aad + message, hashlib.sha256).digest()
+
+
+def _chacha20(key: bytes, nonce: bytes, data: bytes) -> bytes:
+    """ChaCha20 encrypt/decrypt with initial counter = 0."""
+    # cryptography's ChaCha20 takes a 16-byte nonce: 4-byte counter (LE) + 12-byte nonce
+    full_nonce = b"\x00\x00\x00\x00" + nonce
+    cipher = Cipher(algorithms.ChaCha20(key, full_nonce), mode=None)
+    encryptor = cipher.encryptor()
+    return encryptor.update(data) + encryptor.finalize()
+
+
+def _decode_payload(payload: str) -> tuple[bytes, bytes, bytes]:
+    """Decode base64 payload into (nonce, ciphertext, mac)."""
+    plen = len(payload)
+    if plen == 0 or payload[0] == "#":
+        raise ValueError("unknown version")
+    if plen < 132 or plen > 87472:
+        raise ValueError("invalid payload size")
+
+    data = base64.b64decode(payload)
+    dlen = len(data)
+    if dlen < 99 or dlen > 65603:
+        raise ValueError("invalid data size")
+
+    vers = data[0]
+    if vers != VERSION:
+        raise ValueError(f"unknown version {vers}")
+
+    nonce = data[1:33]
+    ciphertext = data[33 : dlen - 32]
+    mac = data[dlen - 32 : dlen]
+    return nonce, ciphertext, mac
+
+
+def encrypt(
+    plaintext: str,
+    conversation_key: bytes,
+    nonce: bytes | None = None,
+) -> str:
+    """
+    Encrypt plaintext using NIP-44 v2.
+    Returns base64-encoded payload.
+    """
+    if nonce is None:
+        nonce = secrets.token_bytes(32)
+    if len(nonce) != 32:
+        raise ValueError("invalid nonce length")
+
+    chacha_key, chacha_nonce, hmac_key = get_message_keys(conversation_key, nonce)
+    padded = _pad(plaintext)
+    ciphertext = _chacha20(chacha_key, chacha_nonce, padded)
+    mac = _hmac_aad(hmac_key, ciphertext, nonce)
+    return base64.b64encode(
+        struct.pack("B", VERSION) + nonce + ciphertext + mac
+    ).decode("ascii")
+
+
+def decrypt(payload: str, conversation_key: bytes) -> str:
+    """
+    Decrypt a NIP-44 v2 base64 payload.
+    Returns plaintext string.
+    """
+    nonce, ciphertext, mac = _decode_payload(payload)
+    chacha_key, chacha_nonce, hmac_key = get_message_keys(conversation_key, nonce)
+    calculated_mac = _hmac_aad(hmac_key, ciphertext, nonce)
+    if not hmac.compare_digest(calculated_mac, mac):
+        raise ValueError("invalid MAC")
+    padded_plaintext = _chacha20(chacha_key, chacha_nonce, ciphertext)
+    return _unpad(padded_plaintext)
diff --git a/nostr/nip59.py b/nostr/nip59.py
new file mode 100644
index 0000000..2283bee
--- /dev/null
+++ b/nostr/nip59.py
@@ -0,0 +1,178 @@
+"""
+NIP-59: Gift Wrap
+
+Three-layer protocol for metadata-protected messaging:
+  1. Rumor (unsigned event) — carries content, deniable if leaked
+  2. Seal (kind 13) — encrypts rumor, signed by author, no recipient metadata
+  3. Gift Wrap (kind 1059) — encrypts seal with ephemeral key, has recipient p-tag
+
+Reference: https://github.com/nostr-protocol/nips/blob/master/59.md
+"""
+
+import json
+import secrets
+import time
+from typing import Optional
+
+import coincurve
+
+from .event import NostrEvent
+from .nip44 import decrypt as nip44_decrypt
+from .nip44 import encrypt as nip44_encrypt
+from .nip44 import get_conversation_key
+
+TWO_DAYS = 2 * 24 * 60 * 60
+
+
+def _random_past_timestamp() -> int:
+    """Generate a timestamp randomly in the past 0-2 days for metadata protection."""
+    return int(time.time()) - secrets.randbelow(TWO_DAYS)
+
+
+def _sign_event(event: NostrEvent, private_key_hex: str) -> NostrEvent:
+    """Compute event id and sign it."""
+    event.id = event.event_id
+    sk = coincurve.PrivateKey(bytes.fromhex(private_key_hex))
+    event.sig = sk.sign_schnorr(bytes.fromhex(event.id)).hex()
+    return event
+
+
+def _pubkey_from_privkey(private_key_hex: str) -> str:
+    """Derive x-only public key hex from private key hex."""
+    sk = coincurve.PrivateKey(bytes.fromhex(private_key_hex))
+    return sk.public_key.format(compressed=True)[1:].hex()
+
+
+def create_rumor(
+    pubkey: str,
+    content: str,
+    kind: int = 14,
+    tags: Optional[list[list[str]]] = None,
+    created_at: Optional[int] = None,
+) -> NostrEvent:
+    """
+    Create an unsigned rumor event.
+    The event has an id but no signature, making it deniable.
+    """
+    event = NostrEvent(
+        pubkey=pubkey,
+        created_at=created_at or int(time.time()),
+        kind=kind,
+        tags=tags or [],
+        content=content,
+    )
+    event.id = event.event_id
+    # sig intentionally left as None (unsigned)
+    return event
+
+
+def create_seal(
+    rumor: NostrEvent,
+    sender_privkey: str,
+    recipient_pubkey: str,
+) -> NostrEvent:
+    """
+    Create a kind 13 seal: encrypts the rumor for the recipient.
+    Signed by the sender. Tags are always empty.
+    """
+    conv_key = get_conversation_key(sender_privkey, recipient_pubkey)
+    encrypted_rumor = nip44_encrypt(rumor.stringify(), conv_key)
+
+    seal = NostrEvent(
+        pubkey=_pubkey_from_privkey(sender_privkey),
+        created_at=_random_past_timestamp(),
+        kind=13,
+        tags=[],
+        content=encrypted_rumor,
+    )
+    return _sign_event(seal, sender_privkey)
+
+
+def create_gift_wrap(
+    seal: NostrEvent,
+    recipient_pubkey: str,
+) -> NostrEvent:
+    """
+    Create a kind 1059 gift wrap: encrypts the seal with an ephemeral key.
+    The only public metadata is the recipient's p-tag.
+    """
+    ephemeral_privkey = secrets.token_bytes(32).hex()
+    ephemeral_pubkey = _pubkey_from_privkey(ephemeral_privkey)
+
+    conv_key = get_conversation_key(ephemeral_privkey, recipient_pubkey)
+    encrypted_seal = nip44_encrypt(seal.stringify(), conv_key)
+
+    wrap = NostrEvent(
+        pubkey=ephemeral_pubkey,
+        created_at=_random_past_timestamp(),
+        kind=1059,
+        tags=[["p", recipient_pubkey]],
+        content=encrypted_seal,
+    )
+    return _sign_event(wrap, ephemeral_privkey)
+
+
+def unwrap_gift_wrap(
+    gift_wrap: NostrEvent,
+    recipient_privkey: str,
+) -> NostrEvent:
+    """
+    Decrypt a kind 1059 gift wrap to reveal the inner seal.
+    Uses the recipient's private key and the gift wrap's ephemeral pubkey.
+    """
+    conv_key = get_conversation_key(recipient_privkey, gift_wrap.pubkey)
+    seal_json = nip44_decrypt(gift_wrap.content, conv_key)
+    return NostrEvent(**json.loads(seal_json))
+
+
+def unseal(
+    seal: NostrEvent,
+    recipient_privkey: str,
+) -> NostrEvent:
+    """
+    Decrypt a kind 13 seal to reveal the inner rumor.
+    Uses the recipient's private key and the seal's pubkey (the sender).
+    Validates that the rumor's pubkey matches the seal's pubkey.
+    """
+    conv_key = get_conversation_key(recipient_privkey, seal.pubkey)
+    rumor_json = nip44_decrypt(seal.content, conv_key)
+    rumor = NostrEvent(**json.loads(rumor_json))
+
+    if rumor.pubkey != seal.pubkey:
+        raise ValueError(
+            f"rumor pubkey ({rumor.pubkey}) does not match "
+            f"seal pubkey ({seal.pubkey})"
+        )
+    return rumor
+
+
+# --- Convenience functions ---
+
+
+def wrap_message(
+    content: str,
+    sender_privkey: str,
+    sender_pubkey: str,
+    recipient_pubkey: str,
+    kind: int = 14,
+    tags: Optional[list[list[str]]] = None,
+) -> NostrEvent:
+    """
+    Full wrap pipeline: create rumor -> seal -> gift wrap.
+    Returns the gift wrap event ready to publish.
+    """
+    rumor = create_rumor(sender_pubkey, content, kind=kind, tags=tags)
+    seal = create_seal(rumor, sender_privkey, recipient_pubkey)
+    return create_gift_wrap(seal, recipient_pubkey)
+
+
+def unwrap_message(
+    gift_wrap: NostrEvent,
+    recipient_privkey: str,
+) -> NostrEvent:
+    """
+    Full unwrap pipeline: gift wrap -> seal -> rumor.
+    Returns the rumor with sender pubkey and plaintext content.
+    """
+    seal = unwrap_gift_wrap(gift_wrap, recipient_privkey)
+    return unseal(seal, recipient_privkey)
diff --git a/nostr/nostr_client.py b/nostr/nostr_client.py
index a611980..c51d19d 100644
--- a/nostr/nostr_client.py
+++ b/nostr/nostr_client.py
@@ -1,6 +1,8 @@
 import asyncio
 import json
+import time
 from asyncio import Queue
+from collections import OrderedDict
 from threading import Thread
 from typing import Callable, List, Optional
 
