diff --git a/DuckDuckGo.xcodeproj/xcshareddata/xcschemes/DuckDuckGo Privacy Browser.xcscheme b/DuckDuckGo.xcodeproj/xcshareddata/xcschemes/DuckDuckGo Privacy Browser.xcscheme
index b272e5bb34..294ba1aeb6 100644
--- a/DuckDuckGo.xcodeproj/xcshareddata/xcschemes/DuckDuckGo Privacy Browser.xcscheme	
+++ b/DuckDuckGo.xcodeproj/xcshareddata/xcschemes/DuckDuckGo Privacy Browser.xcscheme	
@@ -299,6 +299,10 @@
             argument = "-NSConstraintBasedLayoutVisualizeMutuallyExclusiveConstraints YES"
             isEnabled = "YES">
          </CommandLineArgument>
+         <CommandLineArgument
+            argument = "-SUEnableAutomaticChecks NO"
+            isEnabled = "YES">
+         </CommandLineArgument>
          <CommandLineArgument
             argument = "-com.apple.CoreData.ConcurrencyDebug 1"
             isEnabled = "YES">
diff --git a/DuckDuckGo/Preferences/Model/AboutPreferences.swift b/DuckDuckGo/Preferences/Model/AboutPreferences.swift
index 63b5433ce8..c664a6bedb 100644
--- a/DuckDuckGo/Preferences/Model/AboutPreferences.swift
+++ b/DuckDuckGo/Preferences/Model/AboutPreferences.swift
@@ -71,7 +71,7 @@ final class AboutPreferences: ObservableObject, PreferencesTabOpening {
 
 #if SPARKLE
     func checkForUpdate() {
-        updateController?.checkForUpdateIfNeeded()
+        updateController?.checkForUpdateSkippingRollout()
     }
 
     func runUpdate() {
diff --git a/DuckDuckGo/Preferences/View/PreferencesAboutView.swift b/DuckDuckGo/Preferences/View/PreferencesAboutView.swift
index 3ba655735a..d6fe08b06a 100644
--- a/DuckDuckGo/Preferences/View/PreferencesAboutView.swift
+++ b/DuckDuckGo/Preferences/View/PreferencesAboutView.swift
@@ -51,11 +51,6 @@ extension Preferences {
                     }
                 }
             }
-            .onAppear {
-#if SPARKLE && !DEBUG
-                model.checkForUpdate()
-#endif
-            }
         }
     }
 
diff --git a/DuckDuckGo/Updates/ReleaseNotesTabExtension.swift b/DuckDuckGo/Updates/ReleaseNotesTabExtension.swift
index 570ea39d05..d258c5e523 100644
--- a/DuckDuckGo/Updates/ReleaseNotesTabExtension.swift
+++ b/DuckDuckGo/Updates/ReleaseNotesTabExtension.swift
@@ -105,11 +105,11 @@ final class ReleaseNotesTabExtension: NavigationResponder {
 
     @MainActor
     func navigationDidFinish(_ navigation: Navigation) {
-#if !DEBUG
         guard NSApp.runType != .uiTests, navigation.url == .releaseNotes else { return }
         let updateController = Application.appDelegate.updateController!
-        updateController.checkForUpdateIfNeeded()
-#endif
+        if updateController.latestUpdate?.needsLatestReleaseNote == true {
+            updateController.checkForUpdateSkippingRollout()
+        }
     }
 }
 
