Azure Bastion Developer SKU: Unable to connect to any VM due to "Internal server error while requesting session"

edi_smooth 0 Reputation points
2026-10-16T09:26:27.06+00:00

Service: Azure Bastion (Developer SKU), Windows VMs, UK South

Scenario: Connect to Windows VMs over RDP via Azure Portal → Connect → Bastion (VM password auth). This worked until 14 Oct 2026.

Result: A few seconds after clicking Connect: "There was an error in requesting a session. Please try again. Internal server error while requesting session." No connection attempt reaches the VM (no logon events on the target).

Screenshot 2026-10-16 at 11.22.28-c

Environment:

  • 2 Developer Bastion hosts in 2 different subscriptions, same error on both
  • Multiple users, each on a different network
  • Last successful session: 14 Oct 2026, 07:55 UTC

Troubleshooting done:

  • Clean browser profile, all extensions disabled: same error
  • Deleted and recreated the Bastion host: provisioning Succeeded, same error
  • Target VMs: running, VM agent Ready, RDP listening on 3389, NSG allows 3389 from VirtualNetwork, no changes in 30 days
  • Service Health: no Bastion events; Resource Health: "Unknown"

Steps to reproduce:

  1. Azure Portal → VM → Connect → Bastion
  2. Authentication type: VM Password, enter username/password
  3. Click Connect → after a few seconds the error above is shown

Question: Is there a known issue with Bastion Developer SKU in UK South, and is there a workaround other than upgrading to Basic SKU?

Azure Bastion
Azure Bastion

An Azure service that provides private and fully managed Remote Desktop Protocol (RDP) and Secure Shell (SSH) access to virtual machines.

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