SMTP 550 relay not permitted, authentication required

SecCon · November 27, 2023, 10:21am

System Information
System hostname: xservu2 (127.0.1.1)
Operating system: Ubuntu Linux 22.04.3
Webmin version: 2.105
Authentic theme version: 21.09.5
Time on system: Monday, November 27, 2023 10:02 AM
Kernel and CPU: Linux 6.2.0-37-generic on x86_64
Processor information: Intel(R) Xeon(R) CPU E5-2683 v4 @ 2.10GHz, 4 cores
System uptime: 1 hour, 09 minutes
Running processes: 233
CPU load averages: 0.15 (1 min) 0.14 (5 mins) 0.15 (15 mins)
Real memory: 1.42 GiB used / 1.37 GiB cached / 7.74 GiB total
Virtual memory: 0 bytes used / 1.99 GiB total
Local disk space: 57.63 GiB used / 949.66 GiB free / 1007.3 GiB total
Package updates: All installed packages are up to date

I am trying to get Webmin to send me status reports. Monitoring.

When first in the Webmin configuration > Sending e-mail I got this error:

SMTP authentication cannot be enabled unless the Authen::SASL Perl module is installed. Error detailsCan&#39;t locate Authen/SASL.pm in @INC (you may need to install the Authen::SASL module) (@INC contains: /usr/share/webmin/vendor_perl /usr/share/webmin /etc/perl /usr/local/lib/x86_64-linux-gnu/perl/5.34.0 /usr/local/share/perl/5.34.0 /usr/lib/x86_64-linux-gnu/perl5/5.34 /usr/share/perl5 /usr/lib/x86_64-linux-gnu/perl-base /usr/lib/x86_64-linux-gnu/perl/5.34 /usr/share/perl/5.34 /usr/local/lib/site_perl /usr/share/webmin/ . .. ..) at (eval 262) line 1. BEGIN failed--compilation aborted at (eval 262) line 1. : webmin/save_sendmail.cgi (line 43)

Which I guess is ok, since it needed a dependency and I could install it. Then back to the conf.

I use START/TLS SMTP authentification on the mail server. Entered all that. I have it configured and working with similar configuration in other systems, like some virtual machines and my router and firewall. I mostly know how to fill in this to get it working. And it works. Tried while doing this.
But not here.

I enter the required info in all the required fields and sens a TES mail, but that leaves an error

Sending message from security@conram.it to security@conram.it ..
.. sending failed : SMTP command rcpt to: <security@conram.it> failed : 550 relay not permitted, authentication required

It is an external mail server, my web hosts, and I fiddled a bit with different settings that may or may not have an impact , like the

From address for email from Webmin

that I changed back and forth from the default to a known mail address
or
the smtp server address that I tested to put the IP instead of the URL, which seemed to have no effect one way or the other.

My firewall has no logs of blocking anything related to this, and it would block other SMTP entries on my network if so, and it is not.

Any tips on something I may be missing?
Do I need to configure additional mail server options? I do not use them or need them, only this as described above.

SecCon · November 27, 2023, 6:48pm

Could it possibly be related to: Sendmail Mail Server | Webmin

SecCon · November 30, 2023, 7:09am

So I am still getting this and will be monitoring this thread should someone be kind enough to give me some information I can use to troubleshoot this.

jimr1 · November 30, 2023, 7:15am

A “550 Authentication is required for relay” error indicates that your email server requires SMTP authentication in order to send outgoing mail, but the email client used to send email has not been authenticated with your username and password

how are you trying to connect to the server to send the message ?

SecCon · November 30, 2023, 9:00am

Via the Webmin interface. Is that somehow unclear?

jimr1 · November 30, 2023, 9:06am

Very … the webmin interface does not connect to a mail server a mail transport agent (mta) does, normally on a webmin/virtualmin server postfix is the mta, so the reworded question is are you using usermin to attempt to send mail or outlook,thunderbird etc ?

