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Just recently, I have been dealing with this frustrating problem of my apple mail not being able to authenticate my Google account. I tried different gmail accounts, removing and re-adding the accounts, rebooting my Mac etc. Still no use.

Can someone guide me through the process of getting this issue fixed? It is super frustrating for me to not be able to check my email using Apple mail.

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  • Google has added an extra security level toggle - open google on desktop machine, look under security for something like "allow apps to access".
    – Polypipe Wrangler
    Dec 5, 2020 at 1:40
  • The problem is on Google's side. Login to accounts.google.com, go to the Security Tab, click on App Passwords, and set up an app password for your Mac Mail. Use this information to create a new account from Mail (select "Other mail account" as your mail provider and enter your information there).
    – DocOc
    Aug 31, 2021 at 15:28

4 Answers 4

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I too had the exact same issue with Apple's Mail app as you described. Suddenly both my Gmail accounts asked me to re-authenticate. For both accounts I got the "Failed to authenticate with Google" message after entering my passwords. Removing and adding an account gave the same failure message. But every time I authenticated in Safari I got an email from Google saying I've successfully authenticated MacOS. That got me thinking that the issue must be on the Apple side.

The solution that worked for me was:

  1. Open the application "Keychain Access"
  2. Look for application passwords containing the words "gmail" or "google"
  3. Remove all the entries you find and reboot
  4. Authenticate or re-add your Google account
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  • What app is this? I assume the default mail app on macOS?
    – Nathan
    Jun 12, 2020 at 9:47
  • @Nathan, yes my answer applies to the default mail app on macOS. I've edited my answer to clarify that.
    – FoFoCuddlyPoops
    Jun 12, 2020 at 10:01
  • It does not work for me. MacOS Ventura.
    – emeraldhieu
    Jul 4, 2023 at 3:26
  • 1
    VPN is the solution!
    – emeraldhieu
    Jul 4, 2023 at 9:11
  • VPN worked for me
    – truongnm
    Jul 24, 2023 at 15:24
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I had this same issue now, I think. I had updated the password for my gmail account and needed to re-authenticate the Google account in Mac OS. When I went into System Preferences > Internet Accounts I got a dialog saying I needed to re-authenticate and when I clicked the "Open Safari" button in the dialog I just got an error message saying Failed to authenticate with Google.

Solution was to restart my computer, after that it worked just fine.

(I also set my default browser to Safari as recommended on reddit but that didn't help before the restart so I don't think it helped at all)

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I had this issue, more or less as described by Samuel Lindblom, except that the "open browser" button had no result. My solution was to change my default browser to Chrome (in System Preferences: General). Then the authentication worked, and afterwards I changed the default browser back to Safari.

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I spent about 2 hours trying everything (changing default browsers, rebooting, deleting stuff from KeyChain, deleting cookies from browsers, connecting to different networks and VPNs, …) until finally:

The solution was to restart my computer into Safe Mode.

Accounts I added in Safe Mode remained even after leaving Safe Mode, and adding new Gmail accounts started to work normally as well.

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