diff --git a/wpilibc/src/main/native/cpp/framework/OpModeRobot.cpp b/wpilibc/src/main/native/cpp/framework/OpModeRobot.cpp
index 791e7a0ca4..6fff49cf3a 100644
--- a/wpilibc/src/main/native/cpp/framework/OpModeRobot.cpp
+++ b/wpilibc/src/main/native/cpp/framework/OpModeRobot.cpp
@@ -92,7 +92,6 @@ class MonitorThread : public wpi::util::SafeThreadEvent {
 
 void OpModeRobotBase::StartCompetition() {
   fmt::print("********** Robot program startup complete **********\n");
-  HAL_ObserveUserProgramStarting();
 
   wpi::util::Event event;
   struct DSListener {
@@ -108,6 +107,7 @@ void OpModeRobotBase::StartCompetition() {
   HAL_SetNotifierName(m_notifier, "OpModeRobot", &status);
 
   int64_t lastModeId = -1;
+  bool calledObserveUserProgramStarting = false;
   bool calledDriverStationConnected = false;
   std::shared_ptr<OpMode> opMode;
   WPI_EventHandle events[] = {event.GetHandle(),
@@ -116,6 +116,16 @@ void OpModeRobotBase::StartCompetition() {
   for (;;) {
     // Wait for new data from the driver station, with 50 ms timeout
     HAL_SetNotifierAlarm(m_notifier, 50000, 0, false, true, &status);
+
+    // Call HAL_ObserveUserProgramStarting() here as a one-shot to ensure it is
+    // called after the notifier alarm is set.  The notifier alarm is set using
+    // relative time, so tests that wait on the user program to start and then
+    // step time won't work correctly if we call this before setting the alarm.
+    if (!calledObserveUserProgramStarting) {
+      calledObserveUserProgramStarting = true;
+      HAL_ObserveUserProgramStarting();
+    }
+
     auto signaled = wpi::util::WaitForObjects(events, signaledBuf);
     if (signaled.empty()) {
       return;  // handles destroyed
diff --git a/wpilibj/src/main/java/org/wpilib/framework/OpModeRobot.java b/wpilibj/src/main/java/org/wpilib/framework/OpModeRobot.java
index 4bd56590bc..1e37b41c0b 100644
--- a/wpilibj/src/main/java/org/wpilib/framework/OpModeRobot.java
+++ b/wpilibj/src/main/java/org/wpilib/framework/OpModeRobot.java
@@ -566,7 +566,6 @@ public abstract class OpModeRobot extends RobotBase {
   @Override
   public final void startCompetition() {
     System.out.println("********** Robot program startup complete **********");
-    DriverStationJNI.observeUserProgramStarting();
 
     int event = WPIUtilJNI.createEvent(false, false);
     DriverStationJNI.provideNewDataEventHandle(event);
@@ -577,11 +576,22 @@ public abstract class OpModeRobot extends RobotBase {
     try {
       // Implement the opmode lifecycle
       long lastModeId = -1;
+      boolean calledObserveUserProgramStarting = false;
       boolean calledDriverStationConnected = false;
       int[] events = {event, m_notifier};
       while (true) {
         // Wait for new data from the driver station, with 50 ms timeout
         NotifierJNI.setNotifierAlarm(m_notifier, 50000, 0, false, true);
+
+        // Call observeUserProgramStarting() here as a one-shot to ensure it is called after the
+        // notifier alarm is set.  The notifier alarm is set using relative time, so tests that
+        // wait on the user program to start and then step time won't work correctly if we call
+        // this before setting the alarm.
+        if (!calledObserveUserProgramStarting) {
+          calledObserveUserProgramStarting = true;
+          DriverStationJNI.observeUserProgramStarting();
+        }
+
         try {
           int[] signaled = WPIUtilJNI.waitForObjects(events);
           for (int val : signaled) {