Many Mac users complained about not being able to add files to their emails. This problem mainly affects third-party email services such as Gmail, Outlook, Yahoo, and others. In other words, Mac prevents users from adding email attachments when using non-Apple email services on Safari. If you really need to send out an important document, this issue can be quite crippling. So, let’s dive right in and explore how you can troubleshoot the problem.
My Mac Won’t Let Me Attach Files to Emails
Quick Fixes
Use a Different Browser
Since this issue usually affects Safari, you should be able to attach files to emails on a different browser. So, as a quick workaround, download and install Chrome, log in to your email account and check if the issue is gone.
Drag and Drop the File
There’s another quick workaround that you can use if you’re in a hurry. Simply drag and drop your attachments on the Upload File or Attach button. While this method is a bit less convenient, it should get the job done for some users.
Clear the Browsing History and Cookies
Clearing your browsing history and cookies may help you to solve this problem. Temporary files stored as browser cache files may sometimes interfere with the websites you’re visiting.
Launch Safari and navigate to Clear History.
Then select how far back you want to clear your browsing history.
Disable Cross-Site Tracking
Safari has a very handy feature that blocks cross-site tracking so that third-party trackers can’t detect the exact configuration of your device. In this manner, trackers won’t be able to uniquely identify your Mac. Unfortunately, this feature may occasionally trigger various glitches.
Launch Safari and click Preferences.
Then go to Privacy and locate Website tracking.
Uncheck the Prevent cross-site tracking option.
Restart Safari and check if you can attach files to your emails now. Feel free to re-enable the option when you’re done.
Update Safari and macOS
Maybe this is only a temporary issue affecting your current Safari version. Check if there’s a newer browser version available and install it on your Mac. Apple may have already solved this issue on the latest OS update. It doesn’t matter if the problem stems from the macOS source code itself or Safari. Click on the Apple menu, select System Preferences, go to Software Update, and check for updates.
Your Mac will automatically install the latest macOS and Safari versions.
Enable Safe Mode
A number of users reported they managed to attach files to their emails after starting their Mac computers in Safe Mode. They also confirmed the function of attaching files returned in normal mode as well after restarting their devices.
Click the Apple menu and select Shut Down.
Wait 10 seconds and then restart your device.
Press the Shift key as soon as you restart your device and hold it down.
Release it only after the login window appears on the screen.
If you own a Mac with Apple Silicon, after the third step, you need to select your startup disk. Then hold down the Shift key again and select Continue in Safe Mode. Check if you can add email attachments in Safe Mode.
Enable Develop Mode in Safari
Other users bypassed this issue by enabling the Develop mode.
Launch Safari and navigate to Preferences.
Select Advanced and then click on Show Develop menu in menu bar.
Then go to the Develop menu, and enable Disable Local File Restrictions.
Check if Safari lets you add email attachments.
Conclusion
If you can’t attach any files to your emails in Safari, update the browser, disable cross-site tracking, or enable the Develop menu. Do you often experience similar issues when using non-Apple email services on Safari? Let us know in the comments below.
Update to my 16-inch Mac Monsteray 12 on June 23, 2022. Took away the ability to send all type of attachments (rich text even) in all emails and other “Share” like messages. Online support was not able to help. Going to the Apple store to see if a repair can be made. Worked fine before the update, did not not have malware.
I am experiencing this with ALL of my services – chrome as a browser, firefox as a browser, safari as a browser. It’s not pop up blockers, they’re not on. It is definitely crippling my ability to do my job as I cannot attach anything. I can click and drag to email, but I have other services and sites I have to use that require uploading that I cannot use due to this issue.
I just assisted a teacher encountering this problem. Not matter the browser (Safari or Chrome) on a newish MacBook (I didn’t check the OS version before she left my office). The issue was not being able to upload a file to Google Classroom. As soon as she clicked the Browse button, the file dialog box displayed her folders, but everything about the dialog box was disabled — no mouse clicks would register, even the Cancel button. Tried out a different website that accepts uploads, and encountered the same issue, so it’s not site-specific.
just used the proposed work-around, allowable by Google Classroom/Drive, of doing a drag-and-drop from Finder into the upload window **without first clicking the Browse button**. So thanks for the tip.
Wondering now whether a recent OS update may have caused the issue, but I’ll have to check that out later.
Out of the blue I couldn’t attach a word document to my email in yahoo mail, using Safari on mac. I disabled cross-site tracking prevent and am back in business. I have rechecked it – as it always worked before, so will see next time. Thanks!!
Update to my 16-inch Mac Monsteray 12 on June 23, 2022. Took away the ability to send all type of attachments (rich text even) in all emails and other “Share” like messages. Online support was not able to help. Going to the Apple store to see if a repair can be made. Worked fine before the update, did not not have malware.
not able to share docs and photos on whatsapp web or gmail over chome in macbook air m2
Worked! Turned off the computer, restarted while holding down the shift key. Magic! Mahalo!
I am experiencing this with ALL of my services – chrome as a browser, firefox as a browser, safari as a browser. It’s not pop up blockers, they’re not on. It is definitely crippling my ability to do my job as I cannot attach anything. I can click and drag to email, but I have other services and sites I have to use that require uploading that I cannot use due to this issue.
It is not a Safari problem: I have tried Chrome, Firefox and Safari. None have let me upload/attach files using either Gmail or Outlook.
I just assisted a teacher encountering this problem. Not matter the browser (Safari or Chrome) on a newish MacBook (I didn’t check the OS version before she left my office). The issue was not being able to upload a file to Google Classroom. As soon as she clicked the Browse button, the file dialog box displayed her folders, but everything about the dialog box was disabled — no mouse clicks would register, even the Cancel button. Tried out a different website that accepts uploads, and encountered the same issue, so it’s not site-specific.
just used the proposed work-around, allowable by Google Classroom/Drive, of doing a drag-and-drop from Finder into the upload window **without first clicking the Browse button**. So thanks for the tip.
Wondering now whether a recent OS update may have caused the issue, but I’ll have to check that out later.
I cant attach any file anywhere. I can’t get my work done and my manager is unhappy. I don’t know what to do
Unable to upload file on any browser on my mac.Wish to find a solution.Can anyone let me know that you found any solution to that ?
I never had any issues with my attachment button until now, please help resolve this, as Safari do not show any enable in the what you desbriction.
I can’t attach files to gmail or even on web-sites, for example when trying to attach a CV for a job application via a company‘s website.
Did you finally get it to work? I’m using Google Chrome and can’t attach files on any platform.
Out of the blue I couldn’t attach a word document to my email in yahoo mail, using Safari on mac. I disabled cross-site tracking prevent and am back in business. I have rechecked it – as it always worked before, so will see next time. Thanks!!
I can’t select files on WordPress dashboard/backend either… and gmail on Chrome…
I face the same issue on all my browsers.