Known issue.:
Update has been pulled and they are working on a fix.
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After installing KB 5044062 on Exchange 2019, my mail flow rules stopped working
After installing the above, I used HealtChecker and it asked to change the transport service to the following:
Set-TransportService Mailbox1 -MaxPerDomainOutboundConnections 40 (before change 20)
Set-TransportService Mailbox1 -MessageRetryInterval 00:05:00 (before change 15)
If I run the following:
Get-TransportRule -Identity "Spam" | Format-List Name,Priority,State
I receive a message that the rule is enabled.
I need a hint :-)
Known issue.:
Update has been pulled and they are working on a fix.
I have a similar problem with transport rules failing to fire after KB5044062, but I'm still on 2016.
You wouldn't happen to also be running ESET Mail Security would you?
I have gotten the rules working again (for a little while now anyway) by disabling mail transport protection and restarting the exchange transport service.
I have the same problem on Exchange Server 2019.
To workaround it.
Rename the rule to _old for example, and clone it to the original name.
Save the rule, put the rule at the top (i've done this, but maybe it's not necessary) and do not change it anymore.
It worked for me