diff --git a/include/pybind11/functional.h b/include/pybind11/functional.h
index 9cdf21f7ad..7a0988ab05 100644
--- a/include/pybind11/functional.h
+++ b/include/pybind11/functional.h
@@ -54,9 +54,20 @@ struct type_caster<std::function<Return(Args...)>> {
             }
         }
 
-        value = [func](Args... args) -> Return {
+        // ensure GIL is held during functor destruction
+        struct func_handle {
+            function f;
+            func_handle(function&& f_) : f(std::move(f_)) {}
+            func_handle(const func_handle&) = default;
+            ~func_handle() {
+                gil_scoped_acquire acq;
+                function kill_f(std::move(f));
+            }
+        };
+
+        value = [hfunc = func_handle(std::move(func))](Args... args) -> Return {
             gil_scoped_acquire acq;
-            object retval(func(std::forward<Args>(args)...));
+            object retval(hfunc.f(std::forward<Args>(args)...));
             /* Visual studio 2015 parser issue: need parentheses around this expression */
             return (retval.template cast<Return>());
         };
diff --git a/tests/test_callbacks.cpp b/tests/test_callbacks.cpp
index 273eacc30c..71b88c44c7 100644
--- a/tests/test_callbacks.cpp
+++ b/tests/test_callbacks.cpp
@@ -10,6 +10,7 @@
 #include "pybind11_tests.h"
 #include "constructor_stats.h"
 #include <pybind11/functional.h>
+#include <thread>
 
 
 int dummy_function(int i) { return i + 1; }
@@ -146,4 +147,22 @@ TEST_SUBMODULE(callbacks, m) {
     py::class_<CppBoundMethodTest>(m, "CppBoundMethodTest")
         .def(py::init<>())
         .def("triple", [](CppBoundMethodTest &, int val) { return 3 * val; });
+
+    // test async Python callbacks
+    using callback_f = std::function<void(int)>;
+    m.def("test_async_callback", [](callback_f f, py::list work) {
+        // make detached thread that calls `f` with piece of work after a little delay
+        auto start_f = [f](int j) {
+            auto invoke_f = [f, j] {
+                std::this_thread::sleep_for(std::chrono::milliseconds(50));
+                f(j);
+            };
+            auto t = std::thread(std::move(invoke_f));
+            t.detach();
+        };
+
+        // spawn worker threads
+        for (auto i : work)
+            start_f(py::cast<int>(i));
+    });
 }
diff --git a/tests/test_callbacks.py b/tests/test_callbacks.py
index 93c42c22b8..6439c8e72a 100644
--- a/tests/test_callbacks.py
+++ b/tests/test_callbacks.py
@@ -1,5 +1,6 @@
 import pytest
 from pybind11_tests import callbacks as m
+from threading import Thread
 
 
 def test_callbacks():
@@ -105,3 +106,31 @@ def test_function_signatures(doc):
 
 def test_movable_object():
     assert m.callback_with_movable(lambda _: None) is True
+
+
+def test_async_callbacks():
+    # serves as state for async callback
+    class Item:
+        def __init__(self, value):
+            self.value = value
+
+    res = []
+
+    # generate stateful lambda that will store result in `res`
+    def gen_f():
+        s = Item(3)
+        return lambda j: res.append(s.value + j)
+
+    # do some work async
+    work = [1, 2, 3, 4]
+    m.test_async_callback(gen_f(), work)
+    # wait until work is done
+    from time import sleep
+    sleep(0.5)
+    assert sum(res) == sum([x + 3 for x in work])
+
+
+def test_async_async_callbacks():
+    t = Thread(target=test_async_callbacks)
+    t.start()
+    t.join()