Hello Stephen

On 16/01/2026, at 10:18 AM, STEPHEN CHAPE via WAMUG wrote:

>  My step-son has the following issue with Mac Mail.
> 
>   Just wondering if anyone has any ideas please ?
> 
>   He used the “Attach File” option in Mail to send several PDF files to
>   his insurer. He was later informed that the email “attachments” were
>   not actual PDF files, but links to download them. Due to the insurer’s
>   security policies, their staff are not permitted to access such links,
>   and he was asked to resend the documents as email attachments.
>   Unfortunately, despite numerous attempts, none of the online guidance
>   he found enabled him to do this successfully. Is anyone aware of any
>   method or process that allows Mail to attach the actual files
>   themselves, rather than download links?

We have not seen this behaviour with any version of mail. You could try any or 
all of...

Use the attach icon (paperclip) rather than the menu item
Drag and drop the file rather than use the menu
Make sure that the file is at the very end (below the signature) of the mail 
message
It might be a size thing - test with a small PDF
Make sure that you have edit / attachments with "windows-friendly" turned on
Under the format menu (when you are composing a message) make sure it is set to 
plain text

When testing, send the test message to a windows machine (there was, and maybe 
still is, a problem in the way windows handled mail messages)

One more thing you could look at - display the sent message and go to 
view/message/raw source (this is where it is in my very old version of mail - 
they might have moved it but you should find it somewhere). If the contents of 
the PDF are included you should see a large amount of garbage-looking stuff 
which is the PDF contents (this is easier to determine if the PDF is attached 
at the bottom as suggested above). If it is there then it implies that the 
problem lies with the receiver.

Hope this helps

Geoff
---------------------
Kaye and Geoff
[email protected]




-- The WA Macintosh User Group Mailing List --
Archives - <https://www.mail-archive.com/[email protected]/>
Guidelines - <http://www.wamug.org.au/mailinglist/guidelines.shtml>
Settings & Unsubscribe - <https://lists.wamug.org.au/mailman/listinfo/wamug>