diff --git a/BitwardenShared/UI/Billing/BillingCoordinator.swift b/BitwardenShared/UI/Billing/BillingCoordinator.swift
index 7b07a319b4..a1326476c8 100644
--- a/BitwardenShared/UI/Billing/BillingCoordinator.swift
+++ b/BitwardenShared/UI/Billing/BillingCoordinator.swift
@@ -64,6 +64,8 @@ class BillingCoordinator: NSObject, Coordinator, HasStackNavigator {
             }
         case .premiumUpgradeComplete:
             showPremiumUpgradeComplete()
+        case .premiumUpgradeCompleteStandalone:
+            showPremiumUpgradeCompleteStandalone()
         case let .premiumPlan(subscription):
             showPremiumPlan(subscription: subscription)
         case .premiumUpgrade:
@@ -75,7 +77,10 @@ class BillingCoordinator: NSObject, Coordinator, HasStackNavigator {
 
     // MARK: Private Methods
 
-    /// Shows the Premium upgrade complete screen.
+    /// Shows the Premium upgrade complete screen on top of the currently-visible
+    /// `PremiumUpgradeView`, for the synchronous-confirm-while-upgrade-screen-is-open path. Use
+    /// `showPremiumUpgradeCompleteStandalone()` instead when no `PremiumUpgradeView` has been
+    /// shown in this coordinator instance.
     ///
     private func showPremiumUpgradeComplete() {
         premiumUpgradeCompleteOnClose = isUpgradeAsModalRoot
@@ -94,6 +99,21 @@ class BillingCoordinator: NSObject, Coordinator, HasStackNavigator {
         stackNavigator?.present(view)
     }
 
+    /// Shows the Premium upgrade complete screen as the sole content of this coordinator's
+    /// stack, with no `PremiumUpgradeView` shown first. Use this when a Premium upgrade
+    /// resolves outside of the upgrade screen itself — e.g. a "Sync Now" retry succeeding after
+    /// the upgrade screen has already been dismissed — so `.dismiss` can simply close the whole
+    /// modal without any `isUpgradeAsModalRoot`/Settings-plan branching.
+    ///
+    private func showPremiumUpgradeCompleteStandalone() {
+        let processor = PremiumUpgradeCompleteProcessor(
+            coordinator: asAnyCoordinator(),
+            services: services,
+        )
+        let view = PremiumUpgradeCompleteView(store: Store(processor: processor))
+        stackNavigator?.replace(view)
+    }
+
     /// Shows the Premium plan screen.
     ///
     /// - Parameter subscription: An already-fetched subscription; pass `nil` to let the plan screen fetch it.
diff --git a/BitwardenShared/UI/Billing/BillingCoordinatorTests.swift b/BitwardenShared/UI/Billing/BillingCoordinatorTests.swift
index 4dab363ad0..4665cd7d30 100644
--- a/BitwardenShared/UI/Billing/BillingCoordinatorTests.swift
+++ b/BitwardenShared/UI/Billing/BillingCoordinatorTests.swift
@@ -117,6 +117,34 @@ struct BillingCoordinatorTests {
         #expect(action.view is PremiumUpgradeCompleteView)
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeCompleteStandalone` replaces the stack's root with the
+    /// Premium upgrade complete view, rather than presenting it as a child of an existing screen.
+    @Test
+    func navigate_premiumUpgradeCompleteStandalone() throws {
+        subject.navigate(to: .premiumUpgradeCompleteStandalone)
+
+        #expect(stackNavigator.actions.count == 1)
+        let action = try #require(stackNavigator.actions.last)
+        #expect(action.type == .replaced)
+        #expect(action.view is PremiumUpgradeCompleteView)
+    }
+
+    /// `navigate(to:)` with `.dismiss` after `.premiumUpgradeCompleteStandalone` dismisses the
+    /// entire modal directly, without any of the modal-root/settings-context branching that
+    /// `.premiumUpgradeComplete` needs.
+    @Test
+    func navigate_dismiss_afterPremiumUpgradeCompleteStandalone() throws {
+        subject.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator.actions.removeAll()
+
+        stackNavigator.isPresenting = false
+        // viewControllersToPop is empty by default, so pop() returns nil.
+        subject.navigate(to: .dismiss)
+
+        let action = try #require(stackNavigator.actions.last)
+        #expect(action.type == .dismissed)
+    }
+
     /// `navigate(to:)` with `.premiumPlan` pushes the Premium plan view.
     @Test
     func navigate_premiumPlan() throws {
diff --git a/BitwardenShared/UI/Billing/BillingRoute.swift b/BitwardenShared/UI/Billing/BillingRoute.swift
index afb0cbc5fb..fff343b93f 100644
--- a/BitwardenShared/UI/Billing/BillingRoute.swift
+++ b/BitwardenShared/UI/Billing/BillingRoute.swift
@@ -14,4 +14,10 @@ enum BillingRoute: Equatable {
 
