diff --git a/cmd/wfctl/infra_apply.go b/cmd/wfctl/infra_apply.go
index 460339e9..b0ea009d 100644
--- a/cmd/wfctl/infra_apply.go
+++ b/cmd/wfctl/infra_apply.go
@@ -843,7 +843,16 @@ func isIaCNotFound(err error) bool {
 		return true
 	}
 	var platformNotFound *platform.ResourceNotFoundError
-	return errors.As(err, &platformNotFound)
+	if errors.As(err, &platformNotFound) {
+		return true
+	}
+	// gRPC fallback: typed adapter loses sentinel identity across the
+	// wire. The message survives as a wrapped string. Match on the
+	// literal ErrResourceNotFound.Error() value so adoption can still
+	// detect "not present yet, fall back to create" against remote
+	// plugin drivers (workflow-plugin-digitalocean v2+ database
+	// adoption is the original repro path).
+	return strings.Contains(err.Error(), interfaces.ErrResourceNotFound.Error())
 }
 
 func resourceStateFromLiveOutput(spec interfaces.ResourceSpec, providerType string, live *interfaces.ResourceOutput) (interfaces.ResourceState, error) {
diff --git a/cmd/wfctl/infra_apply_isiacnotfound_test.go b/cmd/wfctl/infra_apply_isiacnotfound_test.go
new file mode 100644
index 00000000..ccbebbef
--- /dev/null
+++ b/cmd/wfctl/infra_apply_isiacnotfound_test.go
@@ -0,0 +1,41 @@
+package main
+
+import (
+	"errors"
+	"fmt"
+	"testing"
+
+	"github.com/GoCodeAlone/workflow/interfaces"
+)
+
+// TestIsIaCNotFound_TypedSentinel confirms native wrapping still works.
+func TestIsIaCNotFound_TypedSentinel(t *testing.T) {
+	err := fmt.Errorf("database %q: %w", "multisite-pg", interfaces.ErrResourceNotFound)
+	if !isIaCNotFound(err) {
+		t.Error("expected typed sentinel to be detected")
+	}
+}
+
+// TestIsIaCNotFound_GRPCStringFallback is the regression test for the
+// gocodealone-multisite deploy: the typed gRPC adapter strips sentinel
+// identity, leaving only the wrapped error string. Adoption is meant
+// to be "look up, fall back to create" — without this fallback the
+// remote plugin's not-found returns made apply-prereq fail every run.
+func TestIsIaCNotFound_GRPCStringFallback(t *testing.T) {
+	grpcErr := errors.New(`rpc error: code = Unknown desc = database "multisite-pg": iac: resource not found`)
+	if !isIaCNotFound(grpcErr) {
+		t.Error("expected gRPC-flattened not-found to be detected via string match")
+	}
+}
+
+func TestIsIaCNotFound_NilSafe(t *testing.T) {
+	if isIaCNotFound(nil) {
+		t.Error("nil err must not be reported as not-found")
+	}
+}
+
+func TestIsIaCNotFound_OtherErrorsIgnored(t *testing.T) {
+	if isIaCNotFound(errors.New("permission denied")) {
+		t.Error("non-matching error must not be reported as not-found")
+	}
+}