Gmail Not Working on Mac: All Issues and Solutions?

Any app has the possibility of being misoperated due to different factors, let alone the frequently used mail service, Gmail. As one of the biggest online mail servers, Gmail receives numerous welcomes and commendations for its handyness and ease of use.

However, its popularity fails to make Gmail get around sorts of issues or problems, and that's why this post comes here to help. Today, this post walks you through the issues of Gmail not working on Mac and explore corresponding solutions, just bring your trouble and read on for a way out!

The collections of Gmail issues on Mac

Let's see the command issues happen with Gmail on Mac first, and all of them will be troubleshoot one by one in the following sections:

Before we dig deep into every case separately, please rule out the poor connection from the final culprit. You can check the internet by Apple Menu > System Settings > Network and see if the network shows a green sign -- green means the internet connection is going well. If not, fix the internet connection on your Mac first.

Case 1: You can't log into your Gmail account

Eliminating the network connection from the final factors, the issue that you can't log into the Gmail account can be caused by an operating system bug, mail server error, app glitch, or so on. Running into such a case, you can delete your Gmail account from the Internet Accounts and then re-add it to make everything go on.

Share this post if it helps you out of the Gmail not working trouble!

Case 2: Apple Mail not working with Gmail

First Apple Mail kept asking for a password for Hotmail and Gmail. I kept reentering it, hoping to just move on. It finally worked for Hotmail. As for Gmail. I have deleted the account to try a fresh start... Now the Google log-in serve gives me a 404 error saying the request was malformed and should not be repeated. So I am not even able to try again with a fresh setup. What is happening and how do I fix it? What happened to the days of "It just works?"

Well, the conflict between Gmail and Apple Mail happens unexpectedly sometimes, and it's tough to tell what factors should be blamed since you cannot know the trouble hits on which app. Yet don't worry, once you face Apple Mail not working well with Gmail, try the steps below to get it fixed:

Case 3: Your email client won't connect to Google's servers to check for mail

When your email client won't connect to Google's servers, the priority is to shut down the email client, and then restart it for further working routine. A restart isolates almost strange glitches or bugs and gets itself ready for the following work, you just restart it and then everything will be resolved.

If the restart makes no sense here, scroll up for the steps to remove the Gmail account from Mail and add it back. With your Gmail account being refreshed, the email client will connect to Google's servers to check for emails without a hitch!

Case 4: You can't send an email message

If your email isn't sent in Gmail, the factors can be internet connection (this can be excluded as we checked the network connection beforehand), incorrect SMTP settings, or trouble with the Gmail accounts. Here we can check the SMTP settings with the following steps:

For the Gmail account issues, you can follow the steps mentioned above to remove it from Mail and then add it again. Once the account is updated, mail can be sent via Gmail without any trouble.

Case 5: You can't send an attachment with your email message

Kinds of things can fail to send an attachment, and the most common one is that the attachment you want to send is too big. In this way, you can share this attachment with the recipient via the cloud server. iCloud, OneDrive, Google Cloud, and Dropbox are top-ranking servers that are worth a shot!

Another possible culprit is a damaged attachment, which prevents you from sending an email. If this happens, you can try to repair the damaged picture by asking a professional for help.

One last reason to mention is that the original image you plan to send is moved to the Mac Trash, causing your sending to fail. You can open the Mac Trash to restore the image or launch iBoysoft Data Recovery Software to recover the image emptied from the Mac Trash.

Case 6: You can't sign in to this app because it doesn't comply with Google's OAuth 2.0 policy for keeping apps secure

I try to add my account but I got this message:

Authorisation Error
Error 400: invalid_request

You can't sign in to this app because it doesn't comply with Google's OAuth 2.0 policy for keeping apps secure.

You can let the app developer know that this app doesn't comply with one or more Google validation rules.
Learn more
Request Details
The content in this section has been provided by the app developer. This content has not been reviewed or verified by Google.
If you're the app developer, make sure that these request details comply with Google policies.
redirect_uri: urn:ietf:wg:oauth:2.0:oob

What's wrong with Apple and Google? Google asks to contact the developer, yes Apple...It's so frustrating...

Well, this issue happens due to the insufficient security of old macOS stated by Google. Based on this statement, the only way you can apply is to update macOS. Luckily, however, it is still possible for users running old macOS to ass new Gmail accounts with the following steps:

Final words 

This post gathers common issues happening on Gmail and provides corresponding workarounds to fix them. If you run into Gmail trouble, try the solutions given in this post. Let me know if you fix the Gmail issue with the included solutions or if you have other Gmail trouble!