diff --git a/bindings/pydrake/examples/BUILD.bazel b/bindings/pydrake/examples/BUILD.bazel
index 27ccc5cf34ee..f27cf2c93277 100644
--- a/bindings/pydrake/examples/BUILD.bazel
+++ b/bindings/pydrake/examples/BUILD.bazel
@@ -25,6 +25,7 @@ drake_pybind_library(
     cc_deps = [
         "//bindings/pydrake:documentation_pybind",
         "//bindings/pydrake/common:deprecation_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
     ],
     cc_so_name = "__init__",
     cc_srcs = [
diff --git a/bindings/pydrake/examples/examples_py_acrobot.cc b/bindings/pydrake/examples/examples_py_acrobot.cc
index 8aacf38247fe..247b0a1d9c77 100644
--- a/bindings/pydrake/examples/examples_py_acrobot.cc
+++ b/bindings/pydrake/examples/examples_py_acrobot.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/examples/examples_py.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
@@ -161,8 +162,7 @@ void DefineExamplesAcrobot(py::module m) {
               geometry::SceneGraph<double>*>(&AcrobotGeometry::AddToBuilder),
           py::arg("builder"), py::arg("acrobot_state_port"),
           py::arg("acrobot_params"), py::arg("scene_graph"),
-          // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.AcrobotGeometry.AddToBuilder.doc_4args)
       .def_static("AddToBuilder",
@@ -172,7 +172,7 @@ void DefineExamplesAcrobot(py::module m) {
           py::arg("builder"), py::arg("acrobot_state_port"),
           py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.AcrobotGeometry.AddToBuilder.doc_3args);
 }
diff --git a/bindings/pydrake/examples/examples_py_compass_gait.cc b/bindings/pydrake/examples/examples_py_compass_gait.cc
index dc1c99fa1157..3f3d22b8eda0 100644
--- a/bindings/pydrake/examples/examples_py_compass_gait.cc
+++ b/bindings/pydrake/examples/examples_py_compass_gait.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/examples/examples_py.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
@@ -93,7 +94,7 @@ void DefineExamplesCompassGait(py::module m) {
           py::arg("builder"), py::arg("floating_base_state_port"),
           py::arg("compass_gait_params"), py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.CompassGaitGeometry.AddToBuilder.doc_4args)
       .def_static("AddToBuilder",
@@ -104,7 +105,7 @@ void DefineExamplesCompassGait(py::module m) {
           py::arg("builder"), py::arg("floating_base_state_port"),
           py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.CompassGaitGeometry.AddToBuilder.doc_3args);
 }
diff --git a/bindings/pydrake/examples/examples_py_pendulum.cc b/bindings/pydrake/examples/examples_py_pendulum.cc
index 2e7c953b9a0a..7b070f5a6b70 100644
--- a/bindings/pydrake/examples/examples_py_pendulum.cc
+++ b/bindings/pydrake/examples/examples_py_pendulum.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/examples/examples_py.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
@@ -106,7 +107,7 @@ void DefineExamplesPendulum(py::module m) {
           py::arg("builder"), py::arg("pendulum_state_port"),
           py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.PendulumGeometry.AddToBuilder.doc);
 }
diff --git a/bindings/pydrake/examples/examples_py_quadrotor.cc b/bindings/pydrake/examples/examples_py_quadrotor.cc
index 545034feb83b..b77c5f85e6b6 100644
--- a/bindings/pydrake/examples/examples_py_quadrotor.cc
+++ b/bindings/pydrake/examples/examples_py_quadrotor.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/examples/examples_py.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
@@ -45,7 +46,7 @@ void DefineExamplesQuadrotor(py::module m) {
           py::arg("builder"), py::arg("quadrotor_state_port"),
           py::arg("scene_graph"), py::return_value_policy::reference,
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(), doc.QuadrotorGeometry.AddToBuilder.doc);
+          internal::ref_cycle<0, 1>(), doc.QuadrotorGeometry.AddToBuilder.doc);
 
   m.def("StabilizingLQRController", &StabilizingLQRController,
       py::arg("quadrotor_plant"), py::arg("nominal_position"),
diff --git a/bindings/pydrake/examples/examples_py_rimless_wheel.cc b/bindings/pydrake/examples/examples_py_rimless_wheel.cc
index 34841253adba..575b527c5aa0 100644
--- a/bindings/pydrake/examples/examples_py_rimless_wheel.cc
+++ b/bindings/pydrake/examples/examples_py_rimless_wheel.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/examples/examples_py.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
@@ -82,7 +83,7 @@ void DefineExamplesRimlessWheel(py::module m) {
           py::arg("builder"), py::arg("floating_base_state_port"),
           py::arg("rimless_wheel_params"), py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.RimlessWheelGeometry.AddToBuilder.doc_4args)
       .def_static("AddToBuilder",
@@ -93,7 +94,7 @@ void DefineExamplesRimlessWheel(py::module m) {
           py::arg("builder"), py::arg("floating_base_state_port"),
           py::arg("scene_graph"),
           // Keep alive, ownership: `return` keeps `builder` alive.
-          py::keep_alive<0, 1>(),
+          internal::ref_cycle<0, 1>(),
           // See #11531 for why `py_rvp::reference` is needed.
           py_rvp::reference, doc.RimlessWheelGeometry.AddToBuilder.doc_3args);
 }
diff --git a/bindings/pydrake/geometry/BUILD.bazel b/bindings/pydrake/geometry/BUILD.bazel
index 06133bdd6df2..b2e0bf3519a0 100644
--- a/bindings/pydrake/geometry/BUILD.bazel
+++ b/bindings/pydrake/geometry/BUILD.bazel
@@ -38,6 +38,7 @@ drake_pybind_library(
         "//bindings/pydrake/common:default_scalars_pybind",
         "//bindings/pydrake/common:deprecation_pybind",
         "//bindings/pydrake/common:identifier_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:serialize_pybind",
         "//bindings/pydrake/common:sorted_pair_pybind",
         "//bindings/pydrake/common:type_pack",
diff --git a/bindings/pydrake/geometry/geometry_py_visualizers.cc b/bindings/pydrake/geometry/geometry_py_visualizers.cc
index 184970d33f6f..cd700d89960d 100644
--- a/bindings/pydrake/geometry/geometry_py_visualizers.cc
+++ b/bindings/pydrake/geometry/geometry_py_visualizers.cc
@@ -3,6 +3,7 @@
 
