Timeout SMTP outgoing e-mail

graffx

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Mail from apple. (IMAP). incomming 143 and outgoing 587.

When adding a new email address:
The password can't be send safe to "mail.domain.nl" / server. Continue is possible but password can't be secured.

Message I get when selecting SSL: Control of account name or password failed.
 

Richard G

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The password can't be send safe to "mail.domain.nl" / server. Continue is possible but password can't be secured.
But does it work when using port 143 and 587? Or does it also generate other errors?

Might be an Apple mail bug.
Maybe this will help:
 

graffx

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It works, but not with SSL. As soon as I select SSL it wont save that setting.
`Failed to verify account name or password.`
 

Richard G

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Can you try with a Windows client with a test account? To see if it's an Apple or server issue?

Of ik wil ook wel even voor je testen als je me via pm een testaccountje stuurt.
 

mxroute

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Sounds like you have a CAA record in your DNS that you should probably remove. You might have pasted it at the recommendation of some service at some point, and limited your future use cases by accident.
 

Richard G

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Ah @mxroute nice to see you pop in here too.
I tested this with my windows client and with telnet.

In the beginning via telnet port 993 opened and closed instantly. When using SSL on incoming or outgoing ports, the error notice from Outlook 2013 is:
Login to incoming mail server (POP3): The server does not support the encryption you specified for the connection. Use a different encryption method. Contact your email server administrator or Internet service provider (ISP) for assistance.
Same error for smpt. Encryption method not supported.

I don't know if this can be caused by CAA records which must be removed, but if it is, then this is the confirmation for it.
 

mxroute

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Ah @mxroute nice to see you pop in here too.
I tested this with my windows client and with telnet.

In the beginning via telnet port 993 opened and closed instantly. When using SSL on incoming or outgoing ports, the error notice from Outlook 2013 is:

Same error for smpt. Encryption method not supported.

I don't know if this can be caused by CAA records which must be removed, but if it is, then this is the confirmation for it.

That may indeed be something different. Outdated systems generally don’t support current SSL standards. If your OS is fully up to date and supports current SSL standards you may be able to review the default exim ciphers and cross reference to what your Os version supports to see if you can add a secure one to the system.

But in general I just tell people to stop wanting outdated software to tell them they have a secure connection, because often that means wanting the server to lie to them by supporting insecure standards.
 

graffx

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There where no CAA records before the issue. The system is pretty up to date. CentOS 8 - All updates are done. Server version: 1.61.5.
The only thing I have played with is server dkim keys which seemed to be pretty easy to do in DA and just needed to copy them in the external DNS.
 

Nickske00

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Nov 30, 2015
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Mail from apple. (IMAP). incomming 143 and outgoing 587.

When adding a new email address:
The password can't be send safe to "mail.domain.nl" / server. Continue is possible but password can't be secured.

Message I get when selecting SSL: Control of account name or password failed.

For SSL I use port 993 for incomming and 465 for outgoing. And a valid ssl certificate for the used server ofcourse ;) (I usually use my hostname because these days you use a cert for the hostname anyways).
 

graffx

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That ports don't work (can't save changes) I did notice I can use my reverseDNS vps.somedomain.nl instead of mail.domainname.nl

Really need to do some more testing I guess.
 

Richard G

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Can Reverse DNS be an issue?
This would only cause anti-spam blocks not encryption errors.

You can use either rDNS, but best is to use the name that your mailserver is answering with.
As far as I know your mailserver answers with vps.somedomain.nl so best is to put that rDNS to vps.somedomain.nl for good practice.
 

graffx

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Dec 7, 2020
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Thanks to Richard it seems to be fixed.
The hostname needed to have a certificate.

/usr/local/directadmin/scripts/letsencrypt.sh request_single vps.mydomain.nl 4096
 
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