Office 365 Message Encryption delays for internal recipients

Brass Contributor

Tech community - I have a question for you all. I have deployed Office 365 message encryption and i am seeing some delays and hope to get some feedback or confirmation that this is happening else where. I will post my tests and results below.


My keyword is #Secure in the subject based on the rule.


Test: Send an email with #Secure in the subject to only one/multiple internal recipients

Result: Message is delivered immediately


Test: Send an email with #Secure in the subject to only one/multiple external recipients

Result: Message is delivered immediately




Test: Send an encrypted message to one/multiple external email address and one/multiple internal email addresses.

Result: External recipients get the encrypted message immediately. The internal recipients take a minimum of 30 min to appear in the mailbox. Sometimes it takes hours for the internal recipient to get the message.


Can someone lend any advice or information? I have confirmed that the rule i created is not stopping any more rules from being processed or anything out of the ordinary. 


2 Replies

What does Message trace show? Also check the header information for the internal message, might simply be hitting the same (set of) server with degraded performance. In any case, if you can reliably reproduce the issue, open a support case to have it properly investigated/escalated.

Message trace shows that the message is being delivered. Everything that i can find in logs and traces, shows that everything is functioning as expected. Just the emails are not showing up for long periods of time. The time stamp on the email even shows the correct time when it finally appears in the mailbox.