diff --git a/ray-operator/controllers/ray/utils/util.go b/ray-operator/controllers/ray/utils/util.go
index 00f0242cfcb..8c806d6d413 100644
--- a/ray-operator/controllers/ray/utils/util.go
+++ b/ray-operator/controllers/ray/utils/util.go
@@ -38,6 +38,7 @@ const (
 	ServeName           = "serve"
 	ClusterDomainEnvKey = "CLUSTER_DOMAIN"
 	DefaultDomainName   = "cluster.local"
+	ContainersNotReady  = "ContainersNotReady"
 )
 
 // TODO (kevin85421): Define CRDType here rather than constant.go to avoid circular dependency.
@@ -103,12 +104,36 @@ func FindHeadPodReadyCondition(headPod *corev1.Pod) metav1.Condition {
 			headPodReadyCondition.Reason = reason
 		}
 
+		// If reason is ContainersNotReady, then replace it with an available
+		// container status that may illuminate why the container is not ready.
+		if reason == ContainersNotReady {
+			reason, message, ok := firstNotReadyContainerStatus(headPod)
+			if ok {
+				if headPodReadyCondition.Message != "" {
+					headPodReadyCondition.Message += "; "
+				}
+				headPodReadyCondition.Message += message
+				headPodReadyCondition.Reason = reason
+			}
+		}
+
 		// Since we're only interested in the PodReady condition, break after processing it
 		break
 	}
 	return headPodReadyCondition
 }
 
+func firstNotReadyContainerStatus(pod *corev1.Pod) (reason string, message string, ok bool) {
+	for _, status := range pod.Status.ContainerStatuses {
+		if status.State.Waiting != nil {
+			return status.State.Waiting.Reason, fmt.Sprintf("%s: %s", status.Name, status.State.Waiting.Message), true
+		} else if status.State.Terminated != nil {
+			return status.State.Terminated.Reason, fmt.Sprintf("%s: %s", status.Name, status.State.Terminated.Message), true
+		}
+	}
+	return "", "", false
+}
+
 // FindRayClusterSuspendStatus returns the current suspend status from two conditions:
 //  1. rayv1.RayClusterSuspending
 //  2. rayv1.RayClusterSuspended
diff --git a/ray-operator/controllers/ray/utils/util_test.go b/ray-operator/controllers/ray/utils/util_test.go
index 9a9371acd05..47afa55c85a 100644
--- a/ray-operator/controllers/ray/utils/util_test.go
+++ b/ray-operator/controllers/ray/utils/util_test.go
@@ -328,7 +328,7 @@ func createSomePodWithCondition(typ corev1.PodConditionType, status corev1.Condi
 	}
 }
 
-func createRayHeadPodWithPhaseAndCondition(phase corev1.PodPhase, typ corev1.PodConditionType, status corev1.ConditionStatus) (pod *corev1.Pod) {
+func createRayHeadPodWithPhaseAndCondition(phase corev1.PodPhase, status corev1.ConditionStatus) (pod *corev1.Pod) {
 	return &corev1.Pod{
 		TypeMeta: metav1.TypeMeta{
 			APIVersion: "v1",
@@ -345,8 +345,9 @@ func createRayHeadPodWithPhaseAndCondition(phase corev1.PodPhase, typ corev1.Pod
 			Phase: phase,
 			Conditions: []corev1.PodCondition{
 				{
-					Type:   typ,
+					Type:   corev1.PodReady,
 					Status: status,
+					Reason: ContainersNotReady,
 				},
 			},
 		},
@@ -945,7 +946,7 @@ func TestFindHeadPodReadyCondition(t *testing.T) {
 	}{
 		{
 			name: "condition true if Ray head pod is running and ready",
-			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodRunning, corev1.PodReady, corev1.ConditionTrue),
+			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodRunning, corev1.ConditionTrue),
 			expected: metav1.Condition{
 				Type:   string(rayv1.HeadPodReady),
 				Status: metav1.ConditionTrue,
@@ -953,7 +954,7 @@ func TestFindHeadPodReadyCondition(t *testing.T) {
 		},
 		{
 			name: "condition false if Ray head pod is not running",
-			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodPending, corev1.PodReady, corev1.ConditionFalse),
+			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodPending, corev1.ConditionFalse),
 			expected: metav1.Condition{
 				Type:   string(rayv1.HeadPodReady),
 				Status: metav1.ConditionFalse,
@@ -961,7 +962,7 @@ func TestFindHeadPodReadyCondition(t *testing.T) {
 		},
 		{
 			name: "condition false if Ray head pod is not ready",
-			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodRunning, corev1.PodReady, corev1.ConditionFalse),
+			pod:  createRayHeadPodWithPhaseAndCondition(corev1.PodRunning, corev1.ConditionFalse),
 			expected: metav1.Condition{
 				Type:   string(rayv1.HeadPodReady),
 				Status: metav1.ConditionFalse,
@@ -977,6 +978,88 @@ func TestFindHeadPodReadyCondition(t *testing.T) {
 	}
 }
 
