diff --git a/test/e2e/upgrade/dropped_operand_test.go b/test/e2e/upgrade/dropped_operand_test.go
new file mode 100644
index 000000000..a825ea4dc
--- /dev/null
+++ b/test/e2e/upgrade/dropped_operand_test.go
@@ -0,0 +1,92 @@
+package upgrade
+
+import (
+	"fmt"
+	"testing"
+
+	ispnv1 "github.com/infinispan/infinispan-operator/api/v1"
+	"github.com/infinispan/infinispan-operator/controllers/constants"
+	tutils "github.com/infinispan/infinispan-operator/test/e2e/utils"
+	coreos "github.com/operator-framework/api/pkg/operators/v1alpha1"
+	corev1 "k8s.io/api/core/v1"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+)
+
+func TestUpgradeFromDroppedOperand(t *testing.T) {
+	olm := testKube.OLMTestEnv()
+	olm.PrintManifest()
+	sourceChannel := olm.SourceChannel
+	targetChannel := olm.TargetChannel
+
+	testKube.NewNamespace(tutils.Namespace)
+	sub := &coreos.Subscription{
+		TypeMeta: metav1.TypeMeta{
+			APIVersion: coreos.SubscriptionCRDAPIVersion,
+			Kind:       coreos.SubscriptionKind,
+		},
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      olm.SubName,
+			Namespace: olm.SubNamespace,
+		},
+		Spec: &coreos.SubscriptionSpec{
+			Channel:                olm.SourceChannel.Name,
+			CatalogSource:          olm.CatalogSource,
+			CatalogSourceNamespace: olm.CatalogSourceNamespace,
+			InstallPlanApproval:    coreos.ApprovalManual,
+			Package:                olm.SubPackage,
+			StartingCSV:            olm.SubStartingCSV,
+			Config: coreos.SubscriptionConfig{
+				Env: []corev1.EnvVar{
+					{Name: "THREAD_DUMP_PRE_STOP", Value: "TRUE"},
+				},
+			},
+		},
+	}
+	defer testKube.CleanupOLMTest(t, tutils.TestName(t), olm.SubName, olm.SubNamespace, olm.SubPackage)
+	testKube.CreateSubscriptionAndApproveInitialVersion(olm, sub)
+
+	replicas := 1
+	spec := tutils.DefaultSpec(t, testKube, func(i *ispnv1.Infinispan) {
+		i.Spec.Replicas = int32(replicas)
+		i.Spec.Version = constants.GetEnvWithDefault("TESTING_DROPPED_OPERAND_VERSION", "13.0.10")
+	})
+	testKube.CreateInfinispan(spec, tutils.Namespace)
+	testKube.WaitForInfinispanPods(replicas, tutils.SinglePodTimeout, spec.Name, tutils.Namespace)
+	ispn := testKube.WaitForInfinispanConditionWithTimeout(spec.Name, spec.Namespace, ispnv1.ConditionWellFormed, conditionTimeout)
+
+	// Upgrade the Subscription channel if required
+	if sourceChannel != targetChannel {
+		testKube.UpdateSubscriptionChannel(targetChannel.Name, sub)
+	}
+
+	for testKube.Subscription(sub); sub.Status.InstalledCSV != targetChannel.CurrentCSVName; {
+		testKube.WaitForSubscriptionState(coreos.SubscriptionStateUpgradePending, sub)
+		testKube.ApproveInstallPlan(sub)
+		testKube.WaitForSubscription(sub, func() bool {
+			return sub.Status.InstalledCSV == sub.Status.CurrentCSV
+		})
+		testKube.WaitForCSVSucceeded(sub)
+	}
+
+	versionManager := testKube.VersionManagerFromCSV(sub)
+	latestOperand := versionManager.Latest()
+	tutils.ExpectNoError(
+		testKube.UpdateInfinispan(ispn, func() {
+			ispn.Spec.Version = latestOperand.Ref()
+			fmt.Printf("Upgrading Operand to %s\n", ispn.Spec.Version)
+		}),
+	)
+	testKube.WaitForInfinispanState(spec.Name, spec.Namespace, func(i *ispnv1.Infinispan) bool {
+		return !i.IsConditionTrue(ispnv1.ConditionWellFormed) &&
+			i.Status.Operand.Version == latestOperand.Ref() &&
+			i.Status.Operand.Image == latestOperand.Image &&
+			i.Status.Operand.Phase == ispnv1.OperandPhasePending
+	})
+	testKube.WaitForInfinispanPods(replicas, tutils.SinglePodTimeout, spec.Name, tutils.Namespace)
+	testKube.WaitForInfinispanState(spec.Name, spec.Namespace, func(i *ispnv1.Infinispan) bool {
+		return i.IsConditionTrue(ispnv1.ConditionWellFormed) &&
+			i.Status.Operand.Version == latestOperand.Ref() &&
+			i.Status.Operand.Image == latestOperand.Image &&
+			i.Status.Operand.Phase == ispnv1.OperandPhaseRunning
+	})
+}