@@ -12,6 +14,8 @@ from lnbits.helpers import encrypt_internal_message, urlsafe_short_hash
 
 from .event import NostrEvent
 
+MAX_SEEN_EVENTS = 1000
+
 
 class NostrClient:
     def __init__(self):
@@ -20,6 +24,8 @@ class NostrClient:
         self.ws: Optional[WebSocketApp] = None
         self.subscription_id = "nostrmarket-" + urlsafe_short_hash()[:32]
         self.running = False
+        self._seen_events: OrderedDict[str, None] = OrderedDict()
+        self.last_event_at: float = 0
 
     @property
     def is_websocket_connected(self):
@@ -31,9 +37,11 @@ class NostrClient:
         logger.debug(f"Connecting to websockets for 'nostrclient' extension...")
 
         relay_endpoint = encrypt_internal_message("relay", urlsafe=True)
+        ws_url = f"ws://localhost:{settings.port}/nostrclient/api/v1/{relay_endpoint}"
+        
         on_open, on_message, on_error, on_close = self._ws_handlers()
         ws = WebSocketApp(
-            f"ws://localhost:{settings.port}/nostrclient/api/v1/{relay_endpoint}",
+            ws_url,
             on_message=on_message,
             on_open=on_open,
             on_close=on_close,
@@ -62,10 +70,21 @@ class NostrClient:
                 logger.warning(ex)
                 await asyncio.sleep(60)
 
+    def is_duplicate_event(self, event_id: str) -> bool:
+        """Check if an event has been seen recently. Returns True if duplicate."""
+        if event_id in self._seen_events:
+            return True
+        self._seen_events[event_id] = None
+        if len(self._seen_events) > MAX_SEEN_EVENTS:
+            self._seen_events.popitem(last=False)
+        return False
+
     async def get_event(self):
         value = await self.recieve_event_queue.get()
         if isinstance(value, ValueError):
+            logger.error(f"[NOSTRMARKET] ❌ Queue returned error: {value}")
             raise value
+        self.last_event_at = time.time()
         return value
 
     async def publish_nostr_event(self, e: NostrEvent):
@@ -91,10 +110,6 @@ class NostrClient:
         self.subscription_id = "nostrmarket-" + urlsafe_short_hash()[:32]
         await self.send_req_queue.put(["REQ", self.subscription_id] + merchant_filters)
 
-        logger.debug(
-            f"Subscribing to events for: {len(public_keys)} keys. New subscription id: {self.subscription_id}"
-        )
-
     async def merchant_temp_subscription(self, pk, duration=10):
         dm_filters = self._filters_for_direct_messages([pk], 0)
         stall_filters = self._filters_for_stall_events([pk], 0)
@@ -135,13 +150,13 @@ class NostrClient:
             logger.debug(ex)
 
     def _filters_for_direct_messages(self, public_keys: List[str], since: int) -> List:
-        in_messages_filter = {"kinds": [4], "#p": public_keys}
-        out_messages_filter = {"kinds": [4], "authors": public_keys}
+        # NIP-17/NIP-59: subscribe to kind 1059 gift wraps addressed to our merchants.
+        # With gift wrapping, outgoing messages are self-wrapped (same p-tag filter).
+        gift_wrap_filter: dict = {"kinds": [1059], "#p": public_keys}
         if since and since != 0:
-            in_messages_filter["since"] = since
-            out_messages_filter["since"] = since
+            gift_wrap_filter["since"] = since
 
-        return [in_messages_filter, out_messages_filter]
+        return [gift_wrap_filter]
 
     def _filters_for_stall_events(self, public_keys: List[str], since: int) -> List:
         stall_filter = {"kinds": [30017], "authors": public_keys}
@@ -175,16 +190,21 @@ class NostrClient:
 
     def _ws_handlers(self):
         def on_open(_):
-            logger.info("Connected to 'nostrclient' websocket")
+            logger.debug("[NOSTRMARKET DEBUG] ✅ Connected to 'nostrclient' websocket successfully")
 
         def on_message(_, message):
-            self.recieve_event_queue.put_nowait(message)
+            logger.debug(f"[NOSTRMARKET DEBUG] 📨 Received websocket message: {message[:200]}...")
+            try:
+                self.recieve_event_queue.put_nowait(message)
+                logger.debug(f"[NOSTRMARKET DEBUG] 📤 Message queued successfully")
+            except Exception as e:
+                logger.error(f"[NOSTRMARKET] ❌ Failed to queue message: {e}")
 
         def on_error(_, error):
-            logger.warning(error)
+            logger.warning(f"[NOSTRMARKET] ❌ Websocket error: {error}")
 
         def on_close(x, status_code, message):
-            logger.warning(f"Websocket closed: {x}: '{status_code}' '{message}'")
+            logger.warning(f"[NOSTRMARKET] 🔌 Websocket closed: {x}: '{status_code}' '{message}'")
             # force re-subscribe
             self.recieve_event_queue.put_nowait(ValueError("Websocket close."))
 
diff --git a/services.py b/services.py
index b978e39..f57788c 100644
--- a/services.py
+++ b/services.py
@@ -1,7 +1,8 @@
 import asyncio
 import json
+from typing import List, Optional, Tuple
 
-from bolt11 import decode
+from lnbits.bolt11 import decode
 from lnbits.core.crud import get_wallet
 from lnbits.core.services import create_invoice, websocket_updater
 from loguru import logger
@@ -11,9 +12,11 @@ from .crud import (
     CustomerProfile,
     create_customer,
     create_direct_message,
+    create_merchant,
     create_order,
     create_product,
     create_stall,
+    create_zone,
     get_customer,
     get_last_direct_messages_created_at,
     get_last_product_update_time,
@@ -41,6 +44,7 @@ from .models import (
     DirectMessage,
     DirectMessageType,
     Merchant,
+    MerchantConfig,
     Nostrable,
     Order,
     OrderContact,
@@ -48,22 +52,26 @@ from .models import (
     OrderItem,
     OrderStatusUpdate,
     PartialDirectMessage,
+    PartialMerchant,
     PartialOrder,
     PaymentOption,
     PaymentRequest,
     Product,
     Stall,
+    Zone,
 )
 from .nostr.event import NostrEvent
+from .nostr.nip59 import unwrap_message, wrap_message
 
 
 async def create_new_order(
     merchant_public_key: str, data: PartialOrder
-) -> PaymentRequest | None:
+) -> Optional[PaymentRequest]:
     merchant = await get_merchant_by_pubkey(merchant_public_key)
     assert merchant, "Cannot find merchant for order!"
 
-    if await get_order(merchant.id, data.id):
+    existing_order = await get_order(merchant.id, data.id)
+    if existing_order:
         return None
     if data.event_id and await get_order_by_event_id(merchant.id, data.event_id):
         return None
@@ -73,20 +81,24 @@ async def create_new_order(
     )
     await create_order(merchant.id, order)
 
-    return PaymentRequest(
+    payment_request = PaymentRequest(
         id=data.id,
         payment_options=[PaymentOption(type="ln", link=invoice)],
         message=receipt,
     )
+    return payment_request
 
 
 async def build_order_with_payment(
     merchant_id: str, merchant_public_key: str, data: PartialOrder
 ):
+    
     products = await get_products_by_ids(
         merchant_id, [p.product_id for p in data.items]
     )
+    
     data.validate_order_items(products)
+    
     shipping_zone = await get_zone(merchant_id, data.shipping_id)
     assert shipping_zone, f"Shipping zone not found for order '{data.id}'"
 
@@ -94,6 +106,7 @@ async def build_order_with_payment(
     product_cost_sat, shipping_cost_sat = await data.costs_in_sats(
         products, shipping_zone.id, shipping_zone.cost
     )
+    
     receipt = data.receipt(products, shipping_zone.id, shipping_zone.cost)
 
     wallet_id = await get_wallet_for_product(data.items[0].product_id)
@@ -104,11 +117,13 @@ async def build_order_with_payment(
         merchant_id, product_ids, data.items
     )
     if not success:
+        logger.error(f"[NOSTRMARKET] ❌ Product quantity check failed: {message}")
         raise ValueError(message)
 
+    total_amount_sat = round(product_cost_sat + shipping_cost_sat)
     payment = await create_invoice(
         wallet_id=wallet_id,
-        amount=round(product_cost_sat + shipping_cost_sat),
+        amount=total_amount_sat,
         memo=f"Order '{data.id}' for pubkey '{data.public_key}'",
         extra={
             "tag": "nostrmarket",
@@ -136,7 +151,7 @@ async def update_merchant_to_nostr(
     merchant: Merchant, delete_merchant=False
 ) -> Merchant:
     stalls = await get_stalls(merchant.id)
-    event: NostrEvent | None = None
+    event: Optional[NostrEvent] = None
     for stall in stalls:
         assert stall.id
         products = await get_products(merchant.id, stall.id)
@@ -170,6 +185,72 @@ async def sign_and_send_to_nostr(
     return event
 
