diff --git a/dashboard/tests/test_habits_api.py b/dashboard/tests/test_habits_api.py
index 968d573..39507d2 100644
--- a/dashboard/tests/test_habits_api.py
+++ b/dashboard/tests/test_habits_api.py
@@ -39,14 +39,15 @@ def cleanup_test_env(temp_dir):
     api.HABITS_FILE = original_habits_file
     shutil.rmtree(temp_dir)
 
-def start_test_server(port=8765):
-    """Start test server in background thread."""
-    server = HTTPServer(('localhost', port), api.TaskBoardHandler)
+def start_test_server():
+    """Start test server in background thread with random available port."""
+    server = HTTPServer(('localhost', 0), api.TaskBoardHandler)  # Port 0 = random
+    port = server.server_address[1]  # Get actual assigned port
     thread = threading.Thread(target=server.serve_forever)
     thread.daemon = True
     thread.start()
-    time.sleep(0.5)  # Give server time to start
-    return server
+    time.sleep(0.3)  # Give server time to start
+    return server, port
 
 def http_get(path, port=8765):
     """Make HTTP GET request."""
@@ -103,10 +104,10 @@ def http_delete(path, port=8765):
 # Test 1: GET /api/habits returns empty array when no habits
 def test_get_habits_empty():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, data = http_get('/api/habits')
+        status, data = http_get('/api/habits', port)
         assert status == 200, f"Expected 200, got {status}"
         assert data == [], f"Expected empty array, got {data}"
         print("✓ Test 1: GET /api/habits returns empty array")
@@ -117,7 +118,7 @@ def test_get_habits_empty():
 # Test 2: POST /api/habits creates new habit with valid input
 def test_post_habit_valid():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         habit_data = {
@@ -133,7 +134,7 @@ def test_post_habit_valid():
             }
         }
         
-        status, data = http_post('/api/habits', habit_data)
+        status, data = http_post('/api/habits', habit_data, port)
         assert status == 201, f"Expected 201, got {status}"
         assert 'id' in data, "Response should include habit id"
         assert data['name'] == 'Morning Exercise', f"Name mismatch: {data['name']}"
@@ -149,10 +150,10 @@ def test_post_habit_valid():
 # Test 3: POST validates name is required
 def test_post_habit_missing_name():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, data = http_post('/api/habits', {})
+        status, data = http_post('/api/habits', {}, port)
         assert status == 400, f"Expected 400, got {status}"
         assert 'error' in data, "Response should include error"
         assert 'name' in data['error'].lower(), f"Error should mention name: {data['error']}"
@@ -164,10 +165,10 @@ def test_post_habit_missing_name():
 # Test 4: POST validates name max 100 chars
 def test_post_habit_name_too_long():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, data = http_post('/api/habits', {'name': 'x' * 101})
+        status, data = http_post('/api/habits', {'name': 'x' * 101}, port)
         assert status == 400, f"Expected 400, got {status}"
         assert 'error' in data, "Response should include error"
         assert '100' in data['error'], f"Error should mention max length: {data['error']}"
@@ -179,13 +180,13 @@ def test_post_habit_name_too_long():
 # Test 5: POST validates color hex format
 def test_post_habit_invalid_color():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         status, data = http_post('/api/habits', {
             'name': 'Test',
             'color': 'not-a-hex-color'
-        })
+        }, port)
         assert status == 400, f"Expected 400, got {status}"
         assert 'error' in data, "Response should include error"
         assert 'color' in data['error'].lower(), f"Error should mention color: {data['error']}"
@@ -197,13 +198,13 @@ def test_post_habit_invalid_color():
 # Test 6: POST validates frequency type
 def test_post_habit_invalid_frequency():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         status, data = http_post('/api/habits', {
             'name': 'Test',
             'frequency': {'type': 'invalid_type'}
-        })
+        }, port)
         assert status == 400, f"Expected 400, got {status}"
         assert 'error' in data, "Response should include error"
         assert 'frequency' in data['error'].lower(), f"Error should mention frequency: {data['error']}"
@@ -215,15 +216,15 @@ def test_post_habit_invalid_frequency():
 # Test 7: GET /api/habits returns habits with stats enriched
 def test_get_habits_with_stats():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit first
         habit_data = {'name': 'Daily Reading', 'frequency': {'type': 'daily'}}
-        http_post('/api/habits', habit_data)
+        http_post('/api/habits', habit_data, port)
         
