Tag Archives: Windows 2008 R2

Exchange 2010 and TLS 1.2

In a previous blogpost I discussed an issue I had with Outlook 2010 and TLS 1.2. At the same time this reminded me that Microsoft will enable TLS 1.2 (and remove support for TLS 1.0 and TLS 1.1) in Office 365 on October 31, 2018 as communicated in https://support.microsoft.com/en-us/help/4057306/preparing-for-tls-1-2-in-office-365. This means that when you have communication issues with Office 365 because of an older and weaker protocol, you won’t get any support. Time to do some research….

Existing Exchange 2010 environment

As you may have seen on this side, I still am a big fan of Exchange 2010 and also have an pure Exchange 2010 hybrid environment up-and-running and it looks like this:

Inframan-hybrid

MX records is pointing to my Exchange 2010 Edge Transport Server (running on Windows 2008 R2), webmail and Autodiscover are routed via an F5 LTM load balancer to an Exchange 2010 CAS/HUB/Mailbox server (also running on Windows 2008 R2), and hybrid is configured directly on Exchange 2010 (for hybrid mail flow I’m using a separate FQDN, o365mail.inframan.nl) without any Exchange 2013 or Exchange 2016 server.

So, how do you test which TLS version is used by your Exchange 2010 server? In Exchange 2010 this should be done using the protocol logfiles. Message headers in Exchange 2010 do not contain enough information for showing this TLS information. So, you must enable protocol logging for the appropriate Receive Connectors and Send Connectors. In my environment this means the Default Receive Connector on the Exchange 2010 Edge Transport server (for O365 traffic from other tenants), the Default-First-Site-Name to Internet Send Connector, and both connectors between the Exchange 2010 server and Office 365 for hybrid. Analyzing the protocol logfiles can best be done in Excel (import as CSV files). When analyzing, look for a string like TLS protocol SP_PROT_TLS1_0_SERVER (when receiving) or TLS protocol SP_PROT-TLS1_0_CLIENT (when sending). When TLS 1.2 is used, look for a string like TLS protocol SP_PROT_TLS1_2_SERVER and TLS protocol SP_PROT-TLS1_2_CLIENT.

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Install Exchange 2007 SP3 on Windows 2008 R2

Now with Exchange server 2013 scenario testing on the way it’s time again to install Exchange Server 2007 in our lab again. Since Windows 2008 R2 is fully supported with Exchange Server 2007 SP3 this is my preferred server.

The easiest way to install the prerequisite server roles and features is to use PowerShell. The first server you’re going to install (and that is going to change Active Directory) needs the Remote Server Administration Tools (RSAT). RSAT also includes Active Directory Users and Computers, it can be useful to install it on other servers as well. Use the following command to install RSAT:

Import-Module ServerManager
Add-WindowsFeature RSAT-ADDS
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