Using Safari and recently unable to attach files to Gmail

HI - I've been having same problem (loading photos up to Ebay)

I've read many of the threads concerning this, and have worked through suggestions.

IT IS NOT A MOJAVE issue as such...following advice above I reloaded Mojave 10.14.6... upload worked fine (using the installed Safari 12.1.2)

IT IS NOT A SECURITY UPDATE issue...following reload of Mojave and Safari 12.1.2, I then in sequence loaded the 2 security updates 2020-005 and 2020-006....again no problem upload worked.

IT IS NOT A MOJAVE SUPPLEMENT ISSUE...... I then added the macOS Mojave Supplemental Update....this introduced Safari 14.0....again no problem uploads continued to work.

IT IS....IT IS....a SAFARI 14.0.1 ISSUE....so finally I added the Safari 14.10.1 update... lo and behold uploads stopped working.

So I have no solution, but my workaround keeps me on Safari 14.0 and therefore functional, 14.0.1 clearly doesn't work with Mojave, and maybe not with Catalina (according to some posts).

Hope this helps... I've logged with Apple Support.

It is possible, but you need to reinstall mojave.

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

Ahhh yes, you are correct! I can physically drag attachments into the mail compose window!

While that works well for some documents, it's less useful for PDFs and image files, as they get embedded into the body of the email as opposed to being an attached file. But at least it's something!

Thank you for the insight!

I'm having the same Safari / Gmail attachment issue as well. I'm currently on Safari version 14.0.1 and I'm thinking that it might have something to do with Flash.

This article from April 2020 talks about needing to update Flash when this attachment issue happens.

But then the bottom (item #8) of this Adobe help article says that as of Safari v14, Safari is no longer supporting Flash.

I'm not sure when I went from Safari 13 to 14. Perhaps it just happened today which is the first day I've had this attachment issue.

So I dunno...

I'm having similar issues loading photos to Ebay. For at least last week

Ebay told me to use Chrome which works fine.

I suspect its latest security updates?

Unlike Uncle chichi I'm not sure its Flash, unless Safari support of Flash changed with SecUpdates.

I have just uninstalled Flash, and it's not working, nor was it before uninstalling.

It worked from previous versions like Mac OS Yosemite till Mac OS catalina and above , some different method is open mail application , compose a mail the compose mail window opens minimise the background full window of mail application , simultaneously open finder window , drag and drop the documents from iCloud Drive > documents or copy and pasre works .

The more short cut method is keep the documents literally on the desktop screen , you can directly drag and drop them into mail compose window , its all convenience , some adopt difficult methods others prefer easy .

Updating in App Store ( whatever updates appear always install them ) , prefer the latest versions ( upgrade your Mac ) if the Mac is compatible with that version .

My same problem started after upgrading to Safari 10.14.1, and, as in the case with others in the Community, I <can> attach files in Firefox. I also read about users for whom the problem was resolved by upgrading to Catalina, but it now seems that Apple is suggesting that Mojave users upgrade directly to Big Sur. Is Apple going the way of Microsoft in turning out new operating systems without thoroughly checking them out?

Same. Very frustrating. I have not found any useful information on how to work around this or when it will be fixed. Using another browser for now, and it's working.

I'm glad this worked for you, but that seems like an extreme solution. It would mean that an OS upgrade is necessary just to use Gmail in Safari. I just can't believe such a thing is necessary.

That seems like a complicated workaround. You don't think it's possible to successfully use Gmail (including the ability to use attachments) within Safari any longer?

welcome .