         # Get habits
-        status, data = http_get('/api/habits')
+        status, data = http_get('/api/habits', port)
         assert status == 200, f"Expected 200, got {status}"
         assert len(data) == 1, f"Expected 1 habit, got {len(data)}"
         
@@ -240,16 +241,16 @@ def test_get_habits_with_stats():
 # Test 8: GET /api/habits sorts by priority ascending
 def test_get_habits_sorted_by_priority():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create habits with different priorities
-        http_post('/api/habits', {'name': 'Low Priority', 'priority': 10})
-        http_post('/api/habits', {'name': 'High Priority', 'priority': 1})
-        http_post('/api/habits', {'name': 'Medium Priority', 'priority': 5})
+        http_post('/api/habits', {'name': 'Low Priority', 'priority': 10}, port)
+        http_post('/api/habits', {'name': 'High Priority', 'priority': 1}, port)
+        http_post('/api/habits', {'name': 'Medium Priority', 'priority': 5}, port)
         
         # Get habits
-        status, data = http_get('/api/habits')
+        status, data = http_get('/api/habits', port)
         assert status == 200, f"Expected 200, got {status}"
         assert len(data) == 3, f"Expected 3 habits, got {len(data)}"
         
@@ -265,10 +266,10 @@ def test_get_habits_sorted_by_priority():
 # Test 9: POST returns 400 for invalid JSON
 def test_post_habit_invalid_json():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        url = f'http://localhost:8765/api/habits'
+        url = f'http://localhost:{port}/api/habits'
         req = urllib.request.Request(
             url,
             data=b'invalid json{',
@@ -287,10 +288,10 @@ def test_post_habit_invalid_json():
 # Test 10: POST initializes streak.current=0
 def test_post_habit_initial_streak():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, data = http_post('/api/habits', {'name': 'Test Habit'})
+        status, data = http_post('/api/habits', {'name': 'Test Habit'}, port)
         assert status == 201, f"Expected 201, got {status}"
         assert data['streak']['current'] == 0, "Initial streak.current should be 0"
         assert data['streak']['best'] == 0, "Initial streak.best should be 0"
@@ -303,7 +304,7 @@ def test_post_habit_initial_streak():
 # Test 12: PUT /api/habits/{id} updates habit successfully
 def test_put_habit_valid():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit first
@@ -313,7 +314,7 @@ def test_put_habit_valid():
             'color': '#10b981',
             'priority': 3
         }
-        status, created_habit = http_post('/api/habits', habit_data)
+        status, created_habit = http_post('/api/habits', habit_data, port)
         habit_id = created_habit['id']
         
         # Update the habit
@@ -324,7 +325,7 @@ def test_put_habit_valid():
             'priority': 1,
             'notes': 'New notes'
         }
-        status, updated_habit = http_put(f'/api/habits/{habit_id}', update_data)
+        status, updated_habit = http_put(f'/api/habits/{habit_id}', update_data, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert updated_habit['name'] == 'Updated Name', "Name not updated"
@@ -341,12 +342,12 @@ def test_put_habit_valid():
 # Test 13: PUT /api/habits/{id} does not allow editing protected fields
 def test_put_habit_protected_fields():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit first
         habit_data = {'name': 'Test Habit'}
-        status, created_habit = http_post('/api/habits', habit_data)
+        status, created_habit = http_post('/api/habits', habit_data, port)
         habit_id = created_habit['id']
         original_created_at = created_habit['createdAt']
         