SecCon · November 30, 2023, 4:20pm

I am trying to get this to work:

Webmin > Webmin Configuration > Sending Email

Left some fields empty, see posts above.

Joe · November 30, 2023, 4:50pm

It could only be related to the Sendmail Mail Server module if you’re using the Sendmail Mail Server. You should know if you are. (sendmail the mail injection command is not Sendmail the MTA. Postfix includes a sendmail command, probably other MTAs do, too. That is not the Sendmail mail server.)

SecCon · November 30, 2023, 5:28pm

Hmm, not using anything.

I did only try to set tis up to get some e-mail notifications from the Webmin server itself. Basic monitoring and e-mail alerts.

Nothing else e-mail related configured before. Nada. Zero. Zilch.

SecCon · December 2, 2023, 12:46pm

So I added sendmail to another system in my environment (Zabbix) and it worked without any problem on first attempt.

Since I now have at least 3 different systems configured with this enabled and working in the same network, - my firewall, my Zabbix and Ubiquitis UISP - I must conclude that something is wrong or missing in the Webmin configuration but I do not know what.

Just for the heck of it I configured yet another e-mail alert in my Uptime Monitor:

Works. So that make 4 different systems.

Joe · December 2, 2023, 7:09pm

If I’m understanding your comment here: SMTP 550 relay not permitted, authentication required - #7 by SecCon

You’ve left everything blank. No server, no auth information. I don’t see how you’d expect that to work.

You could install a mail server on the system itself (I would choose Postfix for that, but if you’re familiar with Sendmail, that’s fine, too), and choose “Via SMTP to local mail server”. But if you’re trying to use a remote server, you definitely need to tell it what mail server to use, and you almost certainly need a username and password (unless it’s on your local network and allows relaying without authentication).

SecCon · December 2, 2023, 8:29pm

Joe, come on, that was just a screenshot to show to @jimr1 were I was in Webmin.

Of course I filled in everything as specified. And get the error in post 1.

I now have 4 different apps using the exact same settings that do work and Webmin do not.

So I am repeating my question from my second post, which no one has answered: do I need to start/configure/bribe anything else for Webmin to send me e-mail notifications from webmins monitoring system it self.

No users, no mail server , no mail services at all has been activated or is being used for anything. Yet.

stefan1959 · December 2, 2023, 10:44pm

I use default settings and sends fine. I do have Virtualmin. No authentication set.

Joe · December 3, 2023, 12:27am

Sorry, I misunderstood.

No. At least I never have needed to.

What’s in the log of the mail server you’re trying to use, if you can access it?

I’m not sure what else to look at.

SecCon · December 3, 2023, 9:11am

That is you local mailserver, obviously you have one configured.

I am trying to connect to my webhost mailserver at prime1.inleed.net .

@Joe
I do not think there are any logs since it is not even getting in contact with the mailserver but I did check just in case and there is nothing that I can see that would be relevant.

Wait a second. I see the Time is off by one hour… Correcting. And a kernel update. Rebooting. Trying again. No result.

I found something else

Webmin Actions Log > Notification email options
I checked everything just to see if it somehow triggered an smtp relay action as above and tried to save.

It gave me this error message

Error details
Can't locate List/MoreUtils.pm in @INC (you may need to install the List::MoreUtils module) (@INC contains: /usr/share/webmin/vendor_perl /usr/share/webmin /etc/perl /usr/local/lib/x86_64-linux-gnu/perl/5.34.0 /usr/local/share/perl/5.34.0 /usr/lib/x86_64-linux-gnu/perl5/5.34 /usr/share/perl5 /usr/lib/x86_64-linux-gnu/perl-base /usr/lib/x86_64-linux-gnu/perl/5.34 /usr/share/perl/5.34 /usr/local/lib/site_perl /usr/share/webmin/ . ..) at (eval 569) line 1. BEGIN failed--compilation aborted at (eval 569) line 1. : mailboxes/boxes-lib.pl (line 1388)

So maybe that is somehow relevant?

