diff --git a/server/utils/agents/aibitat/plugins/gmail/lib.js b/server/utils/agents/aibitat/plugins/gmail/lib.js
index 28e52c27b..c751444b4 100644
--- a/server/utils/agents/aibitat/plugins/gmail/lib.js
+++ b/server/utils/agents/aibitat/plugins/gmail/lib.js
@@ -123,15 +123,20 @@ async function parseAttachment(attachment) {
 
 /**
  * Collect attachments from messages and optionally parse them with user approval.
+ * Specific files may not show (images) and are pre-stripped by the app script.
+ * If two attachments have the same name, only the first one will be kept (handling fwd emails)
  * @param {Object} context - The handler context (this) from the aibitat function
  * @param {Array} messages - Array of message objects (single message should be wrapped in array)
  * @returns {Promise<{allAttachments: Array, parsedContent: string}>}
  */
 async function handleAttachments(context, messages) {
   const allAttachments = [];
+  const uniqueAttachments = new Set();
   messages.forEach((msg, msgIndex) => {
     if (msg.attachments?.length > 0) {
       msg.attachments.forEach((att) => {
+        if (uniqueAttachments.has(att.name)) return;
+        uniqueAttachments.add(att.name);
         allAttachments.push({
           ...att,
           messageIndex: msgIndex + 1,
diff --git a/server/utils/agents/aibitat/plugins/outlook/lib.js b/server/utils/agents/aibitat/plugins/outlook/lib.js
index 83ebbc06c..98e969ce6 100644
--- a/server/utils/agents/aibitat/plugins/outlook/lib.js
+++ b/server/utils/agents/aibitat/plugins/outlook/lib.js
@@ -364,9 +364,12 @@ function isParseableMimeType(contentType) {
  */
 async function handleAttachments(context, messages) {
   const allAttachments = [];
+  const uniqueAttachments = new Set();
   messages.forEach((msg, msgIndex) => {
     if (msg.attachments?.length > 0) {
       msg.attachments.forEach((att) => {
+        if (uniqueAttachments.has(att.name)) return;
+        uniqueAttachments.add(att.name);
         allAttachments.push({
           ...att,
           messageIndex: msgIndex + 1,