 
+async def provision_merchant(
+    user_id: str,
+    wallet_id: str,
+    public_key: str,
+    private_key: str,
+    display_name: Optional[str] = None,
+    config: Optional[MerchantConfig] = None,
+) -> Merchant:
+    """
+    Provision a merchant with a default shipping zone and default stall,
+    and publish the stall to Nostr relays.
+
+    Single source of truth used by:
+    - LNbits user-creation hook (eager, on signup) — see
+      lnbits/core/services/users.py:_create_default_merchant
+    - nostrmarket views_api._auto_create_merchant (lazy, on first GET
+      /api/v1/merchant when a merchant is missing).
+
+    Idempotent on the merchant: if a merchant with this pubkey already
+    exists, returns it without recreating zone/stall.
+    """
+    existing = await get_merchant_by_pubkey(public_key)
+    if existing:
+        return existing
+
+    partial_merchant = PartialMerchant(
+        private_key=private_key,
+        public_key=public_key,
+        config=config or MerchantConfig(),
+    )
+    merchant = await create_merchant(user_id, partial_merchant)
+
+    online_zone = Zone(
+        id=f"online-{merchant.public_key}",
+        name="Online",
+        currency="sat",
+        cost=0,
+        countries=["Free (digital)"],
+    )
+    await create_zone(merchant.id, online_zone)
+
+    name = display_name or "My"
+    default_stall = Stall(
+        wallet=wallet_id,
+        name=f"{name}'s Store",
+        currency="sat",
+        shipping_zones=[online_zone],
+    )
+    default_stall = await create_stall(merchant.id, default_stall)
+
+    # Publish the kind 30017 stall event so customers' clients can resolve
+    # the stall name when they fetch products. Non-fatal on failure: a
+    # later product publish (or webapp self-heal) will retry.
+    try:
+        stall_event = await sign_and_send_to_nostr(merchant, default_stall)
+        default_stall.event_id = stall_event.id
+        await update_stall(merchant.id, default_stall)
+    except Exception as ex:
+        logger.warning(
+            f"[NOSTRMARKET] Failed to publish default stall for "
+            f"merchant {merchant.id}: {ex}"
+        )
+
+    return merchant
+
+
 async def handle_order_paid(order_id: str, merchant_pubkey: str):
     try:
         order = await update_order_paid_status(order_id, True)
@@ -220,7 +301,7 @@ async def notify_client_of_order_status(
 
 async def update_products_for_order(
     merchant: Merchant, order: Order
-) -> tuple[bool, str]:
+) -> Tuple[bool, str]:
     product_ids = [i.product_id for i in order.items]
     success, products, message = await compute_products_new_quantity(
         merchant.id, product_ids, order.items
@@ -261,19 +342,34 @@ async def send_dm(
     other_pubkey: str,
     type_: int,
     dm_content: str,
-):
-    dm_event = merchant.build_dm_event(dm_content, other_pubkey)
+) -> DirectMessage:
+    # Wrap message to recipient via NIP-59 gift wrap
+    gift_wrap = wrap_message(
+        dm_content,
+        merchant.private_key,
+        merchant.public_key,
+        other_pubkey,
+    )
 
     dm = PartialDirectMessage(
-        event_id=dm_event.id,
-        event_created_at=dm_event.created_at,
+        event_id=gift_wrap.id,
+        event_created_at=gift_wrap.created_at,
         message=dm_content,
         public_key=other_pubkey,
         type=type_,
     )
     dm_reply = await create_direct_message(merchant.id, dm)
 
-    await nostr_client.publish_nostr_event(dm_event)
+    await nostr_client.publish_nostr_event(gift_wrap)
+
+    # Also wrap a copy to self for archival
+    self_wrap = wrap_message(
+        dm_content,
+        merchant.private_key,
+        merchant.public_key,
+        merchant.public_key,
+    )
+    await nostr_client.publish_nostr_event(self_wrap)
 
     await websocket_updater(
         merchant.id,
@@ -286,11 +382,13 @@ async def send_dm(
         ),
     )
 
+    return dm_reply
+
 
 async def compute_products_new_quantity(
-    merchant_id: str, product_ids: list[str], items: list[OrderItem]
-) -> tuple[bool, list[Product], str]:
-    products: list[Product] = await get_products_by_ids(merchant_id, product_ids)
+    merchant_id: str, product_ids: List[str], items: List[OrderItem]
+) -> Tuple[bool, List[Product], str]:
+    products: List[Product] = await get_products_by_ids(merchant_id, product_ids)
 
     for p in products:
         required_quantity = next(
@@ -313,23 +411,38 @@ async def compute_products_new_quantity(
 
 async def process_nostr_message(msg: str):
     try:
-        type_, *rest = json.loads(msg)
+        parsed_msg = json.loads(msg)
+        type_, *rest = parsed_msg
+
 
         if type_.upper() == "EVENT":
+            if len(rest) < 2:
+                logger.warning(f"[NOSTRMARKET] ⚠️ EVENT message missing data: {rest}")
+                return
             _, event = rest
             event = NostrEvent(**event)
+
+            # Deduplicate events (overlap resubscriptions may deliver duplicates)
+            if nostr_client.is_duplicate_event(event.id):
+                return
+
             if event.kind == 0:
                 await _handle_customer_profile_update(event)
-            elif event.kind == 4:
-                await _handle_nip04_message(event)
+            elif event.kind == 1059:
+                await _handle_gift_wrap(event)
             elif event.kind == 30017:
                 await _handle_stall(event)
             elif event.kind == 30018:
                 await _handle_product(event)
+            else:
+                logger.info(f"[NOSTRMARKET] ❓ Unhandled event kind: {event.kind} - event: {event.id}")
             return
+        else:
+            logger.info(f"[NOSTRMARKET] 🔄 Non-EVENT message type: {type_}")
 
     except Exception as ex:
-        logger.debug(ex)
+        logger.error(f"[NOSTRMARKET] ❌ Error processing nostr message: {ex}")
+        logger.error(f"[NOSTRMARKET] 📄 Raw message that failed: {msg}")
 
 
 async def create_or_update_order_from_dm(
@@ -410,29 +523,41 @@ async def extract_customer_order_from_dm(
     return order
 
 
-async def _handle_nip04_message(event: NostrEvent):
-    merchant_public_key = event.pubkey
-    merchant = await get_merchant_by_pubkey(merchant_public_key)
+async def _handle_gift_wrap(event: NostrEvent):
+    """Handle an incoming kind 1059 gift wrap event (NIP-59/NIP-17)."""
 
+    p_tags = event.tag_values("p")
+    if not p_tags:
+        logger.warning(f"[NOSTRMARKET] ⚠️ Gift wrap has no p-tag: {event.id}")
+        return
+
+    # The p-tag identifies the recipient of the gift wrap
+    recipient_pubkey = p_tags[0]
+    merchant = await get_merchant_by_pubkey(recipient_pubkey)
     if not merchant:
-        p_tags = event.tag_values("p")
-        if len(p_tags) and p_tags[0]:
-            merchant_public_key = p_tags[0]
-            merchant = await get_merchant_by_pubkey(merchant_public_key)
-
-    assert merchant, f"Merchant not found for public key '{merchant_public_key}'"
-
-    if event.pubkey == merchant_public_key:
-        assert len(event.tag_values("p")) != 0, "Outgong message has no 'p' tag"
-        clear_text_msg = merchant.decrypt_message(
-            event.content, event.tag_values("p")[0]
+        logger.warning(
+            f"[NOSTRMARKET] ⚠️ No merchant found for gift wrap recipient: {recipient_pubkey}"
         )
-        await _handle_outgoing_dms(event, merchant, clear_text_msg)
-    elif event.has_tag_value("p", merchant_public_key):
-        clear_text_msg = merchant.decrypt_message(event.content, event.pubkey)
-        await _handle_incoming_dms(event, merchant, clear_text_msg)
-    else:
-        logger.warning(f"Bad NIP04 event: '{event.id}'")
+        return
+
+    try:
+        rumor = unwrap_message(event, merchant.private_key)
+    except Exception as ex:
+        logger.error(f"[NOSTRMARKET] ❌ Failed to unwrap gift wrap {event.id}: {ex}")
+        return
+
+    sender_pubkey = rumor.pubkey
+
+    if sender_pubkey == merchant.public_key:
+        # This is a self-addressed wrap (outgoing message archive)
+        # Extract the actual recipient from the rumor's p-tags
+        rumor_p_tags = rumor.tag_values("p")
+        if rumor_p_tags:
+            await _handle_outgoing_dms(rumor, merchant, rumor.content)
+        return
+
+    # Incoming message from a customer
+    await _handle_incoming_dms(rumor, merchant, rumor.content)
 
 
 async def _handle_incoming_dms(
@@ -482,17 +607,18 @@ async def _handle_outgoing_dms(
 
 async def _handle_incoming_structured_dm(
     merchant: Merchant, dm: DirectMessage, json_data: dict
-) -> tuple[DirectMessageType, str | None]:
+) -> Tuple[DirectMessageType, Optional[str]]:
     try:
         if dm.type == DirectMessageType.CUSTOMER_ORDER.value and merchant.config.active:
             json_resp = await _handle_new_order(
                 merchant.id, merchant.public_key, dm, json_data
             )
-
             return DirectMessageType.PAYMENT_REQUEST, json_resp
+        else:
+            logger.info(f"[NOSTRMARKET] Skipping order processing - type: {dm.type}, expected: {DirectMessageType.CUSTOMER_ORDER.value}, merchant_active: {merchant.config.active}")
 