     /// A route to the Premium upgrade complete screen.
     case premiumUpgradeComplete
+
+    /// A route to the Premium upgrade complete screen, presented as the sole content of a
+    /// freshly-created modal (no `PremiumUpgradeView` shown first in this coordinator instance).
+    /// Used when a Premium upgrade resolves outside of the upgrade screen itself — e.g. a
+    /// "Sync Now" retry succeeding after the upgrade screen has already been dismissed.
+    case premiumUpgradeCompleteStandalone
 }
diff --git a/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift b/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
index b0d6a72d11..82943feb17 100644
--- a/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
+++ b/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
@@ -11,6 +11,11 @@ protocol PremiumUpgradeRoute {
     /// The route to the Premium upgrade screen.
     static var premiumUpgrade: Self { get }
 
+    /// The route to a standalone Premium upgrade complete screen, shown when an upgrade
+    /// resolves outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after
+    /// the upgrade screen has already been dismissed).
+    static var premiumUpgradeComplete: Self { get }
+
     /// The route to dismiss the current screen with an optional action.
     ///
     /// - Parameter action: The action to perform on dismiss.
@@ -24,6 +29,39 @@ extension SettingsRoute: PremiumUpgradeRoute {}
 extension VaultItemRoute: PremiumUpgradeRoute {}
 extension VaultRoute: PremiumUpgradeRoute {}
 
+// MARK: - PremiumUpgradeRetry
+
+/// Shared logic for the two explicit, user-initiated "retry the pending upgrade's sync" entry
+/// points — the "Sync Now" button on the upgrade pending alert, and "Try Again" on the "Sync
+/// unsuccessful" alert — so both react identically to the retry actually resolving the upgrade.
+///
+enum PremiumUpgradeRetry {
+    /// Calls `retry`, then, if the pending upgrade resolved successfully (no longer pending, and
+    /// the retry itself didn't fail), navigates to the standalone Premium upgrade complete
+    /// screen. A still-pending (not yet Premium) or still-failed outcome gets no further UI
+    /// here — the CTA and the "Sync unsuccessful" alert already react to those independently via
+    /// the durable `premiumUpgradePendingStatePublisher()` signal.
+    ///
+    /// - Parameters:
+    ///   - billingService: The service used to check the resulting state after `retry` runs.
+    ///   - coordinator: The coordinator to navigate on success.
+    ///   - retry: The retry action to perform — `reconcileCheckoutSuccess()` for the "Sync Now"
+    ///     alert, `premiumStatusChanged()` for the "Sync unsuccessful" alert's "Try Again".
+    ///
+    @MainActor
+    static func retryAndShowCompleteIfResolved<Route: PremiumUpgradeRoute, Event>(
+        billingService: BillingService,
+        coordinator: any Coordinator<Route, Event>,
+        retry: () async -> Void,
+    ) async {
+        await retry()
+        let state = await billingService.premiumUpgradePendingState()
+        if !state.isPending, !state.lastAttemptFailed {
+            coordinator.navigate(to: .premiumUpgradeComplete)
+        }
+    }
+}
+
 // MARK: - PremiumUpgradeHelper
 
 /// A helper that centralizes the Premium upgrade navigation flow.
@@ -157,12 +195,22 @@ class DefaultPremiumUpgradeHelper<Route: PremiumUpgradeRoute, Event>: PremiumUpg
     // MARK: Private Methods
 
