Issue SMTP Auth not working

[member]

After a fresh install with
Debian 10.7
PLESK Plesk Obsidian 18.0.32

postfix
Outgoing mail mode: Send from domain IP addresses
SSL Certificats are good

When trying to setup a mail account in Outlook or on IOS I get IMAP working fine but SMTP Auth with everyting I tried is not working

Outlook:
Testnachricht senden: Vom Server wird keine der von diesem Client unterstützten Authentifizierungsmethoden unterstützt.

The only thing I got working is a openssl connection

openssl s_client -showcerts -connect MYSERVER:465 -servername domain.tld


I really could use some advice or a good log to look at. I only see a lot of IMAP connections.

 

[Bitpalast]

Tools & Settings > Mail > Mail Server Settings
Is it "closed"?

It should be set like this intead with at least one of the two checkboxes checked.

 

[member]

Tools & Settings > Mail > Mail Server Settings
Is it "closed"?

It should be set like this intead with at least one of the two checkboxes checked.

View attachment 18176

This is set correctly,

I have to use iOS as this is the Device that will use most often. I manged to get it working with the QR Code but then it stopped working.
I tried to re add the Profile and it worked one out of a dozzen tries.

I even had to stop IP Blocking in Plesk as it banned me for trying to often.

But even when trying with Outlook it will tell me no supported Auth method

This thing is driving me nuts

 

[mow]

What's in /var/log/maillog when you try to send?
Did you configure Outlook to use port 465?

 

[member]

Here are 587 and 465 both get ERRORs :/


Outlook

Server

 

[Bitpalast]

A small part of one of your screenshots shows "554 5.7.1" which probably ends in the invisible part "Relay not authorized". Click on the "Postausgangsserver" tab in Outlook and check "Gleiche Einstellungen wie für Posteingangsserver verwenden" or similar (in German). You're not logging in correctly for that reason you cannot send emails through the SMTP server.

Also change the IMAP port to 993 and select SSL/TLS from the encryption options.
Change SMTP port to 465 and select SSL/TLS from the encryption options.

And very important: On the first tab of your Outlook configuration, make sure that you do NOT have the SLA checkbox checked. Because if you do, Outlook might try to use DIGEST_MD5 for password encryption off your mailbox password, and that might not work on your server. If you have an SSL protected connection, it is not absolutely necessary to encrypt the password, too.

 

[mow]

What Peter said.

Also you might want to set Stammordnerpfad to INBOX. Much cleaner that way.

 

[member]

A small part of one of your screenshots shows "554 5.7.1" which probably ends in the invisible part "Relay not authorized". Click on the "Postausgangsserver" tab in Outlook and check "Gleiche Einstellungen wie für Posteingangsserver verwenden" or similar (in German). You're not logging in correctly for that reason you cannot send emails through the SMTP server.

Also change the IMAP port to 993 and select SSL/TLS from the encryption options.
Change SMTP port to 465 and select SSL/TLS from the encryption options.

And very important: On the first tab of your Outlook configuration, make sure that you do NOT have the SLA checkbox checked. Because if you do, Outlook might try to use DIGEST_MD5 for password encryption off your mailbox password, and that might not work on your server. If you have an SSL protected connection, it is not absolutely necessary to encrypt the password, too.

Damn,
If you do too much testing you forget the simplest things in Outlook. Why do I only use Exchange

To set everything to SSL/TLS and change the Ports, worked.

BUT it does not give me a hint WHY all of this is not working in iOS with the QR Code it gives the same settings expect it tells to use SSL.
Use SSL True/False

I managed to get it working with 587




But it will not use 465 that is wortking with outlook and REQUIRED for the QR Profile


Thanx for a first big step

 

[mow]

Probably uses port 587 with STARTTLS. You did use plesk sbin pci_compliance_resolver --enable dovecot or manually changed
disable_plaintext_auth to yes in /etc/dovecot/conf.d/10-plesk-security.conf, right?

 

[member]

Probably uses port 587 with STARTTLS. You did use plesk sbin pci_compliance_resolver --enable dovecot or manually changed
disable_plaintext_auth to yes in /etc/dovecot/conf.d/10-plesk-security.conf, right?

never did anything frome above


I have

disable_plaintext_auth = no

in the mentioned file

 

[mow]

Plaintext passwords are just a bad idea nowadays. There are sniffers everywhere, and with e.g. cisco vulnerabilities becoming a running joke you can't trust the network equipment.

 

[member]

Plaintext passwords are just a bad idea nowadays. There are sniffers everywhere, and with e.g. cisco vulnerabilities becoming a running joke you can't trust the network equipment.

main.cf

smtpd_sasl_auth_enable = yes
smtp_sasl_security_options = noanonymous
smtp_sasl_tls_security_options = noanonymous
smtpd_sasl_security_options = noanonymous
smtpd_sasl_tls_security_options = noanonymous

smtpd_tls_protocols = TLSv1.2
smtpd_tls_mandatory_protocols = TLSv1.2


disable_plaintext_auth to yes in /etc/dovecot/conf.d/10-plesk-security.conf

Did some stuff to make it more secure, but 465 is still not my friend.

Glad the 587 works interrim

 

[Silent3]

I'm having a very similar problem, but I'm trying to set up SMTP on my iPhone. Nothing I've tried works so far, and for now I've given up on using my own SMTP server and instead using a Gmail SMTP server. I had been using courier email, but switched to dovecot just in case that might make a difference. It did not.

Unless I'm not following something above because it's written in German, I think I've tried everything here. I've made the same main.cf changes, set disable_plaintext_auth to yes, tried both ports 465 and 587... no joy. What's especially annoying is that iOS hangs up for several minutes for each failed attempt to get this to work.

 

[Silent3]

I'm having a very similar problem, but I'm trying to set up SMTP on my iPhone. Nothing I've tried works so far, and for now I've given up on using my own SMTP server and instead using a Gmail SMTP server. I had been using courier email, but switched to dovecot just in case that might make a difference. It did not.

Unless I'm not following something above because it's written in German, I think I've tried everything here. I've made the same main.cf changes, set disable_plaintext_auth to yes, tried both ports 465 and 587... no joy. What's especially annoying is that iOS hangs up for several minutes for each failed attempt to get this to work.

I found the problem. I can't believe it was just this. I put "smtp." in from of my domain name. When I removed that, SMTP finally worked.