We are curious to know why an idle Outlook program is trying to reach out to these blocked sites?? The user wasn't even using her laptop at the time and so strikes us as very strange behavior. Is Malwarebytes Endpoint Protection perhaps analyzing emails landing in the Junk folder, triggering a block?
In addition to sendgrid.net, we're also seeing repeated cirrusinsight.com blocks from Outlook. Will that also be addressed?