Fix: Can’t Add Email Attachments on Mac

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.

1. Launch Safari and navigate to Clear History.
2. 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.

1. Launch Safari and click Preferences.
2. Then go to Privacy and locate Website tracking.
3. Uncheck the Prevent cross-site tracking option.
4. 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.

1. Click the Apple menu and select Shut Down.
2. Wait 10 seconds and then restart your device.
3. Press the Shift key as soon as you restart your device and hold it down.
4. 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.

1. Launch Safari and navigate to Preferences.
2. Select Advanced and then click on Show Develop menu in menu bar.
3. Then go to the Develop menu, and enable Disable Local File Restrictions.
4. 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.