diff --git a/include/resize.h b/include/resize.h
index 7b33de90..38634156 100644
--- a/include/resize.h
+++ b/include/resize.h
@@ -11,6 +11,6 @@
 
 #include <config.h>
 
-bool resize_find_tiling_participants(Con **current, Con **other, direction_t direction);
+bool resize_find_tiling_participants(Con **current, Con **other, direction_t direction, bool both_sides);
 
 int resize_graphical_handler(Con *first, Con *second, orientation_t orientation, const xcb_button_press_event_t *event);
diff --git a/src/click.c b/src/click.c
index 78af8a03..b061d0c3 100644
--- a/src/click.c
+++ b/src/click.c
@@ -49,7 +49,7 @@ static bool tiling_resize_for_border(Con *con, border_t border, xcb_button_press
             break;
     }
 
-    bool res = resize_find_tiling_participants(&first, &second, search_direction);
+    bool res = resize_find_tiling_participants(&first, &second, search_direction, false);
     if (!res) {
         LOG("No second container in this direction found.\n");
         return false;
diff --git a/src/commands.c b/src/commands.c
index 162f0892..f9b803f4 100644
--- a/src/commands.c
+++ b/src/commands.c
@@ -511,7 +511,7 @@ static bool cmd_resize_tiling_direction(I3_CMD, Con *current, const char *way, c
     else
         search_direction = D_DOWN;
 
-    bool res = resize_find_tiling_participants(&first, &second, search_direction);
+    bool res = resize_find_tiling_participants(&first, &second, search_direction, false);
     if (!res) {
         LOG("No second container in this direction found.\n");
         ysuccess(false);
@@ -552,19 +552,15 @@ static bool cmd_resize_tiling_direction(I3_CMD, Con *current, const char *way, c
 
 static bool cmd_resize_tiling_width_height(I3_CMD, Con *current, const char *way, const char *direction, int ppt) {
     LOG("width/height resize\n");
+
     /* get the appropriate current container (skip stacked/tabbed cons) */
-    while (current->parent->layout == L_STACKED ||
-           current->parent->layout == L_TABBED)
-        current = current->parent;
-
-    /* Then further go up until we find one with the matching orientation. */
-    orientation_t search_orientation =
-        (strcmp(direction, "width") == 0 ? HORIZ : VERT);
-
-    while (current->type != CT_WORKSPACE &&
-           current->type != CT_FLOATING_CON &&
-           (con_orientation(current->parent) != search_orientation || con_num_children(current->parent) == 1))
-        current = current->parent;
+    Con *dummy = NULL;
+    direction_t search_direction = (strcmp(direction, "width") == 0 ? D_LEFT : D_DOWN);
+    bool search_result = resize_find_tiling_participants(&current, &dummy, search_direction, true);
+    if (search_result == false) {
+        ysuccess(false);
+        return false;
+    }
 
     /* get the default percentage */
     int children = con_num_children(current->parent);
@@ -572,24 +568,6 @@ static bool cmd_resize_tiling_width_height(I3_CMD, Con *current, const char *way
     double percentage = 1.0 / children;
     LOG("default percentage = %f\n", percentage);
 
-    orientation_t orientation = con_orientation(current->parent);
-
-    if ((orientation == HORIZ &&
-         strcmp(direction, "height") == 0) ||
-        (orientation == VERT &&
-         strcmp(direction, "width") == 0)) {
-        LOG("You cannot resize in that direction. Your focus is in a %s split container currently.\n",
-            (orientation == HORIZ ? "horizontal" : "vertical"));
-        ysuccess(false);
-        return false;
-    }
-
-    if (children == 1) {
-        LOG("This is the only container, cannot resize.\n");
-        ysuccess(false);
-        return false;
-    }
-
     /* Ensure all the other children have a percentage set. */
     Con *child;
     TAILQ_FOREACH(child, &(current->parent->nodes_head), nodes) {
diff --git a/src/resize.c b/src/resize.c
index f07fcec6..ee50bfbc 100644
--- a/src/resize.c
+++ b/src/resize.c
@@ -47,7 +47,7 @@ DRAGGING_CB(resize_callback) {
     xcb_flush(conn);
 }
 
-bool resize_find_tiling_participants(Con **current, Con **other, direction_t direction) {
+bool resize_find_tiling_participants(Con **current, Con **other, direction_t direction, bool both_sides) {
     DLOG("Find two participants for resizing container=%p in direction=%i\n", other, direction);
     Con *first = *current;
     Con *second = NULL;
@@ -74,8 +74,14 @@ bool resize_find_tiling_participants(Con **current, Con **other, direction_t dir
         /* get the counterpart for this resizement */
         if (dir_backwards) {
             second = TAILQ_PREV(first, nodes_head, nodes);
+            if (second == NULL && both_sides == true) {
+                second = TAILQ_NEXT(first, nodes);
+            }
         } else {
             second = TAILQ_NEXT(first, nodes);
+            if (second == NULL && both_sides == true) {
+                second = TAILQ_PREV(first, nodes_head, nodes);
+            }
         }
 
         if (second == NULL) {