diff --git a/tools/workspace/pybind11/package.BUILD.bazel b/tools/workspace/pybind11/package.BUILD.bazel
index d29d31706972..bbe7c87d8ef0 100644
--- a/tools/workspace/pybind11/package.BUILD.bazel
+++ b/tools/workspace/pybind11/package.BUILD.bazel
@@ -34,6 +34,7 @@ _HDRS = [
     "include/pybind11/eval.h",
     "include/pybind11/functional.h",
     "include/pybind11/gil.h",
+    "include/pybind11/gil_safe_call_once.h",
     "include/pybind11/iostream.h",
     "include/pybind11/numpy.h",
     "include/pybind11/operators.h",
@@ -44,6 +45,7 @@ _HDRS = [
     "include/pybind11/stl/filesystem.h",
     "include/pybind11/stl_bind.h",
     "include/pybind11/type_caster_pyobject_ptr.h",
+    "include/pybind11/typing.h",
 ]
 
 check_lists_consistency(
diff --git a/tools/workspace/pybind11/repository.bzl b/tools/workspace/pybind11/repository.bzl
index 35fd1e3ef280..45fcbc8d3a41 100644
--- a/tools/workspace/pybind11/repository.bzl
+++ b/tools/workspace/pybind11/repository.bzl
@@ -8,9 +8,9 @@ _REPOSITORY = "RobotLocomotion/pybind11"
 #  https://github.com/RobotLocomotion/pybind11/blob/drake/include/pybind11/detail/common.h
 # and if it has changed, then update the version number in the two
 # pybind11-*.cmake files in the current directory to match.
-_COMMIT = "1f8e0c3c4365ed01f2551d61c8ea3e558f690809"
+_COMMIT = "ef4e178018ca20c1042940c77f0f1c08e42b2191"
 
-_SHA256 = "9de2e78026ddbfbdfd3b28c60d53f8f6021a5512638478692c3677c9f6890fb6"
+_SHA256 = "454988e381f1fc86b03452ddc9de7acbc6e6e22a96f684dd6accd3975088c3df"
 
 def pybind11_repository(
         name,