How to troubleshoot remote connectivity to Exchange

testingA few months ago I wrote a post listing fourteen online resources for email admins that included several of my favourite troubleshooting resources. In this post, I want to take you for a closer look at the best one of the lot for testing remote connectivity to Exchange, the Microsoft Exchange Server Remote Connectivity Analyzer. You can access this test suite by clicking the link above, or directly at its URL, https://www.testexchangeconnectivity.com/. There are several great tests this tool can run through to ensure that you have properly set up remote access to your Exchange infrastructure, and you will want to bookmark this site and refer to it whenever you setup, or change, the external connectivity to Exchange.

Before you begin, create an unprivileged test account in your Active Directory, and make sure it has a valid Exchange mailbox. You can of course use your own account or anyone else’s, but this site requires that you enter valid user credentials, and it’s a best practice not to submit valid credentials for a ‘real’ user to an external site outside of your complete control. If you want to skip that step, that’s on you, but I always keep a test account handy for things like this.

Once you have your test account ready, take a look at the site to see what it offers. There are four categories with two tests each:

  1. Microsoft Exchange ActiveSync Connectivity Tests
    Exchange ActiveSync
    Exchange ActiveSync Autodiscover
  2. Microsoft Exchange Web Services Connectivity Tests
    Synchronization, Notification, Availability, and Automatic Replies (OOF)
    Service Account Access (Developers)
  3. Microsoft Office Outlook Connectivity Tests
    Outlook Anywhere (RPC over HTTP)
    Outlook Autodiscover
  4. Internet E-Mail Tests
    Inbound SMTP E-Mail
    Outbound SMTP E-Mail

The ActiveSync Connectivity tests can validate your DNS records, as well as how you have exposed EAS connections to the Internet (through Microsoft TMG or other reverse proxy, or by passing HTTPS traffic through to your CAS server directly). Both of these tests will in essence configure a mail client using EAS, and requires that valid test account to connect all the way through. In case you are using self-signed certificates, it even gives you the option to not validate certificates.

The EWS tests are useful for admins who need to support Entourage or other applications that require access through Exchange Web Services, and can verify the ability to create/delete messages and other service activities.

The Outlook Connectivity tests basically configure an Outlook client using the RPC over HTTP protocol. It can also validate all your DNS records, whether you are using A or SRV for autodiscovery. See this post for more on Autodiscover.

The Internet E-Mail tests can send a test message to your account from an external sender, and can also confirm your DNS records for MX, PTR, and Sender ID, and make sure your host is not listed on any DNS Reverse Blacklist service.

While all of these could be done using your external Hotmail account, and one or more systems connected to a DSL circuit external to your corporate network, it’s really useful and a great timesaver to have all eight tests available to you with nothing more required than a web browser and a test account. Even if you have a working system now, take these eight tests for a spin to see how things you might not be able to test, like Mac clients, would function, and also to see how your DNS records test. You might be surprised at what you find out. If you pass all eight the first time through, you’ve earned bragging rights; leave a comment and let me know.

Written by Ed Fisher

An InfoTech professional, aficionado of capsaicin, and Coffea canephora (but not together,) I’ve been getting my geek on full-time since 1993, and have worked with information technology in some capacity since 1986. Stated simply, if you need to get information securely from a to b, I’m your guy. I’m like "The Transporter," but for data, and without the car. And with a little more hair.

2 Comments

  1. Akihiro Svetson · July 15, 2011

    I just want to add. testexchangeconnectivity.com also has a connection test for Inbound and Outbound SMTP e-mail. I use this tool to test my POP3 emails and personal Outlook accounts, especially if I have big attachments to send.

    If you’re experiencing slow Internet connection both on your Exchange and Outlook, use testexchangeconnectivity.com. It’s a lifesaver.

  2. Ed Fisher · July 15, 2011

    Good suggestion Akihiro, thanks!
    Ed

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