diff --git a/src/citra_qt/main.cpp b/src/citra_qt/main.cpp
index 1854f442a..57adbc136 100644
--- a/src/citra_qt/main.cpp
+++ b/src/citra_qt/main.cpp
@@ -249,22 +249,73 @@ void GMainWindow::OnDisplayTitleBars(bool show)
     }
 }
 
-void GMainWindow::BootGame(const std::string& filename) {
-    LOG_INFO(Frontend, "Citra starting...");
-
+bool GMainWindow::InitializeSystem() {
     // Shutdown previous session if the emu thread is still active...
     if (emu_thread != nullptr)
         ShutdownGame();
 
     // Initialize the core emulation
-    System::Init(render_window);
+    System::Result system_result = System::Init(render_window);
+    if (System::Result::Success != system_result) {
+        switch (system_result) {
+        case System::Result::ErrorInitVideoCore:
+            QMessageBox::critical(this, tr("Error while starting Citra!"),
+                                  tr("Failed to initialize the video core!\n\n"
+                                     "Please ensure that your GPU supports OpenGL 3.3 and that you have the latest graphics driver."));
+            break;
 
-    // Load the game
-    if (Loader::ResultStatus::Success != Loader::LoadFile(filename)) {
+        default:
+            QMessageBox::critical(this, tr("Error while starting Citra!"),
+                                  tr("Unknown error (please check the log)!"));
+            break;
+        }
+        return false;
+    }
+    return true;
+}
+
+bool GMainWindow::LoadROM(const std::string& filename) {
+    Loader::ResultStatus result = Loader::LoadFile(filename);
+    if (Loader::ResultStatus::Success != result) {
         LOG_CRITICAL(Frontend, "Failed to load ROM!");
         System::Shutdown();
-        return;
+
+        switch (result) {
+        case Loader::ResultStatus::ErrorEncrypted: {
+            // Build the MessageBox ourselves to have clickable link
+            QMessageBox popup_error;
+            popup_error.setTextFormat(Qt::RichText);
+            popup_error.setWindowTitle(tr("Error while loading ROM!"));
+            popup_error.setText(tr("The game that you are trying to load must be decrypted before being used with Citra.<br/><br/>"
+                                  "For more information on dumping and decrypting games, please see: <a href='https://citra-emu.org/wiki/Dumping-Game-Cartridges'>https://citra-emu.org/wiki/Dumping-Game-Cartridges</a>"));
+            popup_error.setIcon(QMessageBox::Critical);
+            popup_error.exec();
+            break;
+        }
+        case Loader::ResultStatus::ErrorInvalidFormat:
+            QMessageBox::critical(this, tr("Error while loading ROM!"),
+                                  tr("The ROM format is not supported."));
+            break;
+        case Loader::ResultStatus::Error:
+
+        default:
+            QMessageBox::critical(this, tr("Error while loading ROM!"),
+                                  tr("Unknown error!"));
+            break;
+        }
+        return false;
     }
+    return true;
+}
+
+void GMainWindow::BootGame(const std::string& filename) {
+    LOG_INFO(Frontend, "Citra starting...");
+
+    if (!InitializeSystem())
+        return;
+
+    if (!LoadROM(filename))
+        return;
 
     // Create and start the emulation thread
     emu_thread = Common::make_unique<EmuThread>(render_window);
diff --git a/src/citra_qt/main.h b/src/citra_qt/main.h
index 8c195f816..945aea0cd 100644
--- a/src/citra_qt/main.h
+++ b/src/citra_qt/main.h
@@ -59,6 +59,8 @@ signals:
     void EmulationStopping();
 
 private:
+    bool InitializeSystem();
+    bool LoadROM(const std::string& filename);
     void BootGame(const std::string& filename);
     void ShutdownGame();
 
diff --git a/src/core/core.cpp b/src/core/core.cpp
index 453c7162d..84d6c392e 100644
--- a/src/core/core.cpp
+++ b/src/core/core.cpp
@@ -73,12 +73,11 @@ void Stop() {
 }
 
 /// Initialize the core
-int Init() {
+void Init() {
     g_sys_core = Common::make_unique<ARM_DynCom>(USER32MODE);
     g_app_core = Common::make_unique<ARM_DynCom>(USER32MODE);
 
     LOG_DEBUG(Core, "Initialized OK");
-    return 0;
 }
 
 void Shutdown() {
diff --git a/src/core/core.h b/src/core/core.h
index 453e0a5f0..ad26dca3f 100644
--- a/src/core/core.h
+++ b/src/core/core.h
@@ -52,7 +52,7 @@ void Halt(const char *msg);
 void Stop();
 
 /// Initialize the core
-int Init();
+void Init();
 
 /// Shutdown the core
 void Shutdown();
diff --git a/src/core/loader/loader.cpp b/src/core/loader/loader.cpp
index 6b88169e1..b1907cd55 100644
--- a/src/core/loader/loader.cpp
+++ b/src/core/loader/loader.cpp
@@ -137,11 +137,11 @@ ResultStatus LoadFile(const std::string& filename) {
         AppLoader_NCCH app_loader(std::move(file), filename);
 
         // Load application and RomFS
-        if (ResultStatus::Success == app_loader.Load()) {
+        ResultStatus result = app_loader.Load();
+        if (ResultStatus::Success == result) {
             Service::FS::RegisterArchiveType(Common::make_unique<FileSys::ArchiveFactory_RomFS>(app_loader), Service::FS::ArchiveIdCode::RomFS);
-            return ResultStatus::Success;
         }
-        break;
+        return result;
     }
 
