diff --git a/apps/server/src/provider/Drivers/ClaudeSkills.test.ts b/apps/server/src/provider/Drivers/ClaudeSkills.test.ts
index 860280aa91e89..0ca376a30e8ac 100644
--- a/apps/server/src/provider/Drivers/ClaudeSkills.test.ts
+++ b/apps/server/src/provider/Drivers/ClaudeSkills.test.ts
@@ -3,10 +3,19 @@ import { assert, it } from "@effect/vitest";
 import * as Effect from "effect/Effect";
 import * as FileSystem from "effect/FileSystem";
 import * as Path from "effect/Path";
+import * as HostProcess from "@t3tools/shared/HostProcess";
 
-import { discoverClaudeSkills } from "./ClaudeSkills.ts";
+import { discoverClaudeSkills as discoverSkills } from "./ClaudeSkills.ts";
 import { planClaudeSkillDispatch } from "./ClaudeSkillDispatch.ts";
 
+// Windows makes the managed directory fixture-controlled without reading host policy or skills.
+const discoverClaudeSkills = (
+  ...[config, cwd, environment = {}]: Parameters<typeof discoverSkills>
+) =>
+  discoverSkills(config, cwd, environment).pipe(
+    Effect.provideService(HostProcess.Platform, "win32"),
+  );
+
 const writeSkill = Effect.fn(function* (
   skillsDir: string,
   directoryName: string,
@@ -399,7 +408,7 @@ it.layer(NodeServices.layer)("discoverClaudeSkills", (it) => {
     }),
   );
 
-  it.effect("prefers user skills on name collisions even with a stray .agents copy", () =>
+  it.effect("prefers managed then user skills on collisions, even with a stray .agents copy", () =>
     Effect.gen(function* () {
       const fs = yield* FileSystem.FileSystem;
       const path = yield* Path.Path;
@@ -434,6 +443,62 @@ it.layer(NodeServices.layer)("discoverClaudeSkills", (it) => {
           description: "User deploy.",
         },
       ]);
+
+      const programFiles = path.join(tempDir, "Program Files");
+      const programData = path.join(tempDir, "ProgramData");
+      yield* writeSkill(
+        path.join(programData, "ClaudeCode", ".claude", "skills"),
+        "legacy-only",
+        "# Legacy skills must not be discovered",
+      );
+      yield* fs.writeFileString(
+        path.join(programData, "ClaudeCode", "managed-settings.json"),
+        '{"skillOverrides":{"deploy":"off"}}',
+      );
+      for (const ProgramFiles of [undefined, "", programFiles]) {
+        const legacySkills = yield* discoverClaudeSkills({ homePath: configDir }, workspace, {
+          PROGRAMDATA: programData,
+          ...(ProgramFiles !== undefined ? { ProgramFiles } : {}),
+        });
+        assert.deepEqual(
+          legacySkills,
+          skills.map((skill) => ({ ...skill, enabled: false })),
+        );
+      }
+      yield* writeSkill(
+        path.join(programFiles, "ClaudeCode", ".claude", "skills"),
+        "deploy",
+        ["---", "name: deploy", "description: Managed deploy.", "---"].join("\n"),
+      );
+      yield* fs.writeFileString(
+        path.join(configDir, "settings.json"),
+        '{"skillOverrides":{"deploy":"off"}}',
+      );
+      yield* fs.writeFileString(
+        path.join(programFiles, "ClaudeCode", "managed-settings.json"),
+        '{"skillOverrides":{"deploy":"on"}}',
+      );
+      const managedSkills = yield* discoverClaudeSkills({ homePath: configDir }, workspace, {
+        ProgramFiles: programFiles,
+        PROGRAMDATA: programData,
+      });
+
+      assert.deepEqual(managedSkills, [
+        {
+          name: "deploy",
+          path: path.join(programFiles, "ClaudeCode", ".claude", "skills", "deploy", "SKILL.md"),
+          enabled: true,
+          scope: "user",
+          description: "Managed deploy.",
+        },
+      ]);
+      assert.deepEqual(
+        yield* discoverClaudeSkills({ homePath: configDir }, workspace, {
+          PROGRAMFILES: ` ${programFiles} `,
+          PROGRAMDATA: programData,
+        }),
+        managedSkills,
+      );
     }),
   );
 
