diff --git a/.gitignore b/.gitignore
index 193c75f6c..2930bdbcb 100644
--- a/.gitignore
+++ b/.gitignore
@@ -97,6 +97,9 @@ xcuserdata/
 .claude/
 **/.claude/settings.local.json
 
+# Worktrees
+.worktrees/
+
 # incremental builds
 Makefile
 buildServer.json
diff --git a/CHANGELOG.md b/CHANGELOG.md
index f657851aa..26f45f79a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,8 @@
 
 ### Added
 
+- Added `toggle_software_keyboard` tool to show or hide the iOS Simulator software keyboard ([#346](https://github.com/getsentry/XcodeBuildMCP/issues/346)).
+- Added `toggle_connect_hardware_keyboard` tool to toggle the iOS Simulator hardware keyboard connection ([#346](https://github.com/getsentry/XcodeBuildMCP/issues/346)).
 - Added `xcodebuildmcp upgrade` command to check for updates and upgrade in place. Supports `--check` (report-only) and `--yes`/`-y` (skip confirmation). Detects install method (Homebrew, npm-global, npx) and queries the appropriate channel source (`brew info`, `npm view`, or GitHub Releases) for the latest version. Non-interactive environments exit 1 when an auto-upgrade is possible but `--yes` was not supplied.
 
 ## [2.3.2]
@@ -433,4 +435,3 @@ Please note that the UI automation features are an early preview and currently i
 - Initial release of XcodeBuildMCP
 - Basic support for building iOS and macOS applications
 
-
diff --git a/docs/TOOLS-CLI.md b/docs/TOOLS-CLI.md
index 87aa254b7..ab508ef79 100644
--- a/docs/TOOLS-CLI.md
+++ b/docs/TOOLS-CLI.md
@@ -2,7 +2,7 @@
 
 This document lists CLI tool names as exposed by `xcodebuildmcp <workflow> <tool>`.
 
-XcodeBuildMCP provides 71 canonical tools organized into 13 workflow groups.
+XcodeBuildMCP provides 73 canonical tools organized into 13 workflow groups.
 
 ## Workflow Groups
 
@@ -128,7 +128,7 @@ XcodeBuildMCP provides 71 canonical tools organized into 13 workflow groups.
 
 
 ### Simulator Management (`simulator-management`)
-**Purpose**: Tools for managing simulators from booting, opening simulators, listing simulators, stopping simulators, erasing simulator content and settings, and setting simulator environment options like location, network, statusbar and appearance. (8 tools)
+**Purpose**: Tools for managing simulators from booting, opening simulators, listing simulators, stopping simulators, erasing simulator content and settings, and setting simulator environment options like location, network, statusbar and appearance. (10 tools)
 
 - `boot` - Boot iOS simulator for manual/non-build flows. Not required before simulator build-and-run (build_run_sim).
 - `erase` - Erase simulator.
@@ -138,6 +138,8 @@ XcodeBuildMCP provides 71 canonical tools organized into 13 workflow groups.
 - `set-appearance` - Set sim appearance.
 - `set-location` - Set sim location.
 - `statusbar` - Set sim status bar network.
+- `toggle-connect-hardware-keyboard` - Toggle whether the iOS Simulator receives Mac hardware keyboard input (Cmd+Shift+K). Disconnecting makes the on-screen keyboard appear for tap-based input. Requires the simulator to be booted and Accessibility permission for the MCP host.
+- `toggle-software-keyboard` - Toggle the iOS Simulator software keyboard (Cmd+K). Shows or hides the on-screen keyboard. Requires the simulator to be booted and Accessibility permission for the MCP host.
 
 
 
@@ -185,10 +187,10 @@ XcodeBuildMCP provides 71 canonical tools organized into 13 workflow groups.
 
 ## Summary Statistics
 
-- **Canonical Tools**: 71
-- **Total Tools**: 99
+- **Canonical Tools**: 73
+- **Total Tools**: 101
 - **Workflow Groups**: 13
 
 ---
 
-*This documentation is automatically generated by `scripts/update-tools-docs.ts` from the tools manifest. Last updated: 2026-04-07T11:23:03.868Z UTC*
+*This documentation is automatically generated by `scripts/update-tools-docs.ts` from the tools manifest. Last updated: 2026-04-19T09:35:05.443Z UTC*
diff --git a/docs/TOOLS.md b/docs/TOOLS.md
index bf9c1b5a1..2d1e088b1 100644
--- a/docs/TOOLS.md
+++ b/docs/TOOLS.md
@@ -1,6 +1,6 @@
 # XcodeBuildMCP MCP Tools Reference
 
-This document lists MCP tool names as exposed to MCP clients. XcodeBuildMCP provides 77 canonical tools organized into 15 workflow groups for comprehensive Apple development workflows.
+This document lists MCP tool names as exposed to MCP clients. XcodeBuildMCP provides 79 canonical tools organized into 15 workflow groups for comprehensive Apple development workflows.
 
