diff --git a/src/PIL/Image.py b/src/PIL/Image.py
index 6062857da06..574980771f9 100644
--- a/src/PIL/Image.py
+++ b/src/PIL/Image.py
@@ -2428,7 +2428,14 @@ def resize(
                     (box[3] - reduce_box[1]) / factor_y,
                 )
 
-        return self._new(self.im.resize(size, resample, box))
+        if self.size[1] > self.size[0] * 100 and size[1] < self.size[1]:
+            im = self.im.resize(
+                (self.size[0], size[1]), resample, (0, box[1], self.size[0], box[3])
+            )
+            im = im.resize(size, resample, (box[0], 0, box[2], size[1]))
+        else:
+            im = self.im.resize(size, resample, box)
+        return self._new(im)
 
     def reduce(
         self,