Certificate Problems in Apple Mail on Monterey

Hi,


I use Apple Mail for my email with my domain through host called Fat Cow. I have used them for over a decade with Apple Mail with no problems. I was previously on a Mac Mini 2018 with Big Sur installed. This week I purchased a Mac Studio with Monterey 12.5.1. Now with Apple Mail I get a certificate error when trying to send messages. It is an smtp problem, as I can still receive messages just fine.


The problem seems to be that Apple Mail is pulling in a security certificate that has nothing to do with my web host. It doesn't have my web host's name, and the expiration date is 2016. I also can't find this certificate in the Keychain Access application. The certificate for my web host is in there, but it's not what Apple Mail is trying to use no matter what I try and do. So I'm stuck with Apple Mail saying the certificate is invalid, and I cannot send any emails.


When I jump back to my Mac Mini 2018 I don't have this problem. Sending email works just fine with same exact settings. My webmail works just fine. AND using Microsoft Outlook on the Mac Studio with Monterey works just fine. There is clearly something wrong with Apple Mail on Monterey that is causing this smtp problem. Can anyone help me with this?

Mac Studio, 12.5

Posted on Sep 2, 2022 6:03 PM

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3 replies

Sep 2, 2022 6:39 PM in response to JD Marlow

I'm sure it has nothing to do with Monterey. It is some problem with that host.


When I searched for this issue, the only meaningful hit was this information on a strange, foreign language web site:


Mail SSL/TLS Support!
PowWeb now supports SSL and/or TLS in the following ways on the new platform:

POP with SSL : port 995
IMAP with SSL : port 993

* The sole caveat for using POP or IMAP with SSL is that using mail.domain.com will result in the security certificate mismatch. To avoid this, use pop.powweb.com or imap.powweb.com instead.

SMTP with TLS : port 25 and 587

* The sole caveat for SMTP with TLS is that the SMTP server must be set to smtp.yourhostingaccount.com to avoid the security warning. NOTE: Do not substitute yourhostingaccount.com for anything else; use smtp.yourhostingaccount.com explicitly.

Thank you for choosing PowWeb!
__________________
Tom S.
PowWeb / Endurance Staff

I have no idea what this means. I found one other result that is readable (en français) but still references powweb


My guess is that their service is all hacked up and you will have to manually override this certificate, with the incorrect host name, to make it work. I recommend a different e-mail provider.

Sep 3, 2022 5:01 AM in response to JD Marlow

I found that on a strange, foreign language site that was otherwise about car racing or something. I have no reason to doubt it. The internet is bigger now, but it still works the same way. Bad ideas have always been shared.


I can assure you there is nothing wrong with Apple Mail. There are maybe 80 million people using Apple Mail. Most of those people use a major email provider like Apple, Microsoft, or Google. You are using Fat Cow. Do the math.

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Certificate Problems in Apple Mail on Monterey

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