diff --git a/editor/editor_node.cpp b/editor/editor_node.cpp
index e94acd28073..9d8b6177c18 100644
--- a/editor/editor_node.cpp
+++ b/editor/editor_node.cpp
@@ -2029,16 +2029,16 @@ void EditorNode::_run(bool p_current, const String &p_custom) {
 
 	args = ProjectSettings::get_singleton()->get("editor/main_run_args");
 	skip_breakpoints = ScriptEditor::get_singleton()->get_debugger()->is_skip_breakpoints();
+	emit_signal("play_pressed");
 
 	Error error = editor_run.run(run_filename, args, breakpoints, skip_breakpoints);
 
 	if (error != OK) {
-
+		emit_signal("stop_pressed");
 		show_accept(TTR("Could not start subprocess!"), TTR("OK"));
 		return;
 	}
 
-	emit_signal("play_pressed");
 	if (p_current) {
 		play_scene_button->set_pressed(true);
 		play_scene_button->set_icon(gui_base->get_icon("Reload", "EditorIcons"));
diff --git a/editor/editor_run.cpp b/editor/editor_run.cpp
index ff7420e19b6..a3f3ce40cc0 100644
--- a/editor/editor_run.cpp
+++ b/editor/editor_run.cpp
@@ -30,6 +30,9 @@
 
 #include "editor_run.h"
 
+#include "plugins/script_editor_plugin.h"
+#include "script_editor_debugger.h"
+
 #include "core/project_settings.h"
 #include "editor_settings.h"
 
@@ -43,8 +46,6 @@ Error EditorRun::run(const String &p_scene, const String &p_custom_args, const L
 	List<String> args;
 
 	String resource_path = ProjectSettings::get_singleton()->get_resource_path();
-	String remote_host = EditorSettings::get_singleton()->get("network/debug/remote_host");
-	int remote_port = (int)EditorSettings::get_singleton()->get("network/debug/remote_port");
 
 	if (resource_path != "") {
 		args.push_back("--path");
@@ -52,8 +53,15 @@ Error EditorRun::run(const String &p_scene, const String &p_custom_args, const L
 	}
 
 	args.push_back("--remote-debug");
-	args.push_back(remote_host + ":" + String::num(remote_port));
 
+	const String conn_string = ScriptEditor::get_singleton()->get_debugger()->get_connection_string();
+	if (!conn_string.empty()) {
+		args.push_back(ScriptEditor::get_singleton()->get_debugger()->get_connection_string());
+	} else { // Try anyway with default settings
+		const String remote_host = EditorSettings::get_singleton()->get("network/debug/remote_host");
+		const int remote_port = (int)EditorSettings::get_singleton()->get("network/debug/remote_port");
+		args.push_back(remote_host + ":" + String::num(remote_port));
+	}
 	args.push_back("--allow_focus_steal_pid");
 	args.push_back(itos(OS::get_singleton()->get_process_id()));
 
diff --git a/editor/script_editor_debugger.cpp b/editor/script_editor_debugger.cpp
index ab4501bb8a7..6384b124018 100644
--- a/editor/script_editor_debugger.cpp
+++ b/editor/script_editor_debugger.cpp
@@ -29,8 +29,8 @@
 /*************************************************************************/
 
 #include "script_editor_debugger.h"
-
 #include "core/io/marshalls.h"
+#include "core/os/os.h"
 #include "core/project_settings.h"
 #include "core/ustring.h"
 #include "editor/plugins/canvas_item_editor_plugin.h"
@@ -1476,13 +1476,25 @@ void ScriptEditorDebugger::start() {
 		perf_max.write[i] = 0;
 	}
 
-	int remote_port = (int)EditorSettings::get_singleton()->get("network/debug/remote_port");
-	if (server->listen(remote_port) != OK) {
-		EditorNode::get_log()->add_message(String("Error listening on port ") + itos(remote_port), EditorLog::MSG_TYPE_ERROR);
-		return;
+	const int max_tries = 6;
+	remote_port = (int)EditorSettings::get_singleton()->get("network/debug/remote_port");
+	int current_try = 0;
+	// Find first available port.
+	Error err = server->listen(remote_port);
+	while (err != OK && current_try < max_tries) {
+		EditorNode::get_log()->add_message(String("Remote debugger failed listening on port: ") + itos(remote_port) + String(" Retrying on new port: " + itos(remote_port + 1)), EditorLog::MSG_TYPE_WARNING);
+		current_try++;
+		remote_port++;
+		OS::get_singleton()->delay_usec(1000);
+		err = server->listen(remote_port);
+	}
+	// No suitable port found.
+	if (err != OK) {
+		EditorNode::get_log()->add_message(String("Error listening on port ") + itos(remote_port), EditorLog::MSG_TYPE_ERROR);
+		EditorNode::get_log()->add_message(String("Remote debugger error listening for connections. No free port"), EditorLog::MSG_TYPE_ERROR);
 	}
-
 	EditorNode::get_singleton()->get_scene_tree_dock()->show_tab_buttons();
+
 	auto_switch_remote_scene_tree = (bool)EditorSettings::get_singleton()->get("debugger/auto_switch_to_remote_scene_tree");
 	if (auto_switch_remote_scene_tree) {
 		EditorNode::get_singleton()->get_scene_tree_dock()->show_remote_tree();
@@ -1517,6 +1529,7 @@ void ScriptEditorDebugger::stop() {
 		reason->set_tooltip("");
 	}
 
+	remote_port = 0;
 	pending_in_queue = 0;
 	message.clear();
 
@@ -2059,6 +2072,11 @@ bool ScriptEditorDebugger::get_debug_with_external_editor() const {
 	return enable_external_editor;
 }
 
+String ScriptEditorDebugger::get_connection_string() const {
+	String remote_host = EditorSettings::get_singleton()->get("network/debug/remote_host");
+	return remote_port ? remote_host + ":" + itos(remote_port) : "";
+}
+
 void ScriptEditorDebugger::set_debug_with_external_editor(bool p_enabled) {
 
 	enable_external_editor = p_enabled;
@@ -2625,6 +2643,7 @@ ScriptEditorDebugger::ScriptEditorDebugger(EditorNode *p_editor) {
 	enable_external_editor = false;
 	last_error_count = 0;
 	last_warning_count = 0;
+	remote_port = 0;
 
 	EditorNode::get_singleton()->get_pause_button()->connect("pressed", this, "_paused");
 }
diff --git a/editor/script_editor_debugger.h b/editor/script_editor_debugger.h
index 589a011bffe..7433b0034f4 100644
--- a/editor/script_editor_debugger.h
+++ b/editor/script_editor_debugger.h
@@ -121,6 +121,7 @@ private:
 	int last_warning_count;
 
 	bool hide_on_stop;
+	int remote_port;
 	bool enable_external_editor;
 
 	bool skip_breakpoints_value = false;
@@ -275,6 +276,7 @@ public:
 	void set_hide_on_stop(bool p_hide);
 
 	bool get_debug_with_external_editor() const;
+	String get_connection_string() const;
 	void set_debug_with_external_editor(bool p_enabled);
 
 	Ref<Script> get_dump_stack_script() const;