@@ -359,7 +360,7 @@ def test_put_habit_protected_fields():
             'lives': 10,
             'completions': [{'date': '2025-01-01'}]
         }
-        status, updated_habit = http_put(f'/api/habits/{habit_id}', update_data)
+        status, updated_habit = http_put(f'/api/habits/{habit_id}', update_data, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert updated_habit['name'] == 'Updated Name', "Name should be updated"
@@ -376,11 +377,11 @@ def test_put_habit_protected_fields():
 # Test 14: PUT /api/habits/{id} returns 404 for non-existent habit
 def test_put_habit_not_found():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         update_data = {'name': 'Updated Name'}
-        status, response = http_put('/api/habits/non-existent-id', update_data)
+        status, response = http_put('/api/habits/non-existent-id', update_data, port)
         
         assert status == 404, f"Expected 404, got {status}"
         assert 'error' in response, "Expected error message"
@@ -392,27 +393,27 @@ def test_put_habit_not_found():
 # Test 15: PUT /api/habits/{id} validates input
 def test_put_habit_invalid_input():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit first
         habit_data = {'name': 'Test Habit'}
-        status, created_habit = http_post('/api/habits', habit_data)
+        status, created_habit = http_post('/api/habits', habit_data, port)
         habit_id = created_habit['id']
         
         # Test invalid color
         update_data = {'color': 'not-a-hex-color'}
-        status, response = http_put(f'/api/habits/{habit_id}', update_data)
+        status, response = http_put(f'/api/habits/{habit_id}', update_data, port)
         assert status == 400, f"Expected 400 for invalid color, got {status}"
         
         # Test empty name
         update_data = {'name': ''}
-        status, response = http_put(f'/api/habits/{habit_id}', update_data)
+        status, response = http_put(f'/api/habits/{habit_id}', update_data, port)
         assert status == 400, f"Expected 400 for empty name, got {status}"
         
         # Test name too long
         update_data = {'name': 'x' * 101}
-        status, response = http_put(f'/api/habits/{habit_id}', update_data)
+        status, response = http_put(f'/api/habits/{habit_id}', update_data, port)
         assert status == 400, f"Expected 400 for long name, got {status}"
         
         print("✓ Test 15: PUT /api/habits/{id} validates input")
@@ -423,24 +424,24 @@ def test_put_habit_invalid_input():
 # Test 16: DELETE /api/habits/{id} removes habit successfully
 def test_delete_habit_success():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit first
         habit_data = {'name': 'Habit to Delete'}
-        status, created_habit = http_post('/api/habits', habit_data)
+        status, created_habit = http_post('/api/habits', habit_data, port)
         habit_id = created_habit['id']
         
         # Verify habit exists
-        status, habits = http_get('/api/habits')
+        status, habits = http_get('/api/habits', port)
         assert len(habits) == 1, "Should have 1 habit"
         
         # Delete the habit
-        status, _ = http_delete(f'/api/habits/{habit_id}')
+        status, _ = http_delete(f'/api/habits/{habit_id}', port)
         assert status == 204, f"Expected 204, got {status}"
         
         # Verify habit is deleted
-        status, habits = http_get('/api/habits')
+        status, habits = http_get('/api/habits', port)
         assert len(habits) == 0, "Should have 0 habits after deletion"
         print("✓ Test 16: DELETE /api/habits/{id} removes habit successfully")
     finally:
@@ -450,10 +451,10 @@ def test_delete_habit_success():
 # Test 17: DELETE /api/habits/{id} returns 404 for non-existent habit
 def test_delete_habit_not_found():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, response = http_delete('/api/habits/non-existent-id')
+        status, response = http_delete('/api/habits/non-existent-id', port)
         
         assert status == 404, f"Expected 404, got {status}"
         assert 'error' in response, "Expected error message"
@@ -465,11 +466,11 @@ def test_delete_habit_not_found():
 # Test 18: do_OPTIONS includes PUT and DELETE methods
 def test_options_includes_put_delete():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Make OPTIONS request
-        url = 'http://localhost:8765/api/habits'
+        url = f'http://localhost:{port}/api/habits'
         req = urllib.request.Request(url, method='OPTIONS')
         with urllib.request.urlopen(req) as response:
             allowed_methods = response.headers.get('Access-Control-Allow-Methods', '')
@@ -483,19 +484,19 @@ def test_options_includes_put_delete():
 # Test 20: POST /api/habits/{id}/check adds completion entry
 def test_check_in_basic():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Morning Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201, f"Failed to create habit: {status}"
         habit_id = habit['id']
         