 ## Workflow Groups
 
@@ -137,7 +137,7 @@ This document lists MCP tool names as exposed to MCP clients. XcodeBuildMCP prov
 
 
 ### Simulator Management (`simulator-management`)
-**Purpose**: Tools for managing simulators from booting, opening simulators, listing simulators, stopping simulators, erasing simulator content and settings, and setting simulator environment options like location, network, statusbar and appearance. (8 tools)
+**Purpose**: Tools for managing simulators from booting, opening simulators, listing simulators, stopping simulators, erasing simulator content and settings, and setting simulator environment options like location, network, statusbar and appearance. (10 tools)
 
 - `boot_sim` - Boot iOS simulator for manual/non-build flows. Not required before simulator build-and-run (build_run_sim).
 - `erase_sims` - Erase simulator.
@@ -147,6 +147,8 @@ This document lists MCP tool names as exposed to MCP clients. XcodeBuildMCP prov
 - `set_sim_appearance` - Set sim appearance.
 - `set_sim_location` - Set sim location.
 - `sim_statusbar` - Set sim status bar network.
+- `toggle_connect_hardware_keyboard` - Toggle whether the iOS Simulator receives Mac hardware keyboard input (Cmd+Shift+K). Disconnecting makes the on-screen keyboard appear for tap-based input. Requires the simulator to be booted and Accessibility permission for the MCP host.
+- `toggle_software_keyboard` - Toggle the iOS Simulator software keyboard (Cmd+K). Shows or hides the on-screen keyboard. Requires the simulator to be booted and Accessibility permission for the MCP host.
 
 
 
@@ -201,10 +203,10 @@ This document lists MCP tool names as exposed to MCP clients. XcodeBuildMCP prov
 
 ## Summary Statistics
 
-- **Canonical Tools**: 77
-- **Total Tools**: 105
+- **Canonical Tools**: 79
+- **Total Tools**: 107
 - **Workflow Groups**: 15
 