     /// Calls `onPendingDismiss`, then shows the upgrade pending alert with "Sync Now" wired to
-    /// `reconcileCheckoutSuccess()`.
+    /// `reconcileCheckoutSuccess()` — navigating to the standalone Premium upgrade complete
+    /// screen if the retry actually resolves the upgrade. A still-pending (not yet Premium) or
+    /// still-failed outcome gets no further UI here: the CTA and the "Sync unsuccessful" alert
+    /// already react to those independently via the durable `premiumUpgradePendingStatePublisher()`
+    /// signal.
     ///
     private func showUpgradePendingAlert() {
         onPendingDismiss?()
         coordinator.showAlert(.upgradePending { [weak self] in
-            await self?.services.billingService.reconcileCheckoutSuccess()
+            guard let self else { return }
+            await PremiumUpgradeRetry.retryAndShowCompleteIfResolved(
+                billingService: services.billingService,
+                coordinator: coordinator,
+            ) {
+                await self.services.billingService.reconcileCheckoutSuccess()
+            }
         })
     }
 
diff --git a/BitwardenShared/UI/Billing/PremiumUpgradeHelperTests.swift b/BitwardenShared/UI/Billing/PremiumUpgradeHelperTests.swift
index bb699d77e2..d977448e8f 100644
--- a/BitwardenShared/UI/Billing/PremiumUpgradeHelperTests.swift
+++ b/BitwardenShared/UI/Billing/PremiumUpgradeHelperTests.swift
@@ -370,6 +370,54 @@ struct PremiumUpgradeHelperTests { // swiftlint:disable:this type_body_length
         }) == 1)
     }
 
+    /// Tapping "Sync Now" on the upgrade pending alert navigates to the standalone Premium
+    /// upgrade complete screen only when the retry actually resolves the pending upgrade — not
+    /// when it's still pending (not yet Premium) or the retry itself failed, both of which are
+    /// covered by PR2's CTA and PR3's "Sync unsuccessful" alert independently, via the durable
+    /// `premiumUpgradePendingStatePublisher()` signal.
+    @Test(arguments: [
+        (PremiumUpgradePendingState(isPending: false, lastAttemptFailed: false), true),
+        (PremiumUpgradePendingState(isPending: true, lastAttemptFailed: false), false),
+        (PremiumUpgradePendingState(isPending: true, lastAttemptFailed: true), false),
+        (PremiumUpgradePendingState(isPending: false, lastAttemptFailed: true), false),
+    ])
+    func subscribeToPremiumCheckoutStatus_pending_syncNow(
+        pendingState: PremiumUpgradePendingState,
+        expectedNavigatesToComplete: Bool,
+    ) async throws {
+        billingRepository.isInAppUpgradeAvailableReturnValue = true
+        let statusSubject = PassthroughSubject<PremiumCheckoutStatus, Never>()
+        billingService.premiumCheckoutStatusPublisherReturnValue = statusSubject.eraseToAnyPublisher()
+        // Not pending yet for `startInAppPremiumUpgrade`'s own already-pending check, so it
+        // navigates to `.premiumUpgrade` normally; `pendingState` only reflects the result of the
+        // "Sync Now" retry itself, checked afterward.
+        billingService.premiumUpgradePendingStateReturnValue = PremiumUpgradePendingState(
+            isPending: false,
+            lastAttemptFailed: false,
+        )
+        let subject = makeSubject()
+        await subject.navigateToPremiumUpgrade()
+        try await waitForAsync { coordinator.routes.last == .premiumUpgrade }
+
+        statusSubject.send(.pending)
+        try await waitForAsync {
+            guard case let .dismiss(action) = coordinator.routes.last else { return false }
+            return action != nil
+        }
+        guard case let .dismiss(action) = coordinator.routes.last else {
+            Issue.record("Expected .dismiss route")
+            return
+        }
+        billingService.premiumUpgradePendingStateReturnValue = pendingState
+        action?.action()
+
+        let alert = try #require(coordinator.alertShown.last)
+        try await alert.tapAction(title: Localizations.syncNow)
+
+        #expect(billingService.reconcileCheckoutSuccessCalled)
+        #expect((coordinator.routes.last == .premiumUpgradeComplete) == expectedNavigatesToComplete)
+    }
+
     /// When the billing service emits `.syncing`, nothing happens (the loading overlay is shown
     /// by `PremiumUpgradeProcessor`).
     @Test
@@ -396,4 +444,4 @@ struct PremiumUpgradeHelperTests { // swiftlint:disable:this type_body_length
 
         #expect(coordinator.routes.count == routeCountBeforeSend)
     }
-}
+} // swiftlint:disable:this file_length
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift b/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
index ef71195967..b1276f4087 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
@@ -210,6 +210,8 @@ final class SettingsCoordinator: Coordinator, HasStackNavigator { // swiftlint:d
             showPremiumPlan(subscription: subscription)
         case .premiumUpgrade:
             showPremiumUpgrade()
+        case .premiumUpgradeComplete:
+            showPremiumUpgradeCompleteScreen()
         case let .selectLanguage(currentLanguage: currentLanguage):
             showSelectLanguage(currentLanguage: currentLanguage, delegate: context as? SelectLanguageDelegate)
         case let .settings(presentationMode):
@@ -518,6 +520,25 @@ final class SettingsCoordinator: Coordinator, HasStackNavigator { // swiftlint:d
         coordinator.navigate(to: .premiumUpgrade)
     }
 
