diff --git a/History.md b/History.md
index 2bbc15c3..1238bd8e 100644
--- a/History.md
+++ b/History.md
@@ -1,3 +1,7 @@
+### Master
+* Bugfixes
+  * Resolve issue with threadpool waiting counter decrement when thread is killed
+
 ## 5.0.0
 
 * Features
diff --git a/lib/puma/thread_pool.rb b/lib/puma/thread_pool.rb
index c0bbedb1..bb6a73c7 100644
--- a/lib/puma/thread_pool.rb
+++ b/lib/puma/thread_pool.rb
@@ -122,8 +122,11 @@ module Puma
                 @out_of_band_pending = false
               end
               not_full.signal
-              not_empty.wait mutex
-              @waiting -= 1
+              begin
+                not_empty.wait mutex
+              ensure
+                @waiting -= 1
+              end
             end
 
             work = todo.shift
diff --git a/test/test_thread_pool.rb b/test/test_thread_pool.rb
index 697f5c46..0e6f7645 100644
--- a/test/test_thread_pool.rb
+++ b/test/test_thread_pool.rb
@@ -266,4 +266,19 @@ class TestThreadPool < Minitest::Test
     assert_equal 2, rescued.length
     refute rescued.compact.any?(&:alive?)
   end
+
+  def test_correct_waiting_count_for_killed_threads
+    pool = new_pool(1, 1) { |_| }
+    sleep 1
+
+    # simulate our waiting worker thread getting killed for whatever reason
+    pool.instance_eval { @workers[0].kill }
+    sleep 1
+    pool.reap
+    sleep 1
+
+    pool << 0
+    sleep 1
+    assert_equal 0, pool.backlog
+  end
 end