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docs(fleet): document Windows enrollment via WS1 NDES bridge#517

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docs(fleet): document Windows enrollment via WS1 NDES bridge#517
tashian wants to merge 2 commits into
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carl/fleet-windows-ndes-bridge

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@tashian tashian commented May 21, 2026

Summary

  • Fleet's native Smallstep CA type doesn't yet support Windows (fleetdm/fleet#28488). The previous Windows SyncML profile in this doc used `$FLEET_VAR_SMALLSTEP_SCEP_*_SMALLSTEP_AGENT` variables that are not wired up for Windows, so it wouldn't actually enroll.
  • Replaces the broken Windows section with a dedicated "Windows: bridge via the Workspace ONE connector" flow: spin up a Smallstep WS1 connector (placeholder OAuth credentials are accepted by the form — verified on the Voyager test tenant), add the resulting NDES endpoints to Fleet as a Dynamic SCEP - Okta CA or Microsoft NDES CA, and deploy the SyncML SCEP + Root CA profiles using `$FLEET_VAR_NDES_SCEP_PROXY_URL` / `$FLEET_VAR_NDES_SCEP_CHALLENGE`.
  • Documents the SHA-1 / SHA-256 fingerprint selector in the Smallstep connector UI and uses the SHA-1 value for Windows `CAThumbprint`.
  • Flags the Fleet 1-hour dynamic-challenge TTL expectation as a confirm-with-Smallstep-support item before testing.

This is meant as proper server-side setup instructions for a Smallstep teammate to test against a Windows endpoint before the workflow gets handed to a customer.

Test plan

  • Following Step W1–W5 in the rewritten doc on the Voyager test tenant + smallstep-nfr.cloud.fleetdm.com, get a Windows host to receive a Smallstep-issued certificate via Fleet
  • Confirm Smallstep support has set the WS1-connector dynamic-challenge TTL to 1 hour (per Integrate with Smallstep via SCEP w/ dynamic challenge fleetdm/fleet#28488 comment)
  • Verify the SHA-1 `CAThumbprint` path installs cleanly (vs. the previous SHA-256 value)
  • Confirm preview renders correctly with `pnpm dev` from the smallstep.com repo

🤖 Generated with Claude Code

Fleet's native Smallstep CA type doesn't yet support Windows
(fleetdm/fleet#28488), so Windows SCEP enrollment has to go through
Fleet's Dynamic SCEP (Okta/NDES) CA type pointed at Smallstep's
NDES-emulating endpoints. Those endpoints are exposed by the Smallstep
Workspace ONE connector, which can be created with placeholder OAuth
credentials when the customer doesn't operate a real WS1 tenant.

Remove the previously documented Windows SyncML profile that used the
SMALLSTEP_* Fleet variables (those aren't wired up for Windows) and
replace it with a dedicated "Windows: bridge via the Workspace ONE
connector" section covering: WS1 connector creation with placeholders,
Fleet NDES CA setup, SyncML SCEP and Root CA profiles using
NDES_SCEP_PROXY_URL and NDES_SCEP_CHALLENGE, GitOps stanza, and a
Windows verification recipe. Also flag the Fleet 1-hour challenge TTL
expectation as a setup item to confirm.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>
@tashian tashian requested a review from a team as a code owner May 21, 2026 23:01
@tashian tashian enabled auto-merge May 21, 2026 23:29
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