diff --git a/croppa/main.py b/croppa/main.py
index 5130fb7..334a4fe 100644
--- a/croppa/main.py
+++ b/croppa/main.py
@@ -157,6 +157,7 @@ class VideoEditor:
         self.crop_border_drag_start_pos = None  # (screen_x, screen_y) when drag started
         self.crop_border_drag_start_rect = None  # (x, y, w, h) in rotated coords when drag started
         self.crop_border_drag_inside = None  # True if drag started inside crop area, False if outside
+        self.crop_border_drag_outside_side = None  # 'left', 'right', 'top', 'bottom' if outside
 
         # Zoom settings
         self.zoom_factor = 1.0
@@ -3126,12 +3127,25 @@ class VideoEditor:
             # Check if cursor is inside crop area
             inside_crop = sx1 <= x <= sx2 and sy1 <= y <= sy2
             
+            # Determine which side we're on if outside (for better contraction logic)
+            outside_side = None
+            if not inside_crop:
+                if x < sx1:
+                    outside_side = 'left'
+                elif x > sx2:
+                    outside_side = 'right'
+                elif y < sy1:
+                    outside_side = 'top'
+                elif y > sy2:
+                    outside_side = 'bottom'
+            
             if event == cv2.EVENT_LBUTTONDOWN:
                 # Start dragging - record position and whether we're inside/outside
                 self.crop_border_dragging = True
                 self.crop_border_drag_start_pos = (x, y)
                 self.crop_border_drag_start_rect = (eff_x, eff_y, eff_w, eff_h)
                 self.crop_border_drag_inside = inside_crop
+                self.crop_border_drag_outside_side = outside_side
             elif event == cv2.EVENT_MOUSEMOVE and self.crop_border_dragging:
                 if self.crop_border_drag_start_pos and self.crop_border_drag_start_rect and self.crop_border_drag_inside is not None:
                     # Convert mouse movement from screen to rotated coords
@@ -3173,17 +3187,21 @@ class VideoEditor:
                                 if new_x + new_w > rot_w:
                                     new_w = rot_w - new_x
                         else:
-                            # Outside crop: drag left -> adjust right border left (contract), drag right -> adjust right border right (expand)
+                            # Outside crop: always contract based on drag direction
+                            # Drag left -> contract right (move right border left)
+                            # Drag right -> contract left (move left border right)
                             if dx_r < 0:
                                 # Dragging left -> move right border left (contract right)
                                 new_w = max(self.CROP_MIN_SIZE, new_w + dx_r)
                                 if new_w < self.CROP_MIN_SIZE:
                                     new_w = self.CROP_MIN_SIZE
                             else:
-                                # Dragging right -> move right border right (expand right)
-                                new_w = max(self.CROP_MIN_SIZE, new_w + dx_r)
-                                if new_x + new_w > rot_w:
-                                    new_w = rot_w - new_x
+                                # Dragging right -> move left border right (contract left)
+                                new_x = max(0, new_x + dx_r)
+                                new_w = new_w - dx_r
+                                if new_w < self.CROP_MIN_SIZE:
+                                    new_w = self.CROP_MIN_SIZE
+                                    new_x = self.crop_border_drag_start_rect[0] + self.crop_border_drag_start_rect[2] - self.CROP_MIN_SIZE
                     else:
                         # Vertical movement
                         if self.crop_border_drag_inside:
@@ -3201,17 +3219,21 @@ class VideoEditor:
                                 if new_y + new_h > rot_h:
                                     new_h = rot_h - new_y
                         else:
-                            # Outside crop: drag up -> adjust bottom border up (contract), drag down -> adjust bottom border down (expand)
+                            # Outside crop: always contract based on drag direction
+                            # Drag up -> contract bottom (move bottom border up)
+                            # Drag down -> contract top (move top border down)
                             if dy_r < 0:
                                 # Dragging up -> move bottom border up (contract bottom)
                                 new_h = max(self.CROP_MIN_SIZE, new_h + dy_r)
                                 if new_h < self.CROP_MIN_SIZE:
                                     new_h = self.CROP_MIN_SIZE
                             else:
-                                # Dragging down -> move bottom border down (expand down)
-                                new_h = max(self.CROP_MIN_SIZE, new_h + dy_r)
-                                if new_y + new_h > rot_h:
-                                    new_h = rot_h - new_y
+                                # Dragging down -> move top border down (contract top)
+                                new_y = max(0, new_y + dy_r)
+                                new_h = new_h - dy_r
+                                if new_h < self.CROP_MIN_SIZE:
+                                    new_h = self.CROP_MIN_SIZE
+                                    new_y = self.crop_border_drag_start_rect[1] + self.crop_border_drag_start_rect[3] - self.CROP_MIN_SIZE
                     
                     # Convert back from rotated to original frame coords
                     self._set_crop_from_rotated_rect((new_x, new_y, new_w, new_h))
@@ -3222,6 +3244,7 @@ class VideoEditor:
                 self.crop_border_drag_start_pos = None
                 self.crop_border_drag_start_rect = None
                 self.crop_border_drag_inside = None
+                self.crop_border_drag_outside_side = None
                 self.save_state()
         
         # Handle crop selection (Shift + click and drag)