diff --git a/rclcpp/test/rclcpp/executors/test_executors.cpp b/rclcpp/test/rclcpp/executors/test_executors.cpp
index 68138eb82b..47bb94c16f 100644
--- a/rclcpp/test/rclcpp/executors/test_executors.cpp
+++ b/rclcpp/test/rclcpp/executors/test_executors.cpp
@@ -36,8 +36,11 @@
 #include "rclcpp/duration.hpp"
 #include "rclcpp/guard_condition.hpp"
 #include "rclcpp/rclcpp.hpp"
+#include "rclcpp/time_source.hpp"
+#include "rcpputils/scope_exit.hpp"
 
 #include "test_msgs/msg/empty.hpp"
+#include "test_msgs/srv/empty.hpp"
 
 using namespace std::chrono_literals;
 
@@ -461,19 +464,32 @@ class TestWaitable : public rclcpp::Waitable
   void
   add_to_wait_set(rcl_wait_set_t * wait_set) override
   {
+    if (trigger_count_ > 0) {
+      // Keep the gc triggered until the trigger count is reduced back to zero.
+      // This is necessary if trigger() results in the wait set waking, but not
+      // executing this waitable, in which case it needs to be re-triggered.
+      gc_.trigger();
+    }
     rclcpp::detail::add_guard_condition_to_rcl_wait_set(*wait_set, gc_);
   }
 
   void trigger()
   {
+    trigger_count_++;
     gc_.trigger();
   }
 
   bool
   is_ready(rcl_wait_set_t * wait_set) override
   {
-    (void)wait_set;
-    return true;
+    is_ready_count_++;
+    for (size_t i = 0; i < wait_set->size_of_guard_conditions; ++i) {
+      auto rcl_guard_condition = wait_set->guard_conditions[i];
+      if (&gc_.get_rcl_guard_condition() == rcl_guard_condition) {
+        return true;
+      }
+    }
+    return false;
   }
 
   std::shared_ptr<void>
@@ -490,11 +506,24 @@ class TestWaitable : public rclcpp::Waitable
   }
 
   void
-  execute(std::shared_ptr<void> & data) override
+  execute(std::shared_ptr<void> &) override
   {
-    (void) data;
+    trigger_count_--;
     count_++;
-    std::this_thread::sleep_for(3ms);
+    if (nullptr != on_execute_callback_) {
+      on_execute_callback_();
+    } else {
+      // TODO(wjwwood): I don't know why this was here, but probably it should
+      //   not be there, or test cases where that is important should use the
+      //   on_execute_callback?
+      std::this_thread::sleep_for(3ms);
+    }
+  }
+
+  void
+  set_on_execute_callback(std::function<void()> on_execute_callback)
+  {
+    on_execute_callback_ = on_execute_callback;
   }
 
   void
@@ -516,14 +545,23 @@ class TestWaitable : public rclcpp::Waitable
   get_number_of_ready_guard_conditions() override {return 1;}
 
   size_t
-  get_count()
+  get_count() const
   {
     return count_;
   }
 
+  size_t
+  get_is_ready_call_count() const
+  {
+    return is_ready_count_;
+  }
+
 private:
-  size_t count_ = 0;
+  std::atomic<size_t> trigger_count_ = 0;
+  std::atomic<size_t> is_ready_count_ = 0;
+  std::atomic<size_t> count_ = 0;
   rclcpp::GuardCondition gc_;
+  std::function<void()> on_execute_callback_ = nullptr;
 };
 
 TYPED_TEST(TestExecutors, spinAll)
@@ -837,6 +875,374 @@ TEST(TestExecutors, testSpinUntilFutureCompleteNodePtr)
   rclcpp::shutdown();
 }
 