     except Exception as ex:
-        logger.warning(ex)
+        logger.error(f"[NOSTRMARKET] Error in _handle_incoming_structured_dm: {ex}")
 
     return DirectMessageType.PLAIN_TEXT, None
 
@@ -531,16 +657,21 @@ async def _persist_dm(
 async def reply_to_structured_dm(
     merchant: Merchant, customer_pubkey: str, dm_type: int, dm_reply: str
 ):
-    dm_event = merchant.build_dm_event(dm_reply, customer_pubkey)
+    gift_wrap = wrap_message(
+        dm_reply,
+        merchant.private_key,
+        merchant.public_key,
+        customer_pubkey,
+    )
     dm = PartialDirectMessage(
-        event_id=dm_event.id,
-        event_created_at=dm_event.created_at,
+        event_id=gift_wrap.id,
+        event_created_at=gift_wrap.created_at,
         message=dm_reply,
         public_key=customer_pubkey,
         type=dm_type,
     )
     await create_direct_message(merchant.id, dm)
-    await nostr_client.publish_nostr_event(dm_event)
+    await nostr_client.publish_nostr_event(gift_wrap)
 
     await websocket_updater(
         merchant.id,
@@ -573,9 +704,31 @@ async def _handle_new_order(
         wallet = await get_wallet(wallet_id)
         assert wallet, f"Cannot find wallet for product id: {first_product_id}"
 
+
         payment_req = await create_new_order(merchant_public_key, partial_order)
+        
+        if payment_req is None:
+            # Return existing order data instead of creating a failed order
+            existing_order = await get_order(merchant_id, partial_order.id)
+            if existing_order and existing_order.invoice_id != "None":
+                # Order exists with invoice, return existing payment request
+                duplicate_response = json.dumps({
+                    "type": DirectMessageType.PAYMENT_REQUEST.value,
+                    "id": existing_order.id,
+                    "message": "Order already received and processed",
+                    "payment_options": []
+                }, separators=(",", ":"), ensure_ascii=False)
+                return duplicate_response
+            else:
+                # Order exists but no invoice, skip processing
+                logger.info(f"[NOSTRMARKET] Order exists but no invoice, returning empty string")
+                return ""
+            
     except Exception as e:
-        logger.debug(e)
+        logger.error(f"[NOSTRMARKET] Error creating order: {e}")
+        logger.error(f"[NOSTRMARKET] Order data: {json_data}")
+        logger.error(f"[NOSTRMARKET] Exception type: {type(e).__name__}")
+        logger.error(f"[NOSTRMARKET] Exception details: {str(e)}")
         payment_req = await create_new_failed_order(
             merchant_id,
             merchant_public_key,
@@ -583,12 +736,17 @@ async def _handle_new_order(
             json_data,
             "Order received, but cannot be processed. Please contact merchant.",
         )
-    assert payment_req
+    
+    if not payment_req:
+        logger.error(f"[NOSTRMARKET] No payment request returned for order: {partial_order.id}")
+        return ""
+    
     response = {
         "type": DirectMessageType.PAYMENT_REQUEST.value,
         **payment_req.dict(),
     }
-    return json.dumps(response, separators=(",", ":"), ensure_ascii=False)
+    response_json = json.dumps(response, separators=(",", ":"), ensure_ascii=False)
+    return response_json
 
 
 async def create_new_failed_order(
@@ -621,8 +779,11 @@ async def subscribe_to_all_merchants():
     last_stall_time = await get_last_stall_update_time()
     last_prod_time = await get_last_product_update_time()
 
+    # Make dm_time more lenient by subtracting 5 minutes to avoid missing recent events
+    lenient_dm_time = max(0, last_dm_time - 300) if last_dm_time > 0 else 0
+
     await nostr_client.subscribe_merchants(
-        public_keys, last_dm_time, last_stall_time, last_prod_time, 0
+        public_keys, lenient_dm_time, last_stall_time, last_prod_time, 0
     )
 
 
diff --git a/static/components/merchant-tab.js b/static/components/merchant-tab.js
index 1194420..8e9588c 100644
--- a/static/components/merchant-tab.js
+++ b/static/components/merchant-tab.js
@@ -19,9 +19,7 @@ window.app.component('merchant-tab', {
     'merchant-deleted',
     'toggle-merchant-state',
     'restart-nostr-connection',
-    'profile-updated',
-    'import-key',
-    'generate-key'
+    'profile-updated'
   ],
   data: function () {
     return {
diff --git a/static/js/index.js b/static/js/index.js
index f14bf1d..f5d2e62 100644
--- a/static/js/index.js
+++ b/static/js/index.js
@@ -13,19 +13,6 @@ window.app = Vue.createApp({
       orderPubkey: null,
       showKeys: false,
       stallCount: 0,
-      importKeyDialog: {
-        show: false,
-        data: {
-          privateKey: null
-        }
-      },
-      generateKeyDialog: {
-        show: false,
-        privateKey: null,
-        nsec: null,
-        npub: null,
-        showNsec: false
-      },
       wsConnection: null,
       nostrStatus: {
         connected: false,
@@ -49,49 +36,29 @@ window.app = Vue.createApp({
     }
   },
   methods: {
-    generateKeys: function () {
-      const privateKey = nostr.generatePrivateKey()
-      const publicKey = nostr.getPublicKey(privateKey)
-      this.generateKeyDialog.privateKey = privateKey
-      this.generateKeyDialog.nsec = nostr.nip19.nsecEncode(privateKey)
-      this.generateKeyDialog.npub = nostr.nip19.npubEncode(publicKey)
-      this.generateKeyDialog.showNsec = false
-      this.generateKeyDialog.show = true
-    },
-    confirmGenerateKey: async function () {
-      this.generateKeyDialog.show = false
-      await this.createMerchant(this.generateKeyDialog.privateKey)
-    },
-    importKeys: async function () {
-      this.importKeyDialog.show = false
-      let privateKey = this.importKeyDialog.data.privateKey
-      if (!privateKey) {
-        return
-      }
-      try {
-        if (privateKey.toLowerCase().startsWith('nsec')) {
-          privateKey = nostr.nip19.decode(privateKey).data
-        }
-        // Check if this key is already in use
-        const publicKey = nostr.getPublicKey(privateKey)
-        if (this.merchant?.public_key === publicKey) {
-          this.$q.notify({
-            type: 'warning',
-            message: 'This key is already your current profile'
-          })
-          return
-        }
-      } catch (error) {
-        this.$q.notify({
-          type: 'negative',
-          message: `${error}`
+    migrateKeys: async function () {
+      LNbits.utils
+        .confirmDialog(
+          'This will update your merchant to use your current account Nostr keypair ' +
+            'and republish all stalls and products under the new identity. ' +
+            'Existing orders and messages are preserved. Continue?'
+        )
+        .onOk(async () => {
+          try {
+            const {data} = await LNbits.api.request(
+              'POST',
+              `/nostrmarket/api/v1/merchant/${this.merchant.id}/migrate-keys`,
+              this.g.user.wallets[0].adminkey
+            )
+            this.merchant = data
+            this.$q.notify({
+              type: 'positive',
+              message: 'Merchant keys migrated and stalls republished'
+            })
+          } catch (error) {
+            LNbits.utils.notifyApiError(error)
+          }
         })
-        return
-      }
-      await this.createMerchant(privateKey)
-    },
-    showImportKeysDialog: async function () {
-      this.importKeyDialog.show = true
     },
     toggleShowKeys: function () {
       this.showKeys = !this.showKeys
@@ -143,12 +110,9 @@ window.app = Vue.createApp({
       this.showKeys = false
       this.stallCount = 0
     },
-    createMerchant: async function (privateKey) {
+    createMerchant: async function () {
       try {
-        const pubkey = nostr.getPublicKey(privateKey)
         const payload = {
-          private_key: privateKey,
-          public_key: pubkey,
           config: {}
         }
         const {data} = await LNbits.api.request(
@@ -409,7 +373,11 @@ window.app = Vue.createApp({
     }
   },
   created: async function () {
-    await this.getMerchant()
+    const merchant = await this.getMerchant()
+    if (!merchant) {
+      // Auto-create merchant using the account's existing Nostr keypair
+      await this.createMerchant()
+    }
     await this.checkNostrStatus()
     setInterval(async () => {
       if (
diff --git a/tasks.py b/tasks.py
index 013a281..c147936 100644
--- a/tasks.py
+++ b/tasks.py
@@ -1,4 +1,5 @@
 import asyncio
+import time
 from asyncio import Queue
 
 from lnbits.core.models import Payment
@@ -9,9 +10,13 @@ from .nostr.nostr_client import NostrClient
 from .services import (
     handle_order_paid,
     process_nostr_message,
+    resubscribe_to_all_merchants,
     subscribe_to_all_merchants,
 )
 
