SSL Connection Error with Azure Hybrid Connection

When we added a hybrid connection to our Azure App Service using an Azure Resource Manager (ARM) template, we were greeted by a very difficult to solve error message, “The SSL connection could not be established.”

The architecture of the application is very similar to the diagram depicted by Microsoft’s documentation on Azure App Service Hybrid Connections. There is a web API hosted in Azure App Service that uses a relay hybrid connection to call an on-premise API.

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Using Azure Cloud Shell

The Azure Cloud Shell allows you to run commands in Azure without installing any additional software on your computer. All that you need is a web browser. If you have the Azure mobile app, then you can run commands in Azure directly from your phone.

For instance, let’s say that you’re waiting for your flight at the airport while traveling to a conference showcasing the latest Azure features when you realize that you forgot to create a virtual machine (VM) as part of your task on a user story. You already have the command saved in a file on your laptop from creating the same VM a week ago, so you pull out your laptop, boot it up, log in to the Azure Portal, then execute the command in Azure Cloud Shell. After that, you close your laptop and board the plane.

Let’s do a walk-through of these steps using Azure Cloud Shell to create a VM. If this is the first time that you’ve used Azure Cloud Shell, then there are some prompts that you need to get through. So, let’s get to it.

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