Cannot drag file to email after Mojave update

Since I installed Mojave, I have a new and strange behavior.

When I drag a file from DTPO to an email, a link appears, but not the file (this worked fine previously).

When I drag that file to Finder, the file appears in Finder.

Is there a setting I need to change, or an add-on I need to reinstall?


To an email in what app?

Sorry, using Apple Mail.

And, FYI, I followed the procedure for installing the Mail Plug-in, and I can see it in plugins within Mail preferences.

You can see it?

I’m not seeing an issue with dragging from DEVONthink into Mail (Send by Email, drag to dock, drag to draft email, etc.)

You may need to allow DEVONthink in System Preferences > Security & Privacy > Privacy > Automation. I was prompted by macOS to allow this…

Thank you for the detailed response.

First, yes, I can see the DTPO plug-in within Mail.

I tried dragging a file from DTPO to the dock icon for Mail, got a new message with the file (not the link).

I tried using the menu item, ‘Send by Email,’ and got a new message with the file, but only AFTER I got the prompt to select the automation for DTPO in Security and Privacy. Compared to your image, there was no checkbox for Mail under DevonThink before I got this prompt.

I checked off the Mail checkbox in this window.

I tried dragging the same file, got the same link.

But then I went to another database, and I could drag different files to a new email window, and it worked.

So at this point, the issue appears to be related to a few files in one database. I am going to repair the database and try again.

I will follow up. Thank you for the help.


I have rebuilt my databases. I still have two files that behave in this strange manner, but to the best of my knowledge, other files are behaving properly.

I have encountered similar situations:
(1) A few pdf files that are saved within DTPO BEFORE the Mojave upgrade cannot be drag and drop to apple mail. The mail shows the name of the pdf, but there is no file attached. I didn’t check every files.
(2) for PDF files that are saved within DTPO AFTER the Mojave upgrade, there is no such problem.

Are they indexed or imported?

Imported files for both case (1) and (2). I haven’t tried rebuilding the database after this happened because I rarely need to drop files from DTPO to apple mail. If the situation happen again I’ll try rebuilding the database.


Further follow-up:

I am still experiencing the issue. Some files can be dragged and dropped as documents, but some still show up in the outgoing email only as links.

So far, this applies to pdfs. Some work, some don’t.

If I drag to finder, and then to email, it works.

Is there something I can check in the properties of the individual files?

Thank you.

Just a quick bump. I am still experiencing this issue, and have not been able to figure out why I can drag or copy some files as files to an email message, but others only move as a link back to DTPO.

Any ideas on what I can test or look into?


Do you always drag the emails from the same mailbox or account? Maybe it depends on the origin.

@sawxray: The files that don’t work have a URL and ones that do work don’t have a URL, correct?


Yessir, you are correct!

I have tried about 20 files, and they do follow that pattern.

I am guessing you have figured out the issue, so I wait with bated breath…




I am dragging a pdf from DTPO into a new email message.


It’s actually an Apple / Mojave issue, not a DEVONtech one.

Thank you for following up.

No problem.