+// The purpose of this test is to check that the order of callbacks happen
+// in some relation to the order of events and the order in which the callbacks
+// were registered.
+// This is not a guarantee of executor API, but it is a bit of UB that some
+// have come to depend on, see:
+//
+//   https://github.com/ros2/rclcpp/issues/2532
+//
+// It should not be changed unless there's a good reason for it (users find it
+// the least surprising out come even if it is not guaranteed), but if there
+// is a good reason for changing it, then the executors effected can be skipped,
+// or the test can be removed.
+// The purpose of this test is to catch this regressions and let the authors of
+// the change read up on the above context and act accordingly.
+TYPED_TEST(TestExecutors, deterministic_execution_order_ub)
+{
+  using ExecutorType = TypeParam;
+
+  // number of each entity to test
+  constexpr size_t number_of_entities = 20;
+  std::vector<size_t> forward(number_of_entities);
+  std::iota(std::begin(forward), std::end(forward), 0);
+  std::vector<size_t> reverse(number_of_entities);
+  std::reverse_copy(std::begin(forward), std::end(forward), std::begin(reverse));
+
+  // The expected results vary based on the registration order (always 0..N-1),
+  // the call order (what this means varies based on the entity type), the
+  // entity types, and in some cases the executor type.
+  // It is also possible that the rmw implementation can play a role in the
+  // ordering, depending on how the executor uses the rmw layer.
+  // The follow structure and logic tries to capture these details.
+  // Each test case represents a case-entity pair,
+  // e.g. "forward call order for waitables" or "reverse call order for timers"
+  struct test_case
+  {
+    // If this is true, then the test case should be skipped.
+    bool should_skip;
+    // Order in which to invoke the entities, where that is possible to control.
+    // For example, the order in which we trigger() the waitables, or the
+    // order in which we set the timers up to execute (using increasing periods).
+    std::vector<size_t> call_order;
+    // Order in which we expect the entities to be executed by the executor.
+    std::vector<size_t> expected_execution_order;
+  };
+  // tests cases are "test_name: {"entity type": {call_order, expected_execution_order}"
+  std::map<std::string, std::map<std::string, test_case>> test_cases = {
+    {
+      "forward call order",
+      {
+        {"waitable", {false, forward, forward}},
+        {"subscription", {false, forward, forward}},
+        {"service", {false, forward, forward}},
+        {"timer", {false, forward, forward}}
+      }
+    },
+    {
+      "reverse call order",
+      {
+        {"waitable", {false, reverse, forward}},
+        {"subscription", {false, reverse, forward}},
+        {"service", {false, reverse, forward}},
+        // timers are always called in order of which expires soonest, so
+        // the registration order doesn't necessarily affect them
+        {"timer", {false, reverse, reverse}}
+      }
+    },
+  };
+
+  // Note use this to exclude or modify expected results for executors if this
+  // undefined behavior doesn't hold for them:
+  if (
+    std::is_same<ExecutorType, rclcpp::experimental::executors::EventsExecutor>())
+  {
+    // for the EventsExecutor the call order is the execution order because it
+    // tracks the individual events (triggers in the case of waitables) and
+    // executes in that order
+    test_cases["reverse call order"]["waitable"] = {false, reverse, reverse};
+    // timers are unaffected by the above about waitables, as they are always
+    // executed in "call order" even in the other executors
+    // but, subscription and service execution order is driven by the rmw impl
+    // due to how the EventsExecutor uses the rmw interface, so we'll skip those
+    for (auto & test_case_pair : test_cases) {
+      for (auto & entity_test_case_pair : test_case_pair.second) {
+        if (
+          entity_test_case_pair.first == "subscription" ||
+          entity_test_case_pair.first == "service")
+        {
+          entity_test_case_pair.second = {true, {}, {}};
+        }
+      }
+    }
+  }
+
+  // Set up a situation with N waitables, added in order (1, ..., N) and then
+  // trigger them in various orders between calls to spin, to see that the order
+  // is impacted by the registration order (in most cases).
+  // Note that we always add/register, trigger, then wait/spin, because this
+  // undefined behavior related to execution order only applies to entities
+  // that were "ready" in between calls to spin, i.e. they appear to become
+  // "ready" to the executor at the "same time".
+  // Also note, that this ordering only applies within entities of the same type
+  // as well, there are other parts of the executor that determine the order
+  // between entity types, e.g. the default scheduling (at the time of writing)
+  // prefers timers, then subscriptions, then service servers, then service
+  // clients, and then waitables, see: Executor::get_next_ready_executable()
+  // But that might be different for different executors and may change in the
+  // future.
