Remote Desktop Gateway prompts twice then fails

Minimal guidance for messy support realities.

Scenario

Users get repeated credential prompts when connecting through RD Gateway and never reach the target host.

Recommended Resolution Path

  1. Verify the gateway certificate name, NPS policy, and backend resource authorization policies.
  2. Check whether saved credentials or password changes are causing a mismatch between gateway and target auth.
  3. Review event logs on the RD Gateway for exact denial reasons.
  4. Test with a new RDP file so legacy settings do not keep reintroducing bad options.

Technician Notes

Document what changed, what confirmed the fix, and whether the issue points to a broader standards gap worth addressing for the client.