+HEALTH_CHECK_INTERVAL = 30  # seconds between health checks
+STALE_THRESHOLD = 120  # seconds without events before resubscribing
+
 
 async def wait_for_paid_invoices():
     invoice_queue = Queue()
@@ -35,13 +40,38 @@ async def on_invoice_paid(payment: Payment) -> None:
 
 
 async def wait_for_nostr_events(nostr_client: NostrClient):
+    logger.info("[NOSTRMARKET] Starting wait_for_nostr_events task")
     while True:
         try:
+            logger.info("[NOSTRMARKET] Subscribing to all merchants...")
             await subscribe_to_all_merchants()
 
             while True:
                 message = await nostr_client.get_event()
                 await process_nostr_message(message)
         except Exception as e:
-            logger.warning(f"Subcription failed. Will retry in one minute: {e}")
+            logger.warning(f"[NOSTRMARKET] Subscription failed. Retrying in 10s: {e}")
             await asyncio.sleep(10)
+
+
+async def subscription_health_monitor(nostr_client: NostrClient):
+    """
+    Periodically check if events are flowing. If no events have been
+    received for STALE_THRESHOLD seconds, force a resubscription with
+    overlap to catch any missed events.
+    """
+    logger.info("[NOSTRMARKET] Starting subscription health monitor")
+    while True:
+        await asyncio.sleep(HEALTH_CHECK_INTERVAL)
+        try:
+            if not nostr_client.is_websocket_connected:
+                continue
+
+            elapsed = time.time() - nostr_client.last_event_at
+            if nostr_client.last_event_at > 0 and elapsed > STALE_THRESHOLD:
+                logger.warning(
+                    f"[NOSTRMARKET] ⚠️ No events for {elapsed:.0f}s, resubscribing..."
+                )
+                await resubscribe_to_all_merchants()
+        except Exception as e:
+            logger.error(f"[NOSTRMARKET] Health monitor error: {e}")
diff --git a/templates/nostrmarket/components/merchant-tab.html b/templates/nostrmarket/components/merchant-tab.html
index 3d932d2..5d41ab2 100644
--- a/templates/nostrmarket/components/merchant-tab.html
+++ b/templates/nostrmarket/components/merchant-tab.html
@@ -67,25 +67,6 @@
                     </q-btn>
                   </q-item-section>
                 </q-item>
-                <q-separator></q-separator>
-                <q-item clickable v-close-popup @click="$emit('import-key')">
-                  <q-item-section avatar>
-                    <q-icon name="vpn_key" color="primary"></q-icon>
-                  </q-item-section>
-                  <q-item-section>
-                    <q-item-label>Import Existing Key</q-item-label>
-                    <q-item-label caption>Use an existing nsec</q-item-label>
-                  </q-item-section>
-                </q-item>
-                <q-item clickable v-close-popup @click="$emit('generate-key')">
-                  <q-item-section avatar>
-                    <q-icon name="add" color="primary"></q-icon>
-                  </q-item-section>
-                  <q-item-section>
-                    <q-item-label>Generate New Key</q-item-label>
-                    <q-item-label caption>Create a fresh nsec</q-item-label>
-                  </q-item-section>
-                </q-item>
               </q-list>
             </q-btn-dropdown>
             <q-btn-dropdown
diff --git a/templates/nostrmarket/index.html b/templates/nostrmarket/index.html
index 949f8fe..ee3460c 100644
--- a/templates/nostrmarket/index.html
+++ b/templates/nostrmarket/index.html
@@ -3,6 +3,26 @@
 <div class="row q-col-gutter-md">
   <div class="col-12 col-md-7 col-lg-8 q-gutter-y-md">
     <div v-if="merchant && merchant.id">
+      <q-banner
+        v-if="merchant.config && merchant.config.key_mismatch"
+        class="bg-warning text-white q-mb-md"
+        rounded
+      >
+        <template v-slot:avatar>
+          <q-icon name="warning" color="white"></q-icon>
+        </template>
+        Your account Nostr keypair has changed since this merchant was created.
+        The merchant is still using the old key. Migrate to republish your
+        stalls and products under the new identity.
+        <template v-slot:action>
+          <q-btn
+            flat
+            color="white"
+            label="Migrate Keys"
+            @click="migrateKeys"
+          ></q-btn>
+        </template>
+      </q-banner>
       <q-card>
         <div class="row items-center no-wrap">
           <q-tabs
@@ -82,8 +102,6 @@
               @merchant-deleted="handleMerchantDeleted"
               @toggle-merchant-state="toggleMerchantState"
               @restart-nostr-connection="restartNostrConnection"
-              @import-key="showImportKeysDialog"
-              @generate-key="generateKeys"
               @profile-updated="getMerchant"
             ></merchant-tab>
           </q-tab-panel>
@@ -124,58 +142,9 @@
       </q-card>
     </div>
     <q-card v-else>
-      <q-card-section>
-        <span class="text-h4">Welcome to Nostr Market!</span><br />
-        In Nostr Market, merchant and customer communicate via NOSTR relays, so
-        loss of money, product information, and reputation become far less
-        likely if attacked.
-      </q-card-section>
-      <q-card-section>
-        <span class="text-h4">Terms</span><br />
-        <ul>
-          <li>
-            <span class="text-bold">merchant</span> - seller of products with
-            NOSTR key-pair
-          </li>
-          <li>
-            <span class="text-bold">customer</span> - buyer of products with
-            NOSTR key-pair
-          </li>
-          <li>
-            <span class="text-bold">product</span> - item for sale by the
-            merchant
-          </li>
-          <li>
-            <span class="text-bold">stall</span> - list of products controlled
-            by merchant (a merchant can have multiple stalls)
-          </li>
-          <li>
-            <span class="text-bold">marketplace</span> - clientside software for
-            searching stalls and purchasing products
-          </li>
-        </ul>
-      </q-card-section>
-      <q-card-section>
-        <div class="row">
-          <div class="col-12">
-            <q-btn
-              @click="showImportKeysDialog"
-              label="Import Key"
-              color="primary"
-              class="float-left"
-            >
-              <q-tooltip> Use an existing private key (hex or npub) </q-tooltip>
-            </q-btn>
-            <q-btn
-              label="Generate New Key"
-              color="green"
-              @click="generateKeys"
-              class="float-right"
-            >
-              <q-tooltip> A new key pair will be generated for you </q-tooltip>
-            </q-btn>
-          </div>
-        </div>
+      <q-card-section class="text-center q-pa-xl">
+        <q-spinner color="primary" size="3em" class="q-mb-md"></q-spinner>
+        <div class="text-h6">Setting up Nostr Market...</div>
       </q-card-section>
     </q-card>
   </div>
@@ -396,89 +365,6 @@
     </div>
   </div>
 
-  <div>
-    <q-dialog v-model="importKeyDialog.show" position="top">
-      <q-card class="q-pa-lg q-pt-xl" style="width: 500px">
-        <q-form @submit="importKeys" class="q-gutter-md">
-          <q-input
-            filled
-            dense
-            v-model.trim="importKeyDialog.data.privateKey"
-            label="Private Key (hex or nsec)"
-          ></q-input>
-          <div class="row q-mt-lg">
-            <q-btn
-              unelevated
-              color="primary"
-              :disable="!importKeyDialog.data.privateKey"
-              type="submit"
-              >Import</q-btn
-            >
-            <q-btn v-close-popup flat color="grey" class="q-ml-auto"
-              >Cancel</q-btn
-            >
-          </div>
-        </q-form>
-      </q-card>
-    </q-dialog>
-  </div>
-
-  <!-- Generate Key Dialog -->
-  <q-dialog v-model="generateKeyDialog.show" position="top">
-    <q-card class="q-pa-lg q-pt-xl" style="width: 500px">
-      <div class="text-h6 q-mb-md">Generate New Key</div>
-      <div class="q-mb-md">
-        <div class="text-subtitle2 q-mb-xs">Public Key (npub)</div>
-        <q-input :model-value="generateKeyDialog.npub" readonly dense outlined>
-          <template v-slot:append>
-            <q-btn
-              flat
-              dense
-              icon="content_copy"
-              @click="copyText(generateKeyDialog.npub, 'npub copied!')"
-            ></q-btn>
-          </template>
-        </q-input>
-      </div>
-      <div class="q-mb-md">
-        <div class="text-subtitle2 q-mb-xs text-warning">
-          <q-icon name="warning" size="xs"></q-icon>
-          Private Key (nsec)
-        </div>
-        <q-input
-          :model-value="generateKeyDialog.showNsec ? generateKeyDialog.nsec : '••••••••••••••••••••••••••••••••••••••••••••••'"
-          readonly
-          dense
-          outlined
-        >
-          <template v-slot:append>
-            <q-btn
-              flat
-              dense
-              :icon="generateKeyDialog.showNsec ? 'visibility_off' : 'visibility'"
-              @click="generateKeyDialog.showNsec = !generateKeyDialog.showNsec"
-            ></q-btn>
-            <q-btn
-              flat
-              dense
-              icon="content_copy"
-              @click="copyText(generateKeyDialog.nsec, 'nsec copied! Keep it safe!')"
-            ></q-btn>
-          </template>
-        </q-input>
-        <div class="text-caption text-negative q-mt-xs">
-          <q-icon name="error" size="xs"></q-icon>
-          Never share your private key!
-        </div>
-      </div>
-      <div class="row q-mt-lg">
-        <q-btn unelevated color="primary" @click="confirmGenerateKey"
-          >Create Merchant</q-btn
-        >
-        <q-btn v-close-popup flat color="grey" class="q-ml-auto">Cancel</q-btn>
-      </div>
-    </q-card>
-  </q-dialog>
 </div>
 {% endblock%}{% block scripts %} {{ window_vars(user) }}
 
