Unable to File - Share - Email - Send attachment from inside a Microsoft application

Hi Jill,

Thanks for posting in the community. We are happy to help you.

According to your description, the Outlook dialog box does appear and allows you to send an email with an attachment, but the recipient does not receive the email and you do not see the email from Sent Items or Outbox. To troubleshoot the problem, I suggest you manually send an email to this recipient and then check again.

Also, I suggest you repair Office via Windows Settings> "Apps & features" (or Apps> Installed apps)> find and select the Office product> Modify> choose Online Repair. After that, please test again.

If you can manually send the email successfully, but the problem still occurs after repair, I would like to gather more information about the situation.

1. Did you check the email in the New Outlook? I suggest you type "Outlook" in the Windows Search bar and check if you can see two Outlook applications (Outlook (new) and Outlook). If you can see two Outlook applications, please run Outlook, check the email, and check the account connectivity in the Status Bar.

2. Check Other Folders

Check other folders such as Drafts to see if the email is stuck there.

3. If you have added multiple accounts in Outlook, I suggest you check other accounts' Outbox or Sent Items. 

4. Are your colleagues experiencing the same problems?

5. Please provide your Office version and Product Information.

Click File> Office Account, please take a full screenshot including Product Information and About Outlook. You can click "Insert Image" to upload it.

We look forward to your response. Thanks for your cooperation.

Sincerely,

George | Microsoft Community Moderator

Hello. Yes, I can manually send the email. After some additional troubleshooting, it seems that this is a feature that the new version of Outlook is not yet supporting. I can still take this action if I switch back to the old version. However, if I try to use the new version of Outlook, the feature does not work and those emails just get stuck sitting in the outbox of the old version of outlook. I hope they will fix some of these things soon. It's frustrating to try to use the new version, only to find out that some of my most used features are no longer / not yet available.

Thanks

Hi Jill,

Thanks for posting back.

I'm glad to know you have found the root cause. I'm afraid the New Outlook doesn't currently support the "Send as Attachment" feature for Office applications. You will need to use the classic Outlook or revert the new Outlook to classic Outlook.

For your reference:

Revert to legacy Outlook

Going back to classic Outlook for Windows

Based on the situation, I suggest you send feedback to Microsoft via Help> Feedback and vote for this suggestion in our Microsoft Feedback Portal other members also posted and voted for the same suggestion. They are the platforms for us to hear your voice and improve our products.

Sorry for the inconvenience that happened to you. Appreciate your understanding and patience.

Sincerely, 

George | Microsoft Community Moderator