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Apple mail issues

A

andyherman

macrumors member
Original poster
Mar 13, 2020
32
28
I changed my Gmail password and now when I try to log onto Gmail, I receive an "connection insecure" error message from mail when it tries to contact the gmail server. I've searched online and tried all the suggested fixes to no avail. I'm able to access my mail via outlook on the Mac but not via Apple mail. I've been using Apple mail for years with no prior issues.

Any suggestions?

Screen Shot 2023-06-09 at 12.02.34 PM.png
 
There is no option to verify the certificate. As soon as I click on OK, everything closes out - the dialog box closes and it sends me back to Mail.
 
I found an Apple Support link for getting a certificate but it isn't helpful as it asks to provide the email address of the certificate authority you want to issue you the certificate, which in my case is Google mail, so how do I get Google's email address? -

Request a certificate from a certificate authority in Keychain Access on Mac

In Keychain Access on your Mac, you can request a certificate from a certificate authority (CA) using Certificate Assistant.
support.apple.com
  1. In the Keychain Access app
    a7cf9b42a4eb346015f47a47546a61a2.png
    on your Mac, choose Keychain Access > Certificate Assistant > Request a Certificate From a Certificate Authority.
  2. Enter your email address, name, and the email address of the certificate authority you want to issue you the certificate, then click Continue.
    To change the way key pairs are generated, click “Let me specify the key pair information.” Then choose the key size and algorithm, and click Continue.
    Note: You can create RSA keys up to 4096 bits. RSA keys smaller than 2048 bits are no longer supported.
  3. Review the certificate, then click Done.
  4. Click Continue.
    The request for a certificate is sent to the certificate authority. If the authority agrees, it creates your certificate and returns it to you as an email attachment.
 
Did you ever find out the email address to use for the certificate authority? I have a different error ("The server response was: Authentication Required. For more information, go tohttps://support.google.com/mail/?p=WantAuthError") It's already set up with authentication, and that link doesn't have anything relevant, but based on this Apple page, I suspect that adding a TLS certificate would be the answer. All the gmail documentation I can find is about Google Workspace, but I just have a regular gmail address and would occasionally like to be able to send from it.
 
LOL. This has the potential of being a very, very, very long thread.

I have no solution for you because I have three Gmail accounts set up in Apple Mail and have no issues like the one you're describing. But to me, that in itself is a problem. This sounds like something that would be widespread, but it's not. "Random" problems like you're experiencing are harder to diagnose and fix.

All I can say is that you should not have to resort to creating security certificates, or even thinking about them.
 
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