 ---
 
-*This documentation is automatically generated by `scripts/update-tools-docs.ts` from the tools manifest. Last updated: 2026-04-07T11:23:03.868Z UTC*
+*This documentation is automatically generated by `scripts/update-tools-docs.ts` from the tools manifest. Last updated: 2026-04-19T09:35:05.443Z UTC*
diff --git a/manifests/tools/toggle_connect_hardware_keyboard.yaml b/manifests/tools/toggle_connect_hardware_keyboard.yaml
new file mode 100644
index 000000000..d29ed3c0c
--- /dev/null
+++ b/manifests/tools/toggle_connect_hardware_keyboard.yaml
@@ -0,0 +1,12 @@
+id: toggle_connect_hardware_keyboard
+module: mcp/tools/simulator-management/toggle_connect_hardware_keyboard
+names:
+  mcp: toggle_connect_hardware_keyboard
+  cli: toggle-connect-hardware-keyboard
+description: Toggle whether the iOS Simulator receives Mac hardware keyboard input (Cmd+Shift+K). Disconnecting makes the on-screen keyboard appear for tap-based input. Requires the simulator to be booted and Accessibility permission for the MCP host.
+annotations:
+  title: Toggle Connect Hardware Keyboard
+  readOnlyHint: false
+  destructiveHint: false
+  openWorldHint: false
+  idempotentHint: false
diff --git a/manifests/tools/toggle_software_keyboard.yaml b/manifests/tools/toggle_software_keyboard.yaml
new file mode 100644
index 000000000..9be4af66d
--- /dev/null
+++ b/manifests/tools/toggle_software_keyboard.yaml
@@ -0,0 +1,12 @@
+id: toggle_software_keyboard
+module: mcp/tools/simulator-management/toggle_software_keyboard
+names:
+  mcp: toggle_software_keyboard
+  cli: toggle-software-keyboard
+description: Toggle the iOS Simulator software keyboard (Cmd+K). Shows or hides the on-screen keyboard. Requires the simulator to be booted and Accessibility permission for the MCP host.
+annotations:
+  title: Toggle Software Keyboard
+  readOnlyHint: false
+  destructiveHint: false
+  openWorldHint: false
+  idempotentHint: false
diff --git a/manifests/workflows/simulator-management.yaml b/manifests/workflows/simulator-management.yaml
index ca55174e3..de0ffa0fd 100644
--- a/manifests/workflows/simulator-management.yaml
+++ b/manifests/workflows/simulator-management.yaml
@@ -10,3 +10,5 @@ tools:
   - reset_sim_location
   - set_sim_appearance
   - sim_statusbar
+  - toggle_software_keyboard
+  - toggle_connect_hardware_keyboard
diff --git a/src/mcp/tools/simulator-management/__tests__/_keyboard_shortcut.test.ts b/src/mcp/tools/simulator-management/__tests__/_keyboard_shortcut.test.ts
new file mode 100644
index 000000000..b2325eed9
--- /dev/null
+++ b/src/mcp/tools/simulator-management/__tests__/_keyboard_shortcut.test.ts
@@ -0,0 +1,216 @@
+import { describe, it, expect } from 'vitest';
+import {
+  createMockCommandResponse,
+  type CommandExecutor,
+} from '../../../../test-utils/mock-executors.ts';
+import { sendKeyboardShortcut } from '../_keyboard_shortcut.ts';
+
+const BOOTED_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'test-uuid-123', name: 'iPhone 15 Pro', state: 'Booted' },
+    ],
+  },
+});
+
+const SHUTDOWN_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'test-uuid-123', name: 'iPhone 15 Pro', state: 'Shutdown' },
+    ],
+  },
+});
+
+const EMPTY_JSON = JSON.stringify({ devices: {} });
+const ESCAPED_NAME_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'escaped-uuid', name: 'Test\\Device"', state: 'Booted' },
+    ],
+  },
+});
+const PREFIX_NAME_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'prefix-uuid', name: 'iPhone 15', state: 'Booted' },
+    ],
+  },
+});
+
+type Call = { command: string[] };
+
+function makeFifoExecutor(
+  responses: Array<{ success: boolean; output?: string; error?: string }>,
+): { executor: CommandExecutor; calls: Call[] } {
+  const calls: Call[] = [];
+  let i = 0;
+  const executor: CommandExecutor = async (command) => {
+    calls.push({ command });
+    const r = responses[i] ?? { success: true, output: '' };
+    i += 1;
+    return createMockCommandResponse({
+      success: r.success,
+      output: r.output ?? '',
+      error: r.error,
+    });
+  };
+  return { executor, calls };
+}
+
+describe('sendKeyboardShortcut', () => {
+  it('sends Cmd+K for software-keyboard when simulator is booted and window exists', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: BOOTED_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'OK' },
+      { success: true, output: '' },
+    ]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(true);
+    expect(calls[0].command).toEqual(['xcrun', 'simctl', 'list', 'devices', '--json']);