+    /// Shows a standalone Premium upgrade complete screen, for when an upgrade resolves outside
+    /// of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the upgrade screen
+    /// has already been dismissed). Unlike `showPremiumUpgrade()`, this presents its own fresh
+    /// modal rather than pushing onto Settings' existing stack, matching every other origin
+    /// screen's treatment of this same screen.
+    ///
+    private func showPremiumUpgradeCompleteScreen() {
+        // Unlike every other origin, Settings pushes `PremiumUpgradeView` (rather than
+        // presenting it as a fresh modal root) — reaching this method always means it's still
+        // the top of this stack, since nothing else pops it. Pop it before presenting the
+        // celebration so closing the celebration reveals the real Settings screen underneath,
+        // not a now-stale "Upgrade now" screen that has no way to notice premium was granted.
+        stackNavigator?.pop(animated: false)
+        let navigationController = module.makeNavigationController()
+        let coordinator = module.makeBillingCoordinator(stackNavigator: navigationController)
+        coordinator.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator?.present(navigationController)
+    }
+
     /// Shows the select language screen.
     ///
     private func showSelectLanguage(
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift b/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
index 52582e9976..6b88fdf904 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
@@ -400,6 +400,20 @@ class SettingsCoordinatorTests: BitwardenTestCase { // swiftlint:disable:this ty
         XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgrade])
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeComplete` pops the pushed Premium upgrade screen —
+    /// unlike every other origin, Settings pushes rather than presents it, so it's otherwise
+    /// still visible underneath the celebration and never re-checks premium status on its own —
+    /// then presents a standalone Premium upgrade complete screen via the billing coordinator.
+    @MainActor
+    func test_navigateTo_premiumUpgradeComplete() throws {
+        subject.navigate(to: .premiumUpgradeComplete)
+
+        XCTAssertEqual(stackNavigator.actions.count, 2)
+        XCTAssertEqual(stackNavigator.actions[0].type, .popped)
+        XCTAssertEqual(stackNavigator.actions[1].type, .presented)
+        XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgradeCompleteStandalone])
+    }
+
     /// `navigate(to:)` with `.selectLanguage()` presents the select language view.
     @MainActor
     func test_navigateTo_selectLanguage() throws {
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift b/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
index 2a54a51feb..713fadbed3 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
@@ -80,6 +80,11 @@ public enum SettingsRoute: Equatable, Hashable {
     /// A route to the Premium upgrade screen.
     case premiumUpgrade
 
+    /// A route to a standalone Premium upgrade complete screen, shown when an upgrade resolves
+    /// outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the
+    /// upgrade screen has already been dismissed).
+    case premiumUpgradeComplete
+
     /// A route to view the select language view.
     ///
     /// - Parameter currentLanguage: The currently selected language option.
diff --git a/BitwardenShared/UI/Tools/Send/Send/SendCoordinator.swift b/BitwardenShared/UI/Tools/Send/Send/SendCoordinator.swift
index 2749978b4f..c9843c2829 100644
--- a/BitwardenShared/UI/Tools/Send/Send/SendCoordinator.swift
+++ b/BitwardenShared/UI/Tools/Send/Send/SendCoordinator.swift
@@ -87,6 +87,8 @@ final class SendCoordinator: Coordinator, HasStackNavigator {
             showList()
         case .premiumUpgrade:
             showPremiumUpgrade()
+        case .premiumUpgradeComplete:
+            showPremiumUpgradeCompleteScreen()
         case let .share(url):
             showShareSheet(for: [url])
         case let .viewItem(sendView):
@@ -169,6 +171,17 @@ final class SendCoordinator: Coordinator, HasStackNavigator {
         stackNavigator?.present(navigationController)
     }
 