 #include "drake/bindings/pydrake/common/default_scalars_pybind.h"
 #include "drake/bindings/pydrake/common/deprecation_pybind.h"
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/serialize_pybind.h"
 #include "drake/bindings/pydrake/common/type_pack.h"
 #include "drake/bindings/pydrake/common/type_safe_index_pybind.h"
@@ -54,9 +55,9 @@ void DefineDrakeVisualizer(py::module m, T) {
             py::arg("lcm") = nullptr,
             py::arg("params") = DrakeVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // Keep alive, reference: `builder` keeps `lcm` alive.
-            py::keep_alive<1, 3>(), py_rvp::reference,
+            internal::ref_cycle<1, 3>(), py_rvp::reference,
             cls_doc.AddToBuilder.doc_4args_builder_scene_graph_lcm_params)
         .def_static("AddToBuilder",
             py::overload_cast<systems::DiagramBuilder<T>*,
@@ -66,9 +67,9 @@ void DefineDrakeVisualizer(py::module m, T) {
             py::arg("lcm") = nullptr,
             py::arg("params") = DrakeVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // Keep alive, reference: `builder` keeps `lcm` alive.
-            py::keep_alive<1, 3>(), py_rvp::reference,
+            internal::ref_cycle<1, 3>(), py_rvp::reference,
             cls_doc.AddToBuilder.doc_4args_builder_query_object_port_lcm_params)
         .def_static("DispatchLoadMessage",
             &DrakeVisualizer<T>::DispatchLoadMessage, py::arg("scene_graph"),
@@ -136,7 +137,7 @@ void DefineMeshcatVisualizer(py::module m, T) {
             py::arg("builder"), py::arg("scene_graph"), py::arg("meshcat"),
             py::arg("params") = MeshcatVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // `meshcat` is a shared_ptr, so does not need a keep_alive.
             py_rvp::reference,
             cls_doc.AddToBuilder.doc_4args_builder_scene_graph_meshcat_params)
@@ -147,7 +148,7 @@ void DefineMeshcatVisualizer(py::module m, T) {
             py::arg("builder"), py::arg("query_object_port"),
             py::arg("meshcat"), py::arg("params") = MeshcatVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // `meshcat` is a shared_ptr, so does not need a keep_alive.
             py_rvp::reference,
             cls_doc.AddToBuilder
diff --git a/bindings/pydrake/lcm_py.cc b/bindings/pydrake/lcm_py.cc
index 5d3973891638..7fb7bd6df591 100644
--- a/bindings/pydrake/lcm_py.cc
+++ b/bindings/pydrake/lcm_py.cc
@@ -26,7 +26,7 @@ PYBIND11_MODULE(lcm, m) {
   {
     using Class = DrakeLcmInterface;
     constexpr auto& cls_doc = doc.DrakeLcmInterface;
-    py::class_<Class>(m, "DrakeLcmInterface", cls_doc.doc)
+    py::class_<Class>(m, "DrakeLcmInterface", py::dynamic_attr(), cls_doc.doc)
         .def("get_lcm_url", &DrakeLcmInterface::get_lcm_url,
             cls_doc.get_lcm_url.doc)
         .def(
diff --git a/bindings/pydrake/manipulation/BUILD.bazel b/bindings/pydrake/manipulation/BUILD.bazel
index 6d02c4cf157c..c1d6e57e3245 100644
--- a/bindings/pydrake/manipulation/BUILD.bazel
+++ b/bindings/pydrake/manipulation/BUILD.bazel
@@ -25,6 +25,7 @@ drake_pybind_library(
     cc_deps = [
         "//bindings/pydrake:documentation_pybind",
         "//bindings/pydrake/common:eigen_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:serialize_pybind",
     ],
     cc_so_name = "__init__",
diff --git a/bindings/pydrake/manipulation/manipulation_py_kuka_iiwa.cc b/bindings/pydrake/manipulation/manipulation_py_kuka_iiwa.cc
index dbf1089626f7..bf93d6c6cc15 100644
--- a/bindings/pydrake/manipulation/manipulation_py_kuka_iiwa.cc
+++ b/bindings/pydrake/manipulation/manipulation_py_kuka_iiwa.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/serialize_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/manipulation/manipulation_py.h"
@@ -180,9 +181,9 @@ void DefineManipulationKukaIiwa(py::module m) {
             py::arg("controller_plant"), py::arg("ext_joint_filter_tau"),
             py::arg("desired_iiwa_kp_gains"), py::arg("control_mode"),
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // Keep alive, reference: `builder` keeps `controller_plant` alive.
-            py::keep_alive<1, 4>(), py_rvp::reference,
+            internal::ref_cycle<1, 4>(), py_rvp::reference,
             cls_doc.AddToBuilder.doc);
   }
 
@@ -198,7 +199,7 @@ void DefineManipulationKukaIiwa(py::module m) {
         py::arg("desired_iiwa_kp_gains") = std::nullopt,
         py::arg("control_mode") = IiwaControlMode::kPositionAndTorque,
         // Keep alive, reference: `builder` keeps `controller_plant` alive.
-        py::keep_alive<5, 3>(), doc.BuildIiwaControl.doc);
+        internal::ref_cycle<5, 3>(), doc.BuildIiwaControl.doc);
   }
 }
 
diff --git a/bindings/pydrake/manipulation/manipulation_py_schunk_wsg.cc b/bindings/pydrake/manipulation/manipulation_py_schunk_wsg.cc
index a9bdb54ce894..f16166e41060 100644
--- a/bindings/pydrake/manipulation/manipulation_py_schunk_wsg.cc
+++ b/bindings/pydrake/manipulation/manipulation_py_schunk_wsg.cc
@@ -122,11 +122,13 @@ void DefineManipulationSchunkWsg(py::module m) {
   {
     using T = double;
 
