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 give 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?"

MacBook Pro (2021)

Posted on Jan 26, 2024 11:59 AM

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Question marked as Top-ranking reply

Posted on Jan 27, 2024 1:10 PM

I had this with Safari 17.3 on macOS 14.3.


The 404 was *after* successful auth with Google and happened when I chose "continue" on the "Sign in to macOS" page shown *after* auth.


I managed to get successfully past the "Sign in to macOS" with these steps:


In Safari, go to "Settings ..." and the "Advanced" tab.


There is a checkbox setting on the "Advanced" tab labelled:


"Use advanced tracking and fingerprinting protection". Uncheck the checkbox.


Go back to "System Settings" > "Internet Accounts" and go through the add account auth process again.


Assuming this gets you logged in, remember to set that checkbox back to checked (once the auth with Google has gone through and you have your email).


Good Luck..

5 replies
Question marked as Top-ranking reply

Jan 27, 2024 1:10 PM in response to mikeinportland

I had this with Safari 17.3 on macOS 14.3.


The 404 was *after* successful auth with Google and happened when I chose "continue" on the "Sign in to macOS" page shown *after* auth.


I managed to get successfully past the "Sign in to macOS" with these steps:


In Safari, go to "Settings ..." and the "Advanced" tab.


There is a checkbox setting on the "Advanced" tab labelled:


"Use advanced tracking and fingerprinting protection". Uncheck the checkbox.


Go back to "System Settings" > "Internet Accounts" and go through the add account auth process again.


Assuming this gets you logged in, remember to set that checkbox back to checked (once the auth with Google has gone through and you have your email).


Good Luck..

Jan 27, 2024 2:24 PM in response to Another_Apple_User_


Another_Apple_User_ said:

In Safari, go to "Settings ..." and the "Advanced" tab.

There is a checkbox setting on the "Advanced" tab labelled:


"Use advanced tracking and fingerprinting protection". Uncheck the checkbox.


Go back to "System Settings" > "Internet Accounts" and go through the add account auth process again.


Assuming this gets you logged in, remember to set that checkbox back to checked (once the auth with Google has gone through and you have your email).

This worked for me, thank you!

Jan 26, 2024 1:05 PM in response to mikeinportland

mikeinportland wrote:

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 give 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?"

Why don't you ask google why, since the error message is coming from them and not Apple.

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Apple mail not working with gmail.

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