How concerned should I be about the Webmin Firewall? Or the lack of IPV6 support? Not that I want any of it.

Joe · December 3, 2023, 6:51pm

There is no such thing as a Webmin Firewall. There are firewall modules in Webmin that manage a variety of firewall tools (e.g. iptables, firewalld, CSF, etc.).

You can install the List::MoreUtils module with:

apt install liblist-moreutils-perl

But, I’m surprised Jamie would use that module. And, also the Read Mail module has nothing to do with sending mail from Webmin.

SecCon · December 5, 2023, 11:37am

So installed.

Got an error in the installation:


...
Setting up liblist-moreutils-perl (0.430-2) ...
debconf: unable to initialize frontend: Dialog
debconf: (No usable dialog-like program is installed, so the dialog based frontend cannot be used. at /usr/share/perl5/Debconf/FrontEnd/Dialog.pm line 78.)

debconf: falling back to frontend: Readline

And then I tried again to configure my settings, include a screenshot just in case:

But did not help.

Just in case I restarted the server… same result.

So I did some additional troubleshooting checking connectivity.

Webmin is after all a guest on Ubuntu Server 22.03 in Hyper-V, and I could telnet the smtp server and the port successfully.

Both from Webmin’s terminal and from the host OS (Ubuntu) bash.

More suggestions?

SecCon · December 5, 2023, 11:50am

And using that, Webmin Actions Log, quoting meself…

### Failed to save notification options : SMTP command rcpt to: <security@conram.it> failed : 550 relay not permitted, authentication required

so no longer that long error, but the same as the other.

forlotto · December 6, 2023, 5:06am

ok irrelevant

SecCon · December 6, 2023, 9:38am

I have checked the logs as best I could. Any particular log that give me more insight? There are a few and I am sure I checked them all but not sure which is the relevant one. But I have looked in ALL.

These are somewhat relevant.

[05/Dec/2023:13:20:26 +0100] Reloading configuration
[05/Dec/2023:12:48:28 +0100] [192.168.1.201] /webminlog/save_notify.cgi : SMTP command rcpt to: <security@conram.it> failed : 550 relay not permitted, authentication required
[05/Dec/2023:12:32:36 +0100] Reloading configuration
[05/Dec/2023:12:24:56 +0100] PAM authentication enabled
[05/Dec/2023:12:24:56 +0100] Using SHA512 module Crypt::SHA
[05/Dec/2023:12:24:56 +0100] Using MD5 module Digest::MD5
[05/Dec/2023:12:24:56 +0100] IPv6 support cannot be enabled without the Socket6 perl module
[05/Dec/2023:12:24:56 +0100] miniserv.pl started
[05/Dec/2023:12:24:23 +0100] Shutting down
[03/Dec/2023:10:26:24 +0100] PAM authentication enabled
[03/Dec/2023:10:26:24 +0100] Using SHA512 module Crypt::SHA
[03/Dec/2023:10:26:24 +0100] Using MD5 module Digest::MD5
[03/Dec/2023:10:26:24 +0100] IPv6 support cannot be enabled without the Socket6 perl module
[03/Dec/2023:10:26:24 +0100] miniserv.pl started
[03/Dec/2023:10:25:49 +0100] Shutting down
[03/Dec/2023:09:50:13 +0100] PAM authentication enabled
[03/Dec/2023:09:50:13 +0100] Using SHA512 module Crypt::SHA
[03/Dec/2023:09:50:13 +0100] Using MD5 module Digest::MD5
[03/Dec/2023:09:50:13 +0100] IPv6 support cannot be enabled without the Socket6 perl module
[03/Dec/2023:09:50:13 +0100] miniserv.pl started
[03/Dec/2023:09:38:17 +0100] Shutting down

I rest my case. The fact that I have 4 other apps working and that I have done connectivity checks with positive results from within Webmin and the host OS, leads me towards something being wrong with Webmin, or something additional should be enabled in Webmin, but that seems to escape the responders.