diff --git a/src/RunGui.cpp b/src/RunGui.cpp
index 523a3c9fa..f4a11b19b 100644
--- a/src/RunGui.cpp
+++ b/src/RunGui.cpp
@@ -8,6 +8,7 @@
 #include <csignal>
 
 #include "Application.hpp"
+#include "common/Modes.hpp"
 #include "common/NetworkManager.hpp"
 #include "singletons/Paths.hpp"
 #include "singletons/Resources.hpp"
diff --git a/src/main.cpp b/src/main.cpp
index 990f6e833..c2c4d9ab6 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -5,6 +5,7 @@
 #include "BrowserExtension.hpp"
 #include "RunGui.hpp"
 #include "common/Args.hpp"
+#include "common/Modes.hpp"
 #include "singletons/Paths.hpp"
 #include "singletons/Settings.hpp"
 #include "util/IncognitoBrowser.hpp"
@@ -28,9 +29,35 @@ int main(int argc, char **argv)
     else
     {
         initArgs(args);
-        Paths paths;
-        Settings settings(paths.settingsDirectory);
+        Paths *paths{};
 
-        runGui(a, paths, settings);
+        try
+        {
+            paths = new Paths;
+        }
+        catch (std::runtime_error &error)
+        {
+            QMessageBox box;
+            if (Modes::getInstance().isPortable)
+            {
+                box.setText(
+                    error.what() +
+                    QStringLiteral(
+                        "\n\nInfo: Portable mode requires the application to "
+                        "be in a writeable location. If you don't want "
+                        "portable mode reinstall the application. "
+                        "https://chatterino.com."));
+            }
+            else
+            {
+                box.setText(error.what());
+            }
+            box.exec();
+            return 1;
+        }
+
+        Settings settings(paths->settingsDirectory);
+
+        runGui(a, *paths, settings);
     }
 }
diff --git a/src/singletons/Paths.cpp b/src/singletons/Paths.cpp
index ea8e2526b..83d7ab5a6 100644
--- a/src/singletons/Paths.cpp
+++ b/src/singletons/Paths.cpp
@@ -11,6 +11,8 @@
 #include "common/Modes.hpp"
 #include "util/CombinePath.hpp"
 
+using namespace std::literals;
+
 namespace chatterino {
 
 Paths *Paths::instance = nullptr;
@@ -22,7 +24,7 @@ Paths::Paths()
     this->initAppFilePathHash();
 
     this->initCheckPortable();
-    this->initAppDataDirectory();
+    this->initRootDirectory();
     this->initSubDirectories();
 }
 
@@ -76,7 +78,7 @@ void Paths::initCheckPortable()
         combinePath(QCoreApplication::applicationDirPath(), "portable"));
 }
 
-void Paths::initAppDataDirectory()
+void Paths::initRootDirectory()
 {
     assert(this->portable_.is_initialized());
 
@@ -95,8 +97,8 @@ void Paths::initAppDataDirectory()
             QStandardPaths::writableLocation(QStandardPaths::AppDataLocation);
         if (path.isEmpty())
         {
-            throw std::runtime_error(
-                "Error finding writable location for settings");
+            throw std::runtime_error("Could not create directory \""s +
+                                     path.toStdString() + "\"");
         }
 
 // create directory Chatterino2 instead of chatterino on windows because the
@@ -123,8 +125,8 @@ void Paths::initSubDirectories()
 
         if (!QDir().mkpath(path))
         {
-            throw std::runtime_error(
-                "Error creating appdata path %appdata%/chatterino/" + name);
+            throw std::runtime_error("Could not create directory \""s +
+                                     path.toStdString() + "\"");
         }
 
         return path;
diff --git a/src/singletons/Paths.hpp b/src/singletons/Paths.hpp
index 1df1fc77f..ea4cb6c2d 100644
--- a/src/singletons/Paths.hpp
+++ b/src/singletons/Paths.hpp
@@ -39,7 +39,7 @@ public:
 private:
     void initAppFilePathHash();
     void initCheckPortable();
-    void initAppDataDirectory();
+    void initRootDirectory();
     void initSubDirectories();
 
     boost::optional<bool> portable_;