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Issue External Email Stopped Working after Upgrading to Plesk Obsidian 18.0.70 Update #2

J.Wick

Regular Pleskian
Server operating system version
Rocky Linux 8.10
Plesk version and microupdate number
Plesk Obsidian 18.0.70 Update #2
Everything has been working great until the latest update.

I've verified the email account settings using a desktop client and re-entered the details into Plesk.

All Plesk emails should be coming from [email protected], but now they are being sent from [email protected], and when they are sent from Plesk it's from [email protected]

When I log in to SSH as root, an email is automatically sent using a script, but it has stopped working as well as Plesk notifications and password resets.

Examining the mail log, it appears that it's attempting to use the server hostname in the HELO and envelope.

My /etc/msmtprc
#ATTENTION!
#
#DO NOT MODIFY THIS FILE BECAUSE IT WAS GENERATED AUTOMATICALLY,
#SO ALL YOUR CHANGES WILL BE LOST THE NEXT TIME THE FILE IS GENERATED.

# MSMTP configuration file. See msmtp(1) for syntax.
# This file was generated by msmtpmng utility.

#
# Global settings section
#
defaults

syslog LOG_MAIL

tls_certcheck off
tls on

# Automatic envelope-from generation.
# Caution: this overrides explicitly set envelope-from via --from.
from %[email protected]
allow_from_override off

# This command sets the argument of the SMTP EHLO (or LMTP LHLO) command.
domain subdomain.domain.com

#
# Default account.
#
account default

host west.exch090.emailserver.net
port 587

auth on
user [email protected]
# Password is actually stored in /etc/psa/private/msmtp-pwdeval.conf
passwordeval /usr/lib64/plesk-9.0/msmtp-pwdeval

When enabled
"Allow user scripts to send mail through this SMTP server (using the specified username and password)"
Doesn't allow users to access or use the relay and I see their [email protected] in the error logs with " smtpstatus=550 smtpmsg='550 5.7.60 SMTP; Client does not have permissions to send as this sender' errormsg='the server did not accept the mail' exitcode=EX_UNAVAILABLE"

There needs to be the ability to set the from email address and domain name.

Everything needs to be sent from [email protected] to properly authenticate and pass email security, SPF, DMARC, etc.

I've uninstalled, reinstalled the External SMTP, and even rebooted the server.

Any suggestions for fixing this would be appreciated.

Additionally, maybe relevant info:
The only other operation on the server was that I upgraded MariaDB from 10.6 to 10.11, and I encountered a PHPMyAdmin error. This error led to the complete removal of PHPMyAdmin, along with the database and user, and the subsequent reinstallation of it, which corrected the problem.
 
To get back to the operational level, I had to modify the /etc/msmtprc

I had to hard-set these values. (Which should be available in the Plesk Panel under settings!! )
  • from email
  • allow_from_override on
  • domain
For my login script, I had to modify it to:

ip_address=$(who am i | awk '{print $5}' | sed 's/[()]//g')
server_hostname=$(hostname)
date_time=$(date)
org_name=$(whois "$ip_address" | grep -i "Organization:" | awk -F':' '{print $2}' | tr -d '\n' | xargs)

{
echo "From: [email protected]"
echo "To: [email protected]"
echo "Subject: Alert: Root Access from $ip_address on $server_hostname"
echo
echo "Root Shell Access Detected"
echo
echo "Date: $date_time"
echo "Server: $server_hostname"
echo "IP: $ip_address"
echo "ISP: $org_name"
} | msmtp --read-envelope-from -C /etc/msmtprc [email protected]

For Plesk Notifications coming from psaadm, I had to add the subdomain to my Exchange server, create a distribution user of [email protected], and add it to the Send As permissions list of [email protected].


I thought Plesk was supposed to save me time, but another afternoon was spent entirely on something that should be a few clicks. Do better, Plesk.
 
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