diff --git a/RELEASE-NOTES.txt b/RELEASE-NOTES.txt
index 1b04183ffe8e..1074eb461074 100644
--- a/RELEASE-NOTES.txt
+++ b/RELEASE-NOTES.txt
@@ -9,6 +9,7 @@
 * [*] [internal] Editor: Only register core blocks when `onlyCoreBlocks` capability is enabled [https://github.com/wordpress-mobile/gutenberg-mobile/pull/5293]
 * [**] [internal] Disable StockPhoto and Tenor media sources when Jetpack features are removed [#19826]
 * [*] [Jetpack-only] Fixed a bug where analytics calls weren't synced to the user account. [#19926]
+* [*] [Jetpack-only] Fixed a bug where the Login flow was restarting every time the app enters the foreground. [#19961]
 
 21.4
 -----
diff --git a/WordPress/Classes/System/WindowManager.swift b/WordPress/Classes/System/WindowManager.swift
index 32611f2c51f0..721919743e9d 100644
--- a/WordPress/Classes/System/WindowManager.swift
+++ b/WordPress/Classes/System/WindowManager.swift
@@ -21,6 +21,12 @@ class WindowManager: NSObject {
     ///
     private(set) var isShowingFullscreenSignIn = false
 
+    /// The root view controller for the window.
+    ///
+    var rootViewController: UIViewController? {
+        return window.rootViewController
+    }
+
     init(window: UIWindow) {
         self.window = window
     }
diff --git a/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift b/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
index 5cd83b9ce774..373218cf54b9 100644
--- a/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
+++ b/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
@@ -139,11 +139,41 @@ private extension JetpackWindowManager {
             !hasFailedExportAttempts,
             let schemeUrl = URL(string: "\(AppScheme.wordpressMigrationV1.rawValue)\(WordPressExportRoute().path.removingPrefix("/"))")
         else {
-            showSignInUI()
+            performSafeRootNavigation { [weak self] in
+                self?.showSignInUI()
+            }
             return
         }
 
         /// WordPress is a compatible version for migrations, but needs to be loaded to prepare the data
-        showLoadWordPressUI(schemeUrl: schemeUrl)
+        performSafeRootNavigation { [weak self] in
+            self?.showLoadWordPressUI(schemeUrl: schemeUrl)
+        }
+    }
+
+    /// This method takes care of preventing screens being abruptly replaced.
+    ///
+    /// Since the import method is called whenever the app is foregrounded, we want to make sure that
+    /// any root view controller replacements only happen where it is "allowed":
+    ///
+    ///   1. When there's no root view controller yet, or
+    ///   2. When the Load WordPress screen is shown.
+    ///
+    /// Note: We should remove this method when the migration phase is concluded and we no longer need
+    /// to perfom the migration.
+    ///
+    /// - Parameter navigationClosure: The closure containing logic that eventually calls the `show` method.
+    func performSafeRootNavigation(with navigationClosure: @escaping () -> Void) {
+        switch rootViewController {
+        case .none:
+            // we can perform the navigation directly when there's no root view controller yet.
+            navigationClosure()
+        case .some(let viewController) where viewController is MigrationLoadWordPressViewController:
+            // allow the Load WordPress view to be replaced in case the migration process fails.
+            viewController.dismiss(animated: true, completion: navigationClosure)
+        default:
+            // do nothing when another root view controller is already displayed.
+            break
+        }
     }
 }