diff --git a/src/data/Thread.js b/src/data/Thread.js
index 334609a..dba4663 100644
--- a/src/data/Thread.js
+++ b/src/data/Thread.js
@@ -32,7 +32,7 @@ class Thread {
    * @param {String} text
    * @param {Eris~MessageFile[]} replyAttachments
    * @param {Boolean} isAnonymous
-   * @returns {Promise<void>}
+   * @returns {Promise<boolean>} Whether we were able to send the reply
    */
   async replyToUser(moderator, text, replyAttachments = [], isAnonymous = false) {
     // Username to reply with
@@ -75,8 +75,16 @@ class Thread {
     try {
       dmMessage = await this.postToUser(dmContent, files);
     } catch (e) {
+      await this.addThreadMessageToDB({
+        message_type: THREAD_MESSAGE_TYPE.COMMAND,
+        user_id: moderator.id,
+        user_name: logModUsername,
+        body: logContent
+      });
+
       await this.postSystemMessage(`Error while replying to user: ${e.message}`);
-      return;
+
+      return false;
     }
 
     // Send the reply to the modmail thread
@@ -96,6 +104,8 @@ class Thread {
       await this.cancelScheduledClose();
       await this.postSystemMessage(`Cancelling scheduled closing of this thread due to new reply`);
     }
+
+    return true;
   }
 
   /**
diff --git a/src/main.js b/src/main.js
index 37e698d..7c767cb 100644
--- a/src/main.js
+++ b/src/main.js
@@ -52,8 +52,9 @@ bot.on('messageCreate', async msg => {
     if (! utils.isStaff(msg.member)) return; // Only staff are allowed to reply
 
     if (msg.attachments.length) await attachments.saveAttachmentsInMessage(msg);
-    await thread.replyToUser(msg.member, msg.content.trim(), msg.attachments, config.alwaysReplyAnon || false);
-    msg.delete();
+
+    const replied = await thread.replyToUser(msg.member, msg.content.trim(), msg.attachments, config.alwaysReplyAnon || false);
+    if (replied) msg.delete();
   } else {
     // Otherwise just save the messages as "chat" in the logs
     thread.saveChatMessage(msg);
diff --git a/src/modules/reply.js b/src/modules/reply.js
index 49d56a1..ac6931a 100644
--- a/src/modules/reply.js
+++ b/src/modules/reply.js
@@ -11,8 +11,9 @@ module.exports = bot => {
 
     const text = args.join(' ').trim();
     if (msg.attachments.length) await attachments.saveAttachmentsInMessage(msg);
-    await thread.replyToUser(msg.member, text, msg.attachments, false);
-    msg.delete();
+
+    const replied = await thread.replyToUser(msg.member, text, msg.attachments, false);
+    if (replied) msg.delete();
   });
 
   bot.registerCommandAlias('r', 'reply');
@@ -23,8 +24,9 @@ module.exports = bot => {
 
     const text = args.join(' ').trim();
     if (msg.attachments.length) await attachments.saveAttachmentsInMessage(msg);
-    await thread.replyToUser(msg.member, text, msg.attachments, true);
-    msg.delete();
+
+    const replied = await thread.replyToUser(msg.member, text, msg.attachments, true);
+    if (replied) msg.delete();
   });
 
   bot.registerCommandAlias('ar', 'anonreply');
diff --git a/src/modules/snippets.js b/src/modules/snippets.js
index 5fcec44..a084871 100644
--- a/src/modules/snippets.js
+++ b/src/modules/snippets.js
@@ -47,8 +47,8 @@ module.exports = bot => {
     const snippet = await snippets.get(trigger);
     if (! snippet) return;
 
-    await thread.replyToUser(msg.member, snippet.body, [], isAnonymous);
-    msg.delete();
+    const replied = await thread.replyToUser(msg.member, snippet.body, [], isAnonymous);
+    if (replied) msg.delete();
   });
 
   // Show or add a snippet