diff --git a/ts/session/messages/outgoing/content/sync/index.ts b/ts/session/messages/outgoing/content/sync/index.ts
index 804f4f561..53cb667a4 100644
--- a/ts/session/messages/outgoing/content/sync/index.ts
+++ b/ts/session/messages/outgoing/content/sync/index.ts
@@ -1,3 +1 @@
-import { SyncMessage } from './SyncMessage';
-
-export { SyncMessage };
+export * from './SyncMessage';
diff --git a/ts/session/sending/MessageQueue.ts b/ts/session/sending/MessageQueue.ts
index c53345fa9..9980195a2 100644
--- a/ts/session/sending/MessageQueue.ts
+++ b/ts/session/sending/MessageQueue.ts
@@ -102,7 +102,13 @@ export class MessageQueue implements MessageQueueInterface {
     // Open groups
     if (message instanceof OpenGroupMessage) {
       // No queue needed for Open Groups; send directly
-      await MessageSender.sendToOpenGroup(message);
+
+      try {
+        await MessageSender.sendToOpenGroup(message);
+        this.events.emit('success', message);
+      } catch (e) {
+        this.events.emit('fail', message, e);
+      }
 
       return true;
     }
@@ -113,7 +119,7 @@ export class MessageQueue implements MessageQueueInterface {
   public async sendSyncMessage(message: ContentMessage, sendTo: Array<PubKey>) {
     // Sync with our devices
     const promises = sendTo.map(async device => {
-      const syncMessage = await SyncMessageUtils.from(message);
+      const syncMessage = SyncMessageUtils.from(message);
 
       return this.process(device, syncMessage);
     });
@@ -124,9 +130,10 @@ export class MessageQueue implements MessageQueueInterface {
   public async processPending(device: PubKey) {
     const messages = this.pendingMessageCache.getForDevice(device);
 
+    // TODO: Simpify the isMediumGroup check to not rely on ANY window objects
+    // const isMediumGroup = messages.some(m => m instanceof MediumGroupMessage);
+    const isMediumGroup = false;
     const hasSession = SessionProtocol.hasSession(device);
-    const conversation = ConversationController.get(device.key);
-    const isMediumGroup = conversation.isMediumGroup();
 
     if (!isMediumGroup && !hasSession) {
       await SessionProtocol.sendSessionRequestIfNeeded(device);
@@ -160,7 +167,13 @@ export class MessageQueue implements MessageQueueInterface {
   }
 
   private async process(device: PubKey, message?: ContentMessage) {
-    if (!message || message instanceof SessionRequestMessage) {
+    if (!message) {
+      return;
+    }
+
+    if (message instanceof SessionRequestMessage) {
+      void SessionProtocol.sendSessionRequest(message, device);
+
       return;
     }
 
diff --git a/ts/session/sending/MessageQueueInterface.ts b/ts/session/sending/MessageQueueInterface.ts
index 9f58357a9..c3ee606aa 100644
--- a/ts/session/sending/MessageQueueInterface.ts
+++ b/ts/session/sending/MessageQueueInterface.ts
@@ -10,8 +10,8 @@ import { PubKey } from '../types';
 type GroupMessageType = OpenGroupMessage | ClosedGroupMessage;
 
 export interface MessageQueueInterfaceEvents {
-  success: (message: RawMessage) => void;
-  fail: (message: RawMessage, error: Error) => void;
+  success: (message: RawMessage | OpenGroupMessage) => void;
+  fail: (message: RawMessage | OpenGroupMessage, error: Error) => void;
 }
 
 export interface MessageQueueInterface {
diff --git a/ts/session/utils/SyncMessageUtils.ts b/ts/session/utils/SyncMessageUtils.ts
index e14c79c24..92c1116c0 100644
--- a/ts/session/utils/SyncMessageUtils.ts
+++ b/ts/session/utils/SyncMessageUtils.ts
@@ -8,9 +8,7 @@ import { ConversationController, Whisper } from '../../window';
 
 import { ContentMessage, SyncMessage } from '../messages/outgoing';
 
-export async function from(
-  message: ContentMessage
-): Promise<SyncMessage | undefined> {
+export function from(message: ContentMessage): SyncMessage | undefined {
   // const { timestamp, identifier } = message;
 
   // Stubbed for now
@@ -20,9 +18,9 @@ export async function from(
 export async function canSync(message: ContentMessage): Promise<boolean> {
   // This function should be agnostic to the device; it shouldn't need
   // to know about the recipient
-  // return Boolean(from(message));
+
   // Stubbed for now
-  return true;
+  return Boolean(from(message));
 }
 
 export async function getSyncContacts(): Promise<Array<any> | undefined> {
diff --git a/ts/test/test-utils/testUtils.ts b/ts/test/test-utils/testUtils.ts
index 4cfbc50ac..481a21e5a 100644
--- a/ts/test/test-utils/testUtils.ts
+++ b/ts/test/test-utils/testUtils.ts
@@ -67,3 +67,4 @@ export function generateChatMessage(): ChatMessage {
     preview: undefined,
   });
 }
+