diff --git a/src/state/messages/convo/agent.ts b/src/state/messages/convo/agent.ts
index 6d59e1369b..3b3a532d30 100644
--- a/src/state/messages/convo/agent.ts
+++ b/src/state/messages/convo/agent.ts
@@ -735,6 +735,8 @@ export class Convo {
     }
   }
 
+  private pendingFailed = false
+
   async sendMessage(message: ChatBskyConvoSendMessage.InputSchema['message']) {
     // Ignore empty messages for now since they have no other purpose atm
     if (!message.text.trim()) return
@@ -748,9 +750,12 @@ export class Convo {
       message,
     })
     // remove on each send, it might go through now without user having to click
+    // TODO do need htis?
     this.footerItems.delete(ConvoItemError.PendingFailed)
     this.commit()
 
+    // TODO maybe ignore if failed?
+
     if (!this.isProcessingPendingMessages) {
       this.processPendingMessages()
     }
@@ -805,16 +810,7 @@ export class Convo {
       this.commit()
     } catch (e: any) {
       logger.error(e, {context: `Convo: failed to send message`})
-      this.footerItems.set(ConvoItemError.PendingFailed, {
-        type: 'error-recoverable',
-        key: ConvoItemError.PendingFailed,
-        code: ConvoItemError.PendingFailed,
-        retry: () => {
-          this.footerItems.delete(ConvoItemError.PendingFailed)
-          this.commit()
-          this.batchRetryPendingMessages()
-        },
-      })
+      this.pendingFailed = true
       this.commit()
     } finally {
       this.isProcessingPendingMessages = false
@@ -868,16 +864,7 @@ export class Convo {
       )
     } catch (e: any) {
       logger.error(e, {context: `Convo: failed to batch retry messages`})
-      this.footerItems.set(ConvoItemError.PendingFailed, {
-        type: 'error-recoverable',
-        key: ConvoItemError.PendingFailed,
-        code: ConvoItemError.PendingFailed,
-        retry: () => {
-          this.footerItems.delete(ConvoItemError.PendingFailed)
-          this.commit()
-          this.batchRetryPendingMessages()
-        },
-      })
+      this.pendingFailed = true
       this.commit()
     }
   }
@@ -968,6 +955,13 @@ export class Convo {
           sender: this.sender!,
         },
         nextMessage: null,
+        retry: this.pendingFailed
+          ? () => {
+              this.pendingFailed = false
+              this.commit()
+              this.batchRetryPendingMessages()
+            }
+          : undefined,
       })
     })
 
diff --git a/src/state/messages/convo/types.ts b/src/state/messages/convo/types.ts
index 6ce4d40bd6..2fcfacabc8 100644
--- a/src/state/messages/convo/types.ts
+++ b/src/state/messages/convo/types.ts
@@ -83,7 +83,7 @@ export type ConvoDispatch =
 
 export type ConvoItem =
   | {
-      type: 'message' | 'pending-message'
+      type: 'message'
       key: string
       message: ChatBskyConvoDefs.MessageView
       nextMessage:
@@ -91,6 +91,19 @@ export type ConvoItem =
         | ChatBskyConvoDefs.DeletedMessageView
         | null
     }
+  | {
+      type: 'pending-message'
+      key: string
+      message: ChatBskyConvoDefs.MessageView
+      nextMessage:
+        | ChatBskyConvoDefs.MessageView
+        | ChatBskyConvoDefs.DeletedMessageView
+        | null
+      /**
+       * Retry sending the message. If present, the message is in a failed state.
+       */
+      retry?: () => void
+    }
   | {
       type: 'deleted-message'
       key: string