diff --git a/controllers/deactivation/deactivation_controller_test.go b/controllers/deactivation/deactivation_controller_test.go
index b271aea4e..32f50dfee 100644
--- a/controllers/deactivation/deactivation_controller_test.go
+++ b/controllers/deactivation/deactivation_controller_test.go
@@ -252,8 +252,29 @@ func TestReconcile(t *testing.T) {
 				userSignupFoobar.Status.ScheduledDeactivationTimestamp = nil
 
 				r, req, cl := prepareReconcile(t, mur.Name, userTier30, mur, userSignupFoobar, config)
+
+				// First cause the status update to fail
+				cl.MockStatusUpdate = func(ctx context.Context, obj runtimeclient.Object, opts ...runtimeclient.UpdateOption) error {
+					switch obj.(type) {
+					case *toolchainv1alpha1.UserSignup:
+						return errors.New("mock error")
+					default:
+						return cl.Client.Status().Update(ctx, obj)
+					}
+				}
+
 				// when
 				res, err := r.Reconcile(context.TODO(), req)
+
+				require.Error(t, err)
+				require.Equal(t, "mock error", err.Error())
+
+				// Remove the mock update
+				cl.MockStatusUpdate = nil
+
+				// Attempt the reconcile again
+				res, err = r.Reconcile(context.TODO(), req)
+
 				// then
 				require.NoError(t, err)
 				require.False(t, res.Requeue)
@@ -291,8 +312,28 @@ func TestReconcile(t *testing.T) {
 
 					r, req, cl := prepareReconcile(t, mur.Name, userTier30, mur, userSignupFoobar, config)
 
+					// First cause the status update to fail
+					cl.MockStatusUpdate = func(ctx context.Context, obj runtimeclient.Object, opts ...runtimeclient.UpdateOption) error {
+						switch obj.(type) {
+						case *toolchainv1alpha1.UserSignup:
+							return errors.New("mock error")
+						default:
+							return cl.Client.Status().Update(ctx, obj)
+						}
+					}
+
 					// when
 					res, err := r.Reconcile(context.TODO(), req)
+
+					require.Error(t, err)
+					require.Equal(t, "mock error", err.Error())
+
+					// Remove the mock update
+					cl.MockStatusUpdate = nil
+
+					// Attempt the reconcile again
+					res, err = r.Reconcile(context.TODO(), req)
+
 					// then
 					require.NoError(t, err)
 					require.False(t, res.Requeue)