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Exchange Mailbag: Examining Outlook connectivity issues

Outlook connectivity can prove troublesome, but don’t worry, help is on the way. This mailbag touches on common problems, as well as the tools you’ll need to get them fixed.

Outlook connectivity can be the bane of many an administrator’s existence. When users can’t effectively access email, business can grind to a halt. I’ve heard about various Outlook connection problems from readers as well as users at various clients. Below are the three most common Outlook connectivity problems I’ve heard about, what you need to understand if you’re experiencing similar issues, helpful diagnostic tools and more.

Outlook shows the “Connected to Exchange” message, but my users cannot send or receive email. What’s the problem?

This particular issue is common in organizations that segment server roles onto separate Exchange servers (whether they’re running on physical or virtual hardware). For example, let’s assume that an organization has two servers -- a mailbox server and a server running the hub transport and client access server (CAS) roles. Now assume that a user connects to the server from Microsoft Outlook, and shortly thereafter, the hub transport/CAS fails. The user is still connected to his mailbox, but he cannot send or receive mail because the hub transport and client access services are unavailable.

This problem is most common with Exchange Server 2007. In Exchange 2007, Outlook communicates directly with the mailbox server role. In Exchange Server 2010, Outlook communicates with the CAS role instead of talking directly to the mailbox server role. The key here is to determine exactly which server role is causing the problem and then fix it properly.

Have a look at our other mail bags:

Addressing Exchange 2010 Global Address List issues

Fixing common Outlook user problems

POP3 settings and other Outlook headaches


My users are having difficulty connecting from outside my organization. Is there an effective tool for diagnosing external connectivity to Outlook?

Connecting users to Exchange through Outlook Anywhere and ActiveSync can be surprisingly challenging. When an initial connection fails, the problem is often traced to a firewall setting or the digital certificates (the client often does not trust the certificate authority that issued the certificate). In either case, a diagnostic tool can make fixing the problem a lot easier.

Microsoft provides two tools for diagnosing external connectivity to Exchange. The first is the Remote Connectivity Analyzer, a Web application you can use to externally connect to your Exchange organization. You can use the Remote Connectivity Analyzer to test ActiveSync, Exchange Web Services, Outlook Anywhere, Autodiscover and SMTP mail.

The other resource Microsoft provides is the Test-OutlookConnectivity cmdlet. You can use this cmdlet to test end-to-end client connectivity. The full command reference is easily found on Microsoft’s website.

Is there any way to retrieve diagnostic information from within Outlook 2010?

Outlook 2010 provides admins the “Connected to Microsoft Exchange” message at the bottom of the window. Unfortunately, this notification is of little help when it comes to troubleshooting connection problems.

You can actually retrieve loads of helpful information directly through Outlook, but most of the connection diagnostics are disabled by default. To enable Outlook 2010’s diagnostic capabilities, hold down the Ctrl key, then right-click on the Outlook icon in the system tray (not the icon on the task bar). When you do, you’ll see a menu that offers several options.

If you select the Test E-Mail AutoConfiguration option, Outlook 2010 will display a dialog box that prompts you to enter your email address and password. Next, click the Test button, and you’ll receive diagnostic information related to how Outlook uses the Autodiscover service.

Another option available via the Outlook shortcut menu is Connection Status. If you click it, you’ll see a dialog box that displays Outlook’s connection activity. You can see connections to domain controllers and Exchange servers.

The nice thing about this box is that it lets you view failure counts, response times and much more. This dialog box can go a long way toward helping you determine exactly where connectivity is breaking down. The dialog box also comes with a Reconnect button that you can use to re-establish a broken connection.

Brien Posey is an eight-time Microsoft MVP with two decades of IT experience. Before becoming a freelance technical writer, Brien worked as a CIO at a national chain of hospitals and health care facilities. He has also served as a network administrator for some of the nation’s largest insurance companies and for the Department of Defense at Fort Knox.

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