This browser is no longer supported.
Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support.
![](data:image/svg+xml, %3Csvg xmlns='http://www.w3.org/2000/svg' height='64' class='font-weight-bold' style='font: 600 30.11764705882353px "SegoeUI", Arial' width='64'%3E%3Ccircle fill='hsl(128, 8%, 22%)' cx='32' cy='32' r='32' /%3E%3Ctext x='50%25' y='55%25' dominant-baseline='middle' text-anchor='middle' fill='%23FFF' %3EA%3C/text%3E%3C/svg%3E)
I have an issue whereby Outlook for Mac is losing attachments when sending emails (typically, but not exclusively, PDF files).
If a file(s) is/are dragged and dropped into an email it is shown as attached and appears to send as normal. There are no error messages or bouncebacks, and the first we know that the email has lost the attachment is when we are advised by the recipient. Then when checking the sent folder, the email is there but again without the attachments.
Doesn't do this every-time though... sometimes the email goes with the attachments as it normally should.
I'm using version 16.62 (22052500)
Has anybody else had this issue and is there a fix? Or is it a software glitch?
Using older versions of Outlook for Mac for personal email and calendar
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
Andreas,
Yes, you are correct. This issue ties directly to New Outlook + digitally signed emails. If the outbound emails are not digitally signed, the attachments deliver successfully.
Andreas,
Yes, you are 100% correct.
This issue ties to "New Outlook" and digitally signed emails.
If the outbound emails are not digitally signed, the attachments deliver successfully.
This issue makes the "New Outlook" simply useless - and probably not only in the professional environment.
Can you please fix this issue asap.
Interesting discovery you made here. I too use S/MIME to sign my emails. I postponed using the New Outlook a long time since this feature was not supported for a long time. I haven't tried sending attachments without S/MIME signing yet but it sounds typically like an issue that makes sense with attachments and "new" products released by MS. Sending email without S/MIME is just as useless for me as not getting attachments sent. But yeah, thanks for sharing this discovery.
Nice catch. Without SMIME no problem.
One thing I have noticed is that when I experience the issue is that Outlook for Mac is showing the size of the attachment at 0 KB. If I click on the attachment before it disappears, I can see the file correctly.