diff --git a/TableProTests/Core/Storage/ConnectionStorageSyncDeleteTests.swift b/TableProTests/Core/Storage/ConnectionStorageSyncDeleteTests.swift
new file mode 100644
index 000000000..f1616eb64
--- /dev/null
+++ b/TableProTests/Core/Storage/ConnectionStorageSyncDeleteTests.swift
@@ -0,0 +1,58 @@
+//
+//  ConnectionStorageSyncDeleteTests.swift
+//  TableProTests
+//
+
+import Foundation
+import TableProPluginKit
+import Testing
+
+@testable import TablePro
+
+@Suite("ConnectionStorage sync delete ordering")
+@MainActor
+struct ConnectionStorageSyncDeleteTests {
+    private let storage: ConnectionStorage
+    private let metadata: SyncMetadataStorage
+    private let storageDirectory: URL
+
+    init() {
+        let unique = UUID().uuidString
+        let fileURL = FileManager.default.temporaryDirectory
+            .appendingPathComponent("tablepro-tests")
+            .appendingPathComponent("connections_\(unique).json")
+        storageDirectory = fileURL.deletingLastPathComponent()
+        try? FileManager.default.createDirectory(at: storageDirectory, withIntermediateDirectories: true)
+
+        let defaults = UserDefaults(suiteName: "com.TablePro.tests.ConnectionStorage.\(unique)")!
+        let syncDefaults = UserDefaults(suiteName: "com.TablePro.tests.Sync.\(unique)")!
+        metadata = SyncMetadataStorage(userDefaults: syncDefaults)
+        storage = ConnectionStorage(
+            fileURL: fileURL,
+            userDefaults: defaults,
+            syncTracker: SyncChangeTracker(metadataStorage: metadata)
+        )
+    }
+
+    @Test("Deleting a connection records a sync tombstone after it is persisted")
+    func deleteRecordsTombstoneAfterPersisting() {
+        let connection = TestFixtures.makeConnection()
+        storage.addConnection(connection)
+        #expect(metadata.tombstones(for: .connection).isEmpty)
+
+        storage.deleteConnection(connection)
+
+        #expect(metadata.tombstones(for: .connection).contains { $0.id == connection.id.uuidString })
+    }
+
+    @Test("A delete that fails to persist records no tombstone (persist before notify)")
+    func failedPersistenceRecordsNoTombstone() {
+        let connection = TestFixtures.makeConnection()
+        storage.addConnection(connection)
+        try? FileManager.default.removeItem(at: storageDirectory)
+
+        storage.deleteConnection(connection)
+
+        #expect(metadata.tombstones(for: .connection).isEmpty)
+    }
+}