@@ -4,6 +4,7 @@ import { ClaudeSettings, type ServerProvider } from "@t3tools/contracts";
 import { vi } from "vite-plus/test";
 import { assert, it } from "@effect/vitest";
 import * as Effect from "effect/Effect";
+import * as HostProcess from "@t3tools/shared/HostProcess";
 import * as FileSystem from "effect/FileSystem";
 import * as Path from "effect/Path";
 import * as Schema from "effect/Schema";
@@ -228,6 +229,27 @@ it.effect("always starts the CLI when its sources cannot be vouched for", () =>
       yield* write(settingsPath, "{}");
     }
 
+    yield* Effect.gen(function* () {
+      const managedCommands = yield* makeCommands({ PROGRAMDATA: root });
+      const dropIn = path.join(root, "ClaudeCode", "managed-settings.d", "plugins.json");
+      yield* write(dropIn, "{}");
+      const beforeManaged = probes();
+      yield* managedCommands.get(machine, cwd);
+      yield* managedCommands.get(machine, cwd);
+      assert.strictEqual(probes(), beforeManaged + 1);
+
+      yield* write(
+        dropIn,
+        JSON.stringify({ env: { CLAUDE_CODE_PLUGIN_CACHE_DIR: redirectedPlugins } }),
+      );
+      yield* probesTwice(managedCommands);
+      const beforeManagedEdit = probes();
+      yield* write(redirectedCommand, "edited command under managed redirect");
+      yield* managedCommands.get(machine, cwd);
+      assert.strictEqual(probes(), beforeManagedEdit + 1);
+      yield* write(dropIn, "{}");
+    }).pipe(Effect.provideService(HostProcess.Platform, "win32"));
+
     const installed = path.join(config, "plugins", "installed_plugins.json");
     yield* write(
       installed,
 
@@ -766,7 +766,16 @@ export const fingerprintClaudeCommandSources = Effect.fn("fingerprintClaudeComma
 
       for (const directory of claudeManagedDirectories(path, platform, environment)) {
         yield* addSettings(path.join(directory, "managed-settings.json"));
-        yield* addStat(path.join(directory, "managed-settings.d"));
+        const managedSettingsDirectory = path.join(directory, "managed-settings.d");
+        yield* addStat(managedSettingsDirectory);
+        const managedSettingsFiles = yield* fileSystem
+          .readDirectory(managedSettingsDirectory)
+          .pipe(Effect.catchReason("PlatformError", "NotFound", () => Effect.succeed([])));
+        for (const file of managedSettingsFiles
+          .filter((file) => file.endsWith(".json") && !file.startsWith("."))
+          .sort()) {
+          yield* addSettings(path.join(managedSettingsDirectory, file));
+        }
         for (const subdirectory of CLAUDE_COMMAND_SUBDIRECTORIES) {
           yield* addStat(path.join(directory, ".claude", subdirectory));
         }