         # Check in on the habit
-        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {})
+        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert len(updated_habit['completions']) == 1, "Expected 1 completion"
@@ -509,14 +510,14 @@ def test_check_in_basic():
 # Test 21: Check-in accepts optional note, rating, mood
 def test_check_in_with_details():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Meditation',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Check in with details
@@ -524,7 +525,7 @@ def test_check_in_with_details():
             'note': 'Felt very relaxed today',
             'rating': 5,
             'mood': 'happy'
-        })
+        }, port)
         
         assert status == 200, f"Expected 200, got {status}"
         completion = updated_habit['completions'][0]
@@ -539,10 +540,10 @@ def test_check_in_with_details():
 # Test 22: Check-in returns 404 if habit not found
 def test_check_in_not_found():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, response = http_post('/api/habits/non-existent-id/check', {})
+        status, response = http_post('/api/habits/non-existent-id/check', {}, port)
         
         assert status == 404, f"Expected 404, got {status}"
         assert 'error' in response
@@ -554,7 +555,7 @@ def test_check_in_not_found():
 # Test 23: Check-in returns 400 if habit not relevant for today
 def test_check_in_not_relevant():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit for specific days (e.g., Monday only)
@@ -568,11 +569,11 @@ def test_check_in_not_relevant():
                 'type': 'specific_days',
                 'days': [different_day]
             }
-        })
+        }, port)
         habit_id = habit['id']
         
         # Try to check in
-        status, response = http_post(f'/api/habits/{habit_id}/check', {})
+        status, response = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         assert status == 400, f"Expected 400, got {status}"
         assert 'not relevant' in response.get('error', '').lower()
@@ -584,22 +585,22 @@ def test_check_in_not_relevant():
 # Test 24: Check-in returns 409 if already checked today
 def test_check_in_already_checked():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Water Plants',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Check in once
-        status, _ = http_post(f'/api/habits/{habit_id}/check', {})
+        status, _ = http_post(f'/api/habits/{habit_id}/check', {}, port)
         assert status == 200, "First check-in should succeed"
         
         # Try to check in again
-        status, response = http_post(f'/api/habits/{habit_id}/check', {})
+        status, response = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         assert status == 409, f"Expected 409, got {status}"
         assert 'already checked' in response.get('error', '').lower()
@@ -611,18 +612,18 @@ def test_check_in_already_checked():
 # Test 25: Streak is recalculated after check-in
 def test_check_in_updates_streak():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Read',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Check in
-        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {})
+        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert updated_habit['streak']['current'] == 1, f"Expected streak 1, got {updated_habit['streak']['current']}"
@@ -635,21 +636,21 @@ def test_check_in_updates_streak():
 # Test 26: lastCheckIn is updated after check-in
 def test_check_in_updates_last_check_in():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Floss',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Initially lastCheckIn should be None
         assert habit['streak']['lastCheckIn'] is None
         
         # Check in
-        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {})
+        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         today = datetime.now().date().isoformat()
         assert updated_habit['streak']['lastCheckIn'] == today
@@ -661,14 +662,14 @@ def test_check_in_updates_last_check_in():
 # Test 27: Lives are restored after 7 consecutive check-ins
 def test_check_in_life_restore():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit and manually set up 6 previous check-ins
         status, habit = http_post('/api/habits', {
             'name': 'Yoga',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Manually add 6 previous check-ins and reduce lives to 2
@@ -687,7 +688,7 @@ def test_check_in_life_restore():
         api.HABITS_FILE.write_text(json.dumps(habits_data, indent=2))
         
