diff --git a/lib/reducers/message-reducer.js b/lib/reducers/message-reducer.js
--- a/lib/reducers/message-reducer.js
+++ b/lib/reducers/message-reducer.js
@@ -59,6 +59,7 @@
   messageStoreOpsHandlers,
   type MessageStoreOperation,
   type ReplaceMessageOperation,
+  type ReplaceMessageStoreLocalMessageInfoOperation,
 } from '../ops/message-store-ops.js';
 import { pendingToRealizedThreadIDsSelector } from '../selectors/thread-selectors.js';
 import {
@@ -1813,7 +1814,12 @@
       messageStore: processedMessageStore,
     };
   } else if (action.type === processDMOpsActionType) {
-    const { rawMessageInfos, updateInfos } = action.payload;
+    const {
+      rawMessageInfos,
+      updateInfos,
+      outboundP2PMessages,
+      messageIDWithoutAutoRetry,
+    } = action.payload;
     if (rawMessageInfos.length === 0 && updateInfos.length === 0) {
       return { messageStoreOperations: [], messageStore };
     }
@@ -1824,12 +1830,44 @@
       {},
     );
 
-    return mergeNewMessages(
-      messageStore,
-      messagesResult.rawMessageInfos,
-      messagesResult.truncationStatuses,
-      newThreadInfos,
-    );
+    const { messageStoreOperations, messageStore: newMessageStore } =
+      mergeNewMessages(
+        messageStore,
+        messagesResult.rawMessageInfos,
+        messagesResult.truncationStatuses,
+        newThreadInfos,
+      );
+
+    if (
+      !messageIDWithoutAutoRetry ||
+      !outboundP2PMessages ||
+      outboundP2PMessages.length === 0
+    ) {
+      return { messageStoreOperations, messageStore: newMessageStore };
+    }
+
+    const newMessageID: string = messageIDWithoutAutoRetry;
+
+    // Messages to other peers that can be retried from UI,
+    // we need to track statuses of each one.
+    const outboundP2PMessageIDs = outboundP2PMessages.map(msg => msg.messageID);
+    const localOperation: ReplaceMessageStoreLocalMessageInfoOperation = {
+      type: 'replace_local_message_info',
+      payload: {
+        id: newMessageID,
+        localMessageInfo: {
+          sendFailed: false,
+          outboundP2PMessageIDs,
+        },
+      },
+    };
+
+    return {
+      messageStoreOperations: [...messageStoreOperations, localOperation],
+      messageStore: processMessageStoreOperations(newMessageStore, [
+        localOperation,
+      ]),
+    };
   }
   return { messageStoreOperations: [], messageStore };
 }
diff --git a/lib/shared/dm-ops/process-dm-ops.js b/lib/shared/dm-ops/process-dm-ops.js
--- a/lib/shared/dm-ops/process-dm-ops.js
+++ b/lib/shared/dm-ops/process-dm-ops.js
@@ -161,6 +161,15 @@
         });
       }
 
+      let messageIDWithoutAutoRetry: ?string = null;
+      if (
+        dmOperationSpecification.type ===
+          dmOperationSpecificationTypes.OUTBOUND &&
+        !dmOpSpecs[dmOperationSpecification.op.type].supportsAutoRetry
+      ) {
+        messageIDWithoutAutoRetry = dmOperationSpecification.op.messageID;
+      }
+
       dispatchWithMetadata(
         {
           type: processDMOpsActionType,
@@ -168,6 +177,7 @@
             rawMessageInfos,
             updateInfos,
             outboundP2PMessages,
+            messageIDWithoutAutoRetry,
           },
         },
         metadata,
diff --git a/lib/types/dm-ops.js b/lib/types/dm-ops.js
--- a/lib/types/dm-ops.js
+++ b/lib/types/dm-ops.js
@@ -352,6 +352,10 @@
   +rawMessageInfos: $ReadOnlyArray<RawMessageInfo>,
   +updateInfos: $ReadOnlyArray<ClientUpdateInfo>,
   +outboundP2PMessages: ?$ReadOnlyArray<OutboundP2PMessage>,
+  // For messages that could be retried from UI, we need to bind DM `messageID`
+  // with `outboundP2PMessages` to keep track of whether all P2P messages
+  // were queued on Tunnelbroker.
+  +messageIDWithoutAutoRetry: ?string,
 };
 
 export const queueDMOpsActionType = 'QUEUE_DM_OPS';