diff --git a/tests/conftest.py b/tests/conftest.py
new file mode 100644
index 0000000..22ffb83
--- /dev/null
+++ b/tests/conftest.py
@@ -0,0 +1,27 @@
+"""
+Stub out the nostrmarket root package and all LNbits dependencies so that
+nostr/* unit tests can run without the full LNbits environment.
+
+pytest walks up from tests/ and tries to import the parent __init__.py,
+which pulls in fastapi, lnbits, websocket, etc. We preemptively register
+the parent package as a simple module so that import never happens.
+"""
+
+import sys
+import types
+from pathlib import Path
+
+# Register 'nostrmarket' as an already-imported namespace package
+# pointing at the extension root, so pytest doesn't try to exec __init__.py
+_ext_root = Path(__file__).resolve().parent.parent
+_pkg = types.ModuleType("nostrmarket")
+_pkg.__path__ = [str(_ext_root)]
+_pkg.__package__ = "nostrmarket"
+sys.modules["nostrmarket"] = _pkg
+
+# Also ensure the nostr subpackage is importable
+_nostr_dir = _ext_root / "nostr"
+_nostr_pkg = types.ModuleType("nostrmarket.nostr")
+_nostr_pkg.__path__ = [str(_nostr_dir)]
+_nostr_pkg.__package__ = "nostrmarket.nostr"
+sys.modules["nostrmarket.nostr"] = _nostr_pkg
diff --git a/tests/test_nip44.py b/tests/test_nip44.py
new file mode 100644
index 0000000..3e767a6
--- /dev/null
+++ b/tests/test_nip44.py
@@ -0,0 +1,139 @@
+"""Tests for NIP-44 v2 encryption against official spec test vectors."""
+
+import coincurve
+import pytest
+
+from nostr.nip44 import (
+    calc_padded_len,
+    decrypt,
+    encrypt,
+    get_conversation_key,
+    get_message_keys,
+)
+
+
+def pubkey_from_secret(secret_hex: str) -> str:
+    """Derive x-only public key hex from secret key hex."""
+    sk = coincurve.PrivateKey(bytes.fromhex(secret_hex))
+    return sk.public_key.format(compressed=True)[1:].hex()
+
+
+# --- Test vector from NIP-44 spec ---
+
+SPEC_VECTOR = {
+    "sec1": "0000000000000000000000000000000000000000000000000000000000000001",
+    "sec2": "0000000000000000000000000000000000000000000000000000000000000002",
+    "conversation_key": "c41c775356fd92eadc63ff5a0dc1da211b268cbea22316767095b2871ea1412d",
+    "nonce": "0000000000000000000000000000000000000000000000000000000000000001",
+    "plaintext": "a",
+    "payload": "AgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAABee0G5VSK0/9YypIObAtDKfYEAjD35uVkHyB0F4DwrcNaCXlCWZKaArsGrY6M9wnuTMxWfp1RTN9Xga8no+kF5Vsb",
+}
+
+
+class TestConversationKey:
+    def test_spec_vector(self):
+        pub2 = pubkey_from_secret(SPEC_VECTOR["sec2"])
+        key = get_conversation_key(SPEC_VECTOR["sec1"], pub2)
+        assert key.hex() == SPEC_VECTOR["conversation_key"]
+
+    def test_symmetric(self):
+        """conv(a, B) == conv(b, A)"""
+        pub1 = pubkey_from_secret(SPEC_VECTOR["sec1"])
+        pub2 = pubkey_from_secret(SPEC_VECTOR["sec2"])
+        key_ab = get_conversation_key(SPEC_VECTOR["sec1"], pub2)
+        key_ba = get_conversation_key(SPEC_VECTOR["sec2"], pub1)
+        assert key_ab == key_ba
+
+
+class TestMessageKeys:
+    def test_returns_correct_lengths(self):
+        conv_key = bytes.fromhex(SPEC_VECTOR["conversation_key"])
+        nonce = bytes.fromhex(SPEC_VECTOR["nonce"])
+        chacha_key, chacha_nonce, hmac_key = get_message_keys(conv_key, nonce)
+        assert len(chacha_key) == 32
+        assert len(chacha_nonce) == 12
+        assert len(hmac_key) == 32
+
+    def test_rejects_bad_key_length(self):
+        with pytest.raises(ValueError):
+            get_message_keys(b"\x00" * 16, b"\x00" * 32)
+
+    def test_rejects_bad_nonce_length(self):
+        with pytest.raises(ValueError):
+            get_message_keys(b"\x00" * 32, b"\x00" * 16)
+
+
+class TestPadding:
+    @pytest.mark.parametrize(
+        "unpadded,expected",
+        [
+            (1, 32),
+            (2, 32),
+            (31, 32),
+            (32, 32),
+            (33, 64),
+            (64, 64),
+            (65, 96),
+            (256, 256),
+            (257, 320),
+            (1024, 1024),
+            (65535, 65536),
+        ],
+    )
+    def test_calc_padded_len(self, unpadded, expected):
+        assert calc_padded_len(unpadded) == expected
+
+    def test_rejects_zero(self):
+        with pytest.raises(ValueError):
+            calc_padded_len(0)
+
+
+class TestEncryptDecrypt:
+    def test_spec_vector(self):
+        conv_key = bytes.fromhex(SPEC_VECTOR["conversation_key"])
+        nonce = bytes.fromhex(SPEC_VECTOR["nonce"])
+        payload = encrypt(SPEC_VECTOR["plaintext"], conv_key, nonce)
+        assert payload == SPEC_VECTOR["payload"]
+
+    def test_spec_vector_decrypt(self):
+        conv_key = bytes.fromhex(SPEC_VECTOR["conversation_key"])
+        plaintext = decrypt(SPEC_VECTOR["payload"], conv_key)
+        assert plaintext == SPEC_VECTOR["plaintext"]
+
+    def test_round_trip_short(self):
+        pub2 = pubkey_from_secret(SPEC_VECTOR["sec2"])
+        conv_key = get_conversation_key(SPEC_VECTOR["sec1"], pub2)
+        msg = "x"
+        assert decrypt(encrypt(msg, conv_key), conv_key) == msg
+
+    def test_round_trip_long(self):
+        pub2 = pubkey_from_secret(SPEC_VECTOR["sec2"])
+        conv_key = get_conversation_key(SPEC_VECTOR["sec1"], pub2)
+        msg = "A" * 65535
+        assert decrypt(encrypt(msg, conv_key), conv_key) == msg
+
+    def test_round_trip_unicode(self):
+        pub2 = pubkey_from_secret(SPEC_VECTOR["sec2"])
+        conv_key = get_conversation_key(SPEC_VECTOR["sec1"], pub2)
+        msg = "hello world! \U0001f680\U0001f30e\U0001f4ac"
+        assert decrypt(encrypt(msg, conv_key), conv_key) == msg
+
+    def test_tampered_mac_rejected(self):
+        conv_key = bytes.fromhex(SPEC_VECTOR["conversation_key"])
+        payload = SPEC_VECTOR["payload"]
+        tampered = payload[:-1] + ("a" if payload[-1] != "a" else "b")
+        with pytest.raises(ValueError, match="invalid MAC"):
+            decrypt(tampered, conv_key)
+
+    def test_empty_plaintext_rejected(self):
+        conv_key = bytes.fromhex(SPEC_VECTOR["conversation_key"])
+        with pytest.raises(ValueError, match="invalid plaintext length"):
+            encrypt("", conv_key)
+
+    def test_unknown_version_rejected(self):
+        with pytest.raises(ValueError, match="unknown version"):
+            decrypt("#invalid", bytes(32))
+
+    def test_short_payload_rejected(self):
+        with pytest.raises(ValueError, match="invalid payload size"):
+            decrypt("AAAA", bytes(32))
diff --git a/tests/test_nip59.py b/tests/test_nip59.py
new file mode 100644
index 0000000..e518abf
--- /dev/null
+++ b/tests/test_nip59.py
@@ -0,0 +1,191 @@
+"""Tests for NIP-59 gift wrap protocol."""
+
+import json
+import time
+
+import coincurve
+import pytest
+
+from nostr.nip59 import (
+    create_gift_wrap,
+    create_rumor,
+    create_seal,
+    unseal,
+    unwrap_gift_wrap,
+    unwrap_message,
+    wrap_message,
+)
+
+
+def _generate_keypair() -> tuple[str, str]:
+    """Generate a (privkey_hex, pubkey_hex) pair."""
+    sk = coincurve.PrivateKey()
+    privkey = sk.secret.hex()
+    pubkey = sk.public_key.format(compressed=True)[1:].hex()
+    return privkey, pubkey
+
+
+SENDER_PRIV, SENDER_PUB = _generate_keypair()
+RECIPIENT_PRIV, RECIPIENT_PUB = _generate_keypair()
+
+
+class TestCreateRumor:
+    def test_has_id_but_no_sig(self):
+        rumor = create_rumor(SENDER_PUB, "hello", kind=14)
+        assert rumor.id != ""
+        assert rumor.sig is None
+
+    def test_kind_and_content(self):
+        rumor = create_rumor(SENDER_PUB, "test message", kind=14, tags=[["p", RECIPIENT_PUB]])
+        assert rumor.kind == 14
+        assert rumor.content == "test message"
+        assert rumor.pubkey == SENDER_PUB
+        assert ["p", RECIPIENT_PUB] in rumor.tags
+
+    def test_custom_timestamp(self):
+        ts = 1700000000
+        rumor = create_rumor(SENDER_PUB, "hello", created_at=ts)
+        assert rumor.created_at == ts
+
+
+class TestCreateSeal:
+    def test_kind_13_with_empty_tags(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        assert seal.kind == 13
+        assert seal.tags == []
+        assert seal.pubkey == SENDER_PUB
+
+    def test_is_signed(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        assert seal.sig is not None
+        assert len(seal.sig) == 128  # 64 bytes hex
+
+    def test_content_is_encrypted(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        # Content should be base64 NIP-44 payload, not plaintext JSON
+        assert "hello" not in seal.content
+
+    def test_timestamp_is_randomized(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        now = int(time.time())
+        # Seal timestamp should be in the past (up to 2 days)
+        assert seal.created_at <= now
+        assert seal.created_at >= now - (2 * 24 * 60 * 60 + 10)
+
+
+class TestCreateGiftWrap:
+    def test_kind_1059_with_p_tag(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        wrap = create_gift_wrap(seal, RECIPIENT_PUB)
+        assert wrap.kind == 1059
+        assert ["p", RECIPIENT_PUB] in wrap.tags
+
+    def test_uses_ephemeral_key(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        wrap = create_gift_wrap(seal, RECIPIENT_PUB)
+        # Gift wrap pubkey should be neither sender nor recipient
+        assert wrap.pubkey != SENDER_PUB
+        assert wrap.pubkey != RECIPIENT_PUB
+
+    def test_different_wraps_have_different_ephemeral_keys(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        wrap1 = create_gift_wrap(seal, RECIPIENT_PUB)
+        wrap2 = create_gift_wrap(seal, RECIPIENT_PUB)
+        assert wrap1.pubkey != wrap2.pubkey
+
+
+class TestUnwrap:
+    def test_unwrap_gift_wrap_returns_seal(self):
+        rumor = create_rumor(SENDER_PUB, "hello")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        wrap = create_gift_wrap(seal, RECIPIENT_PUB)
+
+        recovered_seal = unwrap_gift_wrap(wrap, RECIPIENT_PRIV)
+        assert recovered_seal.kind == 13
+        assert recovered_seal.pubkey == SENDER_PUB
+
+    def test_unseal_returns_rumor(self):
+        rumor = create_rumor(SENDER_PUB, "hello world")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+
+        recovered_rumor = unseal(seal, RECIPIENT_PRIV)
+        assert recovered_rumor.content == "hello world"
+        assert recovered_rumor.pubkey == SENDER_PUB
+        assert recovered_rumor.kind == 14
+
+    def test_wrong_key_fails(self):
+        rumor = create_rumor(SENDER_PUB, "secret")
+        seal = create_seal(rumor, SENDER_PRIV, RECIPIENT_PUB)
+        wrap = create_gift_wrap(seal, RECIPIENT_PUB)
+
+        wrong_priv, _ = _generate_keypair()
+        with pytest.raises(Exception):
+            unwrap_message(wrap, wrong_priv)
+
+
+class TestFullRoundTrip:
+    def test_wrap_unwrap_message(self):
+        content = "Are you going to the party tonight?"
+        wrap = wrap_message(content, SENDER_PRIV, SENDER_PUB, RECIPIENT_PUB)
+
+        assert wrap.kind == 1059
+        assert ["p", RECIPIENT_PUB] in wrap.tags
+
+        rumor = unwrap_message(wrap, RECIPIENT_PRIV)
+        assert rumor.content == content
+        assert rumor.pubkey == SENDER_PUB
+        assert rumor.kind == 14
+        assert rumor.sig is None
+
+    def test_wrap_with_custom_kind_and_tags(self):
+        tags = [["p", RECIPIENT_PUB], ["subject", "test"]]
+        wrap = wrap_message(
+            "order data",
+            SENDER_PRIV,
+            SENDER_PUB,
+            RECIPIENT_PUB,
+            kind=14,
+            tags=tags,
+        )
+
+        rumor = unwrap_message(wrap, RECIPIENT_PRIV)
+        assert rumor.content == "order data"
+        assert rumor.kind == 14
+        assert ["subject", "test"] in rumor.tags
+
+    def test_self_wrap_for_archival(self):
+        """Merchant wraps a copy to self (same sender and recipient)."""
+        content = '{"type": 1, "payment_options": [{"type": "ln", "link": "lnbc..."}]}'
+        wrap = wrap_message(content, SENDER_PRIV, SENDER_PUB, SENDER_PUB)
+
+        rumor = unwrap_message(wrap, SENDER_PRIV)
+        assert rumor.content == content
+        assert rumor.pubkey == SENDER_PUB
+
+    def test_json_content_preserved(self):
+        """Order JSON payloads survive the wrap/unwrap cycle."""
+        order = {
+            "type": 0,
+            "id": "test-order-123",
+            "items": [{"product_id": "abc", "quantity": 2}],
+            "shipping_id": "zone-1",
+        }
+        content = json.dumps(order)
+        wrap = wrap_message(content, SENDER_PRIV, SENDER_PUB, RECIPIENT_PUB)
+
+        rumor = unwrap_message(wrap, RECIPIENT_PRIV)
+        recovered_order = json.loads(rumor.content)
+        assert recovered_order == order
+
+    def test_unicode_content(self):
+        content = "Payment received! \u2705 Your order is being processed \U0001f4e6"
+        wrap = wrap_message(content, SENDER_PRIV, SENDER_PUB, RECIPIENT_PUB)
+        rumor = unwrap_message(wrap, RECIPIENT_PRIV)
+        assert rumor.content == content
diff --git a/views_api.py b/views_api.py
index 1e9f5c5..0e78bc3 100644
--- a/views_api.py
+++ b/views_api.py
@@ -1,15 +1,18 @@
 import json
 from http import HTTPStatus
+from typing import List, Optional
 