diff --git a/DuckDuckGo/Updates/ReleaseNotesUserScript.swift b/DuckDuckGo/Updates/ReleaseNotesUserScript.swift
index 1013958aba..ff07147751 100644
--- a/DuckDuckGo/Updates/ReleaseNotesUserScript.swift
+++ b/DuckDuckGo/Updates/ReleaseNotesUserScript.swift
@@ -113,7 +113,7 @@ extension ReleaseNotesUserScript {
     @MainActor
     private func retryUpdate(params: Any, original: WKScriptMessage) async throws -> Encodable? {
         DispatchQueue.main.async { [weak self] in
-            self?.updateController.checkForUpdateIfNeeded()
+            self?.updateController.checkForUpdateSkippingRollout()
         }
         return nil
     }
diff --git a/DuckDuckGo/Updates/Update.swift b/DuckDuckGo/Updates/Update.swift
index d36a7b10d1..bfa43a8db6 100644
--- a/DuckDuckGo/Updates/Update.swift
+++ b/DuckDuckGo/Updates/Update.swift
@@ -34,6 +34,7 @@ final class Update {
     let date: Date
     let releaseNotes: [String]
     let releaseNotesPrivacyPro: [String]
+    let needsLatestReleaseNote: Bool
 
     var title: String {
         let formatter = DateFormatter()
@@ -47,7 +48,8 @@ final class Update {
                   build: String,
                   date: Date,
                   releaseNotes: [String],
-                  releaseNotesPrivacyPro: [String]) {
+                  releaseNotesPrivacyPro: [String],
+                  needsLatestReleaseNote: Bool) {
         self.isInstalled = isInstalled
         self.type = type
         self.version = version
@@ -55,12 +57,13 @@ final class Update {
         self.date = date
         self.releaseNotes = releaseNotes
         self.releaseNotesPrivacyPro = releaseNotesPrivacyPro
+        self.needsLatestReleaseNote = needsLatestReleaseNote
     }
 
 }
 
 extension Update {
-    convenience init(appcastItem: SUAppcastItem, isInstalled: Bool) {
+    convenience init(appcastItem: SUAppcastItem, isInstalled: Bool, needsLatestReleaseNote: Bool) {
         let isCritical = appcastItem.isCriticalUpdate
         let version = appcastItem.displayVersionString
         let build = appcastItem.versionString
@@ -73,7 +76,8 @@ extension Update {
                   build: build,
                   date: date,
                   releaseNotes: releaseNotes,
-                  releaseNotesPrivacyPro: releaseNotesPrivacyPro)
+                  releaseNotesPrivacyPro: releaseNotesPrivacyPro,
+                  needsLatestReleaseNote: needsLatestReleaseNote)
     }
 }
 
diff --git a/DuckDuckGo/Updates/UpdateController.swift b/DuckDuckGo/Updates/UpdateController.swift
index e45a117790..cd88d87159 100644
--- a/DuckDuckGo/Updates/UpdateController.swift
+++ b/DuckDuckGo/Updates/UpdateController.swift
@@ -42,7 +42,8 @@ protocol UpdateControllerProtocol: AnyObject {
 
     var lastUpdateCheckDate: Date? { get }
 
-    func checkForUpdateIfNeeded()
+    func checkForUpdateRespectingRollout()
+    func checkForUpdateSkippingRollout()
     func runUpdate()
 
     var areAutomaticUpdatesEnabled: Bool { get set }
@@ -64,13 +65,20 @@ final class UpdateController: NSObject, UpdateControllerProtocol {
     struct UpdateCheckResult {
         let item: SUAppcastItem
         let isInstalled: Bool
+        let needsLatestReleaseNote: Bool
+
+        init(item: SUAppcastItem, isInstalled: Bool, needsLatestReleaseNote: Bool = false) {
+            self.item = item
+            self.isInstalled = isInstalled
+            self.needsLatestReleaseNote = needsLatestReleaseNote
+        }
     }
     private var cachedUpdateResult: UpdateCheckResult?
 
