diff --git a/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift b/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
index 413fd74db7..2a8c9ef765 100644
--- a/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
+++ b/BitwardenShared/UI/Billing/PremiumUpgradeHelper.swift
@@ -20,6 +20,7 @@ protocol PremiumUpgradeRoute {
 
 extension SendItemRoute: PremiumUpgradeRoute {}
 extension SendRoute: PremiumUpgradeRoute {}
+extension SettingsRoute: PremiumUpgradeRoute {}
 extension VaultItemRoute: PremiumUpgradeRoute {}
 extension VaultRoute: PremiumUpgradeRoute {}
 
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessor.swift b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessor.swift
index 2feb5e94b7..b7abec9d6c 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessor.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessor.swift
@@ -56,7 +56,7 @@ final class DeleteAccountProcessor: StateProcessor<DeleteAccountState, DeleteAcc
     override func receive(_ action: DeleteAccountAction) {
         switch action {
         case .dismiss:
-            coordinator.navigate(to: .dismiss)
+            coordinator.navigate(to: .dismiss())
         }
     }
 
@@ -158,7 +158,7 @@ final class DeleteAccountProcessor: StateProcessor<DeleteAccountState, DeleteAcc
                 try await services.authRepository.isUserManagedByOrganization()
         } catch {
             await coordinator.showErrorAlert(error: error, onDismissed: {
-                self.coordinator.navigate(to: .dismiss)
+                self.coordinator.navigate(to: .dismiss())
             })
             services.errorReporter.log(error: error)
         }
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessorTests.swift b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessorTests.swift
index 3c0f35642a..c5b36f37a8 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/DeleteAccount/DeleteAccountProcessorTests.swift
@@ -53,7 +53,7 @@ class DeleteAccountProcessorTests: BitwardenTestCase {
     func test_receive_dismiss() {
         subject.receive(.dismiss)
 
-        XCTAssertEqual(coordinator.routes.last, .dismiss)
+        XCTAssertEqual(coordinator.routes.last, .dismiss())
     }
 
     /// Perform with `.deleteAccount` presents the master password prompt alert.
@@ -307,6 +307,6 @@ class DeleteAccountProcessorTests: BitwardenTestCase {
 
         coordinator.alertOnDismissed?()
 
-        XCTAssertEqual(coordinator.routes.last, .dismiss)
+        XCTAssertEqual(coordinator.routes.last, .dismiss())
     }
 }
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessor.swift b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessor.swift
index 83516708d5..af9755372a 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessor.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessor.swift
@@ -66,7 +66,7 @@ final class PendingRequestsProcessor: StateProcessor<
         case .declineAllRequestsTapped:
             confirmDenyAllRequests()
         case .dismiss:
-            coordinator.navigate(to: .dismiss, context: self)
+            coordinator.navigate(to: .dismiss(), context: self)
         case let .requestTapped(request):
             coordinator.navigate(to: .loginRequest(request), context: self)
         case let .toastShown(newValue):
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessorTests.swift b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessorTests.swift
index 2cbb83cc33..c338d2660f 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/AccountSecurity/PendingRequests/PendingRequestsProcessorTests.swift
@@ -122,7 +122,7 @@ class PendingRequestsProcessorTests: BitwardenTestCase {
     @MainActor
     func test_receive_dismiss() {
         subject.receive(.dismiss)
-        XCTAssertEqual(coordinator.routes.last, .dismiss)
+        XCTAssertEqual(coordinator.routes.last, .dismiss())
     }
 
     /// `receive(_:)` with `.requestTapped(_)` shows the login request view.
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessor.swift b/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessor.swift
index 2c95f4fdf0..43706792b7 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessor.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessor.swift
@@ -21,8 +21,10 @@ protocol SettingsProcessorDelegate: AnyObject {
 final class SettingsProcessor: StateProcessor<SettingsState, SettingsAction, SettingsEffect> {
     // MARK: Types
 
-    typealias Services = HasBillingService
+    typealias Services = HasBillingRepository
+        & HasBillingService
         & HasConfigService
+        & HasEnvironmentService
         & HasErrorReporter
         & HasStateService
         & HasStorefrontService
@@ -39,6 +41,13 @@ final class SettingsProcessor: StateProcessor<SettingsState, SettingsAction, Set
     /// A delegate of the processor that is notified when the settings tab badge needs to be updated.
     private weak var delegate: SettingsProcessorDelegate?
 
