Illustrator .ai file attachments don't show in Mail until after send

This is a bit perplexing. Macbook Pro - Mail app -Ventura.


With every other file-type I either get a preview or an icon.


If I copy/paste or drag/drop .ai files into an email, they don't show at all until after I've sent them. The only indication that they are there is the file-size display. After I've sent the email it shows up as an embedded preview just as it should.


The frustration is I can't delete the file if I want to change it - I have to delete the email and start again.


I do, however, get an icon if I go the long way and attach via the "Attach a document" button.


Any ideas?

Posted on Nov 3, 2023 01:55 PM

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Posted on Nov 14, 2023 03:54 PM

I'm also just now having this issue ever since I updated my OS to Ventura. It's happening with both AI and PS files for me. Any other attachment type (especially from Apple programs) show up totally fine within my emails like they always have.

The issue only seems to occur with Adobe program files. They show up for the recipient without issue once sent but the only indication they're in my message on my end is seeing the message size change once I drag and drop them into my email. I'm assuming this is just a weird bug from the update? I really hope they fix it soon...it's super annoying.

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Question marked as Top-ranking reply

Nov 14, 2023 03:54 PM in response to Simonster

I'm also just now having this issue ever since I updated my OS to Ventura. It's happening with both AI and PS files for me. Any other attachment type (especially from Apple programs) show up totally fine within my emails like they always have.

The issue only seems to occur with Adobe program files. They show up for the recipient without issue once sent but the only indication they're in my message on my end is seeing the message size change once I drag and drop them into my email. I'm assuming this is just a weird bug from the update? I really hope they fix it soon...it's super annoying.

Nov 16, 2023 07:33 AM in response to CloudCatArts

I just found out that if you save as a draft and reopen you can see the file. An annoying extra step, but at least you don't have to recreate the entire email if you want to switch out the file.


Interestingly, you can see the file in place just fine when you select the email in Drafts - but it only shows as an icon when you open it fully. But at least there's an icon.



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Illustrator .ai file attachments don't show in Mail until after send

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