+    // XXX probably needs annotations
     m.def("ApplyDriverConfig", &manipulation::schunk_wsg::ApplyDriverConfig,
         py::arg("driver_config"), py::arg("model_instance_name"),
         py::arg("sim_plant"), py::arg("models_from_directives"),
         py::arg("lcms"), py::arg("builder"), doc.ApplyDriverConfig.doc);
 
+    // XXX probably needs annotations
     m.def("BuildSchunkWsgControl",
         &manipulation::schunk_wsg::BuildSchunkWsgControl, py::arg("plant"),
         py::arg("wsg_instance"), py::arg("lcm"), py::arg("builder"),
diff --git a/bindings/pydrake/manipulation/manipulation_py_util.cc b/bindings/pydrake/manipulation/manipulation_py_util.cc
index 33bc083d3a1c..4bda82c0cb69 100644
--- a/bindings/pydrake/manipulation/manipulation_py_util.cc
+++ b/bindings/pydrake/manipulation/manipulation_py_util.cc
@@ -26,6 +26,7 @@ void DefineManipulationUtil(py::module m) {
   }
 
   {
+    // XXX probably needs annotations
     m.def("ApplyDriverConfig", &ApplyDriverConfig, py::arg("driver_config"),
         py::arg("model_instance_name"), py::arg("sim_plant"),
         py::arg("models_from_directives"), py::arg("lcms"), py::arg("builder"),
diff --git a/bindings/pydrake/multibody/BUILD.bazel b/bindings/pydrake/multibody/BUILD.bazel
index 156e1c132da8..342fe7cef67c 100644
--- a/bindings/pydrake/multibody/BUILD.bazel
+++ b/bindings/pydrake/multibody/BUILD.bazel
@@ -131,6 +131,7 @@ drake_pybind_library(
         "//bindings/pydrake/common:deprecation_pybind",
         "//bindings/pydrake/common:eigen_pybind",
         "//bindings/pydrake/common:identifier_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:serialize_pybind",
         "//bindings/pydrake/common:type_pack",
         "//bindings/pydrake/common:type_safe_index_pybind",
@@ -172,6 +173,7 @@ drake_pybind_library(
         "//bindings/pydrake:documentation_pybind",
         "//bindings/pydrake/common:cpp_template_pybind",
         "//bindings/pydrake/common:default_scalars_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:serialize_pybind",
         "//bindings/pydrake/common:type_pack",
     ],
diff --git a/bindings/pydrake/multibody/meshcat_py.cc b/bindings/pydrake/multibody/meshcat_py.cc
index 8c0d8b5e4cf4..d3c4e14ac331 100644
--- a/bindings/pydrake/multibody/meshcat_py.cc
+++ b/bindings/pydrake/multibody/meshcat_py.cc
@@ -1,5 +1,6 @@
 #include "drake/bindings/pydrake/common/cpp_template_pybind.h"
 #include "drake/bindings/pydrake/common/default_scalars_pybind.h"
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/serialize_pybind.h"
 #include "drake/bindings/pydrake/common/type_pack.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
@@ -130,7 +131,7 @@ void DoScalarDependentDefinitions(py::module m, T) {
             py::arg("builder"), py::arg("plant"), py::arg("meshcat"),
             py::arg("params") = ContactVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // `meshcat` is a shared_ptr, so does not need a keep_alive.
             py_rvp::reference,
             cls_doc.AddToBuilder.doc_4args_builder_plant_meshcat_params)
@@ -143,7 +144,7 @@ void DoScalarDependentDefinitions(py::module m, T) {
             py::arg("query_object_port"), py::arg("meshcat"),
             py::arg("params") = ContactVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // `meshcat` is a shared_ptr, so does not need a keep_alive.
             py_rvp::reference,
             cls_doc.AddToBuilder
@@ -156,7 +157,7 @@ void DoScalarDependentDefinitions(py::module m, T) {
             py::arg("builder"), py::arg("contact_results_port"),
             py::arg("meshcat"), py::arg("params") = ContactVisualizerParams{},
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(),
+            internal::ref_cycle<0, 1>(),
             // `meshcat` is a shared_ptr, so does not need a keep_alive.
             py_rvp::reference,
             cls_doc.AddToBuilder
diff --git a/bindings/pydrake/multibody/plant_py.cc b/bindings/pydrake/multibody/plant_py.cc
index 3204186e5e19..ca0e06763228 100644
--- a/bindings/pydrake/multibody/plant_py.cc
+++ b/bindings/pydrake/multibody/plant_py.cc
@@ -3,6 +3,7 @@
 #include "drake/bindings/pydrake/common/deprecation_pybind.h"
 #include "drake/bindings/pydrake/common/eigen_pybind.h"
 #include "drake/bindings/pydrake/common/identifier_pybind.h"
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/serialize_pybind.h"
 #include "drake/bindings/pydrake/common/type_pack.h"
 #include "drake/bindings/pydrake/common/value_pybind.h"
@@ -1374,28 +1375,17 @@ void DoScalarDependentDefinitions(py::module m, T) {
   }
 
