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IDProjectCategoryView StatusDate SubmittedLast Update
0004270SOGoActiveSyncpublic2017-09-04 10:182018-07-09 11:06
Assigned To 
Platform[Client] MicrosoftOSWindowsOS Version7
Product Version3.2.10 
Target VersionFixed in Version 
Summary0004270: Mails stay forever in outbox of Outlook 2016
DescriptionWe have a few clients which connect the Outlook 2016 with ActiveSync to our server. In general it is working fine but sometimes they have the problem that the emails get stuck in the outbox. It is not even possible to delete those emails in Outlook anymore. When syncing they seem to sync but are never sent.

Any ideas how to troubleshoot this situation the best?
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-  Notes
tfu (reporter)
2017-09-05 06:58

- Check whether the stuck mails have something in common. (size/attachments/receipients...)
- Search for errors in sogo.log around: ... POST /SOGo/Microsoft-Server-ActiveSync?Cmd=SendMail&DeviceType=....
john.cameron (reporter)
2017-10-19 08:44

We are having this issue with all ActiveSync clients.
Sendmail returns “user unknown”, but the ActiveSync client keeps retrying.

Oct 19 11:13:29 mail sendmail[1278]: v9J9DT6i001278: <>... User unknown
Oct 19 11:25:37 mail sendmail[4673]: v9J9Pbod004673: <>... User unknown

This happens when sending to a non-existent mailbox hosted locally and any invalid email address.

To resolve this we create a temporary alias to an existing mailbox or ask the user to remove
The invalid email address from the email.
Philipp (reporter)
2017-12-28 04:50

I have same problem. That's for sure bug in SOGo - when mail is sent (via webmail or EAS) it is passed to SMTP server, which can accept or reject it depending on configuration. For example Postfix has option smtpd_recipient_restrictions=reject_unknown_recipient_domain which rejects inbound SMTP from SOGo when non-existent recipient domain in To: field. When SOGo webmail don't even allow to send this message (saying invalid recipient), EAS implementation ignores SMTP rejection and mail sits in Outbox forever and, depending on client, delivery attempts continue.

To work around this, you can create separate submission service without any checks. Heres excerpt from my Postfix

# wmsub_relay
5877 inet n - y - - smtpd
  -o syslog_name=postfix/wmsub_relay
  -o smtpd_sasl_auth_enable=no
  -o smtpd_reject_unlisted_recipient=no
  -o smtpd_client_restrictions=
  -o smtpd_helo_restrictions=
  -o smtpd_sender_restrictions=
  -o smtpd_recipient_restrictions=
  -o mynetworks=
  -o smtpd_relay_restrictions=permit_mynetworks,reject
  -o milter_macro_daemon_name=ORIGINATING

This way instead of rejecting, MTA accepts mail (after that it disapears from EAS outbox) and then after delivery attempt sends non-delivery notification back to sender.

But I hope this issue will be fixed in SOGo in future.

- Issue History
Date Modified Username Field Change
2017-09-04 10:18 modir New Issue
2017-09-05 06:58 tfu Note Added: 0012256
2017-10-19 08:44 john.cameron Note Added: 0012384
2017-12-28 04:50 Philipp Note Added: 0012492

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