diff --git a/toolkit/devtools/client/connection-manager.js b/toolkit/devtools/client/connection-manager.js
index fe636449893d..f94a9f79e2a1 100644
--- a/toolkit/devtools/client/connection-manager.js
+++ b/toolkit/devtools/client/connection-manager.js
@@ -6,7 +6,7 @@
 
 "use strict";
 
-const {Cu} = require("chrome");
+const {Cc, Ci, Cu} = require("chrome");
 const {setTimeout, clearTimeout} = require('sdk/timers');
 const EventEmitter = require("devtools/shared/event-emitter");
 
@@ -25,6 +25,7 @@ Cu.import("resource://gre/modules/devtools/dbg-server.jsm");
  * Methods:
  *  ⬩ Connection createConnection(host, port)
  *  ⬩ void       destroyConnection(connection)
+ *  ⬩ Number     getFreeTCPPort()
  *
  * Properties:
  *  ⬩ Array      connections
@@ -46,6 +47,7 @@ Cu.import("resource://gre/modules/devtools/dbg-server.jsm");
  *  ⬩ port              Port
  *  ⬩ logs              Current logs. "newlog" event notifies new available logs
  *  ⬩ store             Reference to a local data store (see below)
+ *  ⬩ keepConnecting    Should the connection keep trying connecting
  *  ⬩ status            Connection status:
  *                        Connection.Status.CONNECTED
  *                        Connection.Status.DISCONNECTED
@@ -86,6 +88,14 @@ let ConnectionManager = {
   get connections() {
     return [c for (c of this._connections)];
   },
+  getFreeTCPPort: function () {
+    let serv = Cc['@mozilla.org/network/server-socket;1']
+                 .createInstance(Ci.nsIServerSocket);
+    serv.init(-1, true, -1);
+    let port = serv.port;
+    serv.close();
+    return port;
+  },
 }
 
 EventEmitter.decorate(ConnectionManager);
@@ -101,6 +111,7 @@ function Connection(host, port) {
   this._onDisconnected = this._onDisconnected.bind(this);
   this._onConnected = this._onConnected.bind(this);
   this._onTimeout = this._onTimeout.bind(this);
+  this.keepConnecting = false;
 }
 
 Connection.Status = {
@@ -180,15 +191,7 @@ Connection.prototype = {
       let delay = Services.prefs.getIntPref("devtools.debugger.remote-timeout");
       this._timeoutID = setTimeout(this._onTimeout, delay);
 
-      let transport;
-      if (!this._host) {
-        transport = DebuggerServer.connectPipe();
-      } else {
-        transport = debuggerSocketConnect(this._host, this._port);
-      }
-      this._client = new DebuggerClient(transport);
-      this._client.addOneTimeListener("closed", this._onDisconnected);
-      this._client.connect(this._onConnected);
+      this._clientConnect();
     } else {
       let msg = "Can't connect. Client is not fully disconnected";
       this.log(msg);
@@ -199,6 +202,7 @@ Connection.prototype = {
   destroy: function() {
     this.log("killing connection");
     clearTimeout(this._timeoutID);
+    this.keepConnecting = false;
     if (this._client) {
       this._client.close();
       this._client = null;
@@ -206,6 +210,18 @@ Connection.prototype = {
     this._setStatus(Connection.Status.DESTROYED);
   },
 
+  _clientConnect: function () {
+    let transport;
+    if (!this._host) {
+      transport = DebuggerServer.connectPipe();
+    } else {
+      transport = debuggerSocketConnect(this._host, this._port);
+    }
+    this._client = new DebuggerClient(transport);
+    this._client.addOneTimeListener("closed", this._onDisconnected);
+    this._client.connect(this._onConnected);
+  },
+
   get status() {
     return this._status
   },
@@ -219,6 +235,13 @@ Connection.prototype = {
   },
 
   _onDisconnected: function() {
+    this._client = null;
+
+    if (this._status == Connection.Status.CONNECTING && this.keepConnecting) {
+      setTimeout(() => this._clientConnect(), 0);
+      return;
+    }
+
     clearTimeout(this._timeoutID);
     switch (this.status) {
       case Connection.Status.CONNECTED:
@@ -230,7 +253,6 @@ Connection.prototype = {
       default:
         this.log("disconnected");
     }
-    this._client = null;
     this._setStatus(Connection.Status.DISCONNECTED);
   },
 
@@ -242,7 +264,7 @@ Connection.prototype = {
 
   _onTimeout: function() {
     this.log("connection timeout");
-    this.emit(Connection.Events.TIMEOUT, str);
+    this.emit(Connection.Events.TIMEOUT);
     this.disconnect();
   },
 }
diff --git a/toolkit/devtools/server/tests/mochitest/test_connection-manager.html b/toolkit/devtools/server/tests/mochitest/test_connection-manager.html
index 263352789f63..c747f0c9af36 100644
--- a/toolkit/devtools/server/tests/mochitest/test_connection-manager.html
+++ b/toolkit/devtools/server/tests/mochitest/test_connection-manager.html
@@ -20,6 +20,7 @@ window.onload = function() {
 
   Cu.import("resource://gre/modules/devtools/dbg-server.jsm");
   Cu.import("resource://gre/modules/devtools/Loader.jsm");
+  Cu.import("resource://gre/modules/Services.jsm");
 
   DebuggerServer.init(function () { return true; });
   DebuggerServer.addBrowserActors();
@@ -43,7 +44,7 @@ window.onload = function() {
 
     var c = c2;
 
-    var eventsRef = "connecting connected disconnecting disconnected host-changed disconnected destroyed";
+    var eventsRef = "connecting connected disconnecting disconnected host-changed disconnected timeout destroyed";
     var events = [];
 
     var s = Connection.Status;
@@ -70,7 +71,7 @@ window.onload = function() {
     function testError() {
       c.once(Connection.Events.DISCONNECTED, function(e) {
         events.push(e);
-        ConnectionManager.destroyConnection(c);
+        testKeepConnecting();
       });
       c.once(Connection.Events.HOST_CHANGED, function(e) {
         events.push(e);
@@ -80,6 +81,24 @@ window.onload = function() {
       c.host = "localhost";
     }
 
+    function testKeepConnecting() {
+      // ensure that keepConnecting keep trying connecting
+      // until the connection attempts timeout
+      var originalTimeout = Services.prefs.getIntPref("devtools.debugger.remote-timeout");
+      Services.prefs.setIntPref("devtools.debugger.remote-timeout", 1000);
+      c.once("timeout", function (e) {
+        events.push(e);
+        Services.prefs.setIntPref("devtools.debugger.remote-timeout", originalTimeout);
+        ConnectionManager.destroyConnection(