diff --git a/packages/legacy/package.json b/packages/legacy/package.json
index 2656e7e3..074bc96a 100644
--- a/packages/legacy/package.json
+++ b/packages/legacy/package.json
@@ -9,7 +9,8 @@
   ],
   "scripts": {
     "check-types": "tsc --noEmit",
-    "build": "tsc"
+    "build": "tsc",
+    "test": "vitest"
   },
   "repository": {
     "type": "git",
@@ -33,6 +34,7 @@
     "commandkit": "workspace:*",
     "discord.js": "catalog:discordjs",
     "tsconfig": "workspace:*",
-    "typescript": "catalog:build"
+    "typescript": "catalog:build",
+    "vitest": "^4.0.18"
   }
 }
diff --git a/packages/legacy/src/plugin.test.ts b/packages/legacy/src/plugin.test.ts
new file mode 100644
index 00000000..9759cff7
--- /dev/null
+++ b/packages/legacy/src/plugin.test.ts
@@ -0,0 +1,160 @@
+import { afterEach, describe, expect, test } from 'vitest';
+import { ApplicationCommandType } from 'discord.js';
+import { mkdir, mkdtemp, rm, writeFile } from 'node:fs/promises';
+import { join, relative } from 'node:path';
+import { LegacyHandlerPlugin } from './plugin';
+import { loadLegacyCommands } from './loadLegacyCommands';
+import { CommandRegistrar, type LoadedCommand } from 'commandkit';
+
+const tmpRoots: string[] = [];
+const commandkitBaseDir = join(process.cwd(), 'dist');
+const tempBaseDir = join(commandkitBaseDir, '.tmp');
+
+async function createLegacyCommandFixture(
+  fileName: string,
+  type: ApplicationCommandType,
+) {
+  await mkdir(tempBaseDir, { recursive: true });
+  const root = await mkdtemp(join(tempBaseDir, 'legacy-commands-'));
+  tmpRoots.push(root);
+
+  const filePath = join(root, fileName);
+  await writeFile(
+    filePath,
+    `
+import { ApplicationCommandType } from 'discord.js';
+
+export const data = {
+  name: ${JSON.stringify(fileName.replace(/\.[^.]+$/, ''))},
+  type: ApplicationCommandType.${type === ApplicationCommandType.User ? 'User' : 'Message'},
+};
+
+export async function run() {
+  return ${JSON.stringify(type === ApplicationCommandType.User ? 'user' : 'message')};
+}
+`,
+  );
+
+  return root;
+}
+
+async function loadPluginCommands(commandsRoot: string) {
+  const registered: LoadedCommand[] = [];
+  const plugin = new LegacyHandlerPlugin({
+    commandsPath: relative(commandkitBaseDir, commandsRoot).replace(/\\/g, '/'),
+    eventsPath: './events',
+    validationsPath: './validations',
+    skipBuiltInValidations: true,
+    devUserIds: [],
+    devGuildIds: [],
+    devRoleIds: [],
+  });
+
+  await (plugin as any).loadCommands(
+    {
+      commandkit: {
+        commandHandler: {
+          registerExternalLoadedCommands: async (commands: LoadedCommand[]) => {
+            registered.push(...commands);
+          },
+        },
+      },
+    },
+    [],
+  );
+
+  return registered;
+}
+
+function createRegistrarData(commands: LoadedCommand[]) {
+  const registrar = new CommandRegistrar({
+    client: {
+      token: 'test-token',
+    },
+    commandHandler: {
+      getCommandsArray: () => commands,
+    },
+    commandsRouter: null,
+    plugins: {
+      execute: async () => undefined,
+    },
+  } as any);
+
+  return registrar.getCommandsData();
+}
+
+afterEach(async () => {
+  await Promise.all(
+    tmpRoots
+      .splice(0)
+      .map((root) => rm(root, { recursive: true, force: true })),
+  );
+});
+
+describe('legacy context menu command loading', () => {
+  test('maps legacy message context menu commands to modern loaded commands', async () => {
+    const root = await createLegacyCommandFixture(
+      'inspect-message.mjs',
+      ApplicationCommandType.Message,
+    );
+
+    const [legacyCommand] = await loadLegacyCommands(root);
+    const [loadedCommand] = await loadPluginCommands(root);
+
+    expect(legacyCommand.messageContextMenu).toBeTypeOf('function');
+    expect(legacyCommand.userContextMenu).toBeUndefined();
+    expect(loadedCommand.data.messageContextMenu).toBeTypeOf('function');
+    expect(loadedCommand.data.userContextMenu).toBeUndefined();
+  });
+
