diff --git a/ts/session/sending/MessageQueue.ts b/ts/session/sending/MessageQueue.ts
index b675b857a..cbb2e817e 100644
--- a/ts/session/sending/MessageQueue.ts
+++ b/ts/session/sending/MessageQueue.ts
@@ -26,7 +26,7 @@ import { UserUtil } from '../../util';
 
 export class MessageQueue implements MessageQueueInterface {
   public readonly events: TypedEventEmitter<MessageQueueInterfaceEvents>;
-  private readonly jobQueues: Map<PubKey, JobQueue> = new Map();
+  private readonly jobQueues: Map<string, JobQueue> = new Map();
   private readonly pendingMessageCache: PendingMessageCache;
 
   constructor(cache?: PendingMessageCache) {
@@ -162,17 +162,19 @@ export class MessageQueue implements MessageQueueInterface {
       const messageId = String(message.timestamp);
 
       if (!jobQueue.has(messageId)) {
-        try {
-          await jobQueue.addWithId(messageId, async () =>
-            MessageSender.send(message)
-          );
-          this.events.emit('success', message);
-        } catch (e) {
-          this.events.emit('fail', message, e);
-        } finally {
-          // Remove from the cache because retrying is done in the sender
-          void this.pendingMessageCache.remove(message);
-        }
+        // We put the event handling inside this job to avoid sending duplicate events
+        const job = async () => {
+          try {
+            await MessageSender.send(message);
+            this.events.emit('success', message);
+          } catch (e) {
+            this.events.emit('fail', message, e);
+          } finally {
+            // Remove from the cache because retrying is done in the sender
+            void this.pendingMessageCache.remove(message);
+          }
+        };
+        await jobQueue.addWithId(messageId, job);
       }
     });
   }
@@ -203,10 +205,10 @@ export class MessageQueue implements MessageQueueInterface {
   }
 
   private getJobQueue(device: PubKey): JobQueue {
-    let queue = this.jobQueues.get(device);
+    let queue = this.jobQueues.get(device.key);
     if (!queue) {
       queue = new JobQueue();
-      this.jobQueues.set(device, queue);
+      this.jobQueues.set(device.key, queue);
     }
 
     return queue;
diff --git a/ts/session/types/PubKey.ts b/ts/session/types/PubKey.ts
index 0d83ec958..a76e4bf6d 100644
--- a/ts/session/types/PubKey.ts
+++ b/ts/session/types/PubKey.ts
@@ -15,7 +15,7 @@ export class PubKey {
     if (!PubKey.validate(pubkeyString)) {
       throw new Error(`Invalid pubkey string passed: ${pubkeyString}`);
     }
-    this.key = pubkeyString;
+    this.key = pubkeyString.toLowerCase();
   }
 
   /**
@@ -54,7 +54,7 @@ export class PubKey {
   public isEqual(comparator: PubKey | string) {
     return comparator instanceof PubKey
       ? this.key === comparator.key
-      : this.key === comparator;
+      : this.key === comparator.toLowerCase();
   }
 }