diff --git a/src/Intervention/Image/Size.php b/src/Intervention/Image/Size.php
index b559588e..fe5e3219 100644
--- a/src/Intervention/Image/Size.php
+++ b/src/Intervention/Image/Size.php
@@ -109,13 +109,26 @@ class Size
 
     public function fit(Size $size)
     {
-        $width = $size->getRatio() <= 1 ? null : $this->width;
-        $height = $size->getRatio() > 1 ? null : $this->height;
+        $auto_width = clone $size;
+        $auto_height = clone $size;
 
-        $size->resize($width, $height, function ($constraint) {
+        // create size with auto width
+        $auto_width->resize(null, $this->height, function ($constraint) {
             $constraint->aspectRatio();
         });
 
+        // create size with auto height
+        $auto_height->resize($this->width, null, function ($constraint) {
+            $constraint->aspectRatio();
+        });
+
+        // decide which version to use
+        if ($auto_height->fitsInto($this)) {
+            $size = $auto_height;
+        } else {
+            $size = $auto_width;
+        }
+
         $this->align('center');
         $size->align('center');
         $size->setPivot($this->relativePosition($size));
@@ -123,6 +136,11 @@ class Size
         return $size;
     }
 
+    public function fitsInto(Size $size)
+    {
+        return ($this->width <= $size->width) && ($this->height <= $size->height);
+    }
+
     public function align($position, $offset_x = 0, $offset_y = 0)
     {
         switch (strtolower($position)) {
diff --git a/tests/SizeTest.php b/tests/SizeTest.php
index 66094b84..22cec778 100644
--- a/tests/SizeTest.php
+++ b/tests/SizeTest.php
@@ -292,6 +292,44 @@ class SizeTest extends PHPUnit_Framework_TestCase
         $this->assertEquals(300, $fitted->height);
         $this->assertEquals(50, $fitted->pivot->x);
         $this->assertEquals(0, $fitted->pivot->y);
+
+        $box = new Size(600, 800);
+        $fitted = $box->fit(new Size(100, 100));
+        $this->assertEquals(600, $fitted->width);
+        $this->assertEquals(600, $fitted->height);
+        $this->assertEquals(0, $fitted->pivot->x);
+        $this->assertEquals(100, $fitted->pivot->y);
+    }
+
+    public function testFitsInto()
+    {
+        $box = new Size(800, 600);
+        $fits = $box->fitsInto(new Size(100, 100));
+        $this->assertFalse($fits);
+
+        $box = new Size(800, 600);
+        $fits = $box->fitsInto(new Size(1000, 100));
+        $this->assertFalse($fits);
+
+        $box = new Size(800, 600);
+        $fits = $box->fitsInto(new Size(100, 1000));
+        $this->assertFalse($fits);
+
+        $box = new Size(800, 600);
+        $fits = $box->fitsInto(new Size(800, 600));
+        $this->assertTrue($fits);
+
+        $box = new Size(800, 600);
+        $fits = $box->fitsInto(new Size(1000, 1000));
+        $this->assertTrue($fits);
+
+        $box = new Size(100, 100);
+        $fits = $box->fitsInto(new Size(800, 600));
+        $this->assertTrue($fits);
+
+        $box = new Size(100, 100);
+        $fits = $box->fitsInto(new Size(80, 60));
+        $this->assertFalse($fits);
     }
 
     /**