+    expect(calls[1].command).toEqual(['open', '-a', 'Simulator']);
+    expect(calls[2].command[0]).toBe('osascript');
+    expect(calls[2].command.join(' ')).toContain('iPhone 15 Pro');
+    expect(calls[3].command[0]).toBe('osascript');
+    const keystrokeScript = calls[3].command.join(' ');
+    expect(keystrokeScript).toContain('keystroke "k"');
+    expect(keystrokeScript).toContain('command down');
+    expect(keystrokeScript).not.toContain('shift down');
+  });
+
+  it('sends Cmd+Shift+K for connect-hardware-keyboard', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: BOOTED_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'OK' },
+      { success: true, output: '' },
+    ]);
+
+    const result = await sendKeyboardShortcut(
+      'test-uuid-123',
+      'connect-hardware-keyboard',
+      executor,
+    );
+
+    expect(result.success).toBe(true);
+    const keystrokeScript = calls[3].command.join(' ');
+    expect(keystrokeScript).toContain('keystroke "k"');
+    expect(keystrokeScript).toContain('command down');
+    expect(keystrokeScript).toContain('shift down');
+  });
+
+  it('escapes backslashes before embedding simulator names in the focus AppleScript', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: ESCAPED_NAME_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'OK' },
+      { success: true, output: '' },
+    ]);
+
+    const result = await sendKeyboardShortcut('escaped-uuid', 'software-keyboard', executor);
+
+    expect(result.success).toBe(true);
+    expect(calls[2].command[2]).toContain('Test\\\\Device\\"');
+  });
+
+  it('matches the simulator window by exact title or runtime suffix instead of substring contains', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: PREFIX_NAME_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'OK' },
+      { success: true, output: '' },
+    ]);
+
+    const result = await sendKeyboardShortcut('prefix-uuid', 'software-keyboard', executor);
+
+    expect(result.success).toBe(true);
+    expect(calls[2].command[2]).toContain('title is "iPhone 15"');
+    expect(calls[2].command[2]).toContain('title starts with "iPhone 15 –"');
+    expect(calls[2].command[2]).not.toContain('title contains');
+  });
+
+  it('errors when simulator UUID is not found', async () => {
+    const { executor, calls } = makeFifoExecutor([{ success: true, output: EMPTY_JSON }]);
+
+    const result = await sendKeyboardShortcut('missing-uuid', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('missing-uuid');
+      expect(result.error).toContain('not found');
+    }
+    expect(calls).toHaveLength(1);
+  });
+
+  it('errors when simulator is not booted', async () => {
+    const { executor, calls } = makeFifoExecutor([{ success: true, output: SHUTDOWN_JSON }]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('not booted');
+    }
+    expect(calls).toHaveLength(1);
+  });
+
+  it('errors when `open -a Simulator` fails', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: BOOTED_JSON },
+      { success: false, error: 'could not open' },
+    ]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('Simulator app');
+    }
+    expect(calls).toHaveLength(2);
+  });
+
+  it('errors and does not send keystroke when window lookup returns NO_WINDOW', async () => {
+    const { executor, calls } = makeFifoExecutor([
+      { success: true, output: BOOTED_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'NO_WINDOW' },
+    ]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('iPhone 15 Pro');
+    }
+    expect(calls).toHaveLength(3);
+  });
+
+  it('errors when simctl list fails', async () => {
+    const { executor } = makeFifoExecutor([{ success: false, error: 'simctl blew up' }]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('simctl blew up');
+    }
+  });
+
+  it('errors when keystroke osascript fails', async () => {
+    const { executor } = makeFifoExecutor([
+      { success: true, output: BOOTED_JSON },
+      { success: true, output: '' },
+      { success: true, output: 'OK' },
+      { success: false, error: 'accessibility denied' },
+    ]);
+
+    const result = await sendKeyboardShortcut('test-uuid-123', 'software-keyboard', executor);
+
+    expect(result.success).toBe(false);
+    if (!result.success) {
+      expect(result.error).toContain('accessibility denied');
+    }
+  });
+});
diff --git a/src/mcp/tools/simulator-management/__tests__/toggle_connect_hardware_keyboard.test.ts b/src/mcp/tools/simulator-management/__tests__/toggle_connect_hardware_keyboard.test.ts
