Can’t Attach Files to Emails on Chrome Mac?

Mac users are reporting an issue where they cannot attach files to emails on Chrome. However, the problem goes beyond Gmail and most websites with an attachment feature. But, don’t worry—as there’s an easy way to fix this issue. 

Hi, I’m Andreas, and I’ve recently encountered this issue when using Gmail on Google Chrome. While digging a bit deeper, I found this problem to be connected with the macOS 12 Monterey version. If this happens to you, stick around and I will tell you how to fix it.

But before that, let’s look at what seems to be causing the issue.

Possible Reasons Why You Can’t Attach Files to Emails on Chrome Mac

Mac users report that every few weeks, the Gmail attachment feature isn’t working

The feature will flat-out refuse to attach files when sending emails through Chrome every few weeks. The problem is we can’t determine the trigger.

While I can make a case for the browser to be the problem, not everyone agrees with this. 

Some say that the problem persists when uploading files with Safari, Firefox, and even Microsoft Edge. So, is Gmail the problem? Considering Gmail is one of the most popular email services, I highly doubt they’ve messed up something. 

So, to troubleshoot the issue, we have to look at what every Mac user has in common. And every Mac user shares an OS version. The current version for Mac machines is macOS 12 Monterey. Some users report the issue since updating to the latest version.

But, again, there is no way of knowing what causes the problem. So what I did was try different solutions and see what sticks. And if you’re in desperate need of assistance, I’m here to tell you what worked for me. 

Solutions to Allow You to Attach Files to Emails on Chrome Mac

I will explain different solutions and explain how each one worked for me. Then, you can try each one and see whether or not they’re an effective solution for the problem.

Solution 1: Revoking Permissions

The solution involves revoking Chrome’s Downloads Folder permission. Here is how to do that.

Step 1: Go to System Preferences and “Security & Privacy.”

Step 2: Click on “Privacy” and look for “Files and Folders.”

Step 3: Look for “Google Chrome” and untick the “Downloads Folder” to remove the permission. Then, tick it again to grant the permission.

Step 4: Restart Chrome.

Mac users report no pop-up error messages when trying to upload files to any website on Chrome (email services, social media, etc.). With these steps, you give Chrome access to use files and folders. 

Solution 2: Avoid Exceeding Size Limits

The second solution concerns the file(s) you plan on attaching. For example, Gmail will not allow you to send an attachment that exceeds 25 MB in size (source). Instead, it will send it as a Google Drive link.

So when trying to attach a file or a group of files, ensure the attachment doesn’t exceed the size limit. Even if it does, there are ways to work around it. 

You can do the following if you don’t want the email to send a Google Drive link.

Select the file(s) or folder you plan on sending via email, control-click, and select “Compress.”

With the compress option, you lower the size of the document or folder, making it easier to send via email. However, this solution relates to a particular issue that isn’t solely related to Chrome Mac. 

That said, give it a try, as it might be an effective workaround.

Solution 3: Drag The Files or Folders Instead of Attaching

The third solution is straightforward, and this one worked for me. Namely, instead of clicking the attachment icon, why not try and drag the file(s) or folders to the email message?

Even some Mac users have found this solution a successful one. 

Solution 4: Reinstall Google Chrome

If all else fails, a solution that I recommend is to reinstall Google Chrome. Here is how to do that.

Step 1: Go to “Applications,” locate Google Chrome, and put it in Trash.

Step 2: Go to Google Chrome’s download page and download Chrome for Mac.

Step 3: Run the installation, open Gmail, and see if you can upload attachments. This solution works if the issue is with Chrome. 


We don’t know what causes Chrome to prevent you from uploading attachments on Gmail on your Mac. However, the four solutions work with varying success. 

One solution might work for you, while another will work for someone else. Give the solutions a try and see if that solves your problem. Let me know which one worked for you?

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