     @Published private(set) var updateProgress = UpdateCycleProgress.default {
         didSet {
             if let cachedUpdateResult {
-                latestUpdate = Update(appcastItem: cachedUpdateResult.item, isInstalled: cachedUpdateResult.isInstalled)
+                latestUpdate = Update(appcastItem: cachedUpdateResult.item, isInstalled: cachedUpdateResult.isInstalled, needsLatestReleaseNote: cachedUpdateResult.needsLatestReleaseNote)
                 hasPendingUpdate = latestUpdate?.isInstalled == false && updateProgress.isDone && userDriver?.isResumable == true
                 needsNotificationDot = hasPendingUpdate
             }
@@ -101,6 +109,7 @@ final class UpdateController: NSObject, UpdateControllerProtocol {
             if oldValue != areAutomaticUpdatesEnabled {
                 userDriver?.cancelAndDismissCurrentUpdate()
                 try? configureUpdater()
+                checkForUpdateSkippingRollout()
             }
         }
     }
@@ -129,6 +138,7 @@ final class UpdateController: NSObject, UpdateControllerProtocol {
         super.init()
 
         try? configureUpdater()
+        checkForUpdateRespectingRollout()
     }
 
     func checkNewApplicationVersion() {
@@ -142,10 +152,18 @@ final class UpdateController: NSObject, UpdateControllerProtocol {
         }
     }
 
-    func checkForUpdateIfNeeded() {
+    func checkForUpdateRespectingRollout() {
+        guard let updater, !updater.sessionInProgress else { return }
+
+        Logger.updates.log("Checking for updates respecting rollout")
+
+        updater.checkForUpdatesInBackground()
+    }
+
+    func checkForUpdateSkippingRollout() {
         guard let updater, !updater.sessionInProgress else { return }
 
-        Logger.updates.log("Checking for updates")
+        Logger.updates.log("Checking for updates skipping rollout")
 
         updater.checkForUpdates()
     }
@@ -168,14 +186,6 @@ final class UpdateController: NSObject, UpdateControllerProtocol {
             .assign(to: \.updateProgress, onWeaklyHeld: self)
 
         try updater?.start()
-
-#if DEBUG
-        updater?.automaticallyChecksForUpdates = false
-        updater?.automaticallyDownloadsUpdates = false
-        updater?.updateCheckInterval = 0
-#else
-        checkForUpdateIfNeeded()
-#endif
     }
 
     private func showUpdateNotificationIfNeeded() {
@@ -249,12 +259,18 @@ extension UpdateController: SPUUpdaterDelegate {
 
     func updaterDidNotFindUpdate(_ updater: SPUUpdater, error: any Error) {
         let nsError = error as NSError
-        guard let item = nsError.userInfo["SULatestAppcastItemFound"] as? SUAppcastItem else { return }
+        guard let item = nsError.userInfo[SPULatestAppcastItemFoundKey] as? SUAppcastItem else { return }
 
         Logger.updates.log("Updater did not find update: \(String(describing: item.displayVersionString))(\(String(describing: item.versionString)))")
         PixelKit.fire(DebugEvent(GeneralPixel.updaterDidNotFindUpdate, error: error))
 
-        cachedUpdateResult = UpdateCheckResult(item: item, isInstalled: true)
+        // Edge case: User upgrades to latest version within their rollout group
+        // But fetched release notes are outdated due to rollout group reset
+        let needsLatestReleaseNote = {
+            guard let reason = nsError.userInfo[SPUNoUpdateFoundReasonKey] as? Int else { return false }
+            return reason == Int(Sparkle.SPUNoUpdateFoundReason.onNewerThanLatestVersion.rawValue)
+        }()
+        cachedUpdateResult = UpdateCheckResult(item: item, isInstalled: true, needsLatestReleaseNote: needsLatestReleaseNote)
     }
 
     func updater(_ updater: SPUUpdater, didDownloadUpdate item: SUAppcastItem) {
@@ -274,6 +290,9 @@ extension UpdateController: SPUUpdaterDelegate {
         if error == nil {
             Logger.updates.log("Updater did finish update cycle")
             updateProgress = .updateCycleDone
+        } else if let errorCode = (error as? NSError)?.code, errorCode == Int(Sparkle.SUError.noUpdateError.rawValue) {
+            Logger.updates.log("Updater did finish update cycle with no update found")
+            updateProgress = .updateCycleDone
         } else {
             Logger.updates.log("Updater did finish update cycle with error")
         }