   {
-    // TODO(eric.cousineau): Figure out why we need to use this to explicit
-    // keep-alive vs. annotating the return tuple with `py::keep_alive()`.
-    // Most likely due to a bug in our fork of pybind11 for handling of
-    // unique_ptr<> arguments and keep_alive<> behavior for objects that are
-    // not yet registered with pybind11 (#11046).
-    auto cast_workaround = [](auto&& nurse, py::object patient_py) {
-      // Cast to ensure we have the object registered.
-      py::object nurse_py = py::cast(nurse, py_rvp::reference);
-      // Directly leverage pybind11's keep alive mechanism.
-      py::detail::keep_alive_impl(nurse_py, patient_py);
-      return nurse_py;
-    };
-
     auto result_to_tuple =
-        [cast_workaround](systems::DiagramBuilder<T>* builder,
+        [](systems::DiagramBuilder<T>* builder,
             const AddMultibodyPlantSceneGraphResult<T>& pair) {
           py::object builder_py = py::cast(builder, py_rvp::reference);
-          // Keep alive, ownership: `plant` keeps `builder` alive.
-          py::object plant_py = cast_workaround(pair.plant, builder_py);
-          // Keep alive, ownership: `scene_graph` keeps `builder` alive.
+          py::object plant_py = py::cast(pair.plant, py_rvp::reference);
           py::object scene_graph_py =
-              cast_workaround(pair.scene_graph, builder_py);
+              py::cast(pair.scene_graph, py_rvp::reference);
+          internal::make_arbitrary_ref_cycle(
+              builder_py, plant_py, "AddMultibodyPlantSceneGraphResult.plant");
+          internal::make_arbitrary_ref_cycle(builder_py, scene_graph_py,
+              "AddMultibodyPlantSceneGraphResult.scene_graph");
           return py::make_tuple(plant_py, scene_graph_py);
         };
 
@@ -1544,7 +1534,7 @@ void DoScalarDependentDefinitions(py::module m, T) {
             py::arg("X_BodyWing") = math::RigidTransform<double>::Identity(),
             py::arg("fluid_density") = Wing<T>::kDefaultFluidDensity,
             // Keep alive, ownership: `return` keeps `builder` alive.
-            py::keep_alive<0, 1>(), py_rvp::reference,
+            internal::ref_cycle<0, 1>(), py_rvp::reference,
             cls_doc.AddToBuilder.doc);
   }
 
@@ -1599,13 +1589,13 @@ PYBIND11_MODULE(plant, m) {
       py::arg("lcm") = nullptr, py::arg("publish_period") = std::nullopt,
       py_rvp::reference,
       // Keep alive, ownership: `return` keeps `builder` alive.
-      py::keep_alive<0, 1>(),
+      internal::ref_cycle<0, 1>(),
       // Keep alive, transitive: `plant` keeps `builder` alive.
-      py::keep_alive<2, 1>(),
+      internal::ref_cycle<2, 1>(),
       // Keep alive, transitive: `scene_graph` keeps `builder` alive.
-      py::keep_alive<3, 1>(),
+      internal::ref_cycle<3, 1>(),
       // Keep alive, transitive: `lcm` keeps `builder` alive.
-      py::keep_alive<4, 1>(),
+      internal::ref_cycle<4, 1>(),
       doc.ConnectContactResultsToDrakeVisualizer.doc_5args);
 
   {
diff --git a/bindings/pydrake/planning/BUILD.bazel b/bindings/pydrake/planning/BUILD.bazel
index 23168b282df5..e926e13b3757 100644
--- a/bindings/pydrake/planning/BUILD.bazel
+++ b/bindings/pydrake/planning/BUILD.bazel
@@ -96,6 +96,8 @@ drake_py_unittest(
     deps = [
         ":planning",
         "//bindings/pydrake/common/test_utilities:numpy_compare_py",
+        "//bindings/pydrake/systems:analysis_py",
+        "//bindings/pydrake/systems:controllers_py",
     ],
 )
 
diff --git a/bindings/pydrake/planning/planning_py_robot_diagram.cc b/bindings/pydrake/planning/planning_py_robot_diagram.cc
index 97fe087005af..22b272425700 100644
--- a/bindings/pydrake/planning/planning_py_robot_diagram.cc
+++ b/bindings/pydrake/planning/planning_py_robot_diagram.cc
@@ -79,13 +79,7 @@ void DefinePlanningRobotDiagram(py::module m) {
               cls_doc.scene_graph.doc_0args_nonconst)
           .def("IsDiagramBuilt", &Class::IsDiagramBuilt,
               cls_doc.IsDiagramBuilt.doc)
-          .def("Build", &Class::Build,
-              // Keep alive, ownership (tr.): `self` keeps `return` alive.
-              // Any prior reference access to our owned systems (e.g., plant())
-              // must remain valid, so the RobotDiagram cannot be destroyed
-              // until the builder (and all of its internal references) are
-              // finished.
-              py::keep_alive<1, 0>(), cls_doc.Build.doc);
+          .def("Build", &Class::Build, cls_doc.Build.doc);
     }
   };
   type_visit(bind_common_scalar_types, CommonScalarPack{});
diff --git a/bindings/pydrake/planning/test/robot_diagram_test.py b/bindings/pydrake/planning/test/robot_diagram_test.py
index 8249a7d6a306..021ca3f37fac 100644
--- a/bindings/pydrake/planning/test/robot_diagram_test.py
+++ b/bindings/pydrake/planning/test/robot_diagram_test.py
@@ -1,12 +1,16 @@
 import pydrake.planning as mut
 
+import gc
 import unittest
 
+import numpy as np
+
 from pydrake.common import FindResourceOrThrow
 from pydrake.common.test_utilities import numpy_compare
 from pydrake.geometry import SceneGraph_
 from pydrake.multibody.parsing import Parser
 from pydrake.multibody.plant import MultibodyPlant_, MultibodyPlantConfig
+from pydrake.systems.controllers import InverseDynamicsController
 from pydrake.systems.framework import Context_, DiagramBuilder_
 
