1 Topic by dgzagm

  • dgzagm
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Topic: Outlook Malforms Emails to Internal Domain

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 1.0 MARIADB edition
- Deployed with iRedMail Easy or the downloadable installer? downloadable installer
- Linux/BSD distribution name and version: Ubuntu 18.04
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- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? No
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

Hello.  When email is sent using Outlook (O365 v16) within the same domain; from Dan@domain1.com to Matt@domain1.com it tries to send two emails: one to Matthew and one to Lastname. 

Jan 17 22:58:31 mx postfix/postscreen[17454]: CONNECT from [127.0.0.1]:60010 to [127.0.0.1]:25
Jan 17 22:58:31 mx postfix/postscreen[17454]: WHITELISTED [127.0.0.1]:60010
Jan 17 22:58:31 mx postfix/smtpd[17455]: connect from mx.domain1.com[127.0.0.1]
Jan 17 22:58:32 mx postfix/smtpd[17455]: NOQUEUE: reject: RCPT from mx.domain1.com[127.0.0.1]: 504 5.5.2 <Matthew>: Recipient address rejected: need fully-qualified address; from=<dan@domain1.com> to=<Matthew> proto=ESMTP helo=<mx.domain1.com>
Jan 17 22:58:32 mx postfix/smtpd[17455]: NOQUEUE: reject: RCPT from mx.domain1.com[127.0.0.1]: 504 5.5.2 <Lastname>: Recipient address rejected: need fully-qualified address; from=<dan@domain1.com> to=<Lastname> proto=ESMTP helo=<mx.domain1.com>
Jan 17 22:58:32 mx postfix/smtpd[17455]: disconnect from mx.domain1.com[127.0.0.1] ehlo=1 mail=1 rcpt=0/2 quit=1 commands=3/5

No problems sending via iPhone or webmail.
Has anyone experienced a problem like this?
Thanks
Dan

----

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2 Reply by ZhangHuangbin

  • ZhangHuangbin
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Re: Outlook Malforms Emails to Internal Domain

According to the log, Outlook connects to port 25.
Please make sure Outlook is configured to send through port 587 with TLS secure connection.

3 Reply by dgzagm

  • dgzagm
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Re: Outlook Malforms Emails to Internal Domain

ZhangHuangbin wrote:

According to the log, Outlook connects to port 25.
Please make sure Outlook is configured to send through port 587 with TLS secure connection.

I'm using EAS so I don't think there is an option to set the port or TLS, right?

4 Reply by ZhangHuangbin

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Re: Outlook Malforms Emails to Internal Domain

Any related log in Postfix/SOGo log files on iRedMail server?

5 Reply by MuPp3t33r

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Re: Outlook Malforms Emails to Internal Domain

Looks to me like an issue with Outlook's autocomplete cache, try deleting the email address that you are sending to from the cache and then type the full email address in to the recipient

6 Reply by dgzagm

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Re: Outlook Malforms Emails to Internal Domain

So I just sent an email to generate some logs and of course it's working now.  I don't know what changed, but for a couple weeks (since I've created the mail server) it wasn't working. In looking at the SoGo logs I do see some warnings that I'm not sure if I need to address?  Some even show hung as long as 40 min.


Jan 20 17:54:47 sogod [2325]: [WARN] <0x0x562de21a6f90[WOWatchDogChild]> pid 2593 has been hanging in the same request for 40 minutes

Jan 20 18:25:48 sogod [2325]: [WARN] <0x0x562de21e7630[WOWatchDogChild]> pid 2603 has been hanging in the same request for 8 minutes
Jan 20 18:25:48 sogod [2325]: [WARN] <0x0x562de21a7310[WOWatchDogChild]> pid 2591 has been hanging in the same request for 3 minutes
Jan 20 18:26:41 sogod [2325]: [WARN] <0x0x562de2288690[WOWatchDogChild]> pid 2604 has been hanging in the same request for 1 minutes
Jan 20 18:26:56 sogod [2325]: [WARN] <0x0x562de21e7630[WOWatchDogChild]> pid 2603 has been hanging in the same request for 1 minutes
Jan 20 18:27:36 sogod [2325]: [WARN] <0x0x562de21a6ba0[WOWatchDogChild]> pid 2596 has been hanging in the same request for 1 minutes
Jan 20 18:27:41 sogod [2325]: [WARN] <0x0x562de2288690[WOWatchDogChild]> pid 2604 has been hanging in the same request for 2 minutes



Thank you for all you do.
Dan

7 Reply by dgzagm (edited by dgzagm 2020-01-21 20:09:49)

  • dgzagm
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Re: Outlook Malforms Emails to Internal Domain

MuPp3t33r wrote:

Looks to me like an issue with Outlook's autocomplete cache, try deleting the email address that you are sending to from the cache and then type the full email address in to the recipient

Thanks for the suggestion.  I also tried this and it did not matter.  However, for unknown reasons it's working as expected.  I'm thinking it has something to so with EAS because it wasn't easy to get into Outlook 16(O365).  I had to use the Mail setting in Control Panel to get away from the automagical email setup O365 wanted to use.

Thanks again for your suggestion and time!
Dan