diff --git a/RELEASE-NOTES.txt b/RELEASE-NOTES.txt
index 0e39fbe3aec..ab768922c13 100644
--- a/RELEASE-NOTES.txt
+++ b/RELEASE-NOTES.txt
@@ -7,6 +7,7 @@
 - [Internal] Moved the request for push notification authorization after login [https://github.com/woocommerce/woocommerce-ios/pull/16428]
 - [Internal] Cleaned up logic for push notification token registration [https://github.com/woocommerce/woocommerce-ios/pull/16434]
 - [*] Fixed possible sync issue in POS (https://github.com/woocommerce/woocommerce-ios/pull/16423)
+- [*] Enabled site troubleshooting for users authenticated with site credentials [https://github.com/woocommerce/woocommerce-ios/pull/16441]
 
 23.8
 -----
diff --git a/WooCommerce/Classes/ViewRelated/Connectivity Tool/ConnectivityToolViewModel.swift b/WooCommerce/Classes/ViewRelated/Connectivity Tool/ConnectivityToolViewModel.swift
index 0daee2c642e..5120f3b7737 100644
--- a/WooCommerce/Classes/ViewRelated/Connectivity Tool/ConnectivityToolViewModel.swift	
+++ b/WooCommerce/Classes/ViewRelated/Connectivity Tool/ConnectivityToolViewModel.swift	
@@ -44,7 +44,14 @@ final class ConnectivityToolViewModel {
     ///
     private func startConnectivityTest(sinceTest: ConnectivityTest = .internetConnection) async {
 
-        for (index, testCase) in ConnectivityTest.allCases.enumerated().dropFirst(sinceTest.rawValue) {
+        let supportedTests: [ConnectivityTest] = {
+            if ServiceLocator.stores.isAuthenticatedWithoutWPCom == false {
+                [.internetConnection, .wpComServers, .site, .siteOrders]
+            } else {
+                [.internetConnection, .site, .siteOrders]
+            }
+        }()
+        for (index, testCase) in supportedTests.enumerated().dropFirst(sinceTest.rawValue) {
 
             // Add an inProgress card for the current test.
             cards.append(testCase.inProgressCard)
@@ -265,7 +272,7 @@ private extension ConnectivityToolViewModel {
         case readMore = "arrow.up.forward.app"
     }
 
-    enum ConnectivityTest: Int, CaseIterable {
+    enum ConnectivityTest: Int {
         case internetConnection
         case wpComServers
         case site
diff --git a/WooCommerce/Classes/ViewRelated/Dashboard/Settings/Settings/SettingsViewModel.swift b/WooCommerce/Classes/ViewRelated/Dashboard/Settings/Settings/SettingsViewModel.swift
index c85d6953834..b118dc67e1f 100644
--- a/WooCommerce/Classes/ViewRelated/Dashboard/Settings/Settings/SettingsViewModel.swift
+++ b/WooCommerce/Classes/ViewRelated/Dashboard/Settings/Settings/SettingsViewModel.swift
@@ -210,7 +210,6 @@ private extension SettingsViewModel {
             var rows: [Row] = []
 
             if stores.isAuthenticated,
-               stores.isAuthenticatedWithoutWPCom == false,
                stores.sessionManager.defaultSite?.isWordPressComStore == false {
                 rows.append(.connectivity)
             }
diff --git a/WooCommerce/WooCommerceTests/ViewRelated/Settings/SettingsViewModelTests.swift b/WooCommerce/WooCommerceTests/ViewRelated/Settings/SettingsViewModelTests.swift
index 01eb7b34352..634f905eeef 100644
--- a/WooCommerce/WooCommerceTests/ViewRelated/Settings/SettingsViewModelTests.swift
+++ b/WooCommerce/WooCommerceTests/ViewRelated/Settings/SettingsViewModelTests.swift
@@ -318,7 +318,7 @@ final class SettingsViewModelTests: XCTestCase {
         XCTAssertFalse(viewModel.sections.contains { $0.rows.contains(SettingsViewController.Row.connectivity) })
     }
 
-    func test_sections_does_not_contain_connectivity_row_if_user_authenticated_without_wpcom() {
+    func test_sections_contains_connectivity_row_if_user_authenticated_without_wpcom() {
         let testSite = Site.fake().copy(siteID: 123, isJetpackThePluginInstalled: true, isJetpackConnected: true, isWordPressComStore: false)
         let stores = MockStoresManager(sessionManager: .makeForTesting(authenticated: true, isWPCom: false, defaultSite: testSite))
         let viewModel = SettingsViewModel(stores: stores)
@@ -327,7 +327,7 @@ final class SettingsViewModelTests: XCTestCase {
         viewModel.onViewDidLoad()
 
         // Then
-        XCTAssertFalse(viewModel.sections.contains { $0.rows.contains(SettingsViewController.Row.connectivity) })
+        XCTAssertTrue(viewModel.sections.contains { $0.rows.contains(SettingsViewController.Row.connectivity) })
     }
 
     func test_sections_contains_connectivity_row_if_user_authenticated_with_wpcom_to_non_wpcom_site() {