diff --git a/gptel-org.el b/gptel-org.el
index f9a6b17c..9c4d7be8 100644
--- a/gptel-org.el
+++ b/gptel-org.el
@@ -41,6 +41,7 @@
 (defvar org-link-angle-re)
 (defvar org-link-bracket-re)
 (declare-function mailcap-file-name-to-mime-type "mailcap")
+(declare-function org-attach-expand "org-attach")
 (declare-function gptel--model-capable-p "gptel")
 (declare-function gptel--model-mime-capable-p "gptel")
 (declare-function gptel--model-name "gptel")
@@ -365,8 +366,11 @@ for inclusion into the user prompt for the gptel request."
         (when-let* ((link (org-element-context))
                     ((gptel-org--link-standalone-p link))
                     (raw-link (org-element-property :raw-link link))
-                    (path (org-element-property :path link))
+                    (raw-path (org-element-property :path link))
                     (type (org-element-property :type link))
+                    (path (if (string= type "attachment")
+                              (org-attach-expand raw-path)
+                            raw-path))
                     ;; FIXME This is not a good place to check for url capability!
                     ((member type `("attachment" "file"
                                     ,@(and (gptel--model-capable-p 'url)
diff --git a/gptel-request.el b/gptel-request.el
index fded267d..22ea5ad8 100644
--- a/gptel-request.el
+++ b/gptel-request.el
@@ -2033,9 +2033,12 @@ Initiate the request when done."
           (save-excursion (goto-char (point-min))
                           (gptel--parse-list-and-insert (cdr directive))))
         (goto-char (point-max))
-        (setq full-prompt (gptel--parse-buffer ;prompt from buffer or explicitly supplied
-                           gptel-backend (and gptel--num-messages-to-send
-                                              (* 2 gptel--num-messages-to-send))))
+        ;; Parse buffer in original buffer context so org-attach-expand can access
+        ;; Org properties (ID, ATTACH_DIR) not present in the temp copy buffer
+        (setq full-prompt (with-current-buffer (plist-get info :buffer)
+                            (gptel--parse-buffer ;prompt from buffer or explicitly supplied
+                             gptel-backend (and gptel--num-messages-to-send
+                                                (* 2 gptel--num-messages-to-send)))))
         ;; Inject media chunks into the first user prompt if required.  Media
         ;; chunks are always included with the first user message,
         ;; irrespective of the preference in `gptel-use-context'.  This is