diff --git a/lib/fast_cache/cache.rb b/lib/fast_cache/cache.rb
index f8153b7..f90b7c2 100644
--- a/lib/fast_cache/cache.rb
+++ b/lib/fast_cache/cache.rb
@@ -201,8 +201,8 @@ def store_entry(key, entry)
     end
 
     def shrink_if_needed
-      if @data.length > @max_size
-        entry = delete(@data.shift)
+      while @data.length > @max_size
+        entry = @data.shift.last
         @expires_at.delete(entry)
       end
     end
diff --git a/spec/lib/fast_cache/cache_spec.rb b/spec/lib/fast_cache/cache_spec.rb
index a96db3f..df8fa7f 100644
--- a/spec/lib/fast_cache/cache_spec.rb
+++ b/spec/lib/fast_cache/cache_spec.rb
@@ -41,6 +41,14 @@
       subject[:a].should eq 10
     end
 
+    describe '#shrink_if_needed' do
+      it 'deletes the entry correctly' do
+        subject[:d] = 4
+        subject.instance_variable_get('@data').keys.should =~ [ :b, :c, :d ]
+        subject.instance_variable_get('@expires_at').values.should =~ [ :b, :c, :d ]
+      end
+    end
+
     describe '#fetch' do
       it 'fetches from the cache when a key is present' do
         subject.fetch(:a) do