Azure Bastion – End of the Jumpbox?

A common headache facing customers migrating workloads to the public cloud is deciding how best to provide secure remote access to Windows and Linux VMs.

This is normally achieved using Remote Desktop Protocol (RDP) and Secure Shell (SSH) sessions connected over public IP addresses, either directly assigned to individual hosts or a shared Jumpbox. Another option is to only allow remote access from a trusted private network over an inter-site connection such as a site-to-site VPN or ExpressRoute.

Either way, enterprises are forced to compromise security or impact the user’s experience, limiting where they can access from or by forcing them to traverse numerous network levels to gain access to the required service.

The problem with adding public endpoints directly to a host or even to a Jumpbox is that it makes them susceptible to malicious attacks. Amongst other things, it’s possible to use port scanning to discover the public IP and then brute force attacks to compromise the machine.

In efforts to reduce risk, security features such as MFA, Just in Time Access (JiT) and ACL can be implemented, but this can be difficult to manage and not totally infallible.

Azure Bastion

In answer to this problem, Microsoft has released in public preview the Azure Bastion service. Bastion is a new managed PaaS service that provides seamless RDP and SSH connectivity for your VMs over Secure Socket Layer (SSL). The service does this without having to configure each VM with its own public endpoint.

Key features available during the public preview include:

  • RDP and SSH from the Azure portal: Initiate RDP and SSH sessions directly in the Azure portal with a single-click seamless experience
  • Remote session over SSL and firewall traversal for RDP/SSH: HTML5 based web clients are automatically streamed to your local device providing the RDP/SSH session over SSL on port 443
  • No public IP required on Azure Virtual Machines: Azure Bastion opens the RDP/SSH connection to your Azure virtual machine using a private IP, limiting exposure of your infrastructure to the public Internet
  • Simplified secure rules management: Simple one-time configuration of Network Security Groups (NSGs) to allow RDP/SSH from only Azure Bastion
  • Increased protection against port scanning: The limited exposure of virtual machines to the public Internet will help protect against threats, such as external port scanning
  • Hardening in one place to protect against zero-day exploits: Azure Bastion is a managed service maintained by Microsoft. It’s continuously hardened by automatically patching and keeping up to date against known vulnerabilities.

Is it ready for the Enterprise customer?

Whether VNets have been implemented due to project segmentation, business unit, location and so on, it’s very rare to encounter an enterprise customer that does not have to control VMs sprawled over multiple VNets.

At the time of writing, limitations of the Bastion service mean that it does not yet support VNet peering. It is also only possible to deploy a Bastion host within a single VNet.

The service roadmap highlights plans to add great capabilities like Azure AD integration, Seamless Single-Sign-on and Multi-Factor Authentication to the service. Further research of various blogs and community chat suggest that support for peered VNets is another feature also being explored.

For now, when trying to access VMs attached to VNets in unsupported regions or for customers that don’t wish to deploy a Bastion host for each VNet, the workaround is to simply adopt a hub-spoke network architecture. The Bastion host sits in the hub VNet which it shares with a Jumpbox, in essence replacing the need for a secure VPN connection. It’s then from the Jumpbox that remote access can be gained across the network peerings.

Before configuring the service, there are a couple of things with the public preview to bear in mind.

  • During the public preview, the service can only be deployed from the Azure Marketplace when accessed through the Bastion preview portal:
  • The service requires a dedicated subnet called AzureBastionSubnet of at least /27 in size
  • The preview is limited to West US, East US, West Europe, South Central US, Australia East and Japan East
  • Supported browsers are limited to Microsoft Edge (Windows), Google Chrome (Windows, Mac) and Microsoft Edge Chromium (Windows, Mac).

Configuring a Bastion Host

1. Log in to the Bastion preview portal and from the homepage, click on +Create a resource.

2. On the New page, type Bastion in the Search the Marketplace box and then press Enter.

3. Select the Bastion (preview) offering, then click on Create.

4. Fill in the Create a bastion web form and finally click Review + create

Connecting to a VM

1. Now the service has been created, simply choose a VM and click on the Connect button as normal.

2. A new BASTION tab is now active on the Connect to virtual machine blade. Select the tab, fill in the username and password details before finally clicking Connect.

The following image shows the RDP session running within the boundaries of the web browser and the Azure portal.

The user experience is the same for SSH sessions.


With console access lacking in Azure and many planned features on the road map, for the most part, I’m really excited about the service. Whether it completely replaces customers needs for a Jumpbox or just offers an alternative to a secure connection to a Jumpbox in place of the normal VPN or ExpressRoute offering, it’s definitely a big step in the right direction.

The one slight concern I have is that Windows or Linux admins who have previously only had access to the client OS and may know little or nothing about Azure, are suddenly going to be exposed to the Azure portal rather than accessing the client directly. Making sure the portal is locked down and security features are configured and in place will be essential. I’m sure though as the service matures, it’s likely that improvements will address this.

To answer the question above, is the Jumpbox dead? My gut feeling is that for now, probably not. In the not too distant future, well it’s looking possible.

To learn more about the Azure Bastion service, head over to Microsoft docs: