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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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

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Jan 8, 2021 2:24 PM in response to Clueless-senior-7881

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

Nov 24, 2020 9:30 PM in response to Clueless-senior-7881

Clueless-senior-7881 Said:

"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."

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Fix System Files:

Your macOS system files (i.e. caches) may have become corrupted. So, boot into Safe Mode for 30 seconds, then try this once more. Safe Mode fixes many corrupt files.

Steps to Follow:

  1. Boot Up: into Safe Mode [hold down: shift key upon boot.
  2. Wait: 30 Seconds
  3. Shut Down: your Mac
  4. Boot Up: normally
  5. Try this: all once more

Dec 6, 2020 6:24 AM in response to Ch33n0

Hi Ch33n0


To get back to Safari 14.0, I had to reinstall mojave, that returned me to Safari 12.1.2. I then added the macOS supplemental update, and security updates - making sure to not update Safari to 14.0.1



To start the reinstall process Apple provide a macOS installer available from


macOS Mojave 10.14


This will give you mojave 1.14.6 and Safari 12.1.2


If you then goto System Preferences, Software Update. Underneath the Catalina update notification, there will be a sentence "Other updates are available", click on the more info link, and then uncheck the Safari 14.0.1 - you can install/update the rest.


Its a slow process on my old iMac late 2012, but it is straightforward.

Just remember to keep unchecking the Safari 14.0.1 install, in the software update pane (in my case underneath the catalina update blurb) after the mojave reinstall.

Safari 14.0 comes bundled in the macOS supplementary update - and that's where I've left it for now.

The 2 security updates are fine to install.

good luck

Feb 25, 2021 1:53 PM in response to GUP1138

This drove me crazy so I did a soft reset (unplug/replug) cleared all cookies from all browsers ran disk utility and memory clean.

Shutdown, restarted in Safe Mode and the function worked. Shutdown once again, restarted and lo and behold the function of attaching files had magically returned.

I would like to know which of the steps and which of the companies (Apple,Google)was the culprit but happy to be back to normalcy.

I'm going to stick blame to Google for the heck of it.

Hopefully one day Apple will provide a comparable browser and mail function that will allow Apple users to dump the company that follows every move I make from morning to night.

Feb 3, 2021 2:24 AM in response to OT51

It could well be something different then. Have you checked your security settings?


Go to System Preferences > Security & Privacy > Privacy and scroll down the list on the left to Full Disk Access. Check that you have Safari in there and it is ticked.


Failing that you will need to raise a bug with Apple, or use the workaround provided earlier in this topic.

Nov 25, 2020 6:59 PM in response to Clueless-senior-7881

Clueless-senior-7881 Said:

"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."

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Did Safe Mode Work?

If Not, Leave Apple Feedback on This.

  1. Go Here: Feedback - Safari - Apple
  2. Select: "Bug Report" for the "Feedback Type"
  3. Proceed for here as necessary

Dec 15, 2020 11:11 AM in response to Ch33n0

As Clueless-senior-7881 stated on November 28, you can still drag and drop an attachment in Safari 14.0.2. I'm using Mojave 10.14.6


I tried the same attachments at the same websites that Safari wouldn't let me attach files to in Firefox. It worked fine with no problems. No need to drag and drop. I'm convinced that Safari seems to be the problem here.


Clueless-senior-7881


Nov 28, 2020 8:07 AM in response to Mimsey196

This is pretty frustrating Mimsey. In the meantime I can still drag an attachment in Safari or just use Chrome with no problems. Users have to keep reporting this bug. Fix this BUG APPLE!!!

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can't attach files with Safari

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