diff --git a/src/node/retry.rs b/src/node/retry.rs
index 5b25df2..0eb371d 100644
--- a/src/node/retry.rs
+++ b/src/node/retry.rs
@@ -259,6 +259,25 @@ impl Node {
 
             let peer_config = state.peer_config.clone();
 
+            // Refresh the peer's overlay advert before retrying. The cache is
+            // read-only on hit (see fetch_advert), so every retry without a
+            // refetch dials the same cached endpoint — and the most common
+            // reason a peer ended up in retry_pending is that the cached
+            // endpoint just stopped working (NAT rebind, port change, peer
+            // restart on a different port). Without this refresh the retry
+            // loop dials the same dead address forever.
+            //
+            // refetch_advert_for_stale_check uses the relay's advert as
+            // ground truth: replaces the cache if there's a newer one,
+            // evicts if the relay has nothing, otherwise leaves it. Cheap
+            // (one Filter fetch with 2s timeout) and bounded by the retry
+            // backoff cadence.
+            if let Some(bootstrap) = self.nostr_discovery.clone() {
+                let _ = bootstrap
+                    .refetch_advert_for_stale_check(&peer_config.npub)
+                    .await;
+            }
+
             match self.initiate_peer_connection(&peer_config).await {
                 Ok(()) => {
                     // Push retry_after_ms past the handshake timeout window so