+    /// Shows a standalone Premium upgrade complete screen, for when an upgrade resolves outside
+    /// of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the upgrade screen
+    /// has already been dismissed).
+    ///
+    private func showPremiumUpgradeCompleteScreen() {
+        let navigationController = module.makeNavigationController()
+        let coordinator = module.makeBillingCoordinator(stackNavigator: navigationController)
+        coordinator.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator?.present(navigationController)
+    }
+
     /// Presents the system share sheet for the specified items.
     ///
     /// - Parameter items: The items to share using the system share sheet.
diff --git a/BitwardenShared/UI/Tools/Send/Send/SendCoordinatorTests.swift b/BitwardenShared/UI/Tools/Send/Send/SendCoordinatorTests.swift
index 7428319896..672e2d5153 100644
--- a/BitwardenShared/UI/Tools/Send/Send/SendCoordinatorTests.swift
+++ b/BitwardenShared/UI/Tools/Send/Send/SendCoordinatorTests.swift
@@ -166,6 +166,18 @@ class SendCoordinatorTests: BitwardenTestCase {
         XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgrade])
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeComplete` presents a standalone Premium upgrade
+    /// complete screen via the billing coordinator.
+    @MainActor
+    func test_navigateTo_premiumUpgradeComplete() throws {
+        subject.navigate(to: .premiumUpgradeComplete)
+
+        let action = try XCTUnwrap(stackNavigator.actions.last)
+        XCTAssertEqual(action.type, .presented)
+        XCTAssertTrue(action.view is UINavigationController)
+        XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgradeCompleteStandalone])
+    }
+
     /// `navigate(to:)` with `.share` presents the share sheet.
     @MainActor
     func test_navigateTo_share() throws {
diff --git a/BitwardenShared/UI/Tools/Send/Send/SendRoute.swift b/BitwardenShared/UI/Tools/Send/Send/SendRoute.swift
index bfa1cd96a1..beb6592e0d 100644
--- a/BitwardenShared/UI/Tools/Send/Send/SendRoute.swift
+++ b/BitwardenShared/UI/Tools/Send/Send/SendRoute.swift
@@ -31,6 +31,11 @@ public enum SendRoute: Equatable {
     /// A route to the Premium upgrade screen.
     case premiumUpgrade
 
+    /// A route to a standalone Premium upgrade complete screen, shown when an upgrade resolves
+    /// outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the
+    /// upgrade screen has already been dismissed).
+    case premiumUpgradeComplete
+
     /// A route to share the provided URL.
     ///
     /// - Parameter url: The `URL` to share.
diff --git a/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinator.swift b/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinator.swift
index b2abb0bdb9..dd78ce5f6d 100644
--- a/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinator.swift
+++ b/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinator.swift
@@ -106,6 +106,8 @@ final class SendItemCoordinator: Coordinator, HasStackNavigator, ProfileSwitcher
             showGenerator(delegate: delegate)
         case .premiumUpgrade:
             showPremiumUpgrade()
+        case .premiumUpgradeComplete:
+            showPremiumUpgradeCompleteScreen()
         case let .share(url):
             showShareSheet(for: [url])
         case let .view(sendView):
@@ -236,6 +238,17 @@ final class SendItemCoordinator: Coordinator, HasStackNavigator, ProfileSwitcher
         stackNavigator?.present(navigationController)
     }
 
+    /// Shows a standalone Premium upgrade complete screen, for when an upgrade resolves outside
+    /// of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the upgrade screen
+    /// has already been dismissed).
+    ///
+    private func showPremiumUpgradeCompleteScreen() {
+        let navigationController = module.makeNavigationController()
+        let coordinator = module.makeBillingCoordinator(stackNavigator: navigationController)
+        coordinator.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator?.present(navigationController)
+    }
+
     /// Presents the system share sheet for the specified items.
     ///
     /// - Parameter items: The items to share using the system share sheet.
diff --git a/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinatorTests.swift b/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinatorTests.swift
index 37e49815b3..e0396ecf5a 100644
--- a/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinatorTests.swift
+++ b/BitwardenShared/UI/Tools/Send/SendItem/SendItemCoordinatorTests.swift
@@ -209,6 +209,17 @@ class SendItemCoordinatorTests: BitwardenTestCase {
         XCTAssertNil(stackNavigator.actions.last)
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeComplete` presents a standalone Premium upgrade
+    /// complete screen via the billing coordinator.
+    @MainActor
+    func test_navigateTo_premiumUpgradeComplete() throws {
+        subject.navigate(to: .premiumUpgradeComplete)
+
+        let action = try XCTUnwrap(stackNavigator.actions.last)
+        XCTAssertEqual(action.type, .presented)
+        XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgradeCompleteStandalone])
+    }
+
     /// `navigate(to:)` with `.view` shows the view send screen.
     @MainActor
     func test_navigateTo_view() throws {
diff --git a/BitwardenShared/UI/Tools/Send/SendItem/SendItemRoute.swift b/BitwardenShared/UI/Tools/Send/SendItem/SendItemRoute.swift
index a29c8c7c6c..8e4e0cb97c 100644
--- a/BitwardenShared/UI/Tools/Send/SendItem/SendItemRoute.swift
+++ b/BitwardenShared/UI/Tools/Send/SendItem/SendItemRoute.swift
@@ -65,6 +65,11 @@ public enum SendItemRoute: Equatable, Hashable {
     /// A route to the Premium upgrade screen.
     case premiumUpgrade
 
