Azure Bastion Alternatives

I had a project come up where I needed 2 factor auth and no public IP with RDP access. I instantly thought Azure Bastion would be great for this. I can use conditional access and hit my private IP VMs. Well, the VM had to be Ubuntu running Gnome desktop with xRDP. Azure Bastion is tied to the OS profile where it is SSH for Linux or RDP for Windows. There is an open feedback item to allow RDP to Linux. With all of that being said, let me present… Apache Guacamole. Nothing like presenting to executives saying let’s use Guacamole to solve our issue, haha.

I found an Azure marketplace image from Bitnami that provisions a VM with http to https redirection enabled with some dummy certificates and guacamole installed.

Once you provision the image, it has a public ip already assigned with a nsg on the nic opening ports 80, 443 and 22. I’d modify that nsg to remove port 80 and lock down port 22 to your IP or remove it and just use the serial console. Now, going back to my original requirements of 2fa, there is a saml extension you can use. We can easily create a new saml application in Azure Active Directory as well. Before we do this, we want to make sure we add a new user account with admin permissions in the format of user@aadDomain, else when we browse to the UI with our saml configured, we won’t be able to log in unless we use the API with the default guacadmin account. You can certainly use the API to create new saml accounts in Guacamole, but login first using the guacadmin creds to make it easier for testing. In order to get the default guacadmin password, look here. Make sure you change it!

Login and add a new user with admin permissions. For username, put in the fqdn of the user in AAD. Do not set a password.

Once we log in with the AAD creds, we can delete the guacadmin account.

Get on the Guacamole VM and download the saml extension, tar -xf and copy the jar inside /opt/bitnami/guacamole/extensions. When guacamole is restarted, it will automatically load the jar. We don’t want to restart just yet, as we need to configure the file with the saml entries. Let’s create a new Azure Enterprise Application and select Create your own application.

Give your app a new name and hit Create.

You will be taken to your new application which you will now select Single Sign On

Select SAML

Edit the basic configuration.

First, modify the Entity ID and Reply URL. We want to put in the FQDN where end users will access it via their browser. I have a domain I mapped to the public IP of Hit save and we need to grab the Login URL from #4

Back on the VM, edit /opt/bitnami/guacamole/ file and add these 3 lines:

saml-idp-url: login url from our enterprise saml app

saml-entity-id and saml-callback-url is our fqdn mapped to the public ip

Save this file. The last step is we need a valid certificate for our domain. I already have one and replaced the server.crt and server.key in /opt/bitnami/apache/conf/bitnami/certs. There is also a tool from Bitnami that does Let’s Encrypt for you.

Restart the required services with sudo /opt/bitnami/ restart

Now, either add the AAD user to the enterprise application or toggle user assignment required to No

Have your user navigate to the FQDN and they will be redirected to auth against AAD.

A couple of things to note. I took this project one more step where you can use an ARM template and set the secrets to a key vault with your certificate. If you have a WAF in front such as Azure Front Door, assign a custom domain name with tls and setup your AAD application to use that FQDN. I have a custom script extension that preps the VM with the steps we did above. For my project, I just pushed the ARM template to Template Specs for quick and easy provisioning.

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