 
@@ -68,3 +72,50 @@ def test_robot_diagram(self, T):
         self.assertIsInstance(
             dut.scene_graph_context(root_context=root_context),
             Context_[T])
+
+    def test_issue14355_robot(self):
+        """
+        XXX rewrite doc
+        DiagramBuilder.AddSystem() may not propagate keep alive relationships.
+        We use this test to show resolution at a known concrete point of
+        failure.
+        https://github.com/RobotLocomotion/drake/issues/14355
+        """
+
+        def make_diagram():
+            # Use a nested function to ensure that all locals get garbage
+            # collected quickly.
+
+            # Construct a trivial plant and ID controller.
+            # N.B. We explicitly do *not* add this plant to the diagram.
+            controller_plant = MultibodyPlant_[float](time_step=0.002)
+            controller_plant.Finalize()
+            builder = mut.RobotDiagramBuilder()
+            controller = builder.builder().AddSystem(
+                InverseDynamicsController(
+                    controller_plant,
+                    kp=[],
+                    ki=[],
+                    kd=[],
+                    has_reference_acceleration=False,
+                )
+            )
+            # Forward ports for ease of testing.
+            builder.builder().ExportInput(
+                controller.get_input_port_estimated_state(), "x_estimated")
+            builder.builder().ExportInput(
+                controller.get_input_port_desired_state(), "x_desired")
+            builder.builder().ExportOutput(
+                controller.get_output_port_control(), "u")
+            diagram = builder.Build()
+            return diagram
+
+        diagram = make_diagram()
+        gc.collect()
+        # N.B. Without the workaround for #14355, we get a segfault when
+        # creating the context.
+        context = diagram.CreateDefaultContext()
+        diagram.GetInputPort("x_estimated").FixValue(context, [])
+        diagram.GetInputPort("x_desired").FixValue(context, [])
+        u = diagram.GetOutputPort("u").Eval(context)
+        np.testing.assert_equal(u, [])
diff --git a/bindings/pydrake/systems/BUILD.bazel b/bindings/pydrake/systems/BUILD.bazel
index 5f93f193aa11..565375ca3519 100644
--- a/bindings/pydrake/systems/BUILD.bazel
+++ b/bindings/pydrake/systems/BUILD.bazel
@@ -48,6 +48,7 @@ drake_pybind_library(
         "//bindings/pydrake/common:default_scalars_pybind",
         "//bindings/pydrake/common:deprecation_pybind",
         "//bindings/pydrake/common:eigen_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:type_safe_index_pybind",
         "//bindings/pydrake/common:value_pybind",
         "//bindings/pydrake/common:wrap_pybind",
@@ -82,6 +83,7 @@ drake_pybind_library(
         "//bindings/pydrake/common:cpp_template_pybind",
         "//bindings/pydrake/common:default_scalars_pybind",
         "//bindings/pydrake/common:eigen_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
     ],
     cc_srcs = ["primitives_py.cc"],
     package_info = PACKAGE_INFO,
@@ -169,6 +171,7 @@ drake_pybind_library(
         "//bindings/pydrake/common:default_scalars_pybind",
         "//bindings/pydrake/common:deprecation_pybind",
         "//bindings/pydrake/common:eigen_pybind",
+        "//bindings/pydrake/common:ref_cycle_pybind",
         "//bindings/pydrake/common:serialize_pybind",
         "//bindings/pydrake/common:type_pack",
         "//bindings/pydrake/common:value_pybind",
diff --git a/bindings/pydrake/systems/framework_py_semantics.cc b/bindings/pydrake/systems/framework_py_semantics.cc
index a315c7028e4b..304fdc59e575 100644
--- a/bindings/pydrake/systems/framework_py_semantics.cc
+++ b/bindings/pydrake/systems/framework_py_semantics.cc
@@ -3,6 +3,7 @@
 #include "drake/bindings/pydrake/common/cpp_template_pybind.h"
 #include "drake/bindings/pydrake/common/default_scalars_pybind.h"
 #include "drake/bindings/pydrake/common/eigen_pybind.h"
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/type_safe_index_pybind.h"
 #include "drake/bindings/pydrake/common/wrap_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
@@ -588,38 +589,45 @@ void DefineEventAndEventSubclasses(py::module m) {
   }
 }
 
+template <typename T>
+struct BuilderLifeSupport {
+  static constexpr char kKey[] = "_pydrake_internal_life_support";
+
+  static void smuggle(DiagramBuilder<T>* builder) {
+    BuilderLifeSupport<T>::attrs(builder).emplace(kKey, py::cast(builder));
+  }
+
+  static void abandon(DiagramBuilder<T>* builder) {
+    BuilderLifeSupport<T>::attrs(builder).erase(kKey);
+  }
+
+  static auto& attrs(DiagramBuilder<T>* builder) {
+    return builder->get_mutable_life_support().attributes;
+  }
+};
+
 template <typename T>
 void DoDefineFrameworkDiagramBuilder(py::module m) {
-  DefineTemplateClassWithDefault<DiagramBuilder<T>>(
-      m, "DiagramBuilder", GetPyParam<T>(), doc.DiagramBuilder.doc)
+  DefineTemplateClassWithDefault<DiagramBuilder<T>>(m, "DiagramBuilder",
+      GetPyParam<T>(), doc.DiagramBuilder.doc, std::nullopt, py::dynamic_attr())
       .def(py::init<>(), doc.DiagramBuilder.ctor.doc)
       .def(
           "AddSystem",
           [](DiagramBuilder<T>* self, unique_ptr<System<T>> system) {
+            BuilderLifeSupport<T>::smuggle(self);
             return self->AddSystem(std::move(system));
           },
-          py::arg("system"),
-          // TODO(eric.cousineau): These two keep_alive's purposely form a
-          // reference cycle as a workaround for #14355. We should find a
-          // better way?
-          // Keep alive, reference: `self` keeps `return` alive.
-          py::keep_alive<1, 0>(),
-          // Keep alive, ownership: `system` keeps `self` alive.
-          py::keep_alive<2, 1>(), doc.DiagramBuilder.AddSystem.doc)
+          py::arg("system"), internal::ref_cycle<1, 2>(),
+          doc.DiagramBuilder.AddSystem.doc)
       .def(
           "AddNamedSystem",
           [](DiagramBuilder<T>* self, std::string& name,
               unique_ptr<System<T>> system) {
+            BuilderLifeSupport<T>::smuggle(self);
             return self->AddNamedSystem(name, std::move(system));
           },
-          py::arg("name"), py::arg("system"),
-          // TODO(eric.cousineau): These two keep_alive's purposely form a
-          // reference cycle as a workaround for #14355. We should find a
-          // better way?
-          // Keep alive, reference: `self` keeps `return` alive.
-          py::keep_alive<1, 0>(),
-          // Keep alive, ownership: `system` keeps `self` alive.
-          py::keep_alive<3, 1>(), doc.DiagramBuilder.AddNamedSystem.doc)
+          py::arg("name"), py::arg("system"), internal::ref_cycle<1, 3>(),
+          doc.DiagramBuilder.AddNamedSystem.doc)
       .def("RemoveSystem", &DiagramBuilder<T>::RemoveSystem, py::arg("system"),
           doc.DiagramBuilder.RemoveSystem.doc)
       .def("empty", &DiagramBuilder<T>::empty, doc.DiagramBuilder.empty.doc)
@@ -694,12 +702,21 @@ void DoDefineFrameworkDiagramBuilder(py::module m) {
       .def("ExportOutput", &DiagramBuilder<T>::ExportOutput, py::arg("output"),
           py::arg("name") = kUseDefaultName, py_rvp::reference_internal,
           doc.DiagramBuilder.ExportOutput.doc)
-      .def("Build", &DiagramBuilder<T>::Build,
-          // Keep alive, ownership (tr.): `self` keeps `return` alive.
-          py::keep_alive<1, 0>(), doc.DiagramBuilder.Build.doc)
-      .def("BuildInto", &DiagramBuilder<T>::BuildInto, py::arg("target"),
-          // Keep alive, ownership (tr.): `target` keeps `self` alive.
-          py::keep_alive<2, 1>(), doc.DiagramBuilder.BuildInto.doc)
+      .def(
+          "Build",
+          [](DiagramBuilder<T>* self) {
+            BuilderLifeSupport<T>::abandon(self);
+            return self->Build();
+          },
+          internal::ref_cycle<0, 1>(), doc.DiagramBuilder.Build.doc)
+      .def(
+          "BuildInto",
+          [](DiagramBuilder<T>* self, Diagram<T>* target) {
+            BuilderLifeSupport<T>::abandon(self);
+            self->BuildInto(target);
+          },
+          internal::ref_cycle<1, 2>(), py::arg("target"),
+          doc.DiagramBuilder.BuildInto.doc)
       .def("IsConnectedOrExported", &DiagramBuilder<T>::IsConnectedOrExported,
           py::arg("port"), doc.DiagramBuilder.IsConnectedOrExported.doc)
       .def("num_input_ports", &DiagramBuilder<T>::num_input_ports,
@@ -1116,6 +1133,7 @@ void DefineDiscreteValues(py::module m) {
           },
           doc.DiscreteValues.operator_array.doc_1args_idx_nonconst);
 }
+
 }  // namespace
 
