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We are currently seeing some issues sending TLS encrypted mails to Outlook.com hosted email addresses.
This appears to only be affecting some of the Outlook.com hosted server ip addresses intermittently
213.199.154.87 / mail-db34087.inbound.protection.outlook.com
213.199.154.23 / mail-am14023.inbound.protection.outlook.com

If messages fail to be delivered, you will receive a bounce message similar to the following:

TLS connect failed: timed out; connected to 213.199.154.87.
I’m not going to try again; this message has been in the queue too long.

In the interim we have disabled TLS encryption to the affected addresses.
We are currently unsure if this is a Microsoft issue, or a China Firewall Issue, so this may or may not resolve the issue.

We will update this post when we have further information.

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We’re seeing a huge recurrence of spam thats been getting through our spam filters., all coming from @live.com addresses.
I hadn’t seen any personally until one of our clients brought up the fact that she was receiving 20-30 sex related spam a day, all coming from Random name @live.com addresses.

A check of the logs showed that we’ve received at least 100,000 of these spam mails over the last month that have gotten through to our users.
This is something I’d obviously like to remedy.  Not receiving, processing, or storing that much spam free’s up the servers for other things.

As the number of valid addresses using @live.com accounts appears to be minimal (I could only see a handful of legitimate users sending from that domain), I have taken the decision to block any email from the @live.com domain until Microsoft can resolve their spam issues.

If you do have clients using @live.com addresses, you will be able to send email to them, but not receive from them.
We apologize for the inconvenience, but unfortunately there is no other solution that easily mitigates the issue, other than completely blocking them.

For a more technical explanation of whats happening, read below:
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