• Plesk Uservoice will be deprecated by October. Moving forward, all product feature requests and improvement suggestions will be managed through our new platform Plesk Productboard.
    To continue sharing your ideas and feedback, please visit features.plesk.com

Issue not sending via external SMTP (msmtp + Office365)

lema

New Pleskian
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 [email protected]

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=[email protected] from=[email protected] recipients=[email protected] 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 %[email protected]
from [email protected]
allow_from_override off
domain plesk2.domain.gr
account default
host smtp.office365.com
port 587
auth on
user [email protected]
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 [email protected] has explicit “Send As” permission for [email protected] and this has been tested and verified.

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