+func TestFindHeadPodReadyMessage(t *testing.T) {
+	tests := []struct {
+		name        string
+		message     string
+		wantMessage string
+		wantReason  string
+		status      []corev1.ContainerStatus
+	}{{
+		name:       "no message no status want original reason",
+		wantReason: ContainersNotReady,
+	}, {
+		name:        "no container status want original reason",
+		message:     "TooEarlyInTheMorning",
+		wantMessage: "TooEarlyInTheMorning",
+		wantReason:  ContainersNotReady,
+	}, {
+		name:    "one reason one status",
+		message: "containers not ready",
+		status: []corev1.ContainerStatus{{
+			Name: "ray",
+			State: corev1.ContainerState{
+				Waiting: &corev1.ContainerStateWaiting{
+					Reason:  "ImagePullBackOff",
+					Message: `Back-off pulling image royproject/roy:latest: ErrImagePull: rpc error: code = NotFound`,
+				},
+			},
+		}},
+		wantReason:  "ImagePullBackOff",
+		wantMessage: `containers not ready; ray: Back-off pulling image royproject/roy:latest: ErrImagePull: rpc error: code = NotFound`,
+	}, {
+		name:    "one reason two statuses only copy first",
+		message: "aesthetic problems",
+		status: []corev1.ContainerStatus{{
+			Name: "indigo",
+			State: corev1.ContainerState{
+				Waiting: &corev1.ContainerStateWaiting{
+					Reason:  "BadColor",
+					Message: "too blue",
+				},
+			},
+		}, {
+			Name: "circle",
+			State: corev1.ContainerState{
+				Terminated: &corev1.ContainerStateTerminated{
+					Reason:  "BadGeometry",
+					Message: "too round",
+				},
+			},
+		}},
+		wantReason:  "BadColor",
+		wantMessage: "aesthetic problems; indigo: too blue",
+	}, {
+		name: "no reason one status",
+		status: []corev1.ContainerStatus{{
+			Name: "my-image",
+			State: corev1.ContainerState{
+				Terminated: &corev1.ContainerStateTerminated{
+					Reason:  "Crashed",
+					Message: "bash not found",
+				},
+			},
+		}},
+		wantReason:  "Crashed",
+		wantMessage: "my-image: bash not found",
+	}}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			pod := createRayHeadPodWithPhaseAndCondition(corev1.PodPending, corev1.ConditionFalse)
+			pod.Status.Conditions[0].Message = tc.message
+			pod.Status.ContainerStatuses = tc.status
+			cond := FindHeadPodReadyCondition(pod)
+			if cond.Message != tc.wantMessage {
+				t.Errorf("FindHeadPodReadyCondition(...) returned condition with message %q, but wanted %q", cond.Message, tc.wantMessage)
+			}
+			if cond.Reason != tc.wantReason {
+				t.Errorf("FindHeadPodReadyCondition(...) returned condition with reason %q, but wanted %q", cond.Reason, tc.wantReason)
+			}
+		})
+	}
+}
+
 func TestErrRayClusterReplicaFailureReason(t *testing.T) {
 	assert.Equal(t, "FailedDeleteAllPods", RayClusterReplicaFailureReason(ErrFailedDeleteAllPods))
 	assert.Equal(t, "FailedDeleteHeadPod", RayClusterReplicaFailureReason(ErrFailedDeleteHeadPod))