Getting "HTTP error. The request cannot be fulfilled..." when sending emails.

Question

Getting the below error when trying to send emails, and the emails get stored in drafts. 

"HTTP error. The request cannot be fulfilled. Mail could not be sent. The message has been moved to your Drafts folder."

This only seems to occur when sending t certain recipients. Unable to find anything useful online to fix this problem. Any suggestions? 

• Outlook for Mac version 15.13.1 (150807)
• OS X Yosemite version 10.10.3
• Downloaded Outlook via Office365 work account

Answer 1

Hi DanMcAuley,

Some customers resolved the similar issue by uninstalling the Office package and then reinstalling it. So could you please try it to see if it works for you ?

If it doesn’t work for you, I’d like to confirm some information below to troubleshoot the issue:

1. Can you send emails to the certain recipients via OWA (Outlook Web App) ?
2. The entire error message.
3. Can you use another Mac where Outlook works fine to send emails to the certain recipients using your Office 365 account? Also, use another Office 365 account which works well to send emails to the certain recipients on your Outlook for Mac. Then let me know the test results.

Thanks,

Larry

Answer 2

Hi DanMcAuley,

Any updates on the issue? Please provide the information requested when you have time.

Thanks,

Larry

Answer 3

HI Larry,

Re-installing seems to have resolved the issue.

Thanks,

Dan