Issue External SMTP Server Settings

[Ither]

Server operating system version

CentOS Linux 7

Plesk version and microupdate number

Plesk Obsidian Web Host Edition 18.0.67 Update #3

I use Google Workspace for email but I obviously get nothing from Plesk -- errors when scheduled tasks fail/etc.
I read this article: How to configure an external SMTP server in Plesk - Support Cases from Plesk Knowledge Base

I installed MTA, setup the relay, and tested a job that I knew would fail--I got nothing. Password reset--I got nothing.
It doesn't seem like MTA is working at all.

I've scoured this place for topics but nothing jumped out as a resolution.

Anybody got any thoughts? Where might I find logs? I don't see anything in plesk error log (/var/log/plesk/panel.log)

I am using the exact same hostname, port, username, and password I use for my web app to email through the relay (it works without an issue.)

 

[Sebahat.hadzhi]

Hello, @Ither . Is the domain name associated with your administrative email present on the Plesk server? If yes and it is supposed to be using Google Workspace, could you please confirm if the mail service is disabled for the domain name? If that's not the case, please check the mail log at /var/log/maillog and let us know if you see any particular errors.

 

[Ither]

Hello, @Ither . Is the domain name associated with your administrative email present on the Plesk server? If yes and it is supposed to be using Google Workspace, could you please confirm if the mail service is disabled for the domain name? If that's not the case, please check the mail log at /var/log/maillog and let us know if you see any particular errors.

Hello, apologies for the delay.

Yes, the email address I am wanting to send to is also the same domain that is in plesk (hosting.)
I also have that same email set to the Administrator account in Plesk as well.

MTA settings reflect the username for the relay which is also the same email for Administrator.

I do not have a /var/log/maillog folder.

This is all I have setup on the server.

 

[Sebahat.hadzhi]

Thanks for the confirmation, @Ither . I suspect that the SMTP configuration details defined in Tools & Settings > External SMTP Server might not be correct. /var/log/maillog is a file rather than a folder and it should be present if you are on CentOS. Can you please check the /etc/msmtprc and confirm if the following line is present:

syslog LOG_MAIL

If it is, MSMTP should log messages to /var/log/maillog. If there are no messages logged at all, what I can suggest is to test the SMTP configuration:

echo -e "Subject: SMTP config confirmation\n\nEmail to confirm the SMTP configuration in MSMTP." | msmtp --debug --from=yoursmptemail@example.com yourrecipient@example.com

If that doesn't help identify the issue, what I can recommend is to get in touch with our support for further investigation.

 

[Ither]

Thanks for the confirmation, @Ither . I suspect that the SMTP configuration details defined in Tools & Settings > External SMTP Server might not be correct. /var/log/maillog is a file rather than a folder and it should be present if you are on CentOS. Can you please check the /etc/msmtprc and confirm if the following line is present:



If it is, MSMTP should log messages to /var/log/maillog. If there are no messages logged at all, what I can suggest is to test the SMTP configuration:



If that doesn't help identify the issue, what I can recommend is to get in touch with our support for further investigation.

AH, dummy me, you are right--I went right over the file.
Maillog does exist and here is what I see.

I redacted my information (don't need someone spamming my email).
The email address in admin, email address in SMTP relay configuration, and the password are right. This is the same hostname, username, and password I use to send email from my website through phpmail without issue.

Mar  9 02:57:12 atlas msmtp: host=smtp-relay.gmail.com tls=on auth=on user=xxxx@xxxx.us from=psaadm@xxxx.xxxx.us recipients=xxxx@walkerair.us errormsg='the server sent an empty reply' exitcode=EX_PROTOCOL
Mar 10 00:00:15 atlas msmtp: host=smtp-relay.gmail.com tls=on auth=on user=xxxx@xxxx.us from=xxxx.us_w482ikb1mof@xxxx.xxxx.us recipients=xxxx@xxxx.us errormsg='the server sent an empty reply' exitcode=EX_PROTOCOL
Mar 11 00:00:15 atlas msmtp: host=smtp-relay.gmail.com tls=on auth=on user=xxxx@xxxx.us from=xxxx.us_w482ikb1mof@xxxx.xxxx.us recipients=xxxx@xxxx.us errormsg='the server sent an empty reply' exitcode=EX_PROTOCOL
Mar 12 00:00:14 atlas msmtp: host=smtp-relay.gmail.com tls=on auth=on user=xxxx@xxxx.us from=xxxx.us_w482ikb1mof@xxxx.xxxx.us recipients=xxxx@xxxx.us errormsg='the server sent an empty reply' exitcode=EX_PROTOCOL

I tried the test email and it's the same error above.

Is it possible the problem is you are trying to send "from:root@xxxx.xxxx.us"? It should be something@xxxx.us.

 

[Ither]

Thanks for the confirmation, @Ither . I suspect that the SMTP configuration details defined in Tools & Settings > External SMTP Server might not be correct. /var/log/maillog is a file rather than a folder and it should be present if you are on CentOS. Can you please check the /etc/msmtprc and confirm if the following line is present:



If it is, MSMTP should log messages to /var/log/maillog. If there are no messages logged at all, what I can suggest is to test the SMTP configuration:



If that doesn't help identify the issue, what I can recommend is to get in touch with our support for further investigation.

Actually, I got further.
When using the GUI to setup the external relay, it's missing some commands.

I had to add this to the msmtprc file

tls_starttls off <-- this command is missing
auth login <-- this is defaulted to plain

I can now get password reset emails but none of my scheduled tasks will email me; if I set it to "errors only" and force an error, or I set it to "everytime". The email address listed on the notification is my email address.

If I do a debug test; I see it in the maillog. If I do reset password; I see it in the maillog. If I do a scheduled task with notify "every time" it does not show up in maillog and I do not get an email.

 

[Sebahat.hadzhi]

Glad to hear you were able to work it out at least for the system notifications. Do the scheduled tasks in question have any output in STDOUT or STRERR streams?
If not, I believe this could be the issue:

• https://support.plesk.com/hc/en-us/...sent-to-email-indicated-in-cron-task-settings