I have multiple clients and my own mail services on Office 365. A few of us started out on BPOS and migrated, others are newer. BPOS always seemed bulletproof in their delivery of mail to outside recipients. Office365 was that way for a while. Lately though I've had multiple clients report issues with delivery to various 3rd party email services. Specifically it's in the last few months after outgoing sending limits were bumped up to 10,000 recipients daily. Different rejection messages but a majority are messages reporting the mail was rejected as spam due to the poor reputation of the sending MTA.
SPF and other DNS records are all correct and active, general health and proper configuration tests all pass with perfect reports for our domain, but frequently I'll find the final MS outbound server (after FOPE) flagged on a spam blacklist. Microsoft will make some activity to check and possibly remove their servers from those blacklists, but it's all a bit too little too late. I was initially even told by a support rep that I needed to take action with the blacklist service to request removal of Microsoft's server.
While I can appreciate that some users need to send large volumes of mail, bumping the limits just seems to have encouraged users to use their own accounts rather than paid bulk email services and stupid people failing to comply with Can SPAM rules is blacklisting these shared servers.
I'm not sure what it is that big free mail services do to prevent issues like this, but Microsoft's own hotmail/outlook.com has more reliable delivery than office 365 at the moment and I've even had msn reject incoming mail due to poor reputations.
Anyone else seen this, any suggestions besides migrate all my clients away from a service I so highly recommended only a few months ago?
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