 void DefineFrameworkDiagramBuilder(py::module m) {
diff --git a/bindings/pydrake/systems/framework_py_systems.cc b/bindings/pydrake/systems/framework_py_systems.cc
index 8ff30a6f95c4..363b80a619ef 100644
--- a/bindings/pydrake/systems/framework_py_systems.cc
+++ b/bindings/pydrake/systems/framework_py_systems.cc
@@ -302,8 +302,9 @@ struct Impl {
     // TODO(eric.cousineau): Show constructor, but somehow make sure `pybind11`
     // knows this is abstract?
     auto system_cls =
-        DefineTemplateClassWithDefault<System<T>, SystemBase, PySystem>(
-            m, "System", GetPyParam<T>(), doc.System.doc);
+        DefineTemplateClassWithDefault<System<T>, SystemBase, PySystem>(m,
+            "System", GetPyParam<T>(), doc.System.doc, std::nullopt,
+            py::dynamic_attr());
     system_cls
         // Resource allocation and initialization.
         .def("AllocateContext", &System<T>::AllocateContext,
diff --git a/bindings/pydrake/systems/lcm_py.cc b/bindings/pydrake/systems/lcm_py.cc
index 8cfb9d1b2994..0563629c8bc8 100644
--- a/bindings/pydrake/systems/lcm_py.cc
+++ b/bindings/pydrake/systems/lcm_py.cc
@@ -174,6 +174,7 @@ PYBIND11_MODULE(lcm, m) {
             py::keep_alive<1, 3>(), cls_doc.Add.doc);
   }
 
+  // XXX probably needs annotation
   m.def("ApplyLcmBusConfig",
       py::overload_cast<
           const std::map<std::string, std::optional<DrakeLcmParams>>&,
@@ -246,6 +247,7 @@ PYBIND11_MODULE(lcm, m) {
     constexpr auto& cls_doc = doc.LcmScopeSystem;
     py::class_<Class, LeafSystem<double>>(m, "LcmScopeSystem")
         .def(py::init<int>(), py::arg("size"), cls_doc.ctor.doc)
+        // XXX probably needs annotation
         .def_static(
             "AddToBuilder",
             [](systems::DiagramBuilder<double>* builder,
diff --git a/bindings/pydrake/systems/primitives_py.cc b/bindings/pydrake/systems/primitives_py.cc
index 5f974f5ab502..04b3891d2795 100644
--- a/bindings/pydrake/systems/primitives_py.cc
+++ b/bindings/pydrake/systems/primitives_py.cc
@@ -1,6 +1,7 @@
 #include "drake/bindings/pydrake/common/cpp_template_pybind.h"
 #include "drake/bindings/pydrake/common/default_scalars_pybind.h"
 #include "drake/bindings/pydrake/common/eigen_pybind.h"
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/pydrake_pybind.h"
 #include "drake/systems/primitives/adder.h"
@@ -434,6 +435,7 @@ PYBIND11_MODULE(primitives, m) {
           return std::make_unique<SharedPointerSystem<T>>(std::move(wrapped));
         }),
             py::arg("value_to_hold"), doc.SharedPointerSystem.ctor.doc)
+        // XXX probably needs annotation
         .def_static(
             "AddToBuilder",
             [](DiagramBuilder<T>* builder, py::object value_to_hold) {
@@ -557,7 +559,7 @@ PYBIND11_MODULE(primitives, m) {
             &LogVectorOutput<T>),
         py::arg("src"), py::arg("builder"), py::arg("publish_period") = 0.0,
         // Keep alive, ownership: `return` keeps `builder` alive.
-        py::keep_alive<0, 2>(),
+        internal::ref_cycle<0, 2>(),
         // See #11531 for why `py_rvp::reference` is needed.
         py_rvp::reference, doc.LogVectorOutput.doc_3args);
 
