26.3 - Mail/Preview No Longer Asks to Reply to an Email when I sign a PDF Attachment

[ObeseSquirrel]

For work, I frequently need to sign PDFs that I receive and email the signed PDF back in my reply.

The last couple of iterations of MacOs made this extremely easy with Mail/Preview. I could simply open the PDF from Mail (using Preview), add my signature in Preview, and then close the PDF document. Preview/Mail would then automatically ask me if I wanted to Save the File, Reply to the email with the signed PDF attached (without saving to my computer), or Delete this edited PDF copy. It was so easy!

Since updating from 26.2 to 26.3, this option is no longer available. My only options are to Save the File, or Delete the copy. This adds an extra step while I'm also saving unnecessary files to my Mac.

Is there a Setting to turn that feature back on, or is it completely missing from 26.3? (Or is it still there and I just need to restart my computer, lol?)

 

[318iphone]

Hmm. What you describe still works for me... see screen shot below. I filled out the PDF in Preview then clicked on the red "close window" button and got the below popup. It was an iCloud mailbox not that that should matter.

 

[ObeseSquirrel]

Hmm. What you describe still works for me... see screen shot below. I filled out the PDF in Preview then clicked on the red "close window" button and got the below popup. It was an iCloud mailbox not that that should matter.

Strange... your screenshot is EXACTLY what I was trying to describe, but I don't get that anymore. Instead, I get this... I'm wondering if there's a setting I'm missing, or if I just need to restart the computer and try again. Quitting Mail and reopening the app didn't fix it.

 

[318iphone]

try a reboot. certainly can't hurt! But typically not needed with macOS. Also could be something weird with the folder permissions. Maybe try changing the "download" folder in Mail's General settings. Also check the folder Preview is using... click on the name of the file at the top of the Preview window. Change it to something like Documents.

 

[ObeseSquirrel]

Weird... It's working again without a reboot. I'll watch for this in case the bug comes back.