+    /// A route to a standalone Premium upgrade complete screen, shown when an upgrade resolves
+    /// outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the
+    /// upgrade screen has already been dismissed).
+    case premiumUpgradeComplete
+
     /// A route to share the provided URL.
     ///
     /// - Parameter url: The `URL` to share.
diff --git a/BitwardenShared/UI/Vault/Vault/VaultCoordinator.swift b/BitwardenShared/UI/Vault/Vault/VaultCoordinator.swift
index c554d04890..8f9b5b6b9b 100644
--- a/BitwardenShared/UI/Vault/Vault/VaultCoordinator.swift
+++ b/BitwardenShared/UI/Vault/Vault/VaultCoordinator.swift
@@ -269,6 +269,8 @@ final class VaultCoordinator: Coordinator, HasStackNavigator { // swiftlint:disa
             delegate?.switchToSettingsTab(route: .premiumPlan(nil))
         case .premiumUpgrade:
             showPremiumUpgrade()
+        case .premiumUpgradeComplete:
+            showPremiumUpgradeCompleteScreen()
         case let .vaultItemSelection(totpKeyModel):
             showVaultItemSelection(totpKeyModel: totpKeyModel)
         case let .viewItem(id, masterPasswordRepromptCheckCompleted):
@@ -431,6 +433,17 @@ final class VaultCoordinator: Coordinator, HasStackNavigator { // swiftlint:disa
         stackNavigator?.present(navigationController)
     }
 
+    /// Shows a standalone Premium upgrade complete screen, for when an upgrade resolves outside
+    /// of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the upgrade screen
+    /// has already been dismissed).
+    ///
+    private func showPremiumUpgradeCompleteScreen() {
+        let navigationController = module.makeNavigationController()
+        let coordinator = module.makeBillingCoordinator(stackNavigator: navigationController)
+        coordinator.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator?.present(navigationController)
+    }
+
     /// Shows the vault list screen.
     ///
     private func showList() {
diff --git a/BitwardenShared/UI/Vault/Vault/VaultCoordinatorTests.swift b/BitwardenShared/UI/Vault/Vault/VaultCoordinatorTests.swift
index 23dceef66c..c06e012b46 100644
--- a/BitwardenShared/UI/Vault/Vault/VaultCoordinatorTests.swift
+++ b/BitwardenShared/UI/Vault/Vault/VaultCoordinatorTests.swift
@@ -413,6 +413,17 @@ class VaultCoordinatorTests: BitwardenTestCase { // swiftlint:disable:this type_
         XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgrade])
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeComplete` presents a standalone Premium upgrade
+    /// complete screen via the billing coordinator.
+    @MainActor
+    func test_navigateTo_premiumUpgradeComplete() throws {
+        subject.navigate(to: .premiumUpgradeComplete)
+
+        let action = try XCTUnwrap(stackNavigator.actions.last)
+        XCTAssertEqual(action.type, .presented)
+        XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgradeCompleteStandalone])
+    }
+
     /// `navigate(to:)` with `.switchAccount(userId:, isUnlocked: isUnlocked)`calls the associated delegate method.
     @MainActor
     func test_navigateTo_switchAccount() throws {
diff --git a/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessor.swift b/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessor.swift
index a78f74af0d..5211a16f69 100644
--- a/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessor.swift
+++ b/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessor.swift
@@ -763,7 +763,13 @@ extension VaultListProcessor {
                     // transition rather than a duplicate, or this explicit, user-initiated
                     // retry would fail with no feedback at all.
                     lastAttemptFailed = false
-                    await self?.services.billingService.premiumStatusChanged()
+                    guard let self else { return }
+                    await PremiumUpgradeRetry.retryAndShowCompleteIfResolved(
+                        billingService: services.billingService,
+                        coordinator: coordinator,
+                    ) {
+                        await self.services.billingService.premiumStatusChanged()
+                    }
                 })
             }
             lastAttemptFailed = pendingState.lastAttemptFailed
diff --git a/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessorTests.swift b/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessorTests.swift
index dab1da89ae..865efc71b0 100644
--- a/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessorTests.swift
+++ b/BitwardenShared/UI/Vault/Vault/VaultList/VaultListProcessorTests.swift
@@ -1321,6 +1321,10 @@ class VaultListProcessorTests: BitwardenTestCase { // swiftlint:disable:this typ
             PremiumUpgradePendingState(isPending: true, lastAttemptFailed: true),
         )
         billingService.premiumUpgradePendingStatePublisherReturnValue = pendingStateSubject.eraseToAnyPublisher()
+        billingService.premiumUpgradePendingStateReturnValue = PremiumUpgradePendingState(
+            isPending: true,
+            lastAttemptFailed: false,
+        )
 