     // CIA file format...
diff --git a/src/core/system.cpp b/src/core/system.cpp
index b62ebf69e..1e3b2783c 100644
--- a/src/core/system.cpp
+++ b/src/core/system.cpp
@@ -17,14 +17,16 @@
 
 namespace System {
 
-void Init(EmuWindow* emu_window) {
+Result Init(EmuWindow* emu_window) {
     Core::Init();
     CoreTiming::Init();
     Memory::Init();
     HW::Init();
     Kernel::Init();
     HLE::Init();
-    VideoCore::Init(emu_window);
+    if (!VideoCore::Init(emu_window)) {
+        return Result::ErrorInitVideoCore;
+    }
     AudioCore::Init();
     GDBStub::Init();
 }
diff --git a/src/core/system.h b/src/core/system.h
index 59a75ca12..a4a627ea9 100644
--- a/src/core/system.h
+++ b/src/core/system.h
@@ -8,7 +8,14 @@ class EmuWindow;
 
 namespace System {
 
-void Init(EmuWindow* emu_window);
+enum class Result {
+    Success,                ///< Everything is fine
+    Error,                  ///< Something went wrong (no module specified)
+    ErrorInitCore,          ///< Something went wrong during core init
+    ErrorInitVideoCore,     ///< Something went wrong during video core init
+};
+
+Result Init(EmuWindow* emu_window);
 void Shutdown();
 
 }
diff --git a/src/video_core/renderer_base.h b/src/video_core/renderer_base.h
index 506bff815..91a7b7f17 100644
--- a/src/video_core/renderer_base.h
+++ b/src/video_core/renderer_base.h
@@ -38,7 +38,7 @@ public:
     virtual void SetWindow(EmuWindow* window) = 0;
 
     /// Initialize the renderer
-    virtual void Init() = 0;
+    virtual bool Init() = 0;
 
     /// Shutdown the renderer
     virtual void ShutDown() = 0;
diff --git a/src/video_core/renderer_opengl/renderer_opengl.cpp b/src/video_core/renderer_opengl/renderer_opengl.cpp
index ca3a6a6b4..11c4d0daf 100644
--- a/src/video_core/renderer_opengl/renderer_opengl.cpp
+++ b/src/video_core/renderer_opengl/renderer_opengl.cpp
@@ -445,7 +445,7 @@ static void DebugHandler(GLenum source, GLenum type, GLuint id, GLenum severity,
 }
 
 /// Initialize the renderer
-void RendererOpenGL::Init() {
+bool RendererOpenGL::Init() {
     render_window->MakeCurrent();
 
     // TODO: Make frontends initialize this, so they can use gladLoadGLLoader with their own loaders
@@ -462,9 +462,15 @@ void RendererOpenGL::Init() {
     LOG_INFO(Render_OpenGL, "GL_VERSION: %s", glGetString(GL_VERSION));
     LOG_INFO(Render_OpenGL, "GL_VENDOR: %s", glGetString(GL_VENDOR));
     LOG_INFO(Render_OpenGL, "GL_RENDERER: %s", glGetString(GL_RENDERER));
+    if (!GLAD_GL_VERSION_3_3) {
+        return false;
+    }
+
     InitOpenGLObjects();
 
     RefreshRasterizerSetting();
+
+    return true;
 }
 
 /// Shutdown the renderer
diff --git a/src/video_core/renderer_opengl/renderer_opengl.h b/src/video_core/renderer_opengl/renderer_opengl.h
index b42df7654..fe4d142a5 100644
--- a/src/video_core/renderer_opengl/renderer_opengl.h
+++ b/src/video_core/renderer_opengl/renderer_opengl.h
@@ -31,7 +31,7 @@ public:
     void SetWindow(EmuWindow* window) override;
 
     /// Initialize the renderer
-    void Init() override;
+    bool Init() override;
 
     /// Shutdown the renderer
     void ShutDown() override;
diff --git a/src/video_core/video_core.cpp b/src/video_core/video_core.cpp
index 912db91a4..ee5e50df1 100644
--- a/src/video_core/video_core.cpp
+++ b/src/video_core/video_core.cpp
@@ -28,15 +28,19 @@ std::atomic<bool> g_hw_renderer_enabled;
 std::atomic<bool> g_shader_jit_enabled;
 
 /// Initialize the video core
-void Init(EmuWindow* emu_window) {
+bool Init(EmuWindow* emu_window) {
     Pica::Init();
 
     g_emu_window = emu_window;
     g_renderer = Common::make_unique<RendererOpenGL>();
     g_renderer->SetWindow(g_emu_window);
-    g_renderer->Init();
-
-    LOG_DEBUG(Render, "initialized OK");
+    if (g_renderer->Init()) {
+        LOG_DEBUG(Render, "initialized OK");
+    } else {
+        LOG_ERROR(Render, "initialization failed !");
+        return false;
+    }
+    return true;
 }
 
 /// Shutdown the video core
diff --git a/src/video_core/video_core.h b/src/video_core/video_core.h
index accb0a4eb..bca67fb8c 100644
--- a/src/video_core/video_core.h
+++ b/src/video_core/video_core.h
@@ -41,7 +41,7 @@ extern std::atomic<bool> g_shader_jit_enabled;
 void Start();
 
 /// Initialize the video core
-void Init(EmuWindow* emu_window);
+bool Init(EmuWindow* emu_window);
 
 /// Shutdown the video core
 void Shutdown();