Apple Mail Won't Trust SMTP Server

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1

Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. crt.sh | example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.

My domain is:kasdivi.com
I ran this command:
I try to reinstalll my email account on my iPhone and iPad. It never give me a chance to trust it
It produced this outputI
no out out just no action
My web server is (include version):
apache 2.4.5.1
The operating system my web server runs on is (include version):
FreeBSD 13.1

My hosting provider, if applicable, is:

I can login to a root shell on my machine (yes or no, or I don't know):
yes

I'm using a control panel to manage my site (no, or provide the name and version of the control panel):
no
The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):

certbot 1.13.0

The trust certificate for Apple iOS. 2022070700 Includes ISRG Root X2 which I thinks the root for LetsEncyptt

I think it may ba having issue with my certificate covering serval domains. but I have no issue adding email account with another domain , theoceanwindow.com

I know this is an Apple problem but I have gotten no leads except to delete and reinstall which is my new morning routine.

I have been able to send email using this sever using on line tools

I guess my only fix is figure iOS is dead to me and go back to android

2

Highly unlikely. What's your mail server's name? Because that name likely isn't included on the cert it's serving.

5 Likes
3

mail.kssdivi.com. This hs been a continuing problem. It will work a while and trust goes away. My server hasn't changed just another iOS update or tweak I imagine

4

There are no public DNS records for that hostname, but comparing to your OP it's apparently just a typo. If I check mail.kasdivi.com, it returns this certificate:

-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----

...and if I feed that certificate into Certificate Decoder - Decode certificates to view their contents, it confirms my suspicions: mail.kasdivi.com isn't included as a name on that certificate, which is why iOS Mail complains about the certificate.

4 Likes
5

you were right about the typo..my eyesight isn't what it use to be(nor my typing)

Th interesting thing is that my mail server at the theoceanwindow.com \s trusted by iOS

6

Once again, that hostname doesn't seem to exist--there aren't any public DNS records for that hostname. But it (along with www. theoceanwindow.com) is part of the cert I gave above, so it's to be expected that it would be trusted.

The way certificate validation works really is pretty straightforward: if you're connecting to $HOSTNAME, the certificate presented needs to cover $HOSTNAME. If you're trying to connect to mail.kasdivi.com, and the cert doesn't includes that name (which it currently doesn't), you're going to get an error. If you're trying to connect to theoceanwindow.com (once its DNS records exist again), and the cert presented does include that name, then no error.

4 Likes
7

Ok I re-learned the process.. update the certificate... pretty much induced everything in it and Apple MAIL on the iOS devices will not verify the smtp under ssl. Ok so I turned of ssl on Apple Mal for that account and changed port to 25, the old insecure smtp port an outgoing mail works fine. BTW my hostname is triggerfish.theoceanwindow.com.

Got me beat. Like I said my desktop has now issues with this or any other account

8

you should align the domain in server's cert and mx record

4 Likes
9

Interesting, it does for me. I obviously don't have credentials to log in, but my iPhone doesn't give me any cert warnings when I try to set up an account there.

What, exactly, is the error it shows you?

5 Likes
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after I put all the server information in I get "cannot connect Using SSL". I tried reinstalling the account this morning. , ignored that warning and it seems to work ok including sending mail. Thanks. Just more joy dealing with Apple. Thanks for the tips

1 Like
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