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Good mail to Outlook's junk folder

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We are part way through a staged migration.  We are having occasional trouble with mail from users in our own domain ending up in junk folders. 

 

The problem only seems to crop up when mail moves between a user who has been migrated to the cloud and one who has not. Mail moving in either direction may end up in the junk folder of the recipient.

 

So far, we have not found problems between two users in the cloud or two users not yet migrated.

 

We have added our own domain to a whitelist rule in FOPE.  We have also attempted to add our domain to the safe senders list in Outlook. However, within 15 minutes of adding our domain to the safe sender list, the entry disappears.

 

What can we do to keep good mail out of the junk folder?

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  • Hi Bell Nursery,

    To restate the issue:

    • You are performing a staged migration.
    • Mail is being delivered between on-premise users and cloud users successfully
    • However, on occasion, this mail is being marked as junk/spam and delivered to the junk folder.

    Is this correct?
    What phase in the staged migration have you reached? Have you completed a migration batch? Converted to Mail Enabled users on-prem?
    It may be helpful to look at the headers of the messages that have been marked as junk - have you compared to the successful messages?

    Thanks

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  • Correct.  Staged migration.  Approximtely 60 of 300 mailboxes migrated and converted to MEUs. 2-4 mailboxes migrated per batch.

    Have not looked at headers, but have concluded it is an Outlook issue.  A message that ends up in the Junk folder on Outlook does not end up there if using OWA. I used identical messages, so headers would have been the same.

    The messages Outlook moves to Junk might be perceived as risky (no subject line or message body contains only a hyperlink). Outlook appears to be ignoring the safe sender list.

    Ideas?

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  • Hello,

    Thanks for the update.  Can you clarify a bit more on this? What do you mean by "using" Outlook or OWA? are you referring to sending the messages through these programs, or only reading the messages?  If a message is received correctly in OWA and then you start Outlook, does it get moved to the Junk folder?

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  • When I say Outlook, I mean the mail client in the MS Office suite.  When I say OWA, I mean the web based mail client.

    When reading messages, only Outlook appears to exhibit the problem. It does not appear to matter if the message originates from Outlook or OWA.

    After receiving a mail message correctly to the inbox in OWA, Outlook will move the same message to the Junk folder when it opens and syncs with the mail server.

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  • Thanks for the clarification.

    In that case, it does indeed seem to be an Outlook issue.  I would suggest you start by looking at the Outlook rules.  You can back up the existing rules, then run launch Outlook by running "Outlook.exe /cleanrules" from the command line.  This will remove the rules and give you a fresh start, you can then see if the mail still gets moved without rules.

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