diff --git a/ui/src/pages/chat/chat-pane-context.ts b/ui/src/pages/chat/chat-pane-context.ts
index 2c83e6eacafa..b8c16d66b950 100644
--- a/ui/src/pages/chat/chat-pane-context.ts
+++ b/ui/src/pages/chat/chat-pane-context.ts
@@ -190,8 +190,10 @@ export abstract class ChatPaneContext extends ChatPaneLifecycle {
       this.cancelHeaderRename();
       cancelChatScroll(state);
       releaseChatMediaResourceSubscriber(state.requestUpdate);
-      if (state.client) {
-        markQueuedChatSendsWaitingForReconnect(state);
+      if (wasConnected) {
+        if (snapshot.phase === "connected") {
+          markQueuedChatSendsWaitingForReconnect(state);
+        }
         state.chatSending = false;
         state.chatSendingScopeKey = null;
       }