Testing Exchange Connectivity

Missy Koslosky — Thu, 26 Feb 2009 21:22:25 GMT

The Microsoft Exchange Product Group has a pretty cool tool available online (in Beta) that I learned about at the E14 Airlift (don't worry, it's not for Exchange 14), called the Microsoft Exchange Server Remote Connectivity Analyzer. This tool offers several tests that can be run against your Exchange infrastructure to see if things are configured correctly, including:

MS Exchange ActiveSync Test, which simulates a mobile device connecting to Exchange Server
MS Exchange ActiveSync Autodiscover Test, which simulates the steps a mobile device takes to connect to the AutoDiscover service
MS Outlook 2007 Autodiscovery Connectivity Test, which simulates the steps Outlook 2007 takes to connect to the AutoDiscovery service
MS Outlook 2003 RPC/HTTP Connectivity Test, which simulates the steps Outlook 2003 takes to connect to Exchange using RPC over HTTP
Inbound SMTP Email Test, which simulates sending e-mail to your Exchange Server using SMTP

It's a pretty cool tool - you first choose one of the radio buttons, then simply click Next. You're then presented with fields where you enter your server name (obviously, use the Internet-facing name here) and your credentials (they do want a domain password, but they promise to not store it and to use SSL to encrypt it, as always YMMV, and use caution). There's also a challenge in the form of one of those annoyingly garbled strings of letters that are hard to see, but that keep automated systems from using the form. I hate these things and always mess up the first try, but understand why they're there.) Once you've filled out the forms and agreed to the terms of service, a simple click is all it takes to start the test. I just ran through the test, using 3Sharp as the target, and here's a snippet from our results (with some of the fields changed, which I've italicized. My goal is to show you what kind of results you'd see, not to show you everything we do here at 3Sharp):

Attempting to Resolve the host name server.3sharp.com in DNS.
Host successfully Resolved
Additional Details
IP(s) returned: 1.1.1.1

Testing TCP Port 443 on host server.3sharp.com to ensure it is listening/open.
The port was opened successfully.

Testing SSLCertificate for validity.
The certificate passed all validation requirements.
Additional Details
Subject: CN=server.3sharp.com, OU=Domain Control Validated, O=server.3sharp.com, Issuer SERIALNUMBER=12345678, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O="GoDaddy.com, Inc.", L=Scottsdale, S=Arizona, C=US

Testing Http Authentication Methods for URL https://server.3sharp.com/Microsoft-Server-Activesync/
Http Authentication Methods are correct
Additional Details
Found all expected authentication methods and no disallowed methods Methods Found: Basic realm="server.3sharp.com"

Attempting an Activesync session with server
Errors were encountered while testing the ActiveSync session
Test Steps
Attempting to send OPTIONS command to server
Testing the OPTIONS command failed. See Additional Details for more info
Additional Details
A Web Exception occured because an HTTP 401 - Unauthorized response was received from IIS6

All in all, it's a pretty cool tool, and alleviates the need for you to get to a remote desktop to test your environment's connectivity. I was surprised I hadn't heard about it before, and thought I'd share this so more folks can try out the site!

Tips and Tricks

Testing Exchange Connectivity