diff --git a/.github/workflows/windows-free-tests.yml b/.github/workflows/windows-free-tests.yml
index 0c7e69e2..037f1344 100644
--- a/.github/workflows/windows-free-tests.yml
+++ b/.github/workflows/windows-free-tests.yml
@@ -57,6 +57,16 @@ jobs:
         run: bash browse/scripts/build-node-server.sh
         shell: bash
 
+      - name: Generate host SKILL.md outputs (.agents, .factory)
+        # The golden-file regression tests in test/gen-skill-docs.test.ts read
+        # .agents/skills/gstack-ship/SKILL.md and .factory/skills/gstack-ship/
+        # SKILL.md. Both are gitignored — generated on demand by gen:skill-docs.
+        # On Mac/Linux CI the existing eval workflow regenerates these as part
+        # of its own pipeline; the windows-free-tests lane doesn't share that
+        # so it must regenerate explicitly.
+        run: bun run gen:skill-docs --host all
+        shell: bash
+
       - name: Show curated subset (for build log audit trail)
         run: bun run scripts/test-free-shards.ts --windows-only --list
         shell: bash
diff --git a/scripts/test-free-shards.ts b/scripts/test-free-shards.ts
index 94b4d53f..9407c83d 100755
--- a/scripts/test-free-shards.ts
+++ b/scripts/test-free-shards.ts
@@ -86,6 +86,21 @@ const WINDOWS_FRAGILE_PATTERNS: Array<{ pattern: RegExp; reason: string }> = [
   { pattern: /BROWSE_HEADLESS_SKIP|spawn\(\[['"]bun['"],\s*['"]run['"]/, reason: 'spawns the browse server subprocess (Bun-driven path is Windows-broken)' },
 ];
 
+// Explicit known-Windows-incompatible test files that don't fit a regex
+// pattern. Listed here with the precise reason. Prefer adding a pattern above
+// when possible; this list is for environment-/runtime-specific tests where
+// the failure mode is structural rather than detectable via source-file scan.
+const KNOWN_WINDOWS_INCOMPATIBLE: Array<{ file: string; reason: string }> = [
+  {
+    file: 'test/host-config.test.ts',
+    reason: 'asserts "claude" binary on PATH (only true when running inside Claude Code, not on bare CI runner)',
+  },
+  {
+    file: 'browse/test/findport.test.ts',
+    reason: 'asserts Bun.serve.stop() is fire-and-forget — Bun behavior differs on Windows for this polyfill',
+  },
+];
+
 export const DEFAULT_SHARD_COUNT = 20;
 export const FREE_TEST_TIMEOUT_MS = 10_000;
 
@@ -154,7 +169,13 @@ export interface CurationResult {
 export function curateWindowsSafe(files: string[], rootDir = ROOT): CurationResult {
   const safe: string[] = [];
   const excluded: Array<{ file: string; reason: string }> = [];
+  const knownBad = new Map(KNOWN_WINDOWS_INCOMPATIBLE.map((e) => [e.file, e.reason]));
   for (const relativePath of files) {
+    const knownReason = knownBad.get(relativePath);
+    if (knownReason) {
+      excluded.push({ file: relativePath, reason: knownReason });
+      continue;
+    }
     const absolute = path.join(rootDir, relativePath);
     const fragility = detectWindowsFragility(absolute);
     if (fragility) {