diff --git a/src/debugger/gdb-stub.c b/src/debugger/gdb-stub.c
index 0b5145764..e6623fca1 100644
--- a/src/debugger/gdb-stub.c
+++ b/src/debugger/gdb-stub.c
@@ -449,7 +449,7 @@ void GDBStubCreate(struct GDBStub* stub) {
 	stub->untilPoll = GDB_STUB_INTERVAL;
 }
 
-int GDBStubListen(struct GDBStub* stub, int port, const struct Address* bindAddress) {
+bool GDBStubListen(struct GDBStub* stub, int port, const struct Address* bindAddress) {
 	if (!SOCKET_FAILED(stub->socket)) {
 		GDBStubShutdown(stub);
 	}
@@ -458,7 +458,7 @@ int GDBStubListen(struct GDBStub* stub, int port, const struct Address* bindAddr
 		if (stub->d.log) {
 			stub->d.log(&stub->d, DEBUGGER_LOG_ERROR, "Couldn't open socket");
 		}
-		return 0;
+		return false;
 	}
 	if (!SocketSetBlocking(stub->socket, false)) {
 		goto cleanup;
@@ -468,7 +468,7 @@ int GDBStubListen(struct GDBStub* stub, int port, const struct Address* bindAddr
 		goto cleanup;
 	}
 
-	return 1;
+	return true;
 
 cleanup:
 	if (stub->d.log) {
@@ -476,7 +476,7 @@ cleanup:
 	}
 	SocketClose(stub->socket);
 	stub->socket = INVALID_SOCKET;
-	return 0;
+	return false;
 }
 
 void GDBStubHangup(struct GDBStub* stub) {
diff --git a/src/debugger/gdb-stub.h b/src/debugger/gdb-stub.h
index 25b435715..97cb69b22 100644
--- a/src/debugger/gdb-stub.h
+++ b/src/debugger/gdb-stub.h
@@ -37,7 +37,7 @@ struct GDBStub {
 };
 
 void GDBStubCreate(struct GDBStub*);
-int GDBStubListen(struct GDBStub*, int port, const struct Address* bindAddress);
+bool GDBStubListen(struct GDBStub*, int port, const struct Address* bindAddress);
 
 void GDBStubHangup(struct GDBStub*);
 void GDBStubShutdown(struct GDBStub*);
diff --git a/src/platform/qt/GDBController.cpp b/src/platform/qt/GDBController.cpp
index a229a3b66..68511a092 100644
--- a/src/platform/qt/GDBController.cpp
+++ b/src/platform/qt/GDBController.cpp
@@ -58,6 +58,11 @@ void GDBController::listen() {
 	if (!isAttached()) {
 		attach();
 	}
-	GDBStubListen(&m_gdbStub, m_port, &m_bindAddress);
+	if (GDBStubListen(&m_gdbStub, m_port, &m_bindAddress)) {
+		emit listening();
+	} else {
+		detach();
+		emit listenFailed();
+	}
 	m_gameController->threadContinue();
 }
diff --git a/src/platform/qt/GDBController.h b/src/platform/qt/GDBController.h
index ebd80e571..771fabf3d 100644
--- a/src/platform/qt/GDBController.h
+++ b/src/platform/qt/GDBController.h
@@ -35,6 +35,10 @@ public slots:
 	void detach();
 	void listen();
 
+signals:
+	void listening();
+	void listenFailed();
+
 private:
 	GDBStub m_gdbStub;
 	GameController* m_gameController;
diff --git a/src/platform/qt/GDBWindow.cpp b/src/platform/qt/GDBWindow.cpp
index aeb034c80..de467bb12 100644
--- a/src/platform/qt/GDBWindow.cpp
+++ b/src/platform/qt/GDBWindow.cpp
@@ -9,6 +9,7 @@
 #include <QGroupBox>
 #include <QLabel>
 #include <QLineEdit>
+#include <QMessageBox>
 #include <QPushButton>
 #include <QVBoxLayout>
 
@@ -46,6 +47,9 @@ GDBWindow::GDBWindow(GDBController* controller, QWidget* parent)
 
 	m_startStopButton = new QPushButton;
 	mainSegment->addWidget(m_startStopButton);
+	connect(m_gdbController, SIGNAL(listening()), this, SLOT(started()));
+	connect(m_gdbController, SIGNAL(listenFailed()), this, SLOT(failed()));
+
 	if (m_gdbController->isAttached()) {
 		started();
 	} else {
@@ -88,7 +92,6 @@ void GDBWindow::started() {
 	m_bindAddressEdit->setEnabled(false);
 	m_startStopButton->setText(tr("Stop"));
 	disconnect(m_startStopButton, SIGNAL(clicked()), m_gdbController, SLOT(listen()));
-	disconnect(m_startStopButton, SIGNAL(clicked()), this, SLOT(started()));
 	connect(m_startStopButton, SIGNAL(clicked()), m_gdbController, SLOT(detach()));
 	connect(m_startStopButton, SIGNAL(clicked()), this, SLOT(stopped()));
 }
@@ -100,5 +103,12 @@ void GDBWindow::stopped() {
 	disconnect(m_startStopButton, SIGNAL(clicked()), m_gdbController, SLOT(detach()));
 	disconnect(m_startStopButton, SIGNAL(clicked()), this, SLOT(stopped()));
 	connect(m_startStopButton, SIGNAL(clicked()), m_gdbController, SLOT(listen()));
-	connect(m_startStopButton, SIGNAL(clicked()), this, SLOT(started()));
+}
+
+void GDBWindow::failed() {
+	QMessageBox* failure = new QMessageBox(QMessageBox::Warning, tr("Crash"),
+		tr("Could not start GDB server"),
+		QMessageBox::Ok, this,  Qt::Sheet);
+	failure->setAttribute(Qt::WA_DeleteOnClose);
+	failure->show();
 }
diff --git a/src/platform/qt/GDBWindow.h b/src/platform/qt/GDBWindow.h
index 31a8ff5d3..683e7c632 100644
--- a/src/platform/qt/GDBWindow.h
+++ b/src/platform/qt/GDBWindow.h
@@ -28,6 +28,8 @@ private slots:
 	void started();
 	void stopped();
 
+	void failed();
+
 private:
 	GDBController* m_gdbController;