+  test('maps legacy user context menu commands to modern loaded commands', async () => {
+    const root = await createLegacyCommandFixture(
+      'inspect-user.mjs',
+      ApplicationCommandType.User,
+    );
+
+    const [legacyCommand] = await loadLegacyCommands(root);
+    const [loadedCommand] = await loadPluginCommands(root);
+
+    expect(legacyCommand.userContextMenu).toBeTypeOf('function');
+    expect(legacyCommand.messageContextMenu).toBeUndefined();
+    expect(loadedCommand.data.userContextMenu).toBeTypeOf('function');
+    expect(loadedCommand.data.messageContextMenu).toBeUndefined();
+  });
+
+  test('emits user context menu registration data for legacy loaded commands', async () => {
+    const root = await createLegacyCommandFixture(
+      'inspect-user.mjs',
+      ApplicationCommandType.User,
+    );
+
+    const [legacyCommand] = await loadLegacyCommands(root);
+    const [loadedCommand] = await loadPluginCommands(root);
+    const registrationCommands = createRegistrarData([loadedCommand]);
+
+    expect(registrationCommands).toHaveLength(1);
+    expect(registrationCommands[0]).toMatchObject({
+      name: 'inspect-user',
+      type: ApplicationCommandType.User,
+    });
+    expect(registrationCommands[0].description).toBeUndefined();
+    expect(registrationCommands[0].options).toBeUndefined();
+  });
+
+  test('executes the wrapped legacy user context menu runner', async () => {
+    const root = await createLegacyCommandFixture(
+      'inspect-user.mjs',
+      ApplicationCommandType.User,
+    );
+
+    const [legacyCommand] = await loadLegacyCommands(root);
+    const [loadedCommand] = await loadPluginCommands(root);
+    const result = await loadedCommand.data.userContextMenu?.({
+      client: {},
+      interaction: {},
+      commandkit: {},
+    } as any);
+
+    expect(result).toBe('user');
+  });
+});
diff --git a/packages/legacy/src/plugin.ts b/packages/legacy/src/plugin.ts
index 9be90f49..8473d680 100644
--- a/packages/legacy/src/plugin.ts
+++ b/packages/legacy/src/plugin.ts
@@ -192,7 +192,7 @@ export class LegacyHandlerPlugin extends RuntimePlugin<LegacyHandlerPluginOption
                   handler: ctx.commandkit,
                 })
             : undefined,
-          userContextMenu: command.messageContextMenu
+          userContextMenu: command.userContextMenu
             ? (ctx: UserContextMenuCommandContext) =>
                 command.userContextMenu?.({
                   client: ctx.client as any,
diff --git a/packages/legacy/tsconfig.json b/packages/legacy/tsconfig.json
index 53fdb2c1..9df2d979 100644
--- a/packages/legacy/tsconfig.json
+++ b/packages/legacy/tsconfig.json
@@ -14,5 +14,5 @@
     "noEmit": false
   },
   "include": ["src/**/*.ts"],
-  "exclude": ["node_modules"]
+  "exclude": ["node_modules", "src/**/*.test.ts", "src/**/*.spec.ts"]
 }
diff --git a/packages/legacy/vitest.config.ts b/packages/legacy/vitest.config.ts
new file mode 100644
index 00000000..4dbaf432
--- /dev/null
+++ b/packages/legacy/vitest.config.ts
@@ -0,0 +1,24 @@
+import { defineConfig } from 'vitest/config';
+import { join } from 'node:path';
+
+export default defineConfig({
+  test: {
+    include: ['./src/**/*.{test,spec}.?(c|m)[jt]s?(x)'],
+    exclude: ['dist/**', 'node_modules/**'],
+    watch: false,
+    env: {
+      COMMANDKIT_TEST: 'true',
+    },
+  },
+  resolve: {
+    alias: {
+      commandkit: join(
+        import.meta.dirname,
+        '..',
+        'commandkit',
+        'src',
+        'index.ts',
+      ),
+    },
+  },
+});
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 8695b1a4..f13f353a 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -673,6 +673,9 @@ importers:
       typescript:
         specifier: catalog:build
         version: 5.9.3
+      vitest:
+        specifier: ^4.0.18
+        version: 4.0.18(@opentelemetry/api@1.9.0)(@types/node@25.3.2)(esbuild@0.27.3)(jiti@2.6.1)(terser@5.39.2)(tsx@4.21.0)(yaml@2.8.3)
 
   packages/queue:
     devDependencies: