diff --git a/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageManager.swift b/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageManager.swift
index 8076c95..381bfc0 100644
--- a/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageManager.swift
+++ b/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageManager.swift
@@ -40,7 +40,7 @@ enum WorkoutMapImageManager {
     /// - Parameter request: An instance of WorkoutMapImageRequest indicating the type of image being requested
     public static func execute(_ request: WorkoutMapImageRequest) {
         
-        if let id = request.cacheIdentifier, let image = CustomImageCache.mapImageCache.getMapImage(for: id) {
+        if let id = request.cacheIdentifier(), let image = CustomImageCache.mapImageCache.getMapImage(for: id) {
             request.completion(true, image)
             return
         }
@@ -80,8 +80,8 @@ enum WorkoutMapImageManager {
         
         let imageUsesDarkMode = Config.isDarkModeEnabled
         let completion: (Bool, UIImage?) -> Void = { (success, image) in
+            requestQueue.remove(request)
             DispatchQueue.main.async {
-                requestQueue.remove(request)
                 request.completion(success, image)
                 executeNextInQueue()
             }
@@ -137,12 +137,18 @@ enum WorkoutMapImageManager {
                             let resultImage = UIGraphicsGetImageFromCurrentImageContext()
                             UIGraphicsEndImageContext()
                             
-                            if let image = resultImage, let id = request.cacheIdentifier {
+                            if let image = resultImage, let id = request.cacheIdentifier(forDarkAppearance: imageUsesDarkMode) {
                                 CustomImageCache.mapImageCache.set(mapImage: image, for: id)
                             }
                             
                             DispatchQueue.main.async {
+                                
                                 completion(true, resultImage)
+                                
+                                if Config.isDarkModeEnabled != imageUsesDarkMode {
+                                    self.requestQueue.add(request)
+                                }
+                                
                             }
                             
                         } else {
diff --git a/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageRequest.swift b/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageRequest.swift
index b55304b..625ecc6 100644
--- a/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageRequest.swift
+++ b/OutRun/Models/Workout/MapManagement/Images/WorkoutMapImageRequest.swift
@@ -27,13 +27,13 @@ class WorkoutMapImageRequest: Equatable {
     let highPriority: Bool
     var completion: (Bool, UIImage?) -> Void
     
-    var cacheIdentifier: String? {
+    func cacheIdentifier(forDarkAppearance usesDarkAppearance: Bool = Config.isDarkModeEnabled) -> String? {
         guard let uuid = workoutUUID else {
             return nil
         }
         let id = String(describing: uuid)
         let size = self.size.identifier
-        let appearance = Config.isDarkModeEnabled ? "dark" : "light"
+        let appearance = usesDarkAppearance ? "dark" : "light"
         return id + "_" + size + "_" + appearance
     }