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Emails are stuck in my outbox. How do I fix this?

Summary

This document covers 5 reasons email could be stuck and proposes workarounds for each. Every known reason that an email could be stuck should be covered here.

  1. Misconfigured Profile
  2. Never-Ending-Mail-Sending bug (workaround available)
  3. Outlook has Instant Messaging configured (workaround available)
  4. Unknown Antivirus or protocol inspector interfering (workaround available)
  5. Damage to the MAPI store

Details

Mis-configured Profile

Symptoms
  1. The user is trying to use a PST file as the default delivery location in Outlook. This is not supported, and cannot be made to work with the Kerio Outlook Connector.
  2. Archiving turned on. Sometimes Archiving persists in asking the user if they want to turn it on. An unwary user might choose "yes" and a local PST file is created in the profile.
  3. The user is attempting to use POP3 and a Kerio Outlook Connector at the same time. This is a recipe for problems. It is better to use the POP3 downloader in KMS to deliver the messages directly to the user's Kerio store.
  4. The user is preliminarily trying out the Outlook Connector, and does not want to stop using local files. This is better done with a separate profile
Discussion
    Users often try to use other top-level folders besides the "Kerio Outlook Connector" store. The Outlook connector cannot co-exist with other delivery locations in Outlook. The best way to achieve a working Outlook is to use a separate profile. Sometimes, this also happens in combination with a damaged MAPI store. Be sure to read the section on "Damage to the MAPI store" if the problem still happens once this is corrected.

Outlook has Instant Messaging configured

Symptoms
    Mail is stuck in the Outbox. There are no other symptoms.

Discussion

    The Instant Messaging features in Outlook will break Kerio Outlook Connector.

Workaround

    In Outlook 2003 or 2002/XP, click on "Tools->Options->Other" then uncheck the option "Enable the Person Names Smart Tag" in Outlook 2003 or "Enable Instant Messaging in Microsoft Outlook" in Outlook 2002/XP.

Never-Ending-Mail-Sending bug

Symptoms
  1. A message is stuck in your Outbox folder. If you double click on the message in the Outbox, error 0x80040114 is displayed.
  2. User is bombarded with "System Administrator" bounce messages every minute. The bounce messages continue as long as Outlook is open.
  3. If the message is opened up in webmail, you notice the local email address was misspelled or does not exist.
Discussion
    This is a known bug that is fixed in KMS 6.1.0. Please upgrade to that version. If you continue to receive the error, please contact Kerio Support.
Workaround
    There is a workaround. Accept all messages, even if the email address is wrong. The following works very well:
    1. Create a user called "postmaster" with name field of "System Administrator"
    2. Create an alias for * that delivers to the postmaster account.
    3. Log postmaster into webmail, and create a filter rule to autoreply to emails from the local domain. This can give local users an error message. Make sure it only autoreplies to From addresses that contain the local domain. This way, spammers will not receive the autoreply.

    The main drawback to this is that directory harvest attack prevention will not function properly.

Unknown Protocol Inspector or Antivirus Interfering

Symptoms
  1. A message is stuck in your Outbox
  2. You have some kind of antivirus (etrust, norton, AVG) installed on the clients.
  3. You have some sort of internet security solution installed (Norton Internet Security, personal firewall, etc.)
Discussion
    It can be nearly impossible to be sure that no protocol inspectors or AV solutions are conflicting with the MAPI connector. The best way to diagnose this issue is to use the steps in Kerio Knowledge Base article 196. To learn what a protocol inspector is, see Kerio Knowledge Base article 90 . Protocol inspectors are used by any application that does transparing scanning or analysis of protocols such as email protocols. Antivirus, personal firewalls, and internet security solutions can do this without your knowledge.

Damage to the MAPI store

Symptoms
  1. A message is stuck in the Outbox
  2. Restarting Outlook does not fix the problem
  3. You do not have any of the previous mentioned problems
  4. Re-building the MAPI store fixes it
Discussion

Server crashes, Outlook crashes, or unknown problems can cause the MAPI store to become damaged. The MAPI store, when removed, is rebuilt on the fly from data in the IMAP folders.

Fix

Rebuild the MAPI store as follows

  1. Have the user log out of Outlook, Webmail, and all other email client software.
  2. On the mailserver, look in the store folder:
    • Windows: C:\Program Files\Kerio\Mailserver\store\
    • Linux: /opt/kerio/mailserver/store
    • MacOS: /usr/local/kerio/mailserver/store
    So, for kenw@foo.com on Windows, go to C:\Program Files\Kerio\Mailserver\store\mail\foo.com\kenw. This is the user's mailstore folder.
  3. Look for a folder called __keriomapi__STORE. Rename that folder to __keriomapi__STORE-save.
  4. Have the user log back into Outlook. Does the mail go out?
  5. If the mail doesn't goes out, contact Kerio Technical Support and explain the situation.

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