diff --git a/OSBindings/Qt/mainwindow.cpp b/OSBindings/Qt/mainwindow.cpp
index 79cd7dfa8..add5a4183 100644
--- a/OSBindings/Qt/mainwindow.cpp
+++ b/OSBindings/Qt/mainwindow.cpp
@@ -207,14 +207,15 @@ QString MainWindow::getFilename(const char *title) {
 	return fileName;
 }
 
-void MainWindow::insertFile(const QString &fileName) {
-	if(!machine) return;
+bool MainWindow::insertFile(const QString &fileName) {
+	if(!machine) return false;
 
 	auto mediaTarget = machine->media_target();
-	if(!mediaTarget) return;
+	if(!mediaTarget) return false;
 
-	Analyser::Static::Media media = Analyser::Static::GetMedia(fileName.toStdString());
-	mediaTarget->insert_media(media);
+	const Analyser::Static::Media media = Analyser::Static::GetMedia(fileName.toStdString());
+	if(media.empty()) return false;
+	return mediaTarget->insert_media(media);
 }
 
 bool MainWindow::launchFile(const QString &fileName) {
@@ -732,7 +733,10 @@ void MainWindow::dropEvent(QDropEvent* event) {
 		case UIPhase::RunningMachine: {
 			// Attempt to insert into the running machine.
 			const auto fileName = event->mimeData()->urls()[0].toLocalFile();
-			insertFile(fileName);
+			if(!insertFile(fileName)) {
+				deleteMachine();
+				launchFile(fileName);
+			}
 		} break;
 
 		// TODO: permit multiple files dropped at once in both of the above cases.
diff --git a/OSBindings/Qt/mainwindow.h b/OSBindings/Qt/mainwindow.h
index ab02f14e9..24f3593e1 100644
--- a/OSBindings/Qt/mainwindow.h
+++ b/OSBindings/Qt/mainwindow.h
@@ -104,7 +104,7 @@ class MainWindow : public QMainWindow, public Outputs::Speaker::Speaker::Delegat
 		} keyboardInputMode;
 
 		QAction *insertAction = nullptr;
-		void insertFile(const QString &fileName);
+		bool insertFile(const QString &fileName);
 
 		bool launchFile(const QString &fileName);
 		void launchTarget(std::unique_ptr<Analyser::Static::Target> &&);