diff --git a/src/state/messages/convo/agent.ts b/src/state/messages/convo/agent.ts
index fea4630f0f..3e4cabfdc4 100644
--- a/src/state/messages/convo/agent.ts
+++ b/src/state/messages/convo/agent.ts
@@ -288,7 +288,7 @@ export class Convo {
               if (this.convo) {
                 this.status = ConvoStatus.Ready
                 this.refreshConvo()
-                this.batchRetryPendingMessages()
+                this.attemptCleanup()
               } else {
                 this.status = ConvoStatus.Initializing
                 this.setup()
@@ -392,6 +392,12 @@ export class Convo {
     this.dispatch({event: ConvoDispatchEvent.Init})
   }
 
+  private attemptCleanup() {
+    // override what's here in case remote convo state has changed
+    this.pendingMessageFailure = 'recoverable'
+    this.batchRetryPendingMessages()
+  }
+
   private async setup() {
     try {
       const {convo, sender, recipients} = await this.fetchConvo()