@@ -567,7 +569,7 @@ PYBIND11_MODULE(primitives, m) {
         py::arg("src"), py::arg("builder"), py::arg("publish_triggers"),
         py::arg("publish_period") = 0.0,
         // Keep alive, ownership: `return` keeps `builder` alive.
-        py::keep_alive<0, 2>(),
+        internal::ref_cycle<0, 2>(),
         // See #11531 for why `py_rvp::reference` is needed.
         py_rvp::reference, doc.LogVectorOutput.doc_4args);
 
@@ -749,6 +751,7 @@ PYBIND11_MODULE(primitives, m) {
           py::arg("num_outputs"), py::arg("sampling_interval_sec"),
           doc.RandomSource.ctor.doc);
 
+  // XXX annotate???
   m.def("AddRandomInputs", &AddRandomInputs<double>,
        py::arg("sampling_interval_sec"), py::arg("builder"),
        doc.AddRandomInputs.doc)
diff --git a/bindings/pydrake/systems/sensors_py_camera_config.cc b/bindings/pydrake/systems/sensors_py_camera_config.cc
index 966b23b542b1..ee78dcd6ecef 100644
--- a/bindings/pydrake/systems/sensors_py_camera_config.cc
+++ b/bindings/pydrake/systems/sensors_py_camera_config.cc
@@ -1,3 +1,4 @@
+#include "drake/bindings/pydrake/common/ref_cycle_pybind.h"
 #include "drake/bindings/pydrake/common/serialize_pybind.h"
 #include "drake/bindings/pydrake/documentation_pybind.h"
 #include "drake/bindings/pydrake/systems/sensors_py.h"
@@ -64,7 +65,7 @@ void DefineSensorsCameraConfig(py::module m) {
       py::arg("plant") = nullptr, py::arg("scene_graph") = nullptr,
       py::arg("lcm") = nullptr,
       // Keep alive, reference: `builder` keeps `lcm` alive.
-      py::keep_alive<2, 6>(), doc.ApplyCameraConfig.doc);
+      internal::ref_cycle<2, 6>(), doc.ApplyCameraConfig.doc);
 }
 
 }  // namespace internal
diff --git a/bindings/pydrake/test/memory_leak_test.py b/bindings/pydrake/test/memory_leak_test.py
index 4525efb40d2c..59eb3796af54 100644
--- a/bindings/pydrake/test/memory_leak_test.py
+++ b/bindings/pydrake/test/memory_leak_test.py
@@ -43,7 +43,7 @@
 
 
 # Developer-only configuration.
-VERBOSE = False
+VERBOSE = True
 
 
 @functools.cache
@@ -316,18 +316,10 @@ def test_simple_source(self):
         self.do_test(dut=_dut_simple_source, count=10)
 
     def test_trivial_simulator(self):
-        self.do_test(
-            dut=_dut_trivial_simulator,
-            count=5,
-            # TODO(rpoyner-tri): Allow 0 leaks.
-            leaks_allowed=5, leaks_required=1)
+        self.do_test(dut=_dut_trivial_simulator, count=5)
 
     def test_mixed_language_simulator(self):
-        self.do_test(
-            dut=_dut_mixed_language_simulator,
-            count=5,
-            # TODO(rpoyner-tri): Allow 0 leaks.
-            leaks_allowed=5, leaks_required=1)
+        self.do_test(dut=_dut_mixed_language_simulator, count=5)
 
     def test_full_example(self):
         # Note: this test doesn't invoke the #14355 deliberate cycle.
diff --git a/bindings/pydrake/visualization/visualization_py_config.cc b/bindings/pydrake/visualization/visualization_py_config.cc
index fdde46a620e1..d01554a6b740 100644
--- a/bindings/pydrake/visualization/visualization_py_config.cc
+++ b/bindings/pydrake/visualization/visualization_py_config.cc
@@ -25,11 +25,13 @@ void DefineVisualizationConfig(py::module m) {
   }
 
   m  // BR
+     // XXX probably needs annotation
       .def("ApplyVisualizationConfig", &ApplyVisualizationConfig,
           py::arg("config"), py::arg("builder"), py::arg("lcm_buses") = nullptr,
           py::arg("plant") = nullptr, py::arg("scene_graph") = nullptr,
           py::arg("meshcat") = nullptr, py::arg("lcm") = nullptr,
           doc.ApplyVisualizationConfig.doc)
+      // XXX probably needs annotation
       .def("AddDefaultVisualization", &AddDefaultVisualization,
           py::arg("builder"), py::arg("meshcat") = nullptr,
           doc.AddDefaultVisualization.doc);
diff --git a/systems/framework/diagram.cc b/systems/framework/diagram.cc
index 26ce40f4c28a..9b92df762704 100644
--- a/systems/framework/diagram.cc
+++ b/systems/framework/diagram.cc
@@ -1431,6 +1431,10 @@ Diagram<T>::ConvertScalarType() const {
   // Move the new systems into the blueprint.
   blueprint->systems = std::move(new_systems);
 
+  // Do nothing about life_support. Since scalar conversion is effectively a
+  // deep copy, the lifetime extensions provided by life_support are not needed
+  // here.
+
   return blueprint;
 }
 
@@ -1551,6 +1555,7 @@ void Diagram<T>::Initialize(std::unique_ptr<Blueprint> blueprint) {
   connection_map_ = std::move(blueprint->connection_map);
   output_port_ids_ = std::move(blueprint->output_port_ids);
   registered_systems_ = std::move(blueprint->systems);
+  life_support_ = std::move(blueprint->life_support);
 
   // This cache entry just maintains temporary storage. It is only ever used
   // by DoCalcNextUpdateTime(). Since this declaration of the cache entry
diff --git a/systems/framework/diagram.h b/systems/framework/diagram.h
index 4ffaaa985d80..c802805d3358 100644
--- a/systems/framework/diagram.h
+++ b/systems/framework/diagram.h
@@ -1,5 +1,6 @@
 #pragma once
 
