diff --git a/apps/launcher/datafilespage.cpp b/apps/launcher/datafilespage.cpp
index 9e812138c8..8db0076af5 100644
--- a/apps/launcher/datafilespage.cpp
+++ b/apps/launcher/datafilespage.cpp
@@ -301,7 +301,7 @@ void Launcher::DataFilesPage::populateFileViews(const QString& contentModelName)
                               [&](const Config::SettingValue& dir) { return mGameSettings.isUserSetting(dir); }),
             directories.end());
         for (const auto& dir : contentModelDirectories)
-            directories.push_back({ dir });
+            directories.push_back(mGameSettings.procesPathSettingValue({ dir }));
     }
 
     mDataLocal = mGameSettings.getDataLocal();
diff --git a/components/config/gamesettings.cpp b/components/config/gamesettings.cpp
index a7da8fa150..7015f86c04 100644
--- a/components/config/gamesettings.cpp
+++ b/components/config/gamesettings.cpp
@@ -178,9 +178,7 @@ bool Config::GameSettings::readFile(
                     value.originalRepresentation = value.value;
                 }
 
-                std::filesystem::path path = Files::pathFromQString(value.value);
-                mCfgMgr.processPath(path, Files::pathFromQString(context));
-                value.value = Files::pathToQString(path);
+                value = procesPathSettingValue(value);
             }
             if (ignoreContent && (key == QLatin1String("content") || key == QLatin1String("data")))
                 continue;
@@ -588,6 +586,14 @@ bool Config::GameSettings::isUserSetting(const SettingValue& settingValue) const
     return settingValue.context.isEmpty() || settingValue.context == getUserContext();
 }
 
+Config::SettingValue Config::GameSettings::procesPathSettingValue(const SettingValue& value)
+{
+    std::filesystem::path path = Files::pathFromQString(value.value);
+    std::filesystem::path basePath = Files::pathFromQString(value.context.isEmpty() ? getUserContext() : value.context);
+    mCfgMgr.processPath(path, basePath);
+    return SettingValue{ Files::pathToQString(path), value.originalRepresentation, value.context };
+}
+
 void Config::GameSettings::clear()
 {
     mSettings.clear();
diff --git a/components/config/gamesettings.hpp b/components/config/gamesettings.hpp
index 89139ff41a..d31d3bf897 100644
--- a/components/config/gamesettings.hpp
+++ b/components/config/gamesettings.hpp
@@ -118,6 +118,8 @@ namespace Config
         const QString& getUserContext() const { return mContexts.back(); }
         bool isUserSetting(const SettingValue& settingValue) const;
 
+        SettingValue procesPathSettingValue(const SettingValue& value);
+
         void clear();
 
     private:
diff --git a/components/config/launchersettings.cpp b/components/config/launchersettings.cpp
index f4749d0f93..449edd1b89 100644
--- a/components/config/launchersettings.cpp
+++ b/components/config/launchersettings.cpp
@@ -1,6 +1,7 @@
 #include "launchersettings.hpp"
 
 #include <QDebug>
+#include <QDir>
 #include <QMultiMap>
 #include <QRegularExpression>
 #include <QString>
@@ -263,8 +264,17 @@ void Config::LauncherSettings::setContentList(const GameSettings& gameSettings)
     for (const QString& listName : getContentLists())
     {
         const auto& listDirs = getDataDirectoryList(listName);
-        if (!std::ranges::equal(
-                dirs, listDirs, [](const SettingValue& dir, const QString& listDir) { return dir.value == listDir; }))
+#ifdef Q_OS_WINDOWS
+        constexpr auto caseSensitivity = Qt::CaseInsensitive;
+#else
+        constexpr auto caseSensitivity = Qt::CaseSensitive;
+#endif
+        constexpr auto compareDataDirectories = [caseSensitivity](const SettingValue& dir, const QString& listDir) {
+            return dir.originalRepresentation == listDir
+                || QDir::cleanPath(dir.originalRepresentation)
+                       .compare(QDir::cleanPath(listDir), caseSensitivity) == 0;
+        };
+        if (!std::ranges::equal(dirs, listDirs, compareDataDirectories))
             continue;
         constexpr auto compareFiles
             = [](const QString& a, const QString& b) { return a.compare(b, Qt::CaseInsensitive) == 0; };
@@ -281,7 +291,7 @@ void Config::LauncherSettings::setContentList(const GameSettings& gameSettings)
     setCurrentContentListName(newContentListName);
     QStringList newListDirs;
     for (const auto& dir : dirs)
-        newListDirs.push_back(dir.value);
+        newListDirs.push_back(dir.originalRepresentation);
     setContentList(newContentListName, newListDirs, archives, files);
 }