diff --git a/CHANGELOG.md b/CHANGELOG.md
index b4b7f3f9..af33b618 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,9 @@ This project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.htm
 ### Added
 - New window commands `--minimize` and `--deminimize`. Minimized windows are now reported through window queries and there is a new attribute `minimized` to identify the current state [#379](https://github.com/koekeishiya/yabai/issues/379)
 
+### Changed
+- Window commands using cardinal directions use euclidean distance (frame center) to identify best target window [#301](https://github.com/koekeishiya/yabai/issues/301)
+
 ## [2.4.3] - 2020-04-14
 ### Changed
 - Changed how *mouse down* events are handled to reduce cycles spent in macOS event tap callback [#376](https://github.com/koekeishiya/yabai/issues/376)
diff --git a/src/misc/helpers.h b/src/misc/helpers.h
index 2d7214fc..c030e8b7 100644
--- a/src/misc/helpers.h
+++ b/src/misc/helpers.h
@@ -192,47 +192,11 @@ static inline bool psn_equals(ProcessSerialNumber *a, ProcessSerialNumber *b)
 }
 #pragma clang diagnostic pop
 
-static bool rect_is_in_direction(CGRect r1, CGRect r2, int direction)
+static inline int euclidean_distance(CGPoint p1, CGPoint p2)
 {
-    CGPoint r1_max = { CGRectGetMaxX(r1), CGRectGetMaxY(r1) };
-    CGPoint r2_max = { CGRectGetMaxX(r2), CGRectGetMaxY(r2) };
-
-    switch (direction) {
-    case DIR_NORTH: if (r2.origin.y > r1_max.y) return false; break;
-    case DIR_WEST:  if (r2.origin.x > r1_max.x) return false; break;
-    case DIR_SOUTH: if (r2_max.y < r1.origin.y) return false; break;
-    case DIR_EAST:  if (r2_max.x < r1.origin.x) return false; break;
-    }
-
-    switch (direction) {
-    case DIR_NORTH:
-    case DIR_SOUTH:
-        return (r2.origin.x >= r1.origin.x && r2.origin.x <= r1_max.x) ||
-               (r2_max.x >= r1.origin.x && r2_max.x <= r1_max.x) ||
-               (r1.origin.x > r2.origin.x && r1.origin.x < r2_max.x);
-    case DIR_WEST:
-    case DIR_EAST:
-        return (r2.origin.y >= r1.origin.y && r2.origin.y <= r1_max.y) ||
-               (r2_max.y >= r1.origin.y && r2_max.y <= r1_max.y) ||
-               (r1.origin.y > r2.origin.y && r1_max.y < r2_max.y);
-    }
-
-    return false;
-}
-
-static uint32_t rect_distance(CGRect r1, CGRect r2, int direction)
-{
-    CGPoint r1_max = { CGRectGetMaxX(r1), CGRectGetMaxY(r1) };
-    CGPoint r2_max = { CGRectGetMaxX(r2), CGRectGetMaxY(r2) };
-
-    switch (direction) {
-    case DIR_NORTH: return r2_max.y > r1.origin.y ? r2_max.y - r1.origin.y : r1.origin.y - r2_max.y;
-    case DIR_WEST:  return r2_max.x > r1.origin.x ? r2_max.x - r1.origin.x : r1.origin.x - r2_max.x;
-    case DIR_SOUTH: return r2.origin.y < r1_max.y ? r1_max.y - r2.origin.y : r2.origin.y - r1_max.y;
-    case DIR_EAST:  return r2.origin.x < r1_max.x ? r1_max.x - r2.origin.x : r2.origin.x - r1_max.x;
-    }
-
-    return UINT32_MAX;
+    int dx = p1.x - p2.x;
+    int dy = p1.y - p2.y;
+    return dx*dx + dy*dy;
 }
 
 static bool triangle_contains_point(CGPoint t[3], CGPoint p)
diff --git a/src/window_manager.c b/src/window_manager.c
index e16b9c8d..6e930fbe 100644
--- a/src/window_manager.c
+++ b/src/window_manager.c
@@ -678,21 +678,47 @@ struct window *window_manager_find_window_below_cursor(struct window_manager *wm
 
 static struct window *window_manager_find_closest_window_for_direction_in_window_list(struct window_manager *wm, struct window *source, int direction, uint32_t *window_list, int window_count)
 {
-    CGRect source_frame = window_frame(source);
     struct window *best_window = NULL;
-    uint32_t best_distance = UINT32_MAX;
+    int best_distance = INT_MAX;
+
+    CGRect source_frame = window_frame(source);
+    CGPoint source_point = { source_frame.origin.x, source_frame.origin.y };
 
     for (int i = 0; i < window_count; ++i) {
         struct window *window = window_manager_find_window(wm, window_list[i]);
         if (!window || !window_is_standard(window) || window == source) continue;
 
         CGRect frame = window_frame(window);
-        if (!rect_is_in_direction(source_frame, frame, direction))      continue;
+        CGPoint point = { frame.origin.x, frame.origin.y };
+
+        int distance = euclidean_distance(source_point, point);
+        if (distance >= best_distance) continue;
 
-        uint32_t distance = rect_distance(source_frame, frame, direction);
-        if (distance < best_distance) {
-            best_window = window;
-            best_distance = distance;
+        switch (direction) {
+        case DIR_EAST: {
+            if (point.x > source_point.x) {
+                best_window = window;
+                best_distance = distance;
+            }
+        } break;
+        case DIR_SOUTH: {
+            if (point.y > source_point.y) {
+                best_window = window;
+                best_distance = distance;
+            }
+        } break;
+        case DIR_WEST: {
+            if (point.x < source_point.x) {
+                best_window = window;
+                best_distance = distance;
+            }
+        } break;
+        case DIR_NORTH: {
+            if (point.y < source_point.y) {
+                best_window = window;
+                best_distance = distance;
+            }
+        } break;
         }
     }