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Microsoft Entra ID Application Proxy Implementation

· 11 min read

Are you running internal web-based applications that you want to give access to users working remotely securely without the need for a VPN or firewall? Do you want to enforce or use Azure Conditional Access policies to protect and manage access?

Let me introduce the Microsoft Microsoft Entra ID Application Proxy...

Application Proxy is a feature of Azure AD that enables users to access on-premises web applications from a remote client. Application Proxy includes both the Application Proxy service which runs in the cloud, and the Application Proxy connector, which runs on an on-premises server. Azure AD, the Application Proxy service, and the Application Proxy connector work together to securely pass the user sign-on token from Azure AD to the web application. Application Proxy also supports single sign-on.

Application Proxy is recommended for giving remote users access to internal resources. Application Proxy replaces the need for a VPN or reverse proxy.


The Microsoft Entra ID Application Proxyhas been around for a few years, but appears to be a hidden gem; the Application Proxy allows users_(by using Microsoft Entra ID and an Application Proxy Connector(s))_ to connect to internally hosted web applications, by the connector relaying the traffic.

Azure Application Proxy - Network Diagram

Application Proxy supports the following types of applications:

  • Web applications
  • Web APIs that you want to expose to rich applications on different devices
  • Applications hosted behind a Remote Desktop Gateway
  • Rich client apps that are integrated with the Microsoft Authentication Library (MSAL)

Azure Application Proxy can often be overlooked to solve your business requirements without the need to implement costly third-party firewalls (it also doesn't have to be an on-premises workload, for example, if the web application is running on a VM in Azure, it will also work).

The Azure Application proxy connector is a lightweight agent installed on a Windows Server machine that is logically close to the backend service that you want to deliver through the proxy.

The Connector gives access to and relays the information to the Application proxy service in Microsoft Azure via HTTP/HTTPS as long as it has access to the following:

URLPortHow it's used
* * between the connector and the Application Proxy cloud service ocsp.msocsp.com80/HTTPThe connector uses these URLs to verify certificates. * * * * * * * * connector uses these URLs during the registration process.
ctldl.windowsupdate.com80/HTTPThe connector uses this URL during the registration process.

Setup Azure Application Proxy

I will set up an Azure Application Proxy to grant access to my Synology NAS (Network Attached Storage) device web page in this guide.

Although I am using my local NAS web administration page, it can be any webpage (Unifi Controller, hosted on Apache, IIS etc.) accessible from the connector.

  • I have a Windows Server 2022 Domain Controller.
  • Synology NAS (not domain joined, but accessible on the network via a DNS record from the domain)
  • Microsoft 365 Developer subscription with appropriate licenses

Pre-requisites for Azure Application Proxy setup

The following resources and rights will be needed to set up Azure Application Proxy:

  • An Microsoft Entra ID tenant
  • A minimum of Application Administrator rights is required to set up the Application and user and group assignments.
  • A server running Windows Server 2012 R2 or above to install the Application Proxy connector on (and the permissions to install)
  • If you are using a third-party domain (you will need a public SSL certificate) and, of course, the ability to edit external DNS records, the domain will need to be added to Microsoft Entra ID as a custom domain in order to be used.
  • Microsoft Entra ID Premium P1 license or M365 Business Premium/E3 license for each user using Microsoft Entra ID Application Proxy.

Microsoft Entra ID Application Proxy Licensing

(Note: Normal Azure AD service limits and restrictions apply).

I will be configuring the Azure Application Proxy on a domain controller running Windows Server 2022.

Disable IE Enhanced Security Configuration

The Azure Application Proxy connector requires you to log in to Microsoft Azure, and I will be installing this on a Windows Server 2022 domain controller; if this Enhanced Security Configuration is enabled (as it should be), you will have problems authenticating to Microsoft Azure, so the easiest thing is to turn it off temporarily.

