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GMail App on Android handles IMAP certificate change poorly.
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This problem has bothered me for (literally) years. I use Lets Encrypt certificates for my home mail server - both SMTP (using Exim4) and IMAP (using Courier), and Lets Encrypt forces the certificates to change every 90 days or so.  

When I change the IMAP certificate, the GMail App just quietly stops reading from my IMAP server.  No warnings, nothing - it's like I just have no new mail.  This is problem number one - I would assume that if the GMail App noticed that the certificate had changed it could maybe tell the user about it?

Since, I changed the certificate, I'm aware that I need to do something to get the GMail App working again.  Going through the settings for the mail server and re-verifying, the outgoing mail settings (see attached picture 1),  I get the following error:

Certificate not valid
The Gmail app can't guarantee the security of
this email address.  Your messages would be
at risk.
Fair enough, I select "Advanced" which shows the certificate and the warning "Certificate has been changed".  Yes, it has.  At the bottom of the certificate I select "PROCEED ANYWAY".

This only takes me back to to the "Certificate not valid", error.  There is no way out.

The only way I have found to upgrade to the new certificate is to remove the account from my phone, and re-add it and all the accompanying information.  That's not such a huge deal for me, but I need to do my wife's phone and my sons' phones and I really shouldn't have to.

Every other mail application that the family uses - Outlook, Thunderbird, Samsung EMail, WebMail seems to handle this issue without a problem.  It's only the Gmail App that doesn't.

Is there any way I might get this fixed?
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Seriously?  No one has any ideas or a way to fix it?
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I have the same problem and also looking for a solution...
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Just went through this. I have received Godaddy email for years through my phone (pixel). I first tried going to Godaddy for help. They said their cert is up to date. So I contacted support here at Google. I was instructed to delete the email account in question, then install it. That worked. When I asked why it worked (did they do anything on their end, or did I just need to delete and reinstall), the answer was cryptic. Basically it was "sometimes this happens." So IDK. I guess if it happens to you, try uninstalling and reinstalling. If that doesn't work, contact google help, then wait for them to tell you to uninstall and reinstall. Or wave your hands over your head and spin around three times before uninstalling and reinstalling!
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@Linda - Thanks for your thoughts - as I said, my only solution has been to delete the account from the Mail app and re-add it.

Does no one actually supporting the GMail App read this forum?  Is there a "more official" way to get support?
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I'm pretty upset about the silent part. I have an e-mail address that I rarely use so I didn't notice that it stopped working for months and I only see now that I actually received e-mails during that time that I should have answered.

@Google, please let us know how to report this issue so it will get fixed.
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We shouldn't have to delete the account and re-add it every 90 days. When "Proceed Anyway" does not proceed, clearly that's a bug in the app.
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With the cert universe moving to shorter cert lifetimes, this problem will become much more significant. I don't think I should have to live with the "delete and add", but at least the workaround exists.

However, the silent failure of a working system is unacceptable. If I configure the settings for "sync every 30 minutes", then the system needs to tell me when that stops happening.
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I just encountered this problem as well and find it unacceptable. No notification and no way to accept a new certificate is egregious and forces me to abandon Gmail.
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I'm on a Pixel 4a and am experiencing the same issue.
Just as the OP, I experience this as a two part issue:
 - The GMail app doesn't report it when it fails to talk to my IMAP server (due to a changed certificate), it just appears as if no new mail is present.
 - When trying to accept a changed certificate, the "Advanced" => "PROCEED ANYWAY" option is broken.

I find it quite strange that we don't even get an official reply like "we're looking into it" or "please report this issue in this other way".
Hoping that that will change quickly...
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I had this happen last night when I updated the cert on our Mail server.  Swapping to normal SSL/TLS  forces it to actually validate the cert (because it is valid afterall) and then everything works.  Seems something is indeed broken in "Accept All Certs" and it doesn't blindly accept them like it is suppose to.
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