diff --git a/controllers/node_handler.go b/controllers/node_handler.go
index 4e73e05..fcb3213 100644
--- a/controllers/node_handler.go
+++ b/controllers/node_handler.go
@@ -83,7 +83,7 @@ func ApplyProfiles(ctx context.Context, params reconcileParameters, data *state.
 		if err == nil {
 			continue
 		}
-		if errors.Is(err, retryErr) {
+		if errors.As(err, &retryErr) {
 			profilesWithRetryError[ps.Profile.Name] = struct{}{}
 		} else {
 			errs = append(errs, err)
diff --git a/plugin/impl/eviction.go b/plugin/impl/eviction.go
index 0e5e9aa..3e6f9f1 100644
--- a/plugin/impl/eviction.go
+++ b/plugin/impl/eviction.go
@@ -94,7 +94,8 @@ func (e *Eviction) Trigger(params plugin.Parameters) error {
 			ForceEviction: e.ForceEviction,
 		})
 		if err != nil {
-			return err
+			params.Log.Error(err, "Drain encountered errors; will retry next reconcile", "node", params.Node.Name)
+			return &plugin.RetryError{Message: err.Error()}
 		}
 		if !drained {
 			params.Log.Info("Drain still in progress; will continue in next reconcile", "node", params.Node.Name)
diff --git a/plugin/plugin_test.go b/plugin/plugin_test.go
index ff9c94e..5b72de8 100644
--- a/plugin/plugin_test.go
+++ b/plugin/plugin_test.go
@@ -18,7 +18,7 @@ func TestPlugins(t *testing.T) {
 	RunSpecs(t, "Plugin Suite")
 }
 
-var _ = Describe("CheckError", func() {
+var _ = Describe("ChainError", func() {
 	chainErr := ChainError{
 		Message: "msg",
 		Err:     errors.New("err"),
@@ -35,6 +35,25 @@ var _ = Describe("CheckError", func() {
 	})
 })
 
+var _ = Describe("RetryError", func() {
+	It("is extractable via errors.As through ChainError wrapping", func() {
+		retryErr := &RetryError{Message: "drain still in progress"}
+		wrapped := &ChainError{Message: "trigger chain failed", Err: retryErr}
+
+		var extracted *RetryError
+		Expect(errors.As(wrapped, &extracted)).To(BeTrue())
+		Expect(extracted.Message).To(Equal("drain still in progress"))
+	})
+
+	It("is not matched by errors.Is with a different instance", func() {
+		retryErr := &RetryError{Message: "some error"}
+		wrapped := &ChainError{Message: "trigger chain failed", Err: retryErr}
+
+		// errors.Is uses pointer identity for types without Is() method
+		Expect(errors.Is(wrapped, &RetryError{})).To(BeFalse())
+	})
+})
+
 var _ = Describe("Registry", func() {
 	var emptyConfig *ucfgwrap.Config
 
diff --git a/state/state.go b/state/state.go
index 521926a..1c3be5d 100644
--- a/state/state.go
+++ b/state/state.go
@@ -192,7 +192,8 @@ func Apply(state NodeState, node *v1.Node, data *Data, params plugin.Parameters)
 	}
 	if stateInfo.Previous != stateInfo.Current {
 		err := state.Enter(params, data)
-		if errors.Is(err, &plugin.RetryError{}) {
+		var retryErr *plugin.RetryError
+		if errors.As(err, &retryErr) {
 			return result, err
 		}
 		if err != nil {