  1. Open Server Manager
  2. Click on Local Server
  3. Click on: IE Enhanced Security Configuration
  4. Select Off for: Administrators
  5. Close Microsoft Edge (if you have it opened)
  6. Disable IE Enhanced Security Configuration

Install Azure Application Proxy Connector

  1. Login to Azure Portal (on the server that you want to install the Connector on)
  2. Navigate to: Microsoft Entra ID
  3. Select Application Proxy
  4. Azure Portal - Application Proxy
  5. Click on: Download connector service.
  6. Accept the system requirements and click Accept Terms & Download
  7. A file named: 'AADApplicationProxyConnectorInstaller.exe' should have been downloaded. Run it.
  8. Select: I agree to the license terms and conditions and select Install
  9. Microsoft Microsoft Entra ID Application Proxy Connector Installation
  10. Wait for the Microsoft Microsoft Entra ID Application to display and log in with an Microsoft Entra ID account with Application Administrator rights.
  11. The Microsoft Microsoft Entra ID Application Connector will now be registered in your Microsoft Entra ID tenancy.
  12. Microsoft Microsoft Entra ID Application Proxy Connector Installation
  13. Click Close
  14. Now re-enable IE enhanced security configuration.

You should now see two new services appear in services as Automatic (Delayed Start):

  • WAPCsvc - Microsoft AAD Application Proxy Connector
  • WAPCUpdaterSvc - Microsoft AAD Application Proxy Connector Updater

And the following processes running:

  • ApplicationProxyConnectorService
  • ApplicationProxyConnectorUpdateService


If you are running Server Core, Microsoft Microsoft Entra ID Application Proxy can be installed via PowerShell.

The Azure Application Proxy Connector agent gets updated automatically when a new major version is released by Microsoft.

Configure Connector Group

Now that you have created the Connector, the Application Proxy has put our Connector in a group that has defaulted to Asia; because you can have more than one Application Proxy Connector for redundancy and different applications, we will create a new Connector Group that is set to use the Australia region if Asia works for you – feel free to skip this step.

  1. Login to Azure Portal (on any PC/server)
  2. Navigate to: Microsoft Entra ID
  3. Select Application Proxy
  4. You should now see: Default and your Region
  5. If you expand the Default Group, will you see your Connector:
  6. Azure AD Application Proxy Connector Groups
  7. Click on + New Connector Group
  8. Give it a name (i.e., On-premises)
  9. Select the Connector you had earlier and select the region closest to you (currently, the following regions can be chosen: Asia, Australia, Europe, North America)
  10. Azure AD Application Proxy - New Connector Group
  11. Click + Create
  12. Clicking create will create your new On-premises connector group and add the Connector to the group.

Configure your Azure Application Proxy Application

Now that you have your Connector setup, its time to set up your application

  1. Login to Azure Portal (on any PC/server)
  2. Navigate to: Microsoft Entra ID
  3. Select Application Proxy
  4. Click on: + Configure an app
  5. Fill in the details that match your application:
  • Name: This is the application that users will see (i.e. I am going with Pizza, which is the name of my NAS)
  • Internal URL: This is the internal URL used to access your application inside the network (in my example, it is:
  • External Url: This is the external URL that will be created so that users can access the application form; I will go with Pizza. Note this URL down.
  • Pre-Authentication: You don't have to authenticate with Azure AD, you can use passthrough, but it is not something I would recommend without delving into requirements, testing – I am going to select: Microsoft Entra ID.
  • Connector Group: Select the connector group you created earlier or that your Connector is signed to.
  • Leave all Additional Settings as default – they can be changed later if you need to.
    1. Azure Application Proxy
    2. Verify that everything is filled out correctly and, click + Add
    3. Azure Application Proxy has now created a new Enterprise Application for you; based on the name mentioned earlier, if you navigate to the external URL mentioned earlier, you should get a prompt similar to below:
    4. Azure AD Login Error
    5. It is now time to assign the permissions for users to access the Application via Microsoft Entra ID!

Assign rights to your Azure Application Proxy Application

  1. Login to Azure Portal (on any PC/server)
  2. Navigate to: Microsoft Entra ID
  3. Select Enterprise Applications
  4. Find the application that was created earlier by the Azure Application Proxy service.
  5. Microsoft Entra ID, Enterprise Application
  6. Click on the Application
  7. Click on: Users and Groups
  8. Click Add Assignment
  9. Add a user or group (preferred) you want to have access to this application.
  10. Click Assigned
  11. Azure AD Enterprise Applications - User & Group Assignment
  12. Click on Application Proxy
  13. Here you can see and edit the information you created earlier when you created the application, copy the External URL
  14. Open Microsoft Edge (or another browser of your choice)
  15. Paste in the External URL
  16. Log in with the Microsoft Entra ID account that was assigned to the Enterprise application.
  17. You should now have access to your on-premises web application from anywhere in the world, and because you are using Microsoft Entra ID, your conditional access policies and restrictions will be in effect:
  18. Synology Login

Note: Because the Synology web interface was running on port: 5000, I had to go back and add the port to the internal URL, as the Application Proxy was attempting to route to the incorrect port. Note: You may also notice that Microsoft has supplied an * certificate, even if your backend service doesn't have one..

