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.