diff --git a/include/pybind11/detail/type_caster_base.h b/include/pybind11/detail/type_caster_base.h
index 0898be014..d5d86dc6c 100644
--- a/include/pybind11/detail/type_caster_base.h
+++ b/include/pybind11/detail/type_caster_base.h
@@ -117,7 +117,6 @@ PYBIND11_NOINLINE void all_type_info_populate(PyTypeObject *t, std::vector<type_
     for (handle parent : reinterpret_borrow<tuple>(t->tp_bases)) {
         check.push_back((PyTypeObject *) parent.ptr());
     }
-
     auto const &type_dict = get_internals().registered_types_py;
     for (size_t i = 0; i < check.size(); i++) {
         auto *type = check[i];
@@ -176,13 +175,7 @@ PYBIND11_NOINLINE void all_type_info_populate(PyTypeObject *t, std::vector<type_
  * The value is cached for the lifetime of the Python type.
  */
 inline const std::vector<detail::type_info *> &all_type_info(PyTypeObject *type) {
-    auto ins = all_type_info_get_cache(type);
-    if (ins.second) {
-        // New cache entry: populate it
-        all_type_info_populate(type, ins.first->second);
-    }
-
-    return ins.first->second;
+    return all_type_info_get_cache(type).first->second;
 }
 
 /**
diff --git a/include/pybind11/pybind11.h b/include/pybind11/pybind11.h
index 2527d25fa..b4f93f1a6 100644
--- a/include/pybind11/pybind11.h
+++ b/include/pybind11/pybind11.h
@@ -2326,13 +2326,20 @@ keep_alive_impl(size_t Nurse, size_t Patient, function_call &call, handle ret) {
 inline std::pair<decltype(internals::registered_types_py)::iterator, bool>
 all_type_info_get_cache(PyTypeObject *type) {
     auto res = with_internals([type](internals &internals) {
-        return internals
-            .registered_types_py
+        auto ins = internals
+                       .registered_types_py
 #ifdef __cpp_lib_unordered_map_try_emplace
-            .try_emplace(type);
+                       .try_emplace(type);
 #else
-            .emplace(type, std::vector<detail::type_info *>());
+                       .emplace(type, std::vector<detail::type_info *>());
 #endif
+        if (ins.second) {
+            // For free-threading mode, this call must be under
+            // the with_internals() mutex lock, to avoid that other threads
+            // continue running with the empty ins.first->second.
+            all_type_info_populate(type, ins.first->second);
+        }
+        return ins;
     });
     if (res.second) {
         // New cache entry created; set up a weak reference to automatically remove it if the type
diff --git a/tests/pybind11_tests.cpp b/tests/pybind11_tests.cpp
index 3d2d84e77..818d53a54 100644
--- a/tests/pybind11_tests.cpp
+++ b/tests/pybind11_tests.cpp
@@ -128,4 +128,9 @@ PYBIND11_MODULE(pybind11_tests, m, py::mod_gil_not_used()) {
     for (const auto &initializer : initializers()) {
         initializer(m);
     }
+
+    py::class_<TestContext>(m, "TestContext")
+        .def(py::init<>(&TestContext::createNewContextForInit))
+        .def("__enter__", &TestContext::contextEnter)
+        .def("__exit__", &TestContext::contextExit);
 }
diff --git a/tests/pybind11_tests.h b/tests/pybind11_tests.h
index 7be58feb6..0eb0398df 100644
--- a/tests/pybind11_tests.h
+++ b/tests/pybind11_tests.h
@@ -96,3 +96,24 @@ void ignoreOldStyleInitWarnings(F &&body) {
     )",
              py::dict(py::arg("body") = py::cpp_function(body)));
 }
+
+// See PR #5419 for background.
+class TestContext {
+public:
+    TestContext() = delete;
+    TestContext(const TestContext &) = delete;
+    TestContext(TestContext &&) = delete;
+    static TestContext *createNewContextForInit() { return new TestContext("new-context"); }
+
+    pybind11::object contextEnter() {
+        py::object contextObj = py::cast(*this);
+        return contextObj;
+    }
+    void contextExit(const pybind11::object & /*excType*/,
+                     const pybind11::object & /*excVal*/,
+                     const pybind11::object & /*excTb*/) {}
+
+private:
+    explicit TestContext(const std::string &context) : context(context) {}
+    std::string context;
+};
diff --git a/tests/test_class.py b/tests/test_class.py
index f424db5c3..01963d012 100644
--- a/tests/test_class.py
+++ b/tests/test_class.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import sys
 from unittest import mock
 
 import pytest
@@ -508,3 +509,31 @@ def test_pr4220_tripped_over_this():
         m.Empty0().get_msg()
         == "This is really only meant to exercise successful compilation."
     )
+
+
+@pytest.mark.skipif(sys.platform.startswith("emscripten"), reason="Requires threads")
+def test_all_type_info_multithreaded():
+    # See PR #5419 for background.
+    import threading
+
+    from pybind11_tests import TestContext
+
+    class Context(TestContext):
+        pass
+
+    num_runs = 10
+    num_threads = 4
+    barrier = threading.Barrier(num_threads)
+
+    def func():
+        barrier.wait()
+        with Context():
+            pass
+
+    for _ in range(num_runs):
+        threads = [threading.Thread(target=func) for _ in range(num_threads)]
+        for thread in threads:
+            thread.start()
+
+        for thread in threads:
+            thread.join()