Setup Password-based Single-Sign on

Azure Application Proxy supports various single sign-on methods, including Kerberos SPN integration.

However, my Synology NAS uses standalone accounts, so I will set Password-based single sign-on, allowing the MyApps extension to store my credentials (if you want single-sign-on using the password-based sign in, then every user will need to have this extension configured).

  1. Download and install the MyApps Secure Sign-in extension
  2. Log in using your Microsoft account to the MyApps extension
  3. Azure App Proxy
  4. Login to Azure Portal (on any PC/server)
  5. Navigate to: Microsoft Entra ID
  6. Select Enterprise Applications
  7. Find the application that was created earlier by the Azure Application Proxy service.
  8. Click on Single sign-on
  9. Select Password-based
  10. Azure Portal - Single Signon
  11. Type in the URL of the authentication webpage and click Save
  12. Azure App Proxy
  13. The Azure AD Application Proxy didn't find my sign-in login and password fields, so I have to manually configure them, select: Configure Pizza Password Single Sign-on Settings.
  14. Select: Manually detect sign-in fields
  15. Select Capture sign-in fields
  16. Azure Application Proxy - Configure Sign-on
  17. Your MS Edge Extension should show Capture Field:
  18. Azure Application Configure Extension
  19. Enter in your username
  20. Press Enter
  21. Enter in your password
  22. Select the MS Apps extension and select Save
  23. Navigate back to the Azure Portal
  24. Select 'I was able to sign in.'
  25. If successful, Azure AD should now have mapped the fields:
  26. Azure Portal - Signin Fields
  27. Click Save
  28. Next time you log in to the application, the My Apps Secure Sign-in Extension will have cached the credentials. It should automatically log you into the application, meaning you should only log in once with your Azure AD credentials.

Access your Azure Application Proxy published application

  1. You can now go to My Apps (, and you will see your application.
  2. M365 Waffle
  3. Your application will also appear in the Microsoft 365 Waffle (it may take up to an hour to appear):
  4. M365 Waffle

I recommend you go into the Enterprise Application and upload a better image/logo so your users can quickly tell it apart.

Git using Github Desktop on Windows for SysAdmins

· 9 min read

Git (Git is software for tracking changes in any set of files, usually used for coordinating work among programmers collaboratively developing source code during software development, allowing versioning, source control and enablement of continuous Integration and deployment)has been around for years(development and the first release began in 2005 by Linus Torvolds).

Although primary driven and consumed by software developers – it is now a staple of everyday life for an IT professional of many disciplines (i.e. Operations, Delivery), even if a git repository is used to store your PowerShell scripts (hint – it should!).

You don't have to know every single git command line syntax to use Git.

Tools such as Visual Studio Code allows you to utilize git source control efficiently, and of course, you can use Git directly from the command line; however, sometimes you want an easy way to leverage Git through a point and click interface, there a lot of tools out there to give you easy access to Git, but today I will concentrate on Github Desktop.

If you are looking at something a bit more powerful (especially if you are wanting to do submodules), then I suggest Atlassian Sourcetree.

Introducing Github Desktop... "Focus on what matters instead of fighting with Git. Whether you're new to Git or a seasoned user, GitHub Desktop simplifies your development workflow."

Github Desktop - Overview

Github Desktop gives you a clean, light and easy to use tool to work with git repositories that is constantly kept up to date and improved upon!

Although Github Desktop is published by Github – this doesn't mean you cannot use a git repository hosted by another provider, such as Azure DevOps.

This article assumes that you have a Git repository initialized already; you can create free repositories from Azure DevOps or Github. Microsoft owns Azure DevOps and Github; personally, I have moved from Azure DevOps to Github for my git repositories but utilize AzureDevOps pipelines.

