Outbount legitimate customer order email trapped as spam in Exchange online

We run batch jobs early each day that send out customers information regarding the status of their orders (confirmation, updates, shipping details etc). This has worked fine until recently, coinciding with a spike in holiday orders.

Now we find that Exchange online is identifying this outbound email as spam, and although we can unblock the sending address this provides only a temporary solution. We believe this issue is primarily tied to the volume being sent over a short period of time. We have contacted MS support on this (and escalated up through the chain) but as may be expected they have offered little by way of solution (their goal is to protect recipients from spam/maintain reputation with downstream ESP's).

We understand that the underlying issue lies in the design of the sending application (batch job sends out high volume with same sender & subject over short period of time) but we are reluctant to an initiate a system redesign at our busiest time of the year.

We are considering relaying this email directly from our system to a service that may be able to better handle this scenario. Is anyone doing this with success today, can advise on a suitable service? Do you have any other suggestions on how we may be able to get this legitimate order status email to our customers?

We understand the best way to prevent email being trapped as spam is to do what we can to prevent is looking like spam, we're just looking for a short term fix at this point.

Thanks!
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agradminAsked:
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AmitConnect With a Mentor IT ArchitectCommented:
It seems you are breaching EOP limit and that is the reason you are facing this issue.

Read this article: https://technet.microsoft.com/en-in/library/exchange-online-protection-limits.aspx

Number of outbound messages sent   The limit for the number of outbound messages sent through EOP is high enough to ensure that normal email communication is not treated as spam. If you want to send commercial bulk email messages, rather than sending outbound messages through EOP, we recommend that you either use a third-party email service provider (ESP) or send them through your on-premises email servers.


https://technet.microsoft.com/en-in/library/exchange-online-limits.aspx

Check Sending limits across Office 365 options
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FOXActive Directory/Exchange EngineerCommented:
Agradmin,
Is the sending email account on o365?
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agradminAuthor Commented:
Yes, the system has worked fine since we migrated in the spring, it is only now that we are hitting peak period (bulk) email is being detected as spam and the sender blocked. Once unblocked the sender can resume sending until a threshold is exceeded once again.
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FOXActive Directory/Exchange EngineerCommented:
Is the sender getting blocked by the domain of the recipient?
Check to see if your domain is getting blacklisted
https://mxtoolbox.com/blacklists.aspx
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agradminAuthor Commented:
Please read the initial description - the email does not leave our Exchange online server - MICROSOFT is blocking. When unblocked email is being accepted and delivered by downstream ESP's
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AmitIT ArchitectCommented:
You might have received the communication from Microsoft EOP, recently they made the changes in EOP system and EOP now reject non RFC 5322 compliant messages. You need to fix at your end to make it RFS 5322 compliant, else EOP will mark it as SPAM and block it.

Note: If messages that does not have a "from address" or "return-path", those mails are rejected.
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agradminAuthor Commented:
As an update - the (order) email we send to customers is fully CAN-SPAM act (offers unsubscribe links etc) as well as Confirmed opt-in compliant. It seems that the sender of the emails is being blocked purely based on quantity (from sender to individual customer) over a short period of time.
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agradminAuthor Commented:
Amit,
The email is delivered OK outside of the early morning batch job, and has done historically until we reached our peak/high volume season. That would suggest the email itself is compliant and the issue related to volume (over short period of time).

Microsoft are unwilling to provide helpful information, presumably to protect against spammers.
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agradminAuthor Commented:
After further consultation with our application development manager it has been confirmed that the email is fully CAN-Spam compliant, should not be classified as bulk (each order status directed to an individual opted in customer) and has valid unsubscribe links etc.

Microsoft has thus far been totally unhelpful and unwilling to look at the email ( to verify legitimacy, advise on what is causing the false-positive). At this point we can only assume that the batch email is being flagged as spam due to volume alone (only witnessed during our busiest time of the year....), and OUR only solution is to try and change the design of the system (at our busiest time of the year) or look at an alternate ESP.

We are going with option #2. I would recommend that businesses seriously look at other options than Exchange online if wishing to send automated email responses to customers.
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AmitIT ArchitectCommented:
I agree, you should look for option 2. Microsoft is known for creating monopoly in the market. If you see, Microsoft wiped out all other mailing solution from the market in last 10 years. Relying too much on one vendor is always a big mistake. Next cloud services is not suitable for all. You need to look into your business model and then decide. 99% CIO who make these cloud decision doesn't have any knowledge on the technical limitation or product limitation by vendor.

Best you go with on-prem server. Lot of clients are moving back to on-prem server, as cloud is not suitable for them.
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agradminAuthor Commented:
In closing, I am dreadfully disappointed with Microsoft. I can understand and applaud their desire to protect customers from spam, but an unwillingness to work with customers when legitimate email is falsely flagged is unacceptable.
All we have asked of them is to look at a single customer email (order confirmation, status or shipping) and after confirming legitimacy advise on why this may trigger their spam filter so we can correct.

All we know is from our own research - we know it is tied to volume (only flagged when order volumes hit peak) but otherwise the only help Microsoft are willing to provide is that the system is not intended to email in such a way and to look at other (non-Microsoft) solutions.

That is what we are doing..............
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agradminAuthor Commented:
Thanks Amit. We did actually review the rate limit but as NDR's are indicating that the sender is being blocked as spam we have been trying to gain clarification from Microsoft as to what the root cause may be.

I would expect a rate issue would produce a message other than that the sender is a spammer, or at least Microsoft to verify that rate is the actual cause and the sender not blocked.

I believe the doc indicates that a rate issue would cause email to be queued and the sender would have to resend, in this instance the sender was blocked from doing so.
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