Jira Cloud emails to Office 365 hosted domain

[Tim Spencer]

We have a client who recently moved their email to an Office 365 hosted domain. Up until the time they made the move, they had zero issues getting emails from our Jira instance. 

Since making the move, they haven't received a single message. Don't see anything in spam/junk. Tried the send mail option in Jira to trigger a test message...Jira says the send is successful, no indication of bouncing. 

Any known issues sending to Office 365 addresses? 

Thanks,

Tim

[Gregory Van Den Ham]

I like the connector option, going into mailflow and specifying from email server to o365 and spec'ing the IP address.

Alternatively, if you're still hybrid and have a 2016-19 exchange server onprem, push mail through the hybrid connector.

[Josh Steckler]

Hi Tim,

Yes, I have seen problems with office 365. Not necessarily related to Jira Cloud.

What your client may need to do is ask their O365 administrators to whitelist the domain that the notifications are coming from. I also noticed that O365 is particularly interested in having correct SPF records for email senders, and anything not set up to their liking has a higher chance of being blocked. The whitelist is the best option to avoid that.

Unfortunately I'm not an O365 admin myself so I don't know exactly how to do that, but I'm a Jira admin who deals a lot with O365 accounts for incoming and outgoing mail.

[Tim Spencer]

Thanks for the feedback Josh. 

Will try the whitelist option and see if that makes any difference. Results soon....

[Matt Doar]

I've seen problems with scripts trying to connect to o365 once a minute, Sometimes you get a ServerBusy, retry in 5 mins with exponential back off. So make sure your mail handler is not running that often

[Tim Spencer]

Whitelist option didn't work. Jira Cloud sends the message (and thinks it's doing so error free) but the destination server never sees the message