diff --git a/src/xenia/app/emulator_window.cc b/src/xenia/app/emulator_window.cc
index d130bc286..65a6f5e0e 100644
--- a/src/xenia/app/emulator_window.cc
+++ b/src/xenia/app/emulator_window.cc
@@ -864,30 +864,29 @@ void EmulatorWindow::FileClose() {
 }
 
 void EmulatorWindow::InstallContent() {
-  std::filesystem::path path;
+  std::vector<std::filesystem::path> paths;
 
   auto file_picker = xe::ui::FilePicker::Create();
   file_picker->set_mode(ui::FilePicker::Mode::kOpen);
   file_picker->set_type(ui::FilePicker::Type::kFile);
-  file_picker->set_multi_selection(false);
+  file_picker->set_multi_selection(true);
   file_picker->set_title("Select Content Package");
   file_picker->set_extensions({
       {"All Files (*.*)", "*.*"},
   });
   if (file_picker->Show(window_.get())) {
-    auto selected_files = file_picker->selected_files();
-    if (!selected_files.empty()) {
-      path = selected_files[0];
-    }
+    paths = file_picker->selected_files();
   }
 
-  if (!path.empty()) {
-    // Normalize the path and make absolute.
-    auto abs_path = std::filesystem::absolute(path);
-    auto result = emulator_->InstallContentPackage(abs_path);
-    if (XFAILED(result)) {
-      // TODO: Display a message box.
-      XELOGE("Failed to install content: {:08X}", result);
+  if (!paths.empty()) {
+    for (auto path : paths) {
+      // Normalize the path and make absolute.
+      auto abs_path = std::filesystem::absolute(path);
+      auto result = emulator_->InstallContentPackage(abs_path);
+      if (XFAILED(result)) {
+        // TODO: Display a message box.
+        XELOGE("Failed to install content: {:08X}", result);
+      }
     }
   }
 }
diff --git a/src/xenia/ui/file_picker_win.cc b/src/xenia/ui/file_picker_win.cc
index 5cb467ca1..b4364d383 100644
--- a/src/xenia/ui/file_picker_win.cc
+++ b/src/xenia/ui/file_picker_win.cc
@@ -114,7 +114,7 @@ bool Win32FilePicker::Show(Window* parent_window) {
   // TODO(benvanik): FileSaveDialog.
   assert_true(mode() == Mode::kOpen);
 
-  Microsoft::WRL::ComPtr<IFileDialog> file_dialog;
+  Microsoft::WRL::ComPtr<IFileOpenDialog> file_dialog;
   HRESULT hr =
       CoCreateInstance(CLSID_FileOpenDialog, NULL, CLSCTX_INPROC_SERVER,
                        IID_PPV_ARGS(&file_dialog));
@@ -192,23 +192,30 @@ bool Win32FilePicker::Show(Window* parent_window) {
 
   // Obtain the result once the user clicks the 'Open' button.
   // The result is an IShellItem object.
-  Microsoft::WRL::ComPtr<IShellItem> shell_item;
-  hr = file_dialog->GetResult(&shell_item);
+  Microsoft::WRL::ComPtr<IShellItemArray> shell_items;
+  hr = file_dialog->GetResults(&shell_items);
   if (!SUCCEEDED(hr)) {
     return false;
   }
 
-  // We are just going to print out the name of the file for sample sake.
-  PWSTR file_path = nullptr;
-  hr = shell_item->GetDisplayName(SIGDN_FILESYSPATH, &file_path);
-  if (!SUCCEEDED(hr)) {
-    return false;
-  }
   std::vector<std::filesystem::path> selected_files;
-  selected_files.push_back(std::filesystem::path(file_path));
-  set_selected_files(selected_files);
-  CoTaskMemFree(file_path);
 
+  DWORD items_count = 0;
+  shell_items->GetCount(&items_count);
+  // Iterate over selected files
+  for (DWORD i = 0; i < items_count; i++) {
+    Microsoft::WRL::ComPtr<IShellItem> shell_item;
+    shell_items->GetItemAt(i, &shell_item);
+    // We are just going to print out the name of the file for sample sake.
+    PWSTR file_path = nullptr;
+    hr = shell_item->GetDisplayName(SIGDN_FILESYSPATH, &file_path);
+    if (!SUCCEEDED(hr)) {
+      return false;
+    }
+    selected_files.push_back(std::filesystem::path(file_path));
+    CoTaskMemFree(file_path);
+  }
+  set_selected_files(selected_files);
   return true;
 }