Git High level workflow

Install Github Desktop

Installation of Github Desktop is pretty simple, but assuming you have rights to install the software:

  1. In your web browser, navigate to Github Desktop homepage and click on: Download
  2. Github Desktop - Download
  3. Once it's downloaded, you should have a file such as GitHubDesktopSetup-x64.exe (it should only take a few seconds, the file is about 109 MB at the time this article was written), then run it to install.
  4. Github Desktop - Installing

Congratulations, you have now installed Github Desktop!

Add your Azure DevOps repository

If you have an Azure DevOps git repository, then follow the steps below – if you have chosen to go: Github, then feel free to skip this section for the next.

  1. Sign in to Azure DevOps
  2. Navigate to the project you want to add to Github Desktop
  3. Click on Repos, Files
  4. Azure DevOps - Repo
  5. In the address bar, you will see your URL, and it should look like this:
  6. Copy the URL and open Github Desktop
  7. Click on File and Clone a repository
  8. Click on URL
  9. Github Desktop - Clone a Repository
  10. Paste in the repository URL you copied earlier.
  11. Select the Local path of where you want the Git repository to be saved locally on your device
  12. Now we need to generate git credentials to clone your repository, navigate back to Azure DevOps.
  13. Azure DevOps - Clone
  14. Click on Generate Git Credentials
  15. Azure DevOps will now generate the username and password that will be used by Github Desktop to authenticate with your git repository.
  16. Navigate back to Github Desktop
  17. Click Clone
  18. Enter in the username and password that you received from the git credentials, generated by Azure DevOps and click Clone.
  19. Github Desktop should now clone your repository locally.

Congratulations, you have set up an Azure DevOps git repository using Github Desktop.

Add your Github repository.

If you have an Azure DevOps git repository, follow the steps above – otherwise, follow these steps to add your Github repository into Github Desktop.

  1. Open Github Desktop
  2. Click File
  3. Click Clone repository….
  4. Github Desktop - Clone repository
  5. On the tab, enter your Github credentials
  6. Select the Local path of where you want the Git repository to be saved locally on your device
  7. Click Clone

Congratulations, you have now set up a Github git repository using Github Desktop.

Using Github Desktop

Now that you have a git repository cloned locally, it's time to use it.

Initial Commit

Once you have a file created and saved into the folder of your git repository, i.e. a PowerShell script, you will want to commit it to the git repository.

  1. Open Github Desktop
  2. Click on: Current repository to make sure your repository is selected.
  3. Github Desktop - Initial Commit
  4. In my example, I have created a new file called: HelloWorld.ps1 in my PowerShell repository.
  5. What you can see in the screenshot below is the various components that make up the Github Desktop; you can see the changed file (i.e. the new file), the contents of the file and what will be added, the commit title and the all-important commit description.
  6. Github Desktop - Overview
  7. You can change the title to something more appropriate if you want, but with your commit description, this is what you will use for versioning and seeing what changes you made in the future from a quick glance – make sure it's an appropriate description and click Commit to master.
  8. Committing it to master does not push it to its 'Origin'. I.e. the actual remote git repository (stored in Github or Azure DevOps) will commit to the local git repository. This allows you to work on code locally without requiring every change to be uploaded to a local repository. In order to commit to the Origin and remote repository, click on: Push Origin.
  9. Github Desktop - Header
  10. Once it has been committed, you should be able to see the file on the origin git repository, and you can Push multiple local git changes at once.
  11. If you click on: History should now see your commit with your file and description (as you can see, I was using an old PowerShell repository that I had merged into other repositories since then but thought it was worth using it for this article).
  12. Github Desktop - Initial commit

Congratulations, you now committed your first file into Git! It wasn't that difficult!

Restore file from the previous version

One of the benefits of using Git is version control and restoring a file if something stops working, or someone had an 'Oops!' moment! With Github Desktop, restoring a previous version is straightforward.

  1. Open Github Desktop
  2. Click on: Current repository to make sure your repository is selected
  3. Click on History (you may need to click Fetch Origin if files have been updated remotely)
  4. As you can see, someone (i.e. Luke Murray) has made a change to my' HelloWorld. ps1'' file, to be: "I like Unicorn" and changed the background and foreground colour to be both Yellow'.
  5. I can right-click that file and select Revert changes in the commit using Github Desktop.
  6. Github Desktop - Revert changes
  7. You will now have a new entry in the History that will revert the commit, and you can quickly push it back to Origin again.

