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Microsoft, Where's My Email?

 * Problem


PROBLEM


WHAT HAPPENED WHEN SOMEONE TRIED TO SEND AN EMAIL TO A MICROSOFT USER.

Raffaella owns a dog walking service. She serves over 5 clients. This includes
her uncle. Depending on her schedule, she walks his dogs a few times a week.

One day, Raffaella got a call from her uncle:

> Why didn’t you reply to the email I sent last week?

But she did reply to his email! During the call, she did recall receiving a
strange email the week before, saying:

> Unfortunately, messages from [xxx.xxx.xxx.xxx] weren’t sent. Please contact
> your Internet service provider since part of their network is on our block
> list (S3150). You can also refer your provider to
> http://mail.live.com/mail/troubleshooting.aspx#errors.

Understandably, Raffaella was confused. As the message instructed her to, she
contacted her hosting provider.

Phoebe, the hosting provider’s customer service expert, told Raffaella that
Microsoft blocked their IP address. Phoebe promised to fix the problem, because
surely something must have gone wrong on their side.


WHAT’S WRONG?

Phoebe checked the recommendations on the Microsoft help page:

 * Is DKIM set up? Yes!
 * Is SPF set up? Yes!
 * Are we signed up for JMRP? Yes!
 * Are we signed up for SNDS? Yes!

So according to Microsoft’s help page, everything’s fine! Phoebe then asked
Microsoft to unblock the IP address, because surely something must have gone
wrong on their side.

She filled in Microsoft’s form:

Within minutes, Phoebe received a response to her request to unblock the IP
address. Wow, that’s fast!

But the response was disappointing:

Microsoft didn’t unblock the IP address. They did provide Phoebe with
recommendations. But they were the same ones that she checked before. So what’s
the problem?

Also, the email was not signed off by a human, so surely something must have
gone wrong with some automatic system. Phoebe replied to the email asking if a
human could fix the mistake – because all recommendations are already being
followed! – but received the following response:

> We have investigated your deliverability issue. At the current time, these IPs
> are not eligible for mitigation.


WHAT NOW?

According to Microsoft’s own recommendations, nothing was wrong. Yet they
blocked the IP address. But they wouldn’t unblock it. And they wouldn’t say why
it’s blocked. So Phoebe couldn’t fix the issue. Meanwhile, Raffaella still
couldn’t send emails to Microsoft users.

This cost Phoebe’s hosting company a previously happy customer (Raffaella moved
to another hosting provider), $100 in yearly revenue, and lots of time and
money.

(Later, Raffaella new hosting provider’s IP address was blocked too. Microsoft
made it impossible for them to figure out why too. Raffaella now pays Microsoft
$200 per year for email services. )

--------------------------------------------------------------------------------


P.S.

If Phoebe was real, she would have run into even more issues with Microsoft’s
system…

When filling in an alternative unblock request form, Microsoft simply does not
respond after saying “your request has been escalated to Microsoft Support”.
Even after waiting for weeks, and filling in the form over 10 times.

As no-one responds to the form, you may send an email
“delist@messaging.microsoft.com”. But emails to this email address are not
delivered – from an outlook.com email address, no less – saying:

> A custom mail flow rule created by an admin@frontbridge.com has blocked your
> message.

And don’t even think about sending an email to “admin@frontbridge.com” for help.
That email address doesn’t exist.