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Azure DevOps Server–Switch from HTTP to HTTPS–Part 1

With the release of Azure DevOps Server 2022, I thought it would be a good time to finally make the switch to HTTPS for our internal Azure DevOps server. With the idea to minimize downtime, I decided to first introduce the HTTPS endpoint before upgrading the Azure DevOps server. But o boy, what I thought would be an easy task turned out to be quite a journey.

Updating IIS

Let’s start with the simple stuff and update our IIS instance to introduce a second binding:

  • Log in on your Azure DevOps server instance.
  • Open the Internet Information Services (IIS) Manager.

  • Select the Azure DevOps Server site on the left and click on Bindings… on the right.

  • On the Site Bindings window choose Add…

  • On the Add Site Binding window, select HTTPS from the Type dropdown and select the correct SSL certificate. Optionally you can also set a hostname.

  • Click OK and Close.

Now you can already test if the new binding is working by browsing to the HTTPS endpoint you’ve just created.

Updating Azure DevOps Server

Although doing the changes in IIS is already sufficient to be able to start using the HTTPS endpoint, when Azure DevOps itself communicates about its URL it will be still using the old HTTP based endpoint.

To change this, we have to update the Public URL:

  • Open the Azure DevOps Server Administration Console.

  • Click on Change Public URL.
  • Specify our HTTPS endpoint and click on Test. If the test succeeds succesfully, click on OK to apply the change.

More information: Setting up HTTPS - Azure DevOps | Microsoft Learn

So far, so good. But these are only the changes that need to be done on the server. Tomorrow, we’ll have a look at what needs to be done on the client.

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