+    /// The helper used to navigate to the Premium upgrade flow.
+    lazy var premiumUpgradeHelper: PremiumUpgradeHelper = DefaultPremiumUpgradeHelper(
+        services: services,
+        coordinator: coordinator,
+        setURL: { [weak self] url in self?.state.url = url },
+    )
+
     /// The services used by this processor.
     private var services: Services
 
@@ -126,7 +135,7 @@ final class SettingsProcessor: StateProcessor<SettingsState, SettingsAction, Set
         case .clearUrl:
             state.url = nil
         case .dismiss:
-            coordinator.navigate(to: .dismiss)
+            coordinator.navigate(to: .dismiss())
         case .learnMoreAboutPremium:
             state.url = ExternalLinksConstants.learnMoreAboutPremium
             state.shouldShowUpgradedToPremiumActionCard = false
@@ -156,10 +165,10 @@ final class SettingsProcessor: StateProcessor<SettingsState, SettingsAction, Set
             if subscription.status.isTroubleState {
                 coordinator.navigate(to: .premiumPlan(subscription))
             } else {
-                coordinator.navigate(to: .premiumUpgrade)
+                premiumUpgradeHelper.startInAppPremiumUpgrade(onConfirmed: nil)
             }
         } catch is GetSubscriptionRequestError {
-            coordinator.navigate(to: .premiumUpgrade)
+            premiumUpgradeHelper.startInAppPremiumUpgrade(onConfirmed: nil)
         } catch {
             services.errorReporter.log(error: error)
             await coordinator.showErrorAlert(error: error)
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessorTests.swift b/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessorTests.swift
index eeb933bbd6..bcfc57cbc8 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/SettingsProcessorTests.swift
@@ -17,6 +17,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
     var coordinator: MockCoordinator<SettingsRoute, SettingsEvent>!
     var delegate: MockSettingsProcessorDelegate!
     var errorReporter: MockErrorReporter!
+    var premiumUpgradeHelper: MockPremiumUpgradeHelper!
     var subject: SettingsProcessor!
     var stateService: MockStateService!
     var storefrontService: MockStorefrontService!
@@ -34,6 +35,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
         coordinator = MockCoordinator()
         delegate = MockSettingsProcessorDelegate()
         errorReporter = MockErrorReporter()
+        premiumUpgradeHelper = MockPremiumUpgradeHelper()
         stateService = MockStateService()
         storefrontService = MockStorefrontService()
         storefrontService.isUSStorefrontReturnValue = true
@@ -50,6 +52,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
         coordinator = nil
         delegate = nil
         errorReporter = nil
+        premiumUpgradeHelper = nil
         subject = nil
         stateService = nil
         storefrontService = nil
@@ -71,6 +74,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
             ),
             state: SettingsState(presentationMode: presentationMode),
         )
+        subject.premiumUpgradeHelper = premiumUpgradeHelper
     }
 
     // MARK: Tests
@@ -161,7 +165,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
     func test_receive_dismiss() {
         subject.receive(.dismiss)
 
-        XCTAssertEqual(coordinator.routes.last, .dismiss)
+        XCTAssertEqual(coordinator.routes.last, .dismiss())
     }
 
     /// Receiving `.otherPressed` navigates to the other screen.
@@ -221,7 +225,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
 
         await subject.perform(.planPressed)
 
-        XCTAssertEqual(coordinator.routes.last, .premiumUpgrade)
+        XCTAssertTrue(premiumUpgradeHelper.startInAppPremiumUpgradeCalled)
         XCTAssertEqual(coordinator.loadingOverlaysShown, [LoadingOverlayState(title: Localizations.loading)])
         XCTAssertFalse(errorReporter.errors.contains { $0 is GetSubscriptionRequestError })
     }
@@ -249,7 +253,7 @@ class SettingsProcessorTests: BitwardenTestCase { // swiftlint:disable:this type
 
         await subject.perform(.planPressed)
 
-        XCTAssertEqual(coordinator.routes.last, .premiumUpgrade)
+        XCTAssertTrue(premiumUpgradeHelper.startInAppPremiumUpgradeCalled)
         XCTAssertEqual(coordinator.loadingOverlaysShown, [LoadingOverlayState(title: Localizations.loading)])
     }
 