new file mode 100644
index 000000000..385d6b2ab
--- /dev/null
+++ b/src/mcp/tools/simulator-management/__tests__/toggle_connect_hardware_keyboard.test.ts
@@ -0,0 +1,95 @@
+import { describe, it, expect } from 'vitest';
+import * as z from 'zod';
+import {
+  createMockCommandResponse,
+  type CommandExecutor,
+} from '../../../../test-utils/mock-executors.ts';
+import {
+  schema,
+  toggle_connect_hardware_keyboardLogic,
+} from '../toggle_connect_hardware_keyboard.ts';
+import { runLogic } from '../../../../test-utils/test-helpers.ts';
+
+const BOOTED_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'test-uuid-123', name: 'iPhone 15 Pro', state: 'Booted' },
+    ],
+  },
+});
+
+function fifo(responses: Array<{ success: boolean; output?: string; error?: string }>): {
+  executor: CommandExecutor;
+  commands: string[][];
+} {
+  const commands: string[][] = [];
+  let i = 0;
+  const executor: CommandExecutor = async (command) => {
+    commands.push(command);
+    const r = responses[i] ?? { success: true, output: '' };
+    i += 1;
+    return createMockCommandResponse({
+      success: r.success,
+      output: r.output ?? '',
+      error: r.error,
+    });
+  };
+  return { executor, commands };
+}
+
+describe('toggle_connect_hardware_keyboard tool', () => {
+  describe('Schema Validation', () => {
+    it('exposes public schema without simulatorId field', () => {
+      const schemaObj = z.object(schema);
+      expect(schemaObj.safeParse({}).success).toBe(true);
+      const withSimId = schemaObj.safeParse({ simulatorId: 'test-uuid-123' });
+      expect(withSimId.success).toBe(true);
+      expect('simulatorId' in (withSimId.data as object)).toBe(false);
+    });
+  });
+
+  describe('Handler Behavior', () => {
+    it('returns success for a booted simulator', async () => {
+      const { executor } = fifo([
+        { success: true, output: BOOTED_JSON },
+        { success: true, output: '' },
+        { success: true, output: 'OK' },
+        { success: true, output: '' },
+      ]);
+
+      const result = await runLogic(() =>
+        toggle_connect_hardware_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      expect(result.isError).toBeFalsy();
+    });
+
+    it('sends Cmd+Shift+K keystroke', async () => {
+      const { executor, commands } = fifo([
+        { success: true, output: BOOTED_JSON },
+        { success: true, output: '' },
+        { success: true, output: 'OK' },
+        { success: true, output: '' },
+      ]);
+
+      await runLogic(() =>
+        toggle_connect_hardware_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      const keystroke = commands[3].join(' ');
+      expect(keystroke).toContain('keystroke "k"');
+      expect(keystroke).toContain('command down');
+      expect(keystroke).toContain('shift down');
+    });
+
+    it('returns error when simulator not found', async () => {
+      const { executor } = fifo([{ success: true, output: JSON.stringify({ devices: {} }) }]);
+
+      const result = await runLogic(() =>
+        toggle_connect_hardware_keyboardLogic({ simulatorId: 'missing' }, executor),
+      );
+
+      expect(result.isError).toBe(true);
+    });
+  });
+});
diff --git a/src/mcp/tools/simulator-management/__tests__/toggle_software_keyboard.test.ts b/src/mcp/tools/simulator-management/__tests__/toggle_software_keyboard.test.ts
new file mode 100644
index 000000000..42d8ded29
--- /dev/null
+++ b/src/mcp/tools/simulator-management/__tests__/toggle_software_keyboard.test.ts
@@ -0,0 +1,115 @@
+import { describe, it, expect } from 'vitest';
+import * as z from 'zod';
+import {
+  createMockCommandResponse,
+  type CommandExecutor,
+} from '../../../../test-utils/mock-executors.ts';
+import { schema, toggle_software_keyboardLogic } from '../toggle_software_keyboard.ts';
+import { runLogic } from '../../../../test-utils/test-helpers.ts';
+
+const BOOTED_JSON = JSON.stringify({
+  devices: {
+    'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+      { udid: 'test-uuid-123', name: 'iPhone 15 Pro', state: 'Booted' },
+    ],
+  },
+});
+
+function fifo(responses: Array<{ success: boolean; output?: string; error?: string }>): {
+  executor: CommandExecutor;
+  commands: string[][];
+} {
+  const commands: string[][] = [];
+  let i = 0;
+  const executor: CommandExecutor = async (command) => {
+    commands.push(command);
+    const r = responses[i] ?? { success: true, output: '' };
