Fix: Can’t Add Email Attachments on Mac

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Many Mac users have complained that they cannot add files to their emails. This issue mainly affects third party email services like Gmail, Outlook, Yahoo, and others. In other words, Mac prevents users from adding attachments to emails when using non-Apple email services on Safari. If you really need to send an important document, this problem can be quite crippling. So, let’s dive in and explore how you can fix the problem.

My Mac won’t let me attach files to emails

Quick repairs

Use another browser

Since this issue usually affects Safari, you should be able to attach files to emails on a different browser. So, to quickly fix the issue, download and install Chrome, log into your email account, and check if the issue is resolved.

Drag and drop the file

There is another quick workaround that you can use if you are in a rush. Simply drag and drop your attachments onto the Upload a file or To attach button. While this method is a little less convenient, it should get the job done for some users.

Clear browsing history and cookies

Deleting your browsing history and cookies can help you solve this problem. Temporary files stored as browser cache files can sometimes interfere with the websites you visit.

  1. Launch Safari and go to Clear story.
  2. Then select how far you want to clear your browsing history.safari clear browsing history

Turn off cross-site tracking

Safari has a very handy feature that blocks cross-site tracking so that third-party trackers cannot detect your device’s exact configuration. This way, trackers won’t be able to uniquely identify your Mac. Unfortunately, this feature can occasionally trigger various issues.

  1. Launch Safari and click Preferences.
  2. Then go to Private life and locate Website tracking.
  3. Uncheck the box Prevent cross-site tracking option.safari prevents cross-site tracking
  4. Restart Safari and check if you can now attach files to your emails. Feel free to re-enable the option when you’re done.

Update Safari and macOS

This may only be a temporary issue affecting your current version of Safari. Check if a newer browser version is available and install it on your Mac. Apple may have already fixed this issue with the latest operating system update. It doesn’t matter if the problem is with the source code of macOS itself or with Safari. Click on the Apple menu, select System Preferences, go to Software update, and check for updates.

update macOS

Your Mac will automatically install the latest versions of macOS and Safari.

Enable Safe Mode

A number of users have reported successfully attaching files to their emails after starting their Mac computer in Safe Mode. They also confirmed the function of attaching files returned in normal mode after restarting their devices.

  1. Click on the Apple menu and select To close.
  2. Wait 10 seconds, then restart your device.
  3. Press and hold the Shift key as soon as you restart your device.
  4. Do not release it until the login window appears on the screen.

If you have 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 attachments to emails in Safe Mode.

Enable development mode in Safari

Other users have worked around this problem by turning on Develop mode.

  1. Launch Safari and go to Preferences.
  2. To select Advanced then click on Display the Develop menu in the menu bar.safari show development menu
  3. Then go to the Develop menu and activate Disable local file restrictions.
  4. Check if Safari allows you to add attachments to emails.

Conclusion

If you can’t attach files to your emails in Safari, update the browser, turn off cross-site tracking, or turn on the Expand menu. Do you often encounter similar issues when using non-Apple email services on Safari? Let us know in the comments below.

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