1

Topic: Unable to auth using Outlook in latest version

The latest version 0.9.5-1 does not allow Outlook to connect to SMTP with TLS.

I installed it on 3 different servers running CentOs 6 and 7 64bit - all with the same result.

Outlook tries to connect to send email and says the server does not support any authentication methods supported by Outlook.   I enabled logging in outlook to see the SMTP session and if you review the logs below comparing an install on a previous version 0.9.4 and the current version 0.9.5-1 you will see that after the STARTTLS commands it replies and has no 250-AUTH lines.

I'm not sure what I could be doing wrong in my setup or if there is a bug in the latest version.

Thanks


- iRedMail version (check /etc/iredmail-release): iRedMail-0.9.5-1
- Linux/BSD distribution name and version: CentOS 6 and 7 64 bit
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MariaDB
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? No
- Related log if you're reporting an issue:

Current Version SMTP Session (Broken):
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Port: 25, Secure: TLS, SPA: no
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Finding host
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Connecting to host
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Connected to host
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 220 m.XXXXXXXXX.net ESMTP Postfix
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): [tx] EHLO XXXXXXXXXXX
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-m.XXXXXXXXX.net
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-PIPELINING
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-SIZE 15728640
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-ETRN
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-STARTTLS
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-ENHANCEDSTATUSCODES
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250-8BITMIME
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 250 DSN
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Securing connection
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): [tx] STARTTLS
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): <rx> 220 2.0.0 Ready to start TLS
2016.06.15 11:29:47 SMTP (m.XXXXXXXXX.net): Securing connection
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): Connected to host
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): [tx] EHLO XXXXXXXXXXX
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-m.XXXXXXXXX.net
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-PIPELINING
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-SIZE 15728640
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-ETRN
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-ENHANCEDSTATUSCODES
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250-8BITMIME
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): <rx> 250 DSN
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): Authorizing to server
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): Disconnecting from host
2016.06.15 11:29:48 SMTP (m.XXXXXXXXX.net): Disconnected from host


Previous Version SMTP Session (Works):

2016.06.15 11:32:48 SMTP (m.XXXXXXXXX.net): Port: 25, Secure: TLS, SPA: no
2016.06.15 11:32:48 SMTP (m.XXXXXXXXX.net): Finding host
2016.06.15 11:32:48 SMTP (m.XXXXXXXXX.net): Connecting to host
2016.06.15 11:32:48 SMTP (m.XXXXXXXXX.net): Connected to host
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 220 m.XXXXXXXXX.net ESMTP Postfix
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): [tx] EHLO XXXXXXXXXXX
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-m.XXXXXXXXX.net
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-PIPELINING
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-SIZE 15728640
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-ETRN
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-STARTTLS
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-ENHANCEDSTATUSCODES
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250-8BITMIME
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 250 DSN
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): Securing connection
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): [tx] STARTTLS
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): <rx> 220 2.0.0 Ready to start TLS
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): Securing connection
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): Connected to host
2016.06.15 11:32:49 SMTP (m.XXXXXXXXX.net): [tx] EHLO XXXXXXXXXXX
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-m.XXXXXXXXX.net
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-PIPELINING
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-SIZE 15728640
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-ETRN
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-AUTH PLAIN LOGIN
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-AUTH=PLAIN LOGIN
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-ENHANCEDSTATUSCODES
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250-8BITMIME
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 250 DSN
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): Authorizing to server
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): [tx] AUTH LOGIN
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 334 XXXXXXXXXXXXXXXX
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): [tx] XXXXXXXXXXXXXXXXXXXXXXX==
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 334 XXXXXXXXXXXXXXXX
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): [tx] *****
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): <rx> 235 2.7.0 Authentication successful
2016.06.15 11:32:50 SMTP (m.XXXXXXXXX.net): Authorized to host


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2

Re: Unable to auth using Outlook in latest version

Use port 587 with starttls please.