Resolved not sending via external SMTP (msmtp + Office365)

[lema]

Server operating system version

Debian 12.12

Plesk version and microupdate number

Plesk Obsidian 18.0.73 Update #3 Web Host Edition

Hello everyone,

On my Debian 12 server (Plesk 18.0.73, mail service not installed),
I’m using the built-in msmtp integration to send outgoing messages through Office 365 (smtp.office365.com:587).

When I test manually from Debian shell, it works perfectly:
echo "Subject: Test" | msmtp -v myaddress@domain.com

However, messages sent *from Plesk itself* (e.g. scheduled tasks) are not delivered.
The /var/log/maillog shows:

Oct 20 12:08:15 plesk2 msmtp[221934]: host=smtp.office365.com tls=on auth=on user=smtp-user-004@domain.onmicrosoft.com from=smtp-user-004@domain.onmicrosoft.com recipients=someuser@gmail.com errormsg='the server sent an invalid reply' exitcode=EX_PROTOCOL

my /etc/msmtprc file looks like:

defaults
syslog LOG_MAIL
tls_certcheck on
tls on
#from %U@plesk2.domain.gr
from noreply@domain.gr
allow_from_override off
domain plesk2.domain.gr
account default
host smtp.office365.com
port 587
auth on
user smtp-user-004@domain.onmicrosoft.com
passwordeval /usr/lib/plesk-9.0/msmtp-pwdeval

I have already checked the thread Resolved - External SMTP Server Settings but unfortunately it didn’t solve the problem in my case.
The Office 365 account smtp-user-004@domain.onmicrosoft.com has explicit “Send As” permission for noreply@domain.gr and this has been tested and verified.

Has anyone managed to make outgoing emails from Plesk itself work with Office 365 via msmtp?

 

[Sebahat.hadzhi]

Hello, @lema . Could you please try adding the following lines to the panel.ini file:

[notification]
senderAddress=<custom email address>

 

[lema]

@Sebahat.hadzhi , Thanks a lot, that solved the issue!

[notification]
senderAddress = noreply@domain.com