+#include <any>
 #include <functional>
 #include <map>
 #include <memory>
@@ -12,6 +13,7 @@
 #include "drake/common/default_scalars.h"
 #include "drake/common/drake_copyable.h"
 #include "drake/common/pointer_cast.h"
+#include "drake/common/string_map.h"
 #include "drake/systems/framework/diagram_context.h"
 #include "drake/systems/framework/diagram_continuous_state.h"
 #include "drake/systems/framework/diagram_discrete_values.h"
@@ -27,9 +29,9 @@ namespace systems {
 
 namespace internal {
 
-/// Destroys owned systems in the reverse order they were added; this enables
-/// Systems to refer to each other during destruction, in the usual "undo"
-/// resource order one would expect for C++.
+// Destroys owned systems in the reverse order they were added; this enables
+// Systems to refer to each other during destruction, in the usual "undo"
+// resource order one would expect for C++.
 template <typename T>
 class OwnedSystems {
  public:
@@ -60,6 +62,17 @@ class OwnedSystems {
   std::vector<std::unique_ptr<System<T>>> vec_;
 };
 
+// External life support data for the diagram. The data will be moved to the
+// diagram at Build() time. Data stored here will have a life-cycle that is the
+// union of the builder and the diagram.
+//
+// This mechanism is particularly useful for the Python FFI. It can be used to
+// extend the lifetime of Python-wrapped systems, when the Build() call occurs
+// in C++ that is not exposed to the Python bindings.
+struct DiagramLifeSupport {
+  string_map<std::any> attributes;
+};
+
 }  // namespace internal
 
 template <typename T>
@@ -528,6 +541,8 @@ class Diagram : public System<T>, internal::SystemParentServiceInterface {
     std::map<InputPortLocator, OutputPortLocator> connection_map;
     // All of the systems to be included in the diagram.
     internal::OwnedSystems<T> systems;
+
+    internal::DiagramLifeSupport life_support;
   };
 
   // Constructs a Diagram from the Blueprint that a DiagramBuilder produces.
@@ -603,6 +618,8 @@ class Diagram : public System<T>, internal::SystemParentServiceInterface {
   // allocated as a cache entry to avoid heap operations during simulation.
   CacheIndex event_times_buffer_cache_index_{};
 
+  internal::DiagramLifeSupport life_support_;
+
   // For all T, Diagram<T> considers DiagramBuilder<T> a friend, so that the
   // builder can set the internal state correctly.
   friend class DiagramBuilder<T>;
diff --git a/systems/framework/diagram_builder.cc b/systems/framework/diagram_builder.cc
index fa7d209a80ff..52c5172a974b 100644
--- a/systems/framework/diagram_builder.cc
+++ b/systems/framework/diagram_builder.cc
@@ -681,6 +681,7 @@ std::unique_ptr<typename Diagram<T>::Blueprint> DiagramBuilder<T>::Compile() {
   blueprint->output_port_names = output_port_names_;
   blueprint->connection_map = connection_map_;
   blueprint->systems = std::move(registered_systems_);
+  blueprint->life_support = std::move(life_support_);
 
   already_built_ = true;
 
diff --git a/systems/framework/diagram_builder.h b/systems/framework/diagram_builder.h
index e1acfa825414..ba9cb0390614 100644
--- a/systems/framework/diagram_builder.h
+++ b/systems/framework/diagram_builder.h
@@ -467,6 +467,14 @@ class DiagramBuilder {
   /// as more ports are exported.
   int num_output_ports() const;
 
+  /// (Internal use only). Returns a mutable reference to life support data for
+  /// the diagram. The data will be moved to the diagram at Build() time. Data
+  /// stored here will have a life-cycle that is the union of the builder and
+  /// the diagram.
+  internal::DiagramLifeSupport& get_mutable_life_support() {
+    return life_support_;
+  }
+
  private:
   // Declares a new input to the entire Diagram, using @p model_input to
   // supply the data type. @p name is an optional name for the input port; if
@@ -533,6 +541,8 @@ class DiagramBuilder {
   std::unordered_set<const System<T>*> systems_;
   // The Systems in this DiagramBuilder, in the order they were registered.
   internal::OwnedSystems<T> registered_systems_;
+
+  internal::DiagramLifeSupport life_support_;
 };
 
 }  // namespace systems
diff --git a/systems/framework/test/diagram_test.cc b/systems/framework/test/diagram_test.cc
index 82493be5269c..765aa47f051f 100644
--- a/systems/framework/test/diagram_test.cc
+++ b/systems/framework/test/diagram_test.cc
@@ -4084,6 +4084,35 @@ GTEST_TEST(ImplicitTimeDerivatives, DiagramProcessing) {
   EXPECT_EQ(residual, expected_result);
 }
 
+// Life support data has a lifetime that is the union of the builder and the
+// resulting diagram.
+GTEST_TEST(LifeSupport, Lifetime) {
+  std::weak_ptr<int> spy;
+  {
+    auto do_build = [&]() {
+      auto thing = std::make_shared<int>(42);
+      spy = thing;
+      DiagramBuilder<double> builder;
+      builder.get_mutable_life_support().attributes.emplace("thing",
+                                                            std::move(thing));
+      // Thing is living inside builder.
+      EXPECT_FALSE(builder.get_mutable_life_support().attributes.empty());
+      EXPECT_FALSE(spy.expired());
+      builder.AddSystem<EmptySystem<double>>();
+      auto result = builder.Build();
+      // Thing has been transferred to diagram.
+      EXPECT_TRUE(builder.get_mutable_life_support().attributes.empty());
+      EXPECT_FALSE(spy.expired());
+      return result;
+    };
+    auto diagram = do_build();
+    // Builder is gone; thing remains.
+    EXPECT_FALSE(spy.expired());
+  }
+  // Diagram is gone; thing is now also gone.
+  EXPECT_TRUE(spy.expired());
+}
+
 }  // namespace
 }  // namespace systems
 }  // namespace drake