diff --git a/tests/parallel-sleep.test.mjs b/tests/parallel-sleep.test.mjs
new file mode 100644
index 0000000..a02cac9
--- /dev/null
+++ b/tests/parallel-sleep.test.mjs
@@ -0,0 +1,147 @@
+import { test, expect, describe, beforeEach, afterEach } from 'bun:test';
+import './test-helper.mjs'; // Automatically sets up beforeEach/afterEach cleanup
+import { $, shell, disableVirtualCommands } from '../src/$.mjs';
+
+// Reset shell settings before each test to prevent interference
+beforeEach(() => {
+  shell.errexit(false);
+  shell.verbose(false);
+  shell.xtrace(false);
+  shell.pipefail(false);
+  shell.nounset(false);
+  // Disable virtual commands for these tests to ensure system command behavior
+  disableVirtualCommands();
+});
+
+// Reset shell settings after each test to prevent interference with other test files
+afterEach(() => {
+  shell.errexit(false);
+  shell.verbose(false);
+  shell.xtrace(false);
+  shell.pipefail(false);
+  shell.nounset(false);
+});
+
+describe('Parallel Sleep Commands Execution', () => {
+  test('should execute 2 sleep commands in parallel', async () => {
+    const startTime = Date.now();
+    
+    // Start 2 parallel sleep commands with 0.5 second delay each
+    const promises = [
+      $`sleep 0.5`,
+      $`sleep 0.5`
+    ];
+    
+    const results = await Promise.all(promises);
+    const endTime = Date.now();
+    const duration = endTime - startTime;
+    
+    // Both commands should complete successfully
+    expect(results[0].code).toBe(0);
+    expect(results[1].code).toBe(0);
+    
+    // Total duration should be closer to 0.5s (parallel) than 1.0s (sequential)
+    // Allow some tolerance for system overhead
+    expect(duration).toBeLessThan(800); // Should be much less than 800ms if truly parallel
+    expect(duration).toBeGreaterThan(400); // Should be at least 400ms since sleep is 0.5s
+  });
+
+  test('should execute 3 sleep commands in parallel', async () => {
+    const startTime = Date.now();
+    
+    // Start 3 parallel sleep commands with 0.3 second delay each
+    const promises = [
+      $`sleep 0.3`,
+      $`sleep 0.3`,
+      $`sleep 0.3`
+    ];
+    
+    const results = await Promise.all(promises);
+    const endTime = Date.now();
+    const duration = endTime - startTime;
+    
+    // All commands should complete successfully
+    expect(results[0].code).toBe(0);
+    expect(results[1].code).toBe(0);
+    expect(results[2].code).toBe(0);
+    
+    // Total duration should be closer to 0.3s (parallel) than 0.9s (sequential)
+    // Allow some tolerance for system overhead
+    expect(duration).toBeLessThan(600); // Should be much less than 600ms if truly parallel
+    expect(duration).toBeGreaterThan(250); // Should be at least 250ms since sleep is 0.3s
+  });
+
+  test('should execute mixed duration sleep commands in parallel', async () => {
+    const startTime = Date.now();
+    
+    // Start 3 parallel sleep commands with different durations
+    const promises = [
+      $`sleep 0.2`,
+      $`sleep 0.4`, 
+      $`sleep 0.3`
+    ];
+    
+    const results = await Promise.all(promises);
+    const endTime = Date.now();
+    const duration = endTime - startTime;
+    
+    // All commands should complete successfully
+    expect(results[0].code).toBe(0);
+    expect(results[1].code).toBe(0);
+    expect(results[2].code).toBe(0);
+    
+    // Total duration should be determined by the longest sleep (0.4s), not the sum (0.9s)
+    // Allow some tolerance for system overhead
+    expect(duration).toBeLessThan(650); // Should be much less than 650ms if truly parallel
+    expect(duration).toBeGreaterThan(350); // Should be at least 350ms since longest sleep is 0.4s
+  });
+
+  test('should handle parallel sleep commands with output verification', async () => {
+    const startTime = Date.now();
+    
+    // Start 2 parallel sleep commands that also produce output
+    const promises = [
+      $`sh -c 'echo "command1 start"; sleep 0.2; echo "command1 end"'`,
+      $`sh -c 'echo "command2 start"; sleep 0.3; echo "command2 end"'`
+    ];
+    
+    const results = await Promise.all(promises);
+    const endTime = Date.now();
+    const duration = endTime - startTime;
+    
+    // Both commands should complete successfully
+    expect(results[0].code).toBe(0);
+    expect(results[1].code).toBe(0);
+    
+    // Verify output content
+    expect(results[0].stdout.trim()).toContain('command1 start');
+    expect(results[0].stdout.trim()).toContain('command1 end');
+    expect(results[1].stdout.trim()).toContain('command2 start');
+    expect(results[1].stdout.trim()).toContain('command2 end');
+    
+    // Duration should be closer to max(0.2s, 0.3s) = 0.3s, not sum = 0.5s
+    expect(duration).toBeLessThan(550); // Should be much less than 550ms if truly parallel
+    expect(duration).toBeGreaterThan(250); // Should be at least 250ms since longest sleep is 0.3s
+  });
+
+  test('should maintain individual command execution context in parallel', async () => {
+    // Test that each parallel command maintains its own execution environment
+    const commands = [
+      $`sh -c 'VAR="value1"; sleep 0.1; echo "Command 1: $VAR"'`,
+      $`sh -c 'VAR="value2"; sleep 0.1; echo "Command 2: $VAR"'`,
+      $`sh -c 'VAR="value3"; sleep 0.1; echo "Command 3: $VAR"'`
+    ];
+    
+    const results = await Promise.all(commands);
+    
+    // All commands should succeed
+    results.forEach(result => {
+      expect(result.code).toBe(0);
+    });
+    
+    // Each should have its own variable value
+    expect(results[0].stdout.trim()).toBe('Command 1: value1');
+    expect(results[1].stdout.trim()).toBe('Command 2: value2');
+    expect(results[2].stdout.trim()).toBe('Command 3: value3');
+  });
+});
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