Congratulations, you have successfully reverted a commit to a previous version using Github Desktop.

Working with branches

A significant function of Git is the ability to create and use branches. Branches allow you to work on features without touching the main or master branch (where you can have your production or thoroughly tested resources, for example).

  1. Open Github Desktop
  2. Click on: Current repository to make sure your repository is selected
  3. To create a branch, click on the Current branch and select New branch and give it a name, i.e. Dev
  4. Make a change to the file like you typically would and save
  5. Github Desktop has automatically added your changes, and you can commit them to the dev branch without touching master.
  6. Github Desktop - Branch commit
  7. If you navigate to the master branch, you can see that the file has remained untouched. All the control and versioning is done by Git!
  8. When you are ready to merge the dev branch into master, click the current branch.
  9. Select: Choose a branch to merge into master
  10. Select your branch, i.e. Dev
  11. Github Desktop - Merge branch
  12. Click on create a merge commit.
  13. You should see a message in Github notifying that the merge was successful, and you can push your changes to the origin repository.
  14. Github Desktop should redirect you to the master branch, and you can now see your changes:
  15. Github Desktop
  16. You can go back to using Dev to develop additional features, testing etc. and repeat the same process.

Using a master branch allows others to get production-ready scripts or code, or avoid automation around continuous deployment to production resources, while you may be still working on functionality that you don't quite want to be released yet.

Hopefully, this article gives you an excellent base to start your git journey!

There is a lot more functionality built into Github Desktop, especially around branching, but for day to day use, the above should give you all you need!

It is also worth reading this article on the .gitignore file, to make sure your git repositories don't end up bloated by unwanted files and you are only committing the files you need to be.

Azure Bicep and Insert Resource

· 3 min read

Azure Bicep is a Domain Specific Language (DSL) for deploying Azure resources declaratively. Azure Bicep is a transparent abstraction over ARM and ARM templates, which means anything that can be done in an ARM Template can be done in Bicep.

Azure Bicep has recently (December 2021) been updated to: v0.4.1124, along with various other hotfixes and enhancements; this version supports 'Insert Resource' functionality.

Insert Resource simplifies ARM to Bicep conversion without exporting entire ARM templates, then compiles them to Bicep when you are only after export for a single resource.

To use Insert Resource, you will need to have:

  • Bicep version greater than v0.4.1124
  • Azure CLI
  • Visual Studio Code with the Bicep extension

You can easily install both or upgrade following the Microsoft documentation on the: Install Bicep tools page. You can also review the Bicep changes and latest release notes on Github here: Azure Bicep releases

Import Resources into Bicep using Azure CLI and Bicep

  1. Open a new file in Visual Studio Code
  2. Set the Language mode to Bicep
  3. Visual Studio Code - Bicep
  4. Now we need to login to Azure; in Visual Studio code, click View and Terminal.
  5. In the terminal, type in: az login
  6. Login to Azure using the credentials that have read access to the Resource you want to export.
  7. Once you are logged in, type in: az resource list
  8. In the JSON output in the terminal, copy the resource ID (inside the double quotes from the id value)
  9. Now we need to open the Command Palette, press: CTRL+Shift+P on your keyboard (or click on View, Command Palette)
  10. Start typing in Bicep; if you have the latest version, you should see: Bicep: Insert Resource., select this
  11. Azure Bicep - Insert Resource
  12. Enter in the resource ID you copied earlier.
  13. Azure Bicep - Insert Resource
  14. Azure Bicep should have connected and exported your Resource straight into Bicep! As below, it had imported a Log Analytics workspace in my subscription straight into Bicep.
  15. Azure Bicep - Insert Resource

To find the resource ID using the Azure Portal.

You can use the Azure CLI to find the Resource ID, but you can also use the Azure Portal by navigating to it below:

  1. Log in to the Azure Portal
  2. Navigate to the Resource you want to export to Bicep
  3. On the Overview pane, click on JSON view

I had problems connecting to export an App Service and App Service plan, so for some resources with multiple dependencies, you may be better off exporting the ARM template from the resources/resource groups and decompiling that way, but the Insert Resource functionality is a very quick way to bring your resources into Bicep!

