diff --git a/lib/tunnelbroker/peer-to-peer-context.js b/lib/tunnelbroker/peer-to-peer-context.js
--- a/lib/tunnelbroker/peer-to-peer-context.js
+++ b/lib/tunnelbroker/peer-to-peer-context.js
@@ -38,7 +38,9 @@
     outboundMessageIDs: ?$ReadOnlyArray<string>,
     dmOpID: ?string,
   ) => void,
-  +sendDMOperation: (op: OutboundDMOperationSpecification) => Promise<void>,
+  +sendDMOperation: (
+    op: OutboundDMOperationSpecification,
+  ) => Promise<$ReadOnlyArray<string>>,
   +broadcastEphemeralMessage: (
     contentPayload: string,
     recipients: $ReadOnlyArray<{ +userID: string, +deviceID: string }>,
@@ -61,14 +63,19 @@
   identityContext: IdentityClientContextType,
   peerOlmSessionsCreator: (userID: string, deviceID: string) => Promise<void>,
   messageIDs: ?$ReadOnlyArray<string>,
-): Promise<void> {
-  const authMetadata = await identityContext.getAuthMetadata();
+): Promise<$ReadOnlyArray<string>> {
+  let authMetadata;
+  try {
+    authMetadata = await identityContext.getAuthMetadata();
+  } catch (e) {
+    return [];
+  }
   if (
     !authMetadata.deviceID ||
     !authMetadata.userID ||
     !authMetadata.accessToken
   ) {
-    return;
+    return [];
   }
 
   const { olmAPI, sqliteAPI } = getConfig();
@@ -90,31 +97,38 @@
     }
   }
 
+  const sentMessagesMap: { [messageID: string]: boolean } = {};
+
   const sendMessageToPeer = async (
     message: OutboundP2PMessage,
   ): Promise<void> => {
     if (!authMetadata.deviceID || !authMetadata.userID) {
       return;
     }
-    const encryptedMessage: EncryptedMessage = {
-      type: peerToPeerMessageTypes.ENCRYPTED_MESSAGE,
-      senderInfo: {
-        deviceID: authMetadata.deviceID,
-        userID: authMetadata.userID,
-      },
-      encryptedData: JSON.parse(message.ciphertext),
-    };
-    await sendMessage(
-      {
-        deviceID: message.deviceID,
-        payload: JSON.stringify(encryptedMessage),
-      },
-      message.messageID,
-    );
-    await sqliteAPI.markOutboundP2PMessageAsSent(
-      message.messageID,
-      message.deviceID,
-    );
+    try {
+      const encryptedMessage: EncryptedMessage = {
+        type: peerToPeerMessageTypes.ENCRYPTED_MESSAGE,
+        senderInfo: {
+          deviceID: authMetadata.deviceID,
+          userID: authMetadata.userID,
+        },
+        encryptedData: JSON.parse(message.ciphertext),
+      };
+      await sendMessage(
+        {
+          deviceID: message.deviceID,
+          payload: JSON.stringify(encryptedMessage),
+        },
+        message.messageID,
+      );
+      await sqliteAPI.markOutboundP2PMessageAsSent(
+        message.messageID,
+        message.deviceID,
+      );
+      sentMessagesMap[message.messageID] = true;
+    } catch (e) {
+      console.error(e);
+    }
   };
 
   for (const peerDeviceID in devicesMap) {
@@ -157,9 +171,14 @@
         }
       } else if (message.status === outboundP2PMessageStatuses.encrypted) {
         await sendMessageToPeer(message);
+      } else if (message.status === outboundP2PMessageStatuses.sent) {
+        // Handle edge-case when message was sent, but it wasn't updated
+        // in the message store.
+        sentMessagesMap[message.messageID] = true;
       }
     }
   }
+  return Object.keys(sentMessagesMap);
 }
 
 const AUTOMATIC_RETRY_FREQUENCY = 30 * 1000;
@@ -173,15 +192,24 @@
 
   const dispatch = useDispatch();
   const dmOpsSendingPromiseResolvers = React.useRef<
-    Map<string, { +resolve: () => mixed, +reject: Error => mixed }>,
+    Map<
+      string,
+      {
+        +resolve: ($ReadOnlyArray<string>) => mixed,
+        +reject: Error => mixed,
+      },
+    >,
   >(new Map());
   const allPeerUserIDAndDeviceIDs = useSelector(getAllPeerUserIDAndDeviceIDs);
   const currentUserInfo = useSelector(state => state.currentUserInfo);
 
+  // This returns a promise that will be resolved with arrays of successfully
+  // sent messages, so in case of failing all messages (e.g. no internet
+  // connection) it will still resolve but with an empty array.
   const sendDMOperation = React.useCallback(
     async (op: OutboundDMOperationSpecification) => {
       const dmOpID = uuid.v4();
-      const promise = new Promise<void>((resolve, reject) => {
+      const promise = new Promise<$ReadOnlyArray<string>>((resolve, reject) => {
         dmOpsSendingPromiseResolvers.current.set(dmOpID, { resolve, reject });
       });
 
@@ -223,7 +251,7 @@
           do {
             const queueFront = processingQueue.current.shift();
             try {
-              await processOutboundP2PMessages(
+              const sentMessagesIDs = await processOutboundP2PMessages(
                 sendMessageToDevice,
                 identityContext,
                 peerOlmSessionsCreator,
@@ -232,7 +260,7 @@
               if (queueFront.dmOpID) {
                 dmOpsSendingPromiseResolvers.current
                   .get(queueFront.dmOpID)
-                  ?.resolve?.();
+                  ?.resolve?.(sentMessagesIDs);
               }
             } catch (e) {
               console.log(