1 Topic by jwdaigle

  • jwdaigle
  • Member
  • Offline
  • Registered: 2016-02-16
  • Posts: 3

Topic: "Theres a problem connecting to the POP3 mail server" outlook.com

==== Required information ====
- iRedMail version (check /etc/iredmail-release): 0.9.4
- Linux/BSD distribution name and version: Ubuntu 14.04
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
- Web server (Apache or Nginx): Apache
- Manage mail accounts with iRedAdmin-Pro? No
- Related log if you're reporting an issue: None
====

Just completed setting up my first iRedMail installation, pretty much went with all default trying to be safe.  The end goal for doing this was to be able to have iRedMail accept SMTP connections for emails, and have outlook.com use POP3 to get them into my outlook.com account.

outlook.com account specifies the DNS name of the iRedMail server, port 995, with username@domain.com and correct password specified (using advanced options), along with Requires a secure connection (SSL), and "Leave a copy of messages on server".

It churns for a while and then gives me the ever so useful "There's a problem connecting to the POP3 mail server".

Theres nothing logged on the iRedmail side.  I know the server is up and running and accessible by telnet'ing from my desktop to 25 and 110 and typing raw SMTP & POP3 commands like EHLO, MAIL FROM etc.  Dont think I can test the same works for the SSL port equivalents?

No idea how to proceed, please help?

Thank you -

Joe

----

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

2 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,170

Re: "Theres a problem connecting to the POP3 mail server" outlook.com

Not sure whether outlook.com requires your server to have a purchased SSL cert. Maybe you can do a TESTING like this:

*) Change 'ssl = required' to 'ssl = yes' in /etc/dovecot/dovecot.conf. It will allow insecure pop3/imap connection through port 110/143. Note: restarting dovecot service is required.
*) Update your outlook setup to use port 110 for pop3 connection.

if insecure connection works, then it might be caused by your self-signed ssl cert.

3 Reply by jwdaigle

  • jwdaigle
  • Member
  • Offline
  • Registered: 2016-02-16
  • Posts: 3

Re: "Theres a problem connecting to the POP3 mail server" outlook.com

ZhangHuangbin wrote:

Not sure whether outlook.com requires your server to have a purchased SSL cert. Maybe you can do a TESTING like this:

*) Change 'ssl = required' to 'ssl = yes' in /etc/dovecot/dovecot.conf. It will allow insecure pop3/imap connection through port 110/143. Note: restarting dovecot service is required.
*) Update your outlook setup to use port 110 for pop3 connection.

if insecure connection works, then it might be caused by your self-signed ssl cert.

Hi there - thanks for your help, but changing the referenced line from ssl = required to ssl = yes didnt allow Outlook to pop3 into my server.  The error is different though, making me think that I have not done something correctly.

The new error is :

We couldn't sign in to your POP3 server. Please make sure your username and password are correct. 

[ Server Response: -ERR [AUTH] Plaintext authentication disallowed on non-secure (SSL/TLS) connections. ]

If I look in /var/log/dovecot.log, I see :

Feb 21 16:03:59 pop3-login: Info: Aborted login (tried to use disallowed plaintext auth): user=<>, rip=176.61.139.39, lip=xx.xx.xx.xxx, session=<z3A23UksLwCwPYsn>

It seems to be complaining that there is still a problem related to types of allowed authentications?

Is there another setting I need to change to allow this?

I have changed my outlook to try on port 110, and deselected the "require ssl" checkbox for incoming email.

Thanks for any additional help

4 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,170

Re: "Theres a problem connecting to the POP3 mail server" outlook.com

jwdaigle wrote:

[ Server Response: -ERR [AUTH] Plaintext authentication disallowed on non-secure (SSL/TLS) connections. ]

Please check this tutorial:
http://www.iredmail.org/docs/allow.inse … onnections

5 Reply by jwdaigle

  • jwdaigle
  • Member
  • Offline
  • Registered: 2016-02-16
  • Posts: 3

Re: "Theres a problem connecting to the POP3 mail server" outlook.com

ZhangHuangbin wrote:

Not sure whether outlook.com requires your server to have a purchased SSL cert. Maybe you can do a TESTING like this:

*) Change 'ssl = required' to 'ssl = yes' in /etc/dovecot/dovecot.conf. It will allow insecure pop3/imap connection through port 110/143. Note: restarting dovecot service is required.
*) Update your outlook setup to use port 110 for pop3 connection.

if insecure connection works, then it might be caused by your self-signed ssl cert.

Bingo!  You're exactly right.  Its caused by the self signed cert installed by default.  For my benefit, and other noobs who might be reading this, what are my options (ie, can I get one for free :-)) to getting outlook.com & RedMail to play nicely together?

Thank you very much, coffee on the way!

6 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,170

Re: "Theres a problem connecting to the POP3 mail server" outlook.com

I'm not very sure what the situation is now. Does your Outlook work fine with insecure connection?

If it does, i'm afraid that you need to get/buy a valid SSL certificate and use it on your iRedMail server. We have a tutorial for you:
http://www.iredmail.org/docs/use.a.boug … icate.html

By the way, you may want to try Let's Encrypt, it's free:
https://letsencrypt.org