+    i += 1;
+    return createMockCommandResponse({
+      success: r.success,
+      output: r.output ?? '',
+      error: r.error,
+    });
+  };
+  return { executor, commands };
+}
+
+describe('toggle_software_keyboard tool', () => {
+  describe('Schema Validation', () => {
+    it('exposes public schema without simulatorId field', () => {
+      const schemaObj = z.object(schema);
+      expect(schemaObj.safeParse({}).success).toBe(true);
+      const withSimId = schemaObj.safeParse({ simulatorId: 'test-uuid-123' });
+      expect(withSimId.success).toBe(true);
+      expect('simulatorId' in (withSimId.data as object)).toBe(false);
+    });
+  });
+
+  describe('Handler Behavior', () => {
+    it('returns success for a booted simulator', async () => {
+      const { executor } = fifo([
+        { success: true, output: BOOTED_JSON },
+        { success: true, output: '' },
+        { success: true, output: 'OK' },
+        { success: true, output: '' },
+      ]);
+
+      const result = await runLogic(() =>
+        toggle_software_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      expect(result.isError).toBeFalsy();
+    });
+
+    it('returns an error when the simulator is not booted', async () => {
+      const { executor } = fifo([
+        {
+          success: true,
+          output: JSON.stringify({
+            devices: {
+              'com.apple.CoreSimulator.SimRuntime.iOS-17-0': [
+                { udid: 'test-uuid-123', name: 'iPhone 15 Pro', state: 'Shutdown' },
+              ],
+            },
+          }),
+        },
+      ]);
+
+      const result = await runLogic(() =>
+        toggle_software_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      expect(result.isError).toBe(true);
+    });
+
+    it('sends Cmd+K keystroke without shift modifier', async () => {
+      const { executor, commands } = fifo([
+        { success: true, output: BOOTED_JSON },
+        { success: true, output: '' },
+        { success: true, output: 'OK' },
+        { success: true, output: '' },
+      ]);
+
+      await runLogic(() =>
+        toggle_software_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      const keystroke = commands[3].join(' ');
+      expect(keystroke).toContain('keystroke "k"');
+      expect(keystroke).toContain('command down');
+      expect(keystroke).not.toContain('shift down');
+    });
+
+    it('returns error when executor throws', async () => {
+      const executor: CommandExecutor = async () => {
+        throw new Error('boom');
+      };
+
+      const result = await runLogic(() =>
+        toggle_software_keyboardLogic({ simulatorId: 'test-uuid-123' }, executor),
+      );
+
+      expect(result.isError).toBe(true);
+    });
+  });
+});
diff --git a/src/mcp/tools/simulator-management/_keyboard_shortcut.ts b/src/mcp/tools/simulator-management/_keyboard_shortcut.ts
new file mode 100644
index 000000000..130af9777
--- /dev/null
+++ b/src/mcp/tools/simulator-management/_keyboard_shortcut.ts
@@ -0,0 +1,147 @@
+import type { CommandExecutor } from '../../../utils/execution/index.ts';
+import { log } from '../../../utils/logging/index.ts';
+
+export type KeyboardShortcut = 'software-keyboard' | 'connect-hardware-keyboard';
+
+export type KeyboardShortcutResult = { success: true } | { success: false; error: string };
+
+type SimctlDevice = { udid: string; name: string; state: string };
+type SimctlList = { devices: Record<string, SimctlDevice[]> };
+
+function escapeAppleScriptStringLiteral(value: string): string {
+  return value
+    .replace(/\\/g, '\\\\')
+    .replace(/"/g, '\\"')
+    .replace(/\n/g, '\\n')
+    .replace(/\r/g, '\\r')
+    .replace(/\t/g, '\\t');
+}
+
+function resolveDevice(list: SimctlList, simulatorId: string): SimctlDevice | undefined {
+  for (const runtime in list.devices) {
+    const found = list.devices[runtime]?.find((d) => d.udid === simulatorId);
+    if (found) return found;
+  }
+  return undefined;
+}
+
+function buildFocusScript(deviceName: string): string {
+  const safeName = escapeAppleScriptStringLiteral(deviceName);
+  return [
+    'tell application "System Events"',
+    '  tell process "Simulator"',
+    '    set frontmost to true',
+    '    set matchingWindows to (every window whose (title is "' +
+      safeName +
+      '" or title starts with "' +
+      safeName +
+      ' –" or title starts with "' +
+      safeName +
+      ' -"))',
+    '    if (count of matchingWindows) is 0 then',