         let task = Task {
             await subject.perform(.streamPremiumUpgradePendingState)
@@ -1334,6 +1338,41 @@ class VaultListProcessorTests: BitwardenTestCase { // swiftlint:disable:this typ
             try await alert.tapAction(title: Localizations.tryAgain)
         }
         waitFor(billingService.premiumStatusChangedCallsCount == 1)
+
+        // Still pending (not yet Premium) — no celebration screen, matching "Sync Now"'s own
+        // still-pending boundary.
+        XCTAssertNotEqual(coordinator.routes.last, .premiumUpgradeComplete)
+    }
+
+    /// `perform(_:)` with `.streamPremiumUpgradePendingState` navigates to the standalone Premium
+    /// upgrade complete screen when the user's own "Try again" retry actually resolves the
+    /// pending upgrade — matching "Sync Now"'s own behavior on the pending alert, so the two
+    /// explicit retry entry points behave identically.
+    @MainActor
+    func test_perform_streamPremiumUpgradePendingState_syncUnsuccessfulAlert_tryAgainResolves() throws {
+        let pendingStateSubject = CurrentValueSubject<PremiumUpgradePendingState, Never>(
+            PremiumUpgradePendingState(isPending: true, lastAttemptFailed: true),
+        )
+        billingService.premiumUpgradePendingStatePublisherReturnValue = pendingStateSubject.eraseToAnyPublisher()
+        billingService.premiumUpgradePendingStateReturnValue = PremiumUpgradePendingState(
+            isPending: false,
+            lastAttemptFailed: false,
+        )
+
+        let task = Task {
+            await subject.perform(.streamPremiumUpgradePendingState)
+        }
+        defer { task.cancel() }
+
+        waitFor(!coordinator.alertShown.isEmpty)
+        let alert = try XCTUnwrap(coordinator.alertShown.last)
+
+        Task {
+            try await alert.tapAction(title: Localizations.tryAgain)
+        }
+        waitFor(coordinator.routes.last == .premiumUpgradeComplete)
+
+        XCTAssertEqual(billingService.premiumStatusChangedCallsCount, 1)
     }
 
     /// `perform(_:)` with `.streamPremiumUpgradePendingState` re-shows the "Sync Unsuccessful"
@@ -1345,6 +1384,10 @@ class VaultListProcessorTests: BitwardenTestCase { // swiftlint:disable:this typ
             PremiumUpgradePendingState(isPending: true, lastAttemptFailed: true),
         )
         billingService.premiumUpgradePendingStatePublisherReturnValue = pendingStateSubject.eraseToAnyPublisher()
+        billingService.premiumUpgradePendingStateReturnValue = PremiumUpgradePendingState(
+            isPending: true,
+            lastAttemptFailed: true,
+        )
         billingService.premiumStatusChangedClosure = {
             pendingStateSubject.send(PremiumUpgradePendingState(isPending: true, lastAttemptFailed: true))
         }
@@ -1363,6 +1406,7 @@ class VaultListProcessorTests: BitwardenTestCase { // swiftlint:disable:this typ
         waitFor(coordinator.alertShown.count == 2)
 
         XCTAssertEqual(coordinator.alertShown.last?.title, Localizations.syncUnsuccessful)
+        XCTAssertNotEqual(coordinator.routes.last, .premiumUpgradeComplete)
     }
 
