1

Topic: SMTP TLS not working for some clients

==== Required information ====
- iRedMail version (check /etc/iredmail-release):
- Linux/BSD distribution name and version:
- Store mail accounts in which backend (LDAP/MySQL/PGSQL):
- Web server (Apache or Nginx):
- Manage mail accounts with iRedAdmin-Pro?
- Related log if you're reporting an issue:
======== Required information ====
- iRedMail version (check /etc/iredmail-release): 0.9.5-1
- Linux/BSD distribution name and version: CentOS 7
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
- Web server (Apache or Nginx): Apache
- Manage mail accounts with iRedAdmin-Pro? v2.4.1 (MySQL)
- Related log if you're reporting an issue:

Thunderbird sending mail -> /var/log/maillog:
Nov 17 13:00:07 michael1 postfix/submission/smtpd[12668]: connect from c-73-173-197-215.hsd1.md.comcast.net[73.173.197.215]

connect is received but does not negotiate TLS when using SSL/TLS option resulting in failure to send.
====

This is a totally fresh install of iRedMail and iRedAdmin-Pro.  Most users are sending mail without a problem.  Some are experiencing problems negotiating TLS.

Outlook 2010 sends mail fine choosing TLS on port 587

However, Thunderbird (v45) does not send when using the SSL/TLS option.  It does work when StartTLS is chosen and TLS is negotiated.

Windows smartphone will not send using TLS.  StartTLS is not an option with the Windows smartphone.

Thanks - Jack

----

Spider Email Archiver: On-Premises, lightweight email archiving software developed by iRedMail team. Supports Amazon S3 compatible storage and custom branding.

2

Re: SMTP TLS not working for some clients

jack wrote:

However, Thunderbird (v45) does not send when using the SSL/TLS option.  It does work when StartTLS is chosen and TLS is negotiated.

Could you please show us the SMTP settings in Thunderbird (those don't work)? Please make sure they're configured to use port 587 with STARTTLS encryption.

Also, make sure those clients are not blocked in iptables firewall (triggered by Fail2ban).

jack wrote:

Windows smartphone will not send using TLS.  StartTLS is not an option with the Windows smartphone.

You can enable legacy SMTP over SSL (port 465) in Postfix for those clients. FYI:
http://www.iredmail.org/docs/enable.smtps.html