diff --git a/apps/server/src/provider/Drivers/ClaudeSkills.ts b/apps/server/src/provider/Drivers/ClaudeSkills.ts
index 6aff76d250a76..9df3c484020ff 100644
--- a/apps/server/src/provider/Drivers/ClaudeSkills.ts
+++ b/apps/server/src/provider/Drivers/ClaudeSkills.ts
@@ -104,19 +104,21 @@ function parseSkillFrontmatter(contents: string): SkillFrontmatter {
   };
 }
 
-function claudeManagedSettingsPath(
+function claudeManagedDirectory(
   path: Path.Path,
   platform: NodeJS.Platform,
   environment: NodeJS.ProcessEnv,
 ): string | undefined {
   if (platform === "darwin") {
-    return "/Library/Application Support/ClaudeCode/managed-settings.json";
+    return "/Library/Application Support/ClaudeCode";
   }
   if (platform === "win32") {
-    const programData = environment.PROGRAMDATA?.trim();
-    return programData ? path.join(programData, "ClaudeCode", "managed-settings.json") : undefined;
+    const programFiles = Object.entries(environment)
+      .find(([key]) => key.toLowerCase() === "programfiles")?.[1]
+      ?.trim();
+    return programFiles ? path.join(programFiles, "ClaudeCode") : undefined;
   }
-  return "/etc/claude-code/managed-settings.json";
+  return "/etc/claude-code";
 }
 
 /** Claude Code settings files, lowest precedence first. */
@@ -128,7 +130,8 @@ function claudeSettingsPaths(
   environment: NodeJS.ProcessEnv,
   repositoryRoot?: string,
 ): ReadonlyArray<string> {
-  const managedPath = claudeManagedSettingsPath(path, platform, environment);
+  const managedDirectory = claudeManagedDirectory(path, platform, environment);
+  const programData = platform === "win32" ? environment.PROGRAMDATA?.trim() : undefined;
   const root = repositoryRoot !== undefined && repositoryRoot !== cwd ? repositoryRoot : undefined;
   return [
     path.join(configDirPath, "settings.json"),
@@ -139,7 +142,8 @@ function claudeSettingsPaths(
         ]
       : []),
     ...(root ? [path.join(root, ".claude", "settings.local.json")] : []),
-    ...(managedPath ? [managedPath] : []),
+    ...(programData ? [path.join(programData, "ClaudeCode", "managed-settings.json")] : []),
+    ...(managedDirectory ? [path.join(managedDirectory, "managed-settings.json")] : []),
   ];
 }
 
@@ -485,7 +489,7 @@ export function claudeLaunchArgDirectories(launchArgs?: string): ReadonlyArray<s
   return directories;
 }
 
-/** First name wins, matching Claude Code's precedence of user skills over project skills. */
+/** First name wins: managed skills, then user skills, then project skills. */
 export const discoverClaudeSkills = Effect.fn("discoverClaudeSkills")(function* (
   config: Pick<ClaudeSettings, "homePath"> & Partial<Pick<ClaudeSettings, "launchArgs">>,
   cwd?: string,
@@ -499,8 +503,16 @@ export const discoverClaudeSkills = Effect.fn("discoverClaudeSkills")(function*
     cwd,
     environment ?? process.env,
   );
+  const managedDirectory = claudeManagedDirectory(
+    path,
+    yield* HostProcess.Platform,
+    environment ?? process.env,
+  );
 
   const roots: ReadonlyArray<ClaudeSkillRoot> = [
+    ...(managedDirectory
+      ? [{ directory: path.join(managedDirectory, ".claude", "skills"), scope: "user" as const }]
+      : []),
     { directory: path.join(configDirPath, "skills"), scope: "user" },
     ...(cwd ? [{ directory: path.join(cwd, ".claude", "skills"), scope: "project" as const }] : []),
     ...claudeLaunchArgDirectories(config.launchArgs)