+    '      return "NO_WINDOW"',
+    '    end if',
+    '    perform action "AXRaise" of (item 1 of matchingWindows)',
+    '    return "OK"',
+    '  end tell',
+    'end tell',
+  ].join('\n');
+}
+
+function buildKeystrokeScript(shortcut: KeyboardShortcut): string {
+  const modifiers =
+    shortcut === 'connect-hardware-keyboard' ? '{command down, shift down}' : '{command down}';
+  return [
+    'tell application "System Events"',
+    '  tell process "Simulator"',
+    '    keystroke "k" using ' + modifiers,
+    '  end tell',
+    'end tell',
+  ].join('\n');
+}
+
+export async function sendKeyboardShortcut(
+  simulatorId: string,
+  shortcut: KeyboardShortcut,
+  executor: CommandExecutor,
+): Promise<KeyboardShortcutResult> {
+  log('info', `Sending keyboard shortcut "${shortcut}" to simulator ${simulatorId}`);
+
+  const listResult = await executor(
+    ['xcrun', 'simctl', 'list', 'devices', '--json'],
+    'List Simulators',
+    false,
+  );
+  if (!listResult.success) {
+    return {
+      success: false,
+      error: `Failed to list simulators: ${listResult.error ?? 'unknown error'}`,
+    };
+  }
+
+  let parsed: SimctlList;
+  try {
+    parsed = JSON.parse(listResult.output) as SimctlList;
+  } catch (e) {
+    return {
+      success: false,
+      error: `Failed to parse simulator list: ${(e as Error).message}`,
+    };
+  }
+
+  const device = resolveDevice(parsed, simulatorId);
+  if (!device) {
+    return {
+      success: false,
+      error: `Simulator ${simulatorId} not found. Use list_sims to see available simulators.`,
+    };
+  }
+
+  if (device.state !== 'Booted') {
+    return {
+      success: false,
+      error: `Simulator ${simulatorId} is not booted. Boot it first with boot_sim.`,
+    };
+  }
+
+  const openResult = await executor(['open', '-a', 'Simulator'], 'Open Simulator App', false);
+  if (!openResult.success) {
+    return {
+      success: false,
+      error: `Failed to open Simulator app: ${openResult.error ?? 'unknown error'}`,
+    };
+  }
+
+  const focusResult = await executor(
+    ['osascript', '-e', buildFocusScript(device.name)],
+    'Focus Simulator Window',
+    false,
+  );
+  if (!focusResult.success) {
+    return {
+      success: false,
+      error: `Failed to focus Simulator window: ${focusResult.error ?? 'unknown error'}`,
+    };
+  }
+
+  if (focusResult.output.trim() === 'NO_WINDOW') {
+    return {
+      success: false,
+      error: `No Simulator window found for "${device.name}". Is the simulator window visible?`,
+    };
+  }
+
+  const keystrokeResult = await executor(
+    ['osascript', '-e', buildKeystrokeScript(shortcut)],
+    'Send Keyboard Shortcut',
+    false,
+  );
+  if (!keystrokeResult.success) {
+    return {
+      success: false,
+      error: `Failed to send keyboard shortcut: ${keystrokeResult.error ?? 'unknown error'}`,
+    };
+  }
+
+  return { success: true };
+}
diff --git a/src/mcp/tools/simulator-management/toggle_connect_hardware_keyboard.ts b/src/mcp/tools/simulator-management/toggle_connect_hardware_keyboard.ts
new file mode 100644
index 000000000..814393a94
--- /dev/null
+++ b/src/mcp/tools/simulator-management/toggle_connect_hardware_keyboard.ts
@@ -0,0 +1,77 @@
+import * as z from 'zod';
+import { log } from '../../../utils/logging/index.ts';
+import type { CommandExecutor } from '../../../utils/execution/index.ts';
+import { getDefaultCommandExecutor } from '../../../utils/execution/index.ts';
+import {
+  createSessionAwareTool,
+  getSessionAwareToolSchemaShape,
+  getHandlerContext,
+} from '../../../utils/typed-tool-factory.ts';
+import { withErrorHandling } from '../../../utils/tool-error-handling.ts';
+import { header, statusLine } from '../../../utils/tool-event-builders.ts';
+import { sendKeyboardShortcut } from './_keyboard_shortcut.ts';
+
+const toggleConnectHardwareKeyboardSchema = z.object({
+  simulatorId: z.uuid().describe('UUID of the simulator to use (obtained from list_simulators)'),
+});
+
+type ToggleConnectHardwareKeyboardParams = z.infer<typeof toggleConnectHardwareKeyboardSchema>;
+
+export async function toggle_connect_hardware_keyboardLogic(
+  params: ToggleConnectHardwareKeyboardParams,
+  executor: CommandExecutor,
+): Promise<void> {
+  log('info', `Toggling hardware keyboard connection on simulator ${params.simulatorId}`);
+
+  const headerEvent = header('Toggle Connect Hardware Keyboard', [
+    { label: 'Simulator', value: params.simulatorId },
+  ]);
+
