diff --git a/backend/src/Queue.ts b/backend/src/Queue.ts
index 2ca63d2f..a8505411 100644
--- a/backend/src/Queue.ts
+++ b/backend/src/Queue.ts
@@ -29,10 +29,14 @@ export class Queue<TQueueFunction extends AnyFn = AnyFn> {
   }
 
   public add(fn: TQueueFunction): Promise<any> {
-    const promise = new Promise<any>((resolve) => {
+    const promise = new Promise<any>((resolve, reject) => {
       this.queue.push(async () => {
-        const result = await fn();
-        resolve(result);
+        try {
+          const result = await fn();
+          resolve(result);
+        } catch (err) {
+          reject(err);
+        }
       });
 
       if (!this.running) this.next();
diff --git a/backend/src/plugins/Cases/functions/postToCaseLogChannel.ts b/backend/src/plugins/Cases/functions/postToCaseLogChannel.ts
index 6c1342d7..594f0852 100644
--- a/backend/src/plugins/Cases/functions/postToCaseLogChannel.ts
+++ b/backend/src/plugins/Cases/functions/postToCaseLogChannel.ts
@@ -24,7 +24,7 @@ export async function postToCaseLogChannel(
   // This doesn't use `!isText() || isThread()` because TypeScript had some issues inferring types from it
   if (!caseLogChannel || !(caseLogChannel instanceof TextChannel || caseLogChannel instanceof NewsChannel)) return null;
 
-  let result;
+  let result: InternalPosterMessageResult | null = null;
   try {
     if (file != null) {
       content.files = file;
diff --git a/backend/src/plugins/InternalPoster/functions/sendMessage.ts b/backend/src/plugins/InternalPoster/functions/sendMessage.ts
index a5ce27d9..aecd7735 100644
--- a/backend/src/plugins/InternalPoster/functions/sendMessage.ts
+++ b/backend/src/plugins/InternalPoster/functions/sendMessage.ts
@@ -10,6 +10,16 @@ export type InternalPosterMessageResult = {
   channelId: string;
 };
 
+async function sendDirectly(
+  channel: TextChannel | NewsChannel,
+  content: MessageOptions,
+): Promise<InternalPosterMessageResult | null> {
+  return channel.send(content).then((message) => ({
+    id: message.id,
+    channelId: message.channelId,
+  }));
+}
+
 /**
  * Sends a message using a webhook or direct API requests, preferring webhooks when possible.
  */
@@ -17,7 +27,7 @@ export async function sendMessage(
   pluginData: GuildPluginData<InternalPosterPluginType>,
   channel: TextChannel | NewsChannel,
   content: MessageOptions,
-): Promise<InternalPosterMessageResult> {
+): Promise<InternalPosterMessageResult | null> {
   return pluginData.state.queue.add(async () => {
     if (!pluginData.state.webhookClientCache.has(channel.id)) {
       const webhookInfo = await getOrCreateWebhookForChannel(pluginData, channel);
@@ -53,19 +63,13 @@ export async function sendMessage(
             pluginData.state.webhookClientCache.delete(channel.id);
 
             // Fallback to regular message for this log message
-            return channel.send(content).then((message) => ({
-              id: message.id,
-              channelId: message.channelId,
-            }));
+            return sendDirectly(channel, content);
           }
 
           throw err;
         });
     }
 
-    return channel.send(content).then((message) => ({
-      id: message.id,
-      channelId: message.channelId,
-    }));
+    return sendDirectly(channel, content);
   });
 }