diff --git a/nostr/nostr_client.py b/nostr/nostr_client.py
index 4de332f..e0ae70f 100644
--- a/nostr/nostr_client.py
+++ b/nostr/nostr_client.py
@@ -19,6 +19,9 @@ from websocket import WebSocketApp
 from .event import NostrEvent
 
 MAX_SEEN_EVENTS = 500
+# How many times a dequeued req is retried before it is dropped. Bounded
+# so one unsendable message can't block every later publish behind it.
+MAX_SEND_ATTEMPTS = 3
 
 
 class NostrClient:
@@ -78,17 +81,37 @@ class NostrClient:
 
     async def run_forever(self):
         self.running = True
+        # A req that was dequeued but whose send raised. It is already
+        # off the queue, so dropping it loses the publish outright and
+        # the caller has long since been told it succeeded (the queue
+        # put returns immediately). Hold it across the reconnect and
+        # retry instead.
+        held_req: list | None = None
+        held_attempts = 0
         while self.running:
             try:
                 if not self.is_websocket_connected:
                     self.ws = await self.connect()
                     await asyncio.sleep(5)
 
-                req = await self.send_req_queue.get()
+                if held_req is not None:
+                    req = held_req
+                else:
+                    req = await self.send_req_queue.get()
+                held_req, held_attempts = req, held_attempts + 1
                 assert self.ws
                 self.ws.send(json.dumps(req))
+                held_req, held_attempts = None, 0
             except Exception as ex:
                 logger.warning(f"[EVENTS] NostrClient error: {ex}")
+                if held_req is not None and held_attempts >= MAX_SEND_ATTEMPTS:
+                    # Bounded: a req the relay or the socket will never
+                    # accept must not wedge the queue behind it forever.
+                    logger.error(
+                        f"[EVENTS] Dropping req after {held_attempts} "
+                        f"failed sends: {held_req[0]}"
+                    )
+                    held_req, held_attempts = None, 0
                 await asyncio.sleep(60)
 
     def is_duplicate_event(self, event_id: str) -> bool: