can't attach files with Safari

Safari (Mojave 10.14.6.) will not allow me to attach files through Gmail or Yahoo with the paper clip icon. Today is the first time this problem occurred. I have cleared my cache and history. I can attach files only by drag and drop.


I do not have this problem when using Chrome.




MacBook Air 13″, macOS 10.14

Posted on Nov 24, 2020 9:20 PM

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Question marked as Top-ranking reply

Posted on Jan 8, 2021 2:24 PM

Originally I thought the problem was just with my email, which I have reported about seven times over the past few months. It seems to stem from the November 2020 Security update. Anyway, I am unable to attach anything in my email from Safari, or from other websites (Faxzero, Hartford, among others), so it is obviously a Safari error. How do I know? Because after doing all of the normal clearing cache and all, and still no benefit. I downloaded Firefox at the suggestion from one of the companies mentioned. Although I have only used Safari for years, and did not want to download another browser, I reluctantly did so, and I was able to attache files in each of the three above mentioned companies, as well as others. It is obviously a Safari issue. I am using Mojave 10.14.6 and Safari 14.0.2

60 replies

Dec 6, 2020 3:51 PM in response to Mark4785

I have reported the Bug twice and based on what I have read here and other outlets I am one of 2000s (?).

I have “not” received a response to either of my reports.

Extremely frustrating and I was not aware it was affecting photo attachment as well until today.

You cannot attach photos either inline or attachment unless you drag and drop.


Dec 6, 2020 7:25 PM in response to Clueless-senior-7881

Apple doesn’t routinely monitor the discussions. These are mostly user to user discussions.


If you want to, you can send Apple feedback. They won't answer, but at least will know there is a problem or a suggestion for change. If enough people send feedback, it may get the problem/suggested change solved sooner. Pick the closest topic you can find.


Safari Feedback   

Dec 6, 2020 2:44 PM in response to remlub101

Seems to me Apple should be aggressively focused on resolving this issue that is obviously affecting a mass group of users.

Users should not be expected to downgrade, reinstall to fix an Apple bug

There are many users that are unfamiliar with a reinstall or having to dive into a fix that’s a bandaid only, not guaranteed to work causing other issues and leaves them open to possible security issues.


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can't attach files with Safari

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