 from fastapi import Depends
 from fastapi.exceptions import HTTPException
-from lnbits.core.models import WalletTypeInfo
+from lnbits.core.crud import get_account, update_account
 from lnbits.core.services import websocket_updater
 from lnbits.decorators import (
+    WalletTypeInfo,
     require_admin_key,
     require_invoice_key,
 )
 from lnbits.utils.exchange_rates import currencies
+from lnbits.utils.nostr import generate_keypair
 from loguru import logger
 
 from . import nostr_client, nostrmarket_ext
@@ -36,6 +39,7 @@ from .crud import (
     get_last_direct_messages_time,
     get_merchant_by_pubkey,
     get_merchant_for_user,
+    update_merchant_keys,
     get_order,
     get_order_by_event_id,
     get_orders,
@@ -58,6 +62,7 @@ from .crud import (
 )
 from .helpers import normalize_public_key
 from .models import (
+    CreateMerchantRequest,
     Customer,
     DirectMessage,
     DirectMessageType,
@@ -78,8 +83,10 @@ from .models import (
 from .services import (
     build_order_with_payment,
     create_or_update_order_from_dm,
+    provision_merchant,
     reply_to_structured_dm,
     resubscribe_to_all_merchants,
+    send_dm,
     sign_and_send_to_nostr,
     subscribe_to_all_merchants,
     update_merchant_to_nostr,
@@ -88,34 +95,54 @@ from .services import (
 ######################################## MERCHANT ######################################
 
 
+async def _auto_create_merchant(
+    wallet: WalletTypeInfo,
+    config: MerchantConfig | None = None,
+) -> Merchant:
+    """
+    Lazy fallback: provision a merchant from the user's account keypair when
+    the LNbits-side eager provisioning didn't run (e.g., older accounts, or
+    upstream LNbits without our signup hook).
+
+    Delegates to services.provision_merchant — the canonical implementation.
+    """
+    account = await get_account(wallet.wallet.user)
+    assert account, "User account not found"
+
+    # In our fork, accounts always have keypairs. Generate as fallback only
+    # if somehow missing (e.g., upstream LNbits where this isn't auto-set).
+    if not account.pubkey or not account.prvkey:
+        private_key, public_key = generate_keypair()
+        account.pubkey = public_key
+        account.prvkey = private_key
+        await update_account(account)
+
+    merchant = await provision_merchant(
+        user_id=wallet.wallet.user,
+        wallet_id=wallet.wallet.id,
+        public_key=account.pubkey,
+        private_key=account.prvkey,
+        display_name=account.username,
+        config=config,
+    )
+
+    await resubscribe_to_all_merchants()
+    await nostr_client.merchant_temp_subscription(account.pubkey)
+
+    return merchant
+
+
 @nostrmarket_ext.post("/api/v1/merchant")
 async def api_create_merchant(
-    data: PartialMerchant,
+    data: CreateMerchantRequest,
     wallet: WalletTypeInfo = Depends(require_admin_key),
 ) -> Merchant:
 
     try:
-        merchant = await get_merchant_by_pubkey(data.public_key)
-        assert merchant is None, "A merchant already uses this public key"
+        merchant = await get_merchant_for_user(wallet.wallet.user)
+        assert merchant is None, "A merchant already exists for this user"
 
-        merchant = await create_merchant(wallet.wallet.user, data)
-
-        await create_zone(
-            merchant.id,
-            Zone(
-                id=f"online-{merchant.public_key}",
-                name="Online",
-                currency="sat",
-                cost=0,
-                countries=["Free (digital)"],
-            ),
-        )
-
-        await resubscribe_to_all_merchants()
-
-        await nostr_client.merchant_temp_subscription(data.public_key)
-
-        return merchant
+        return await _auto_create_merchant(wallet, data.config)
     except AssertionError as ex:
         raise HTTPException(
             status_code=HTTPStatus.BAD_REQUEST,
@@ -132,12 +159,13 @@ async def api_create_merchant(
 @nostrmarket_ext.get("/api/v1/merchant")
 async def api_get_merchant(
     wallet: WalletTypeInfo = Depends(require_invoice_key),
-) -> Merchant | None:
+) -> Merchant:
 
