Outlook Connectivity Guided Walkthrough(s)

In order to help troubleshoot connectivity issues an end-user might experience, Microsoft has released two walk-throughs for Outlook connecting to either an On-Premise Exchange or Office 365 Tenant.

On-Premises Outlook Connectivity Walkthrough

Office 365 Outlook Connectivity Guided Walk-through

So let’s take a walk through one of the scenarios for Outlook On-Premises, specifically the “Outlook is displaying a certificate error” scenario:

For this example, I chose the last option “The name on the security certificate is invalid or does not match the name on the site.”

Click ‘Next’.

Check your AutoDiscover URLs, take note of them, and click ‘Next’.

Check your Exchange Web Services URLs, take note of them, and click ‘Next’.

Check your Outlook Address Book URLs, take note of them, and click ‘Next’.

I chose “No” as a name was missing from certificate for my example.

Selected “Request a new certificate….” because I want to correct the certificate and am assuming my URLs are all correct.

Selected Exchange 2010 as this is the newest on the Wizard.

Make sure to click on the link included to see how to generate an actual request. Although it would have been better to display this information within the Wizard frame, the external link is understandable in case guidance from Microsoft changes.

At this point in my scenario I’ve replaced the certificate, but I am still experiencing a certificate error.
I then selected “No” as I wanted to see if the wizard could accommodate for this possibility.

I answer ‘Yes’ because the first issue was resolved with the corrected certificate.

In my scenario I would check the Hardware Load Balancer and realize that the certificates are different due to the fact that I just changed them on Exchange. I would then correct that and answer ‘No’ as I am no longer experiencing the issue.


Now that your issue has been resolved you can give feedback as to how helpful your solution was or save your solutions progress.
Other Scenarios
This same Walk-through wizard has scenarios for users getting prompted for their credentials, Outlook disconnections, not being able to download the Offline Address Book (OAB), and AutoDiscover issues. I commend Microsoft for making a tool that, if used correctly, could potentially help the Exchange support engineer in resolving common errors.
For the cloud based scenarios, you can check how to troubleshoot an archive, a shared mailbox or a user mailbox. With a users mailbox you can troubleshoot Intermittent connectivity, profile issues, disconnects, performance and credential issues. For archive and shared mailboxes you can troubleshoot being able to connect to them via Outlook.

Now, while this tool can be of good use, I find that an Experienced Exchange engineer should know almost all of these scenarios an how to begin troubleshooting them. For example, things to remember when connecting to Exchange 2007+ with Outlook, there are a few items I would look at first before coming to this site.

  • Create a new Outlook profile to see if this resolves your issue.
  • Review all URL names and the certificate to make sure all names match.
  • Is the certificate used self-signed and if so, has it been imported on all machines.
  • Remove the Hardware Load Balancer from the equation if you have one by using hosts files for name resolution.

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