Day in the Life of a Technical Lead

· 4 min read

Being a 'Technical Lead' or 'Tech Lead' means different things to some people and organizations; based on definitions found online, a Technical Lead is:

"A technical lead is a professional who oversees a team of technical personnel at a software or technology company. They often lead software development or software engineering teams and troubleshoot technical issues that involve software development, engineering tasks and product releases."

Although I agree with this, I would flesh out a bit more around architectural governance (or technical assurance, which is what the problem this role or function is for) across it - it also doesn't need to be software development heavy; it can sit in the operational and delivery spaces as well (waterfall or agile) and is more than a specific role, but a frame of mind.

Tech Lead - Venn diagram

At a very high level, this is what a day in the life of a technical lead means to me:

Day in the Life of a Tech Lead

  • Work alongside: Technical Product Owners, Chapter Members, Architecture, Business stakeholders and Service Partners to develop/roadmap/architect and improve technology.
  • Manage delivery and operational risks and dependencies, and remove impediments to the achievement of the team objectives
  • Test and develop roadmaps for preview Cloud capabilities for immediate or future value
  • Act as a Subject Matter Expert (or Consultant) to assist in Design Decisions, Monitoring, Cost and Capacity Requirements
  • Develop Governance processes for onboarding services into BAU, enabling Technology Infrastructure and Operations staff to use technology in a consistent and secure manner
  • Work alongside Security and Developers to enable cross-team visibility and collaboration
  • Champion improvements in People/Processes and ways of working
  • Work alongside Chapter Members and Chapter Lead to develop Training/Skill programs for Technical areas
  • Develop and promote an 'everything as code', 'everything is automated' mindset
  • Problem/Incident Management (i.e. Continous improvement)

A Technical lead mindset may look like below

  • Automate what's trivial, boring, mundane, and belittling
  • Build what you can't buy. Buy what you can't live without
  • Make your work visible. Shift your value to performance.
  • Work is never completed. Establish feedback loops.
  • Target high impact problems.
  • Get out of the way of the work, think outside of the box, don't limit others.
  • Try, Learn, Adapt, Try again
  • Agile is about speed to adapt, not velocity
  • Log what's useful, monitor what matters, alert on what's actionable
  • Empower others while making sure that everything is auditable, standardised.
  • We live in a VUCA (Volatile, Uncertain, Complexity, Ambiguity) world, you will never see perfect.

The views above are my own, but shout out to Teal Unicorn for independent consulting on Ways of Working, Continuous improvement; I attended a few of their workshops on Ways of Working, Ways of Managing and Ways of Consulting, and it helped me take a step back and look at what this kind of mindset may look like, or should be and current blockers.

Overall, I have noticed that Information Technology roles are now blending disciplines that once required specific job roles (ie Business Analyst, Service Delivery Manager, Developer, Architect), although pure technical roles still exist with Cloud technologies, different skillsets are required to get the most value out of technology stacks, as technology becomes more consumable. You may also be interesting in reading my thoughts on: The Cloud Frame of Mind

Hopefully this has helped or at least encouraged looking at problems differently, or areas of improvements for any readers out there!

Azure Storage Account SFTP errors

· 2 min read

As part of standing up and using an Azure Storage account as an SFTP service, I ran into a few issues. This blog post is merely intended to show my findings in case others run into similar issues.

PTY allocation request failed on channel 0

Even though you appear to have connected successfully, you may see the following errors:

  • PTY allocation request failed on channel 0
  • shell request failed on channel 0

You may laugh, but the solution for this was very simple, switch from SSH to SFTP!

If you were like me, I just flicked to SSH as a habit.

Home Directory is not accessible

Make sure that the Home directory (Folder) is created in your container, SFTP won't create this for you.

Also make sure that the Home directory for the user, references Container/Folder, like the below:

Azure Portal - Enable SFTP

Wrong username, authentication failed

When attempting to connect to SFTP using a tool such as WinSCP, I got:

  • Using username "lukeftpuser".
  • Authentication failed.

The username is actually comprised of:

STORAGEACCOUNTNAME+FTPNAME, ie: sftpstorageacc1337.lukeftpuser

WinSCP Connection Azure SFTP

Unable to find Azure Storage SSH Keys

This is not an error, but Azure Keyvault, does not currently support SSH keypairs, so once they are created by Azure, they are stored in a Microsoft.Compute.sshPublicKeys resource found here: SSH Keys