     /// `perform(_:)` with `.streamShowWebIcons` requests the value of the show
diff --git a/BitwardenShared/UI/Vault/Vault/VaultRoute.swift b/BitwardenShared/UI/Vault/Vault/VaultRoute.swift
index bccb72e461..76750ed4bd 100644
--- a/BitwardenShared/UI/Vault/Vault/VaultRoute.swift
+++ b/BitwardenShared/UI/Vault/Vault/VaultRoute.swift
@@ -77,6 +77,11 @@ public enum VaultRoute: Equatable, Hashable {
     /// A route to the Premium upgrade view.
     case premiumUpgrade
 
+    /// A route to a standalone Premium upgrade complete screen, shown when an upgrade resolves
+    /// outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the
+    /// upgrade screen has already been dismissed).
+    case premiumUpgradeComplete
+
     /// A route to switch accounts.
     ///
     /// - Parameter userId: The user id of the selected account.
diff --git a/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinator.swift b/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinator.swift
index 7eeaf3e26b..fea8dd7f7a 100644
--- a/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinator.swift
+++ b/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinator.swift
@@ -143,6 +143,8 @@ class VaultItemCoordinator: NSObject, Coordinator, HasStackNavigator { // swiftl
             showPasswordHistory(passwordHistory)
         case .premiumUpgrade:
             showPremiumUpgrade()
+        case .premiumUpgradeComplete:
+            showPremiumUpgradeCompleteScreen()
         case let .saveFile(temporaryUrl):
             showSaveFile(temporaryUrl)
         case .setupTotpManual:
@@ -462,6 +464,17 @@ class VaultItemCoordinator: NSObject, Coordinator, HasStackNavigator { // swiftl
         stackNavigator?.present(navigationController)
     }
 
+    /// Shows a standalone Premium upgrade complete screen, for when an upgrade resolves outside
+    /// of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the upgrade screen
+    /// has already been dismissed).
+    ///
+    private func showPremiumUpgradeCompleteScreen() {
+        let navigationController = module.makeNavigationController()
+        let coordinator = module.makeBillingCoordinator(stackNavigator: navigationController)
+        coordinator.navigate(to: .premiumUpgradeCompleteStandalone)
+        stackNavigator?.present(navigationController)
+    }
+
     /// Present the `UIDocumentPickerViewController` that allows users to save the newly downloaded file.
     ///
     /// - Parameter temporaryUrl: The temporary url where the file is currently stored.
diff --git a/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinatorTests.swift b/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinatorTests.swift
index 3691ee813c..4a13176e80 100644
--- a/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinatorTests.swift
+++ b/BitwardenShared/UI/Vault/VaultItem/VaultItemCoordinatorTests.swift
@@ -456,6 +456,17 @@ class VaultItemCoordinatorTests: BitwardenTestCase { // swiftlint:disable:this t
         XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgrade])
     }
 
+    /// `navigate(to:)` with `.premiumUpgradeComplete` presents a standalone Premium upgrade
+    /// complete screen via the billing coordinator.
+    @MainActor
+    func test_navigateTo_premiumUpgradeComplete() throws {
+        subject.navigate(to: .premiumUpgradeComplete)
+
+        let action = try XCTUnwrap(stackNavigator.actions.last)
+        XCTAssertEqual(action.type, .presented)
+        XCTAssertEqual(module.billingCoordinator.routes, [.premiumUpgradeCompleteStandalone])
+    }
+
     /// `navigate(to:)` with `.setupTotpCamera` with context without conformance fails to present.
     @MainActor
     func test_navigateTo_setupTotpCamera_noConformance() async throws {
diff --git a/BitwardenShared/UI/Vault/VaultItem/VaultItemRoute.swift b/BitwardenShared/UI/Vault/VaultItem/VaultItemRoute.swift
index 05b9fca649..befaecf781 100644
--- a/BitwardenShared/UI/Vault/VaultItem/VaultItemRoute.swift
+++ b/BitwardenShared/UI/Vault/VaultItem/VaultItemRoute.swift
@@ -88,6 +88,11 @@ enum VaultItemRoute: Equatable, Hashable {
     /// A route to the Premium upgrade screen.
     case premiumUpgrade
 
+    /// A route to a standalone Premium upgrade complete screen, shown when an upgrade resolves
+    /// outside of the upgrade screen itself (e.g. a "Sync Now" retry succeeding after the
+    /// upgrade screen has already been dismissed).
+    case premiumUpgradeComplete
+
     /// A route to the file saving view.
     ///
     /// - Parameter temporaryUrl: The url where the file is currently stored.