Using Safari and recently unable to attach files to Gmail

I've used a MacBookPro for years, currently running macOS Mojave. I regularly download security updates. And, I've been using Safari and my Gmail account without any problems, until yesterday.

After downloading the most recent security update, I now cannot attach documents to my Gmail email account. When I click on the paperclip icon to attach an item nothing is happening; I'm not taken to 'Documents' to select files.

I'm not sure if there a causal connection between the latest security update and inability to attach files to Gmail. I can attach files via Firefox and my iPhone.

How do I fix this problem, thanks?

Posted on Nov 29, 2020 9:08 PM

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Apple-Support-01 Author

Level 1

9 points

Posted on Dec 1, 2020 8:17 PM

Thanks all for your help.

I think I may have solved the Gmail file attaching problem by updating from macOS Mojave to macOS Catalina version 10.15.7.

I can now attach documents to my Gmail email when clicking on the paperclip icon.

If there are any further problems, I'll post again.

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18 replies

Dec 4, 2020 10:13 PM in response to remlub101

This seems correct to me. Is it possible to downgrade to Safari 14.0?

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Level 9

65,010 points

Dec 1, 2020 8:30 PM in response to Apple-Support-01

Make sure iCloud Drive and desktops box is turned as on https://support.apple.com/en-in/guide/mac-help/mchle5a61431/10.14/mac/10.14

Open mail app , compose a mail use command and N keys , click on paper clip icon , and click on documents , select it and click on choose file .

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Dec 1, 2020 11:55 PM in response to tygb

I don't use iCloud Drive. It seems I've found a solution with Catalina - hopefully no more issues.

Thanks for your help, tygb.

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Using Safari and recently unable to attach files to Gmail

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