For New Outlook, I can't drag and drop attachment.

Thanks for sharing. My issue with this functionality is not within the Outlook online app, but dragging attachments into other apps. I can't drag an attachment from Outlook online to the Teams (fat client) app, for example. Or into our other web-based HR app. I CAN do these things from the Outlook fat client app without issue.

For those who are unable to drag attachments into the Outlook App, like I ran into recently, what I found to be the culprit (at least for me) was the email I was sent and replying to was sent as "Plain Text". This didn't allow me to drag files into the email with normal results (adding it as an attachment) when I replied.

The email needs to be in "HTML" format in order to be able to just drag files without issue. This works fine if you use the Outlook Web App.  That seems to always reply in “HTML” format and you don’t have to do anything different.

Unfortunately though, you cannot automatically reply all the time in “HTML” format (from what I’ve found anyway) when using the Outlook App on desktop.  If you want or have to use the Outlook App, then when you reply to an email sent to you in “Plain Text”, you have to:

1. Click “Reply” or “Reply All”
2. Click “Pop Out” to open the reply in a separate pop out window (you can set this to automatically occur in Settings btw)
3. Click “Format Text” at the top of the newly opened reply window
4. Click the 3 dots (…) at the top right of the window to get a drop down
5. Then click “Message Format” > “HTML”
6. Things should work as expected now!

Definitely annoying and a lot of steps, but it gets the results we’re looking for, or at least what I was looking for, haha. Hopefully this helps someone.

I second this.

I agree, I receive lots of documents as attachments that need to be filed on another program