         # Check in for today (7th consecutive)
-        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {})
+        status, updated_habit = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert updated_habit['lives'] == 3, f"Expected 3 lives restored, got {updated_habit['lives']}"
@@ -699,20 +700,20 @@ def test_check_in_life_restore():
 # Test 28: Check-in validates rating range
 def test_check_in_invalid_rating():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Journal',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Try to check in with invalid rating
         status, response = http_post(f'/api/habits/{habit_id}/check', {
             'rating': 10  # Invalid, should be 1-5
-        })
+        }, port)
         
         assert status == 400, f"Expected 400, got {status}"
         assert 'rating' in response.get('error', '').lower()
@@ -724,20 +725,20 @@ def test_check_in_invalid_rating():
 # Test 29: Check-in validates mood values
 def test_check_in_invalid_mood():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a daily habit
         status, habit = http_post('/api/habits', {
             'name': 'Gratitude',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Try to check in with invalid mood
         status, response = http_post(f'/api/habits/{habit_id}/check', {
             'mood': 'excited'  # Invalid, should be happy/neutral/sad
-        })
+        }, port)
         
         assert status == 400, f"Expected 400, got {status}"
         assert 'mood' in response.get('error', '').lower()
@@ -749,19 +750,19 @@ def test_check_in_invalid_mood():
 # Test 30: Skip basic - decrements lives
 def test_skip_basic():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
         # Skip a day
-        status, response = http_post(f'/api/habits/{habit_id}/skip', {})
+        status, response = http_post(f'/api/habits/{habit_id}/skip', {}, port)
         
         assert status == 200, f"Expected 200, got {status}"
         assert response['lives'] == 2, f"Expected 2 lives, got {response['lives']}"
@@ -780,28 +781,28 @@ def test_skip_basic():
 # Test 31: Skip preserves streak
 def test_skip_preserves_streak():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
         # Check in to build a streak
-        http_post(f'/api/habits/{habit_id}/check', {})
+        http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         # Get current streak
-        status, habits = http_get('/api/habits')
+        status, habits = http_get('/api/habits', port)
         current_streak = habits[0]['current_streak']
         assert current_streak > 0
         
         # Skip the next day (simulate by adding skip manually and checking streak doesn't break)
         # Since we can't time travel, we'll verify that skip doesn't recalculate streak
-        status, response = http_post(f'/api/habits/{habit_id}/skip', {})
+        status, response = http_post(f'/api/habits/{habit_id}/skip', {}, port)
         
         assert status == 200, f"Expected 200, got {status}"
         # Verify lives decremented
@@ -821,10 +822,10 @@ def test_skip_preserves_streak():
 # Test 32: Skip returns 404 for non-existent habit
 def test_skip_not_found():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
-        status, response = http_post('/api/habits/nonexistent-id/skip', {})
+        status, response = http_post('/api/habits/nonexistent-id/skip', {}, port)
         
         assert status == 404, f"Expected 404, got {status}"
         assert 'not found' in response.get('error', '').lower()
@@ -837,25 +838,25 @@ def test_skip_not_found():
 # Test 33: Skip returns 400 when no lives remaining
 def test_skip_no_lives():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
         # Use all 3 lives
         for i in range(3):
-            status, response = http_post(f'/api/habits/{habit_id}/skip', {})
+            status, response = http_post(f'/api/habits/{habit_id}/skip', {}, port)
             assert status == 200, f"Skip {i+1} failed with status {status}"
             assert response['lives'] == 2 - i, f"Expected {2-i} lives, got {response['lives']}"
         
         # Try to skip again with no lives
-        status, response = http_post(f'/api/habits/{habit_id}/skip', {})
+        status, response = http_post(f'/api/habits/{habit_id}/skip', {}, port)
         
         assert status == 400, f"Expected 400, got {status}"
         assert 'no lives remaining' in response.get('error', '').lower()
@@ -868,20 +869,20 @@ def test_skip_no_lives():
 # Test 34: Skip returns updated habit with new lives count
 def test_skip_returns_updated_habit():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         original_updated_at = habit['updatedAt']
         
