Using classic Outlook for Windows in business environments
Hi @Julia O
Thank you for posting your question in the Microsoft Q&A forum.
Based on the information you have provided, looks like you cannot send emails with PDF attachments.
I am so sorry about the inconvenience you are facing. We have received some reports about this known issue.
To resolve the root cause of this issue, you need to contact MS support team, they will collect logs and data and troubleshoot from the backend.
Meanwhile, you can try this work around in the picture below.
Or in your case, you can convert PDF file to PNG. It will be sent normally.
Since this bug doesn't affect mobile device, you can draft an email on your computer, then send it with your phone. It will be delivered successfully.
Once again, I apologize for the inconvenience this might cause you. I totally understand how frustrating and time consuming this would be for you.
We will try our best to resolve this issue to enhance customers' experience.
Thank you for your understanding.
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