+  // So here we just test order withing a few different waitable instances only.
+  // Further down we test similar set ups with other entities like subscriptions
+  // and timers.
+
+  constexpr bool automatically_add_to_executor_with_node = false;
+  auto isolated_callback_group = this->node->create_callback_group(
+    rclcpp::CallbackGroupType::MutuallyExclusive,
+    automatically_add_to_executor_with_node);
+
+  // perform each of the test cases for waitables
+  {
+    auto waitable_interfaces = this->node->get_node_waitables_interface();
+
+    std::vector<std::shared_ptr<TestWaitable>> waitables;
+    for (size_t i = 0; i < number_of_entities; ++i) {
+      auto my_waitable = std::make_shared<TestWaitable>();
+      waitable_interfaces->add_waitable(my_waitable, isolated_callback_group);
+      waitables.push_back(my_waitable);
+    }
+
+    for (const auto & test_case_pair : test_cases) {
+      const std::string & test_case_name = test_case_pair.first;
+      const auto & test_case = test_case_pair.second.at("waitable");
+      if (test_case.should_skip) {
+        continue;
+      }
+
+      ExecutorType executor;
+      executor.add_callback_group(isolated_callback_group, this->node->get_node_base_interface());
+
+      RCPPUTILS_SCOPE_EXIT(
+      {
+        for (size_t i = 0; i < number_of_entities; ++i) {
+          waitables[i]->set_on_execute_callback(nullptr);
+        }
+      });
+
+      std::vector<size_t> actual_order;
+      for (size_t i : test_case.call_order) {
+        waitables[i]->set_on_execute_callback([&actual_order, i]() {actual_order.push_back(i);});
+        waitables[i]->trigger();
+      }
+
+      while (actual_order.size() < number_of_entities && rclcpp::ok()) {
+        executor.spin_once(10s);  // large timeout because it should normally exit quickly
+      }
+
+      EXPECT_EQ(actual_order, test_case.expected_execution_order)
+        << "callback call order of waitables in test case '" << test_case_name
+        << "' different than expected, this may be a false positive, see test "
+        << "description";
+    }
+  }
+
+  // perform each of the test cases for subscriptions
+  {
+    const std::string test_topic_name = "~/deterministic_execution_order_ub";
+    std::map<rclcpp::SubscriptionBase *, std::function<void()>> on_sub_data_callbacks;
+    std::vector<rclcpp::Subscription<test_msgs::msg::Empty>::SharedPtr> subscriptions;
+    rclcpp::SubscriptionOptions so;
+    so.callback_group = isolated_callback_group;
+    for (size_t i = 0; i < number_of_entities; ++i) {
+      size_t next_sub_index = subscriptions.size();
+      auto sub = this->node->template create_subscription<test_msgs::msg::Empty>(
+        test_topic_name,
+        10,
+        [&on_sub_data_callbacks, &subscriptions, next_sub_index](const test_msgs::msg::Empty &) {
+          auto this_sub_pointer = subscriptions[next_sub_index].get();
+          auto callback_for_sub_it = on_sub_data_callbacks.find(this_sub_pointer);
+          ASSERT_NE(callback_for_sub_it, on_sub_data_callbacks.end());
+          auto on_sub_data_callback = callback_for_sub_it->second;
+          if (on_sub_data_callback) {
+            on_sub_data_callback();
+          }
+        },
+        so);
+      subscriptions.push_back(sub);
+    }
+
+    for (const auto & test_case_pair : test_cases) {
+      const std::string & test_case_name = test_case_pair.first;
+      const auto & test_case = test_case_pair.second.at("subscription");
+      if (test_case.should_skip) {
+        continue;
+      }
+
+      ExecutorType executor;
+      executor.add_callback_group(isolated_callback_group, this->node->get_node_base_interface());
+
+      RCPPUTILS_SCOPE_EXIT(
+      {
+        on_sub_data_callbacks.clear();
+      });
+
+      std::vector<size_t> actual_order;
+      for (size_t i = 0; i < number_of_entities; ++i) {
+        auto sub = subscriptions[i];
+        on_sub_data_callbacks[sub.get()] = [&actual_order, i]() {
+            actual_order.push_back(i);
+          };
+      }
+
+      // create publisher and wait for all of the subscriptions to match
+      auto pub = this->node->template create_publisher<test_msgs::msg::Empty>(test_topic_name, 10);
+      size_t number_of_matches = pub->get_subscription_count();
+      while (number_of_matches < number_of_entities && rclcpp::ok()) {
+        executor.spin_once(10s);  // large timeout because it should normally exit quickly
+        number_of_matches = pub->get_subscription_count();
+      }
+
+      // publish once and wait for all subscriptions to be handled
+      pub->publish(test_msgs::msg::Empty());
+      while (actual_order.size() < number_of_entities && rclcpp::ok()) {
+        executor.spin_once(10s);  // large timeout because it should normally exit quickly
+      }
+
+      EXPECT_EQ(actual_order, test_case.expected_execution_order)
+        << "callback call order of subscriptions in test case '" << test_case_name
+        << "' different than expected, this may be a false positive, see test "
+        << "description";
+    }
+  }
+
+  // perform each of the test cases for service servers
+  {
+    const std::string test_service_name = "~/deterministic_execution_order_ub";
+    std::map<rclcpp::ServiceBase *, std::function<void()>> on_request_callbacks;