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessor.swift b/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessor.swift
index aee60dff6e..301f38525e 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessor.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessor.swift
@@ -64,7 +64,7 @@ final class ExportVaultProcessor: StateProcessor<ExportVaultState, ExportVaultAc
         switch action {
         case .dismiss:
             services.exportVaultService.clearTemporaryFiles()
-            coordinator.navigate(to: .dismiss)
+            coordinator.navigate(to: .dismiss())
         case let .fileFormatTypeChanged(fileFormat):
             state.fileFormat = fileFormat
         case let .filePasswordTextChanged(newValue):
diff --git a/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessorTests.swift b/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessorTests.swift
index f6c643e822..d6f9dd0d06 100644
--- a/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/Settings/Vault/ExportVault/ExportVaultToFile/ExportVaultProcessorTests.swift
@@ -125,7 +125,7 @@ class ExportVaultProcessorTests: BitwardenTestCase { // swiftlint:disable:this t
         subject.receive(.dismiss)
 
         XCTAssertTrue(exportService.didClearFiles)
-        XCTAssertEqual(coordinator.routes.last, .dismiss)
+        XCTAssertEqual(coordinator.routes.last, .dismiss())
     }
 
     /// `.receive()` with  `.exportVaultTapped` shows the confirm alert for encrypted formats and
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift b/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
index 187c777a5d..21f1f7aeb3 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsCoordinator.swift
@@ -69,6 +69,7 @@ final class SettingsCoordinator: Coordinator, HasStackNavigator { // swiftlint:d
         & HasAuthRepository
         & HasAuthService
         & HasAutofillCredentialService
+        & HasBillingRepository
         & HasBillingService
         & HasBiometricsRepository
         & HasConfigService
@@ -170,8 +171,16 @@ final class SettingsCoordinator: Coordinator, HasStackNavigator { // swiftlint:d
             showAutoFill()
         case .deleteAccount:
             showDeleteAccount()
-        case .dismiss:
-            stackNavigator?.dismiss()
+        case let .dismiss(action):
+            // If we're presenting a more complicated stack of view controllers (in particular, this could happen
+            // if the user navigates to the Premium upgrade flow) then we only want to dismiss the presented one,
+            // not the full stack.
+            let completion = action?.action
+            if let presentedViewController = stackNavigator?.rootViewController?.presentedViewController {
+                presentedViewController.dismiss(animated: UI.animated, completion: completion)
+            } else {
+                stackNavigator?.dismiss(completion: completion)
+            }
         case .exportVault:
             showExportVault()
         case .exportVaultToApp:
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift b/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
index 4f4e2c68f3..bf4ef826fe 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsCoordinatorTests.swift
@@ -169,10 +169,23 @@ class SettingsCoordinatorTests: BitwardenTestCase { // swiftlint:disable:this ty
     /// `navigate(to:)` with `.dismiss` dismisses the view.
     @MainActor
     func test_navigate_dismiss() throws {
-        subject.navigate(to: .dismiss)
+        subject.navigate(to: .dismiss())
 
         let action = try XCTUnwrap(stackNavigator.actions.last)
-        XCTAssertEqual(action.type, .dismissed)
+        XCTAssertEqual(action.type, .dismissedWithCompletionHandler)
+    }
+
+    /// `navigate(to:)` with `.dismiss` and a `DismissAction` passes the completion to the
+    /// underlying dismiss call and invokes it when dismissal completes.
+    @MainActor
+    func test_navigate_dismiss_withDismissAction() throws {
+        var completionCalled = false
+
+        subject.navigate(to: .dismiss(DismissAction { completionCalled = true }))
+
+        XCTAssertTrue(completionCalled)
+        let action = try XCTUnwrap(stackNavigator.actions.last)
+        XCTAssertEqual(action.type, .dismissedWithCompletionHandler)
     }
 
     /// `navigate(to:)` with `.exportVault` pushes the export settings view.
diff --git a/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift b/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
index d261a4957e..978361f2ee 100644
--- a/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
+++ b/BitwardenShared/UI/Platform/Settings/SettingsRoute.swift
@@ -33,7 +33,10 @@ public enum SettingsRoute: Equatable, Hashable {
     case deleteAccount
 
     /// A route that dismisses the current view.
-    case dismiss
+    ///
+    /// - Parameter action: The action to perform on dismiss.
+    ///
+    case dismiss(_ action: DismissAction? = nil)
 
     /// A route to the export vault settings view or export to file view depending on feature flag.
     case exportVault