+  const ctx = getHandlerContext();
+
+  return withErrorHandling(
+    ctx,
+    async () => {
+      const result = await sendKeyboardShortcut(
+        params.simulatorId,
+        'connect-hardware-keyboard',
+        executor,
+      );
+
+      if (!result.success) {
+        log('error', `Failed to toggle hardware keyboard: ${result.error}`);
+        ctx.emit(headerEvent);
+        ctx.emit(statusLine('error', result.error));
+        return;
+      }
+
+      ctx.emit(headerEvent);
+      ctx.emit(statusLine('success', 'Sent Connect Hardware Keyboard (Cmd+Shift+K)'));
+    },
+    {
+      header: headerEvent,
+      errorMessage: ({ message }) => `Failed to toggle hardware keyboard: ${message}`,
+      logMessage: ({ message }) =>
+        `Error toggling hardware keyboard for simulator ${params.simulatorId}: ${message}`,
+    },
+  );
+}
+
+const publicSchemaObject = z.strictObject(
+  toggleConnectHardwareKeyboardSchema.omit({ simulatorId: true } as const).shape,
+);
+
+export const schema = getSessionAwareToolSchemaShape({
+  sessionAware: publicSchemaObject,
+  legacy: toggleConnectHardwareKeyboardSchema,
+});
+
+export const handler = createSessionAwareTool<ToggleConnectHardwareKeyboardParams>({
+  internalSchema: toggleConnectHardwareKeyboardSchema as unknown as z.ZodType<
+    ToggleConnectHardwareKeyboardParams,
+    unknown
+  >,
+  logicFunction: toggle_connect_hardware_keyboardLogic,
+  getExecutor: getDefaultCommandExecutor,
+  requirements: [{ allOf: ['simulatorId'], message: 'simulatorId is required' }],
+});
diff --git a/src/mcp/tools/simulator-management/toggle_software_keyboard.ts b/src/mcp/tools/simulator-management/toggle_software_keyboard.ts
new file mode 100644
index 000000000..749437a41
--- /dev/null
+++ b/src/mcp/tools/simulator-management/toggle_software_keyboard.ts
@@ -0,0 +1,73 @@
+import * as z from 'zod';
+import { log } from '../../../utils/logging/index.ts';
+import type { CommandExecutor } from '../../../utils/execution/index.ts';
+import { getDefaultCommandExecutor } from '../../../utils/execution/index.ts';
+import {
+  createSessionAwareTool,
+  getSessionAwareToolSchemaShape,
+  getHandlerContext,
+} from '../../../utils/typed-tool-factory.ts';
+import { withErrorHandling } from '../../../utils/tool-error-handling.ts';
+import { header, statusLine } from '../../../utils/tool-event-builders.ts';
+import { sendKeyboardShortcut } from './_keyboard_shortcut.ts';
+
+const toggleSoftwareKeyboardSchema = z.object({
+  simulatorId: z.uuid().describe('UUID of the simulator to use (obtained from list_simulators)'),
+});
+
+type ToggleSoftwareKeyboardParams = z.infer<typeof toggleSoftwareKeyboardSchema>;
+
+export async function toggle_software_keyboardLogic(
+  params: ToggleSoftwareKeyboardParams,
+  executor: CommandExecutor,
+): Promise<void> {
+  log('info', `Toggling software keyboard on simulator ${params.simulatorId}`);
+
+  const headerEvent = header('Toggle Software Keyboard', [
+    { label: 'Simulator', value: params.simulatorId },
+  ]);
+
+  const ctx = getHandlerContext();
+
+  return withErrorHandling(
+    ctx,
+    async () => {
+      const result = await sendKeyboardShortcut(params.simulatorId, 'software-keyboard', executor);
+
+      if (!result.success) {
+        log('error', `Failed to toggle software keyboard: ${result.error}`);
+        ctx.emit(headerEvent);
+        ctx.emit(statusLine('error', result.error));
+        return;
+      }
+
+      ctx.emit(headerEvent);
+      ctx.emit(statusLine('success', 'Sent Toggle Software Keyboard (Cmd+K)'));
+    },
+    {
+      header: headerEvent,
+      errorMessage: ({ message }) => `Failed to toggle software keyboard: ${message}`,
+      logMessage: ({ message }) =>
+        `Error toggling software keyboard for simulator ${params.simulatorId}: ${message}`,
+    },
+  );
+}
+
+const publicSchemaObject = z.strictObject(
+  toggleSoftwareKeyboardSchema.omit({ simulatorId: true } as const).shape,
+);
+
+export const schema = getSessionAwareToolSchemaShape({
+  sessionAware: publicSchemaObject,
+  legacy: toggleSoftwareKeyboardSchema,
+});
+
+export const handler = createSessionAwareTool<ToggleSoftwareKeyboardParams>({
+  internalSchema: toggleSoftwareKeyboardSchema as unknown as z.ZodType<
+    ToggleSoftwareKeyboardParams,
+    unknown
+  >,
+  logicFunction: toggle_software_keyboardLogic,
+  getExecutor: getDefaultCommandExecutor,
+  requirements: [{ allOf: ['simulatorId'], message: 'simulatorId is required' }],
+});