         # Skip a day
-        status, response = http_post(f'/api/habits/{habit_id}/skip', {})
+        status, response = http_post(f'/api/habits/{habit_id}/skip', {}, port)
         
         assert status == 200
         assert response['id'] == habit_id
@@ -899,26 +900,26 @@ def test_skip_returns_updated_habit():
 # Test 35: DELETE uncheck - removes completion for specified date
 def test_uncheck_removes_completion():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
         # Check in on a specific date
         today = datetime.now().date().isoformat()
-        status, response = http_post(f'/api/habits/{habit_id}/check', {})
+        status, response = http_post(f'/api/habits/{habit_id}/check', {}, port)
         assert status == 200
         assert len(response['completions']) == 1
         assert response['completions'][0]['date'] == today
         
         # Uncheck the habit for today
-        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}')
+        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}', port)
         assert status == 200
         assert len(response['completions']) == 0, "Completion should be removed"
         assert response['id'] == habit_id
@@ -931,20 +932,20 @@ def test_uncheck_removes_completion():
 # Test 36: DELETE uncheck - returns 404 if no completion for date
 def test_uncheck_no_completion_for_date():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit (but don't check in)
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
         # Try to uncheck a date with no completion
         today = datetime.now().date().isoformat()
-        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}')
+        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}', port)
         assert status == 404
         assert 'error' in response
         assert 'No completion found' in response['error']
@@ -957,11 +958,11 @@ def test_uncheck_no_completion_for_date():
 # Test 37: DELETE uncheck - returns 404 if habit not found
 def test_uncheck_habit_not_found():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         today = datetime.now().date().isoformat()
-        status, response = http_delete(f'/api/habits/nonexistent-id/check?date={today}')
+        status, response = http_delete(f'/api/habits/nonexistent-id/check?date={today}', port)
         assert status == 404
         assert 'error' in response
         assert 'Habit not found' in response['error']
@@ -974,14 +975,14 @@ def test_uncheck_habit_not_found():
 # Test 38: DELETE uncheck - recalculates streak correctly
 def test_uncheck_recalculates_streak():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         assert status == 201
         habit_id = habit['id']
         
@@ -999,14 +1000,14 @@ def test_uncheck_recalculates_streak():
                 json.dump(data, f)
         
         # Get habit to verify streak is 3
-        status, habit = http_get('/api/habits')
+        status, habit = http_get('/api/habits', port)
         assert status == 200
         habit = [h for h in habit if h['id'] == habit_id][0]
         assert habit['current_streak'] == 3
         
         # Uncheck the middle day
         middle_date = (today - timedelta(days=1)).isoformat()
-        status, response = http_delete(f'/api/habits/{habit_id}/check?date={middle_date}')
+        status, response = http_delete(f'/api/habits/{habit_id}/check?date={middle_date}', port)
         assert status == 200
         
         # Streak should now be 1 (only today counts)
@@ -1020,21 +1021,21 @@ def test_uncheck_recalculates_streak():
 # Test 39: DELETE uncheck - returns updated habit object
 def test_uncheck_returns_updated_habit():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create and check in
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         today = datetime.now().date().isoformat()
-        status, _ = http_post(f'/api/habits/{habit_id}/check', {})
+        status, _ = http_post(f'/api/habits/{habit_id}/check', {}, port)
         
         # Uncheck and verify response structure
-        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}')
+        status, response = http_delete(f'/api/habits/{habit_id}/check?date={today}', port)
         assert status == 200
         assert 'id' in response
         assert 'name' in response
@@ -1050,18 +1051,18 @@ def test_uncheck_returns_updated_habit():
 # Test 40: DELETE uncheck - requires date parameter
 def test_uncheck_requires_date():
     temp_dir = setup_test_env()
-    server = start_test_server()
+    server, port = start_test_server()
     
     try:
         # Create a habit
         status, habit = http_post('/api/habits', {
             'name': 'Daily Exercise',
             'frequency': {'type': 'daily'}
-        })
+        }, port)
         habit_id = habit['id']
         
         # Try to uncheck without date parameter
-        status, response = http_delete(f'/api/habits/{habit_id}/check')
+        status, response = http_delete(f'/api/habits/{habit_id}/check', port)
         assert status == 400
         assert 'error' in response
         assert 'date parameter is required' in response['error']