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         if not merchant:
-            return None
+            # Auto-provision merchant from the user's account keypair
+            merchant = await _auto_create_merchant(wallet)
 
         merchant = await touch_merchant(wallet.wallet.user, merchant.id)
         assert merchant
@@ -145,6 +173,11 @@ async def api_get_merchant(
         assert merchant.time
         merchant.config.restore_in_progress = (merchant.time - last_dm_time) < 30
 
+        # Detect keypair rotation: account key no longer matches merchant key
+        account = await get_account(wallet.wallet.user)
+        if account and account.pubkey and account.pubkey != merchant.public_key:
+            merchant.config.key_mismatch = True
+
         return merchant
     except Exception as ex:
         logger.warning(ex)
@@ -190,6 +223,76 @@ async def api_delete_merchant(
         await subscribe_to_all_merchants()
 
 
+@nostrmarket_ext.post("/api/v1/merchant/{merchant_id}/migrate-keys")
+async def api_migrate_merchant_keys(
+    merchant_id: str,
+    wallet: WalletTypeInfo = Depends(require_admin_key),
+) -> Merchant:
+    """
+    Migrate a merchant to the current account keypair.
+
+    When a user rotates their Nostr keypair, the merchant still holds the old
+    key. This endpoint updates the merchant's keys to match the account,
+    then republishes all stalls and products under the new identity.
+
+    Orders and DM history are preserved (they reference customer pubkeys,
+    not the merchant key). Old stall/product events on relays become
+    orphaned — clients following the new pubkey will see the fresh events.
+    """
+    try:
+        merchant = await get_merchant_for_user(wallet.wallet.user)
+        assert merchant, "Merchant cannot be found"
+        assert merchant.id == merchant_id, "Wrong merchant ID"
+
+        account = await get_account(wallet.wallet.user)
+        assert account and account.pubkey and account.prvkey, (
+            "Account has no Nostr keypair"
+        )
+
+        if account.pubkey == merchant.public_key:
+            return merchant  # already in sync
+
+        # Check no other merchant is using the new pubkey
+        existing = await get_merchant_by_pubkey(account.pubkey)
+        assert existing is None, (
+            "Another merchant already uses this public key"
+        )
+
+        old_pubkey = merchant.public_key
+
+        # Update merchant keys in DB
+        merchant = await update_merchant_keys(
+            wallet.wallet.user, merchant.id,
+            account.prvkey, account.pubkey,
+        )
+        assert merchant
+
+        # Republish all stalls and products under the new key
+        merchant = await update_merchant_to_nostr(merchant)
+
+        logger.info(
+            f"[NOSTRMARKET] Migrated merchant {merchant.id} "
+            f"from {old_pubkey[:16]}... to {account.pubkey[:16]}..."
+        )
+
+        # Resubscribe with new pubkey
+        await resubscribe_to_all_merchants()
+
+        return merchant
+
+    except AssertionError as ex:
+        raise HTTPException(
+            status_code=HTTPStatus.BAD_REQUEST,
+            detail=str(ex),
+        ) from ex
+    except Exception as ex:
+        logger.warning(ex)
+        raise HTTPException(
+            status_code=HTTPStatus.INTERNAL_SERVER_ERROR,
+            detail="Cannot migrate merchant keys",
+        ) from ex
+
+
 @nostrmarket_ext.patch("/api/v1/merchant/{merchant_id}")
 async def api_update_merchant(
     merchant_id: str,
@@ -329,7 +432,7 @@ async def api_delete_merchant_on_nostr(
 @nostrmarket_ext.get("/api/v1/zone")
 async def api_get_zones(
     wallet: WalletTypeInfo = Depends(require_invoice_key),
-) -> list[Zone]:
+) -> List[Zone]:
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"
@@ -529,7 +632,7 @@ async def api_get_stall(
 
 @nostrmarket_ext.get("/api/v1/stall")
 async def api_get_stalls(
-    pending: bool | None = False,
+    pending: Optional[bool] = False,
     wallet: WalletTypeInfo = Depends(require_invoice_key),
 ):
     try:
@@ -553,7 +656,7 @@ async def api_get_stalls(
 @nostrmarket_ext.get("/api/v1/stall/product/{stall_id}")
 async def api_get_stall_products(
     stall_id: str,
-    pending: bool | None = False,
+    pending: Optional[bool] = False,
     wallet: WalletTypeInfo = Depends(require_invoice_key),
 ):
     try:
@@ -577,9 +680,9 @@ async def api_get_stall_products(
 @nostrmarket_ext.get("/api/v1/stall/order/{stall_id}")
 async def api_get_stall_orders(
     stall_id: str,
-    paid: bool | None = None,
-    shipped: bool | None = None,
-    pubkey: str | None = None,
+    paid: Optional[bool] = None,
+    shipped: Optional[bool] = None,
+    pubkey: Optional[str] = None,
     wallet: WalletTypeInfo = Depends(require_invoice_key),
 ):
     try:
@@ -652,6 +755,21 @@ async def api_create_product(
         assert stall, "Stall missing for product"
         data.config.currency = stall.currency
 
+        # Re-publish the parent stall before publishing the product. NIP-33
+        # parameterized replaceable events make this idempotent on relays.
+        # This guarantees the customer client never sees a product whose
+        # parent stall isn't on the relay (e.g., when the original stall
+        # publish failed transiently or never ran).
+        try:
+            stall_event = await sign_and_send_to_nostr(merchant, stall)
+            stall.event_id = stall_event.id
+            await update_stall(merchant.id, stall)
+        except Exception as ex:
+            logger.warning(
+                f"[NOSTRMARKET] Failed to refresh stall {stall.id} "
+                f"before product publish: {ex}"
+            )
+
         product = await create_product(merchant.id, data=data)
 
         event = await sign_and_send_to_nostr(merchant, product)
@@ -713,7 +831,7 @@ async def api_update_product(
 async def api_get_product(
     product_id: str,
     wallet: WalletTypeInfo = Depends(require_invoice_key),
-) -> Product | None:
+) -> Optional[Product]:
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"
@@ -798,9 +916,9 @@ async def api_get_order(
 
 @nostrmarket_ext.get("/api/v1/order")
 async def api_get_orders(
-    paid: bool | None = None,
-    shipped: bool | None = None,
-    pubkey: str | None = None,
+    paid: Optional[bool] = None,
+    shipped: Optional[bool] = None,
+    pubkey: Optional[str] = None,
     wallet: WalletTypeInfo = Depends(require_invoice_key),
 ):
     try:
@@ -844,27 +962,11 @@ async def api_update_order_status(
             ensure_ascii=False,
         )
 
-        dm_event = merchant.build_dm_event(dm_content, order.public_key)
-
-        dm = PartialDirectMessage(
-            event_id=dm_event.id,
-            event_created_at=dm_event.created_at,
-            message=dm_content,
-            public_key=order.public_key,
-            type=DirectMessageType.ORDER_PAID_OR_SHIPPED.value,
-        )
-        await create_direct_message(merchant.id, dm)
-
-        await nostr_client.publish_nostr_event(dm_event)
-        await websocket_updater(
-            merchant.id,
-            json.dumps(
-                {
-                    "type": f"dm:{dm.type}",
-                    "customerPubkey": order.public_key,
-                    "dm": dm.dict(),
-                }
-            ),
+        await send_dm(
+            merchant,
+            order.public_key,
+            DirectMessageType.ORDER_PAID_OR_SHIPPED.value,
+            dm_content,
         )
 
         return order
@@ -886,7 +988,7 @@ async def api_update_order_status(
 async def api_restore_order(
     event_id: str,
     wallet: WalletTypeInfo = Depends(require_admin_key),
-) -> Order | None:
+) -> Optional[Order]:
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"
@@ -1013,7 +1115,7 @@ async def api_reissue_order_invoice(
 @nostrmarket_ext.get("/api/v1/message/{public_key}")
 async def api_get_messages(
     public_key: str, wallet: WalletTypeInfo = Depends(require_invoice_key)
-) -> list[DirectMessage]:
+) -> List[DirectMessage]:
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"
@@ -1042,14 +1144,13 @@ async def api_create_message(
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"
 
-        dm_event = merchant.build_dm_event(data.message, data.public_key)
-        data.event_id = dm_event.id
-        data.event_created_at = dm_event.created_at
-
-        dm = await create_direct_message(merchant.id, data)
-        await nostr_client.publish_nostr_event(dm_event)
-
-        return dm
+        dm_reply = await send_dm(
+            merchant,
+            data.public_key,
+            data.type,
+            data.message,
+        )
+        return dm_reply
     except AssertionError as ex:
         raise HTTPException(
             status_code=HTTPStatus.BAD_REQUEST,
@@ -1069,7 +1170,7 @@ async def api_create_message(
 @nostrmarket_ext.get("/api/v1/customer")
 async def api_get_customers(
     wallet: WalletTypeInfo = Depends(require_invoice_key),
-) -> list[Customer]:
+) -> List[Customer]:
     try:
         merchant = await get_merchant_for_user(wallet.wallet.user)
         assert merchant, "Merchant cannot be found"