diff --git a/src/xenia/app/emulator_window.cc b/src/xenia/app/emulator_window.cc
index 65a6f5e0e..0a1537bea 100644
--- a/src/xenia/app/emulator_window.cc
+++ b/src/xenia/app/emulator_window.cc
@@ -883,9 +883,9 @@ void EmulatorWindow::InstallContent() {
       // Normalize the path and make absolute.
       auto abs_path = std::filesystem::absolute(path);
       auto result = emulator_->InstallContentPackage(abs_path);
-      if (XFAILED(result)) {
+      if (result != X_STATUS_SUCCESS) {
         // TODO: Display a message box.
-        XELOGE("Failed to install content: {:08X}", result);
+        XELOGE("Failed to install content! Error code: {:08X}", result);
       }
     }
   }
diff --git a/src/xenia/emulator.cc b/src/xenia/emulator.cc
index e9a671c87..f4400fb25 100644
--- a/src/xenia/emulator.cc
+++ b/src/xenia/emulator.cc
@@ -374,7 +374,12 @@ X_STATUS Emulator::InstallContentPackage(const std::filesystem::path& path) {
     // TODO: Popup
     // Do you want to overwrite already existing data?
   } else {
-    std::filesystem::create_directories(installation_path / path.filename());
+    std::error_code error_code;
+    std::filesystem::create_directories(installation_path / path.filename(),
+                                        error_code);
+    if (error_code) {
+      return error_code.value();
+    }
   }
 
   // Run through all the files, breadth-first style.
@@ -396,7 +401,11 @@ X_STATUS Emulator::InstallContentPackage(const std::filesystem::path& path) {
     auto dest_name =
         installation_path / path.filename() / xe::to_path(entry->path());
     if (entry->attributes() & vfs::kFileAttributeDirectory) {
-      std::filesystem::create_directories(dest_name);
+      std::error_code error_code;
+      std::filesystem::create_directories(dest_name, error_code);
+      if (error_code) {
+        return error_code.value();
+      }
       continue;
     }