+    std::vector<rclcpp::Service<test_msgs::srv::Empty>::SharedPtr> services;
+    std::vector<rclcpp::Client<test_msgs::srv::Empty>::SharedPtr> clients;
+    for (size_t i = 0; i < number_of_entities; ++i) {
+      size_t next_srv_index = services.size();
+      auto srv = this->node->template create_service<test_msgs::srv::Empty>(
+        test_service_name + "_" + std::to_string(i),
+        [&on_request_callbacks, &services, next_srv_index](
+          std::shared_ptr<test_msgs::srv::Empty::Request>,
+          std::shared_ptr<test_msgs::srv::Empty::Response>
+        ) {
+          auto this_srv_pointer = services[next_srv_index].get();
+          auto callback_for_srv_it = on_request_callbacks.find(this_srv_pointer);
+          ASSERT_NE(callback_for_srv_it, on_request_callbacks.end());
+          auto on_request_callback = callback_for_srv_it->second;
+          if (on_request_callback) {
+            on_request_callback();
+          }
+        },
+        10,
+        isolated_callback_group);
+      services.push_back(srv);
+      auto client = this->node->template create_client<test_msgs::srv::Empty>(
+        test_service_name + "_" + std::to_string(i),
+        10,
+        isolated_callback_group
+      );
+      clients.push_back(client);
+    }
+
+    for (const auto & test_case_pair : test_cases) {
+      const std::string & test_case_name = test_case_pair.first;
+      const auto & test_case = test_case_pair.second.at("service");
+      if (test_case.should_skip) {
+        continue;
+      }
+
+      ExecutorType executor;
+      executor.add_callback_group(isolated_callback_group, this->node->get_node_base_interface());
+
+      RCPPUTILS_SCOPE_EXIT(
+      {
+        on_request_callbacks.clear();
+      });
+
+      std::vector<size_t> actual_order;
+      for (size_t i = 0; i < number_of_entities; ++i) {
+        auto srv = services[i];
+        on_request_callbacks[srv.get()] = [&actual_order, i]() {
+            actual_order.push_back(i);
+          };
+      }
+
+      // wait for all of the services to match
+      for (const auto & client : clients) {
+        bool matched = client->wait_for_service(10s);  // long timeout, but should be quick
+        ASSERT_TRUE(matched);
+      }
+
+      // send requests in order
+      for (size_t i : test_case.call_order) {
+        clients[i]->async_send_request(std::make_shared<test_msgs::srv::Empty::Request>());
+      }
+
+      // wait for all the requests to be handled
+      while (actual_order.size() < number_of_entities && rclcpp::ok()) {
+        executor.spin_once(10s);  // large timeout because it should normally exit quickly
+      }
+
+      EXPECT_EQ(actual_order, test_case.expected_execution_order)
+        << "callback call order of service servers in test case '" << test_case_name
+        << "' different than expected, this may be a false positive, see test "
+        << "description";
+    }
+  }
+
+  // perform each of the test cases for timers
+  {
+    for (const auto & test_case_pair : test_cases) {
+      const std::string & test_case_name = test_case_pair.first;
+      const auto & test_case = test_case_pair.second.at("timer");
+      if (test_case.should_skip) {
+        continue;
+      }
+
+      std::map<rclcpp::TimerBase *, std::function<void()>> timer_callbacks;
+      std::vector<rclcpp::TimerBase::SharedPtr> timers;
+      for (size_t i = 0; i < number_of_entities; ++i) {
+        // "call order" for timers will be simulated by setting them at different
+        // periods, with the "first" ones having the smallest period.
+        auto period = 1ms + std::chrono::milliseconds(test_case.call_order[i]);
+        auto timer = this->node->create_timer(
+          period,
+          [&timer_callbacks](rclcpp::TimerBase & timer) {
+            auto timer_callback_it = timer_callbacks.find(&timer);
+            ASSERT_NE(timer_callback_it, timer_callbacks.end());
+            if (nullptr != timer_callback_it->second) {
+              timer_callback_it->second();
+            }
+          },
+          isolated_callback_group);
+        timers.push_back(timer);
+      }
+
+      ExecutorType executor;
+      executor.add_callback_group(isolated_callback_group, this->node->get_node_base_interface());
+
+      RCPPUTILS_SCOPE_EXIT(
+      {
+        timer_callbacks.clear();
+      });
+
+      std::vector<size_t> actual_order;
+      for (size_t i = 0; i < number_of_entities; ++i) {
+        ASSERT_LT(i, timers.size());
+        auto & timer = timers[i];
+        timer_callbacks[timer.get()] = [&actual_order, &timer, i]() {
+            actual_order.push_back(i);
+            // only allow execution once
+            timer->cancel();
+          };
+      }
+
+      while (actual_order.size() < number_of_entities && rclcpp::ok()) {
+        executor.spin_once(10s);  // large timeout because it should normally exit quickly
+      }
+
+      EXPECT_EQ(actual_order, test_case.expected_execution_order)
+        << "callback call order of timers in test case '" << test_case_name
+        << "' different than expected, this may be a false positive, see test "
+        << "description";
+    }
+  }
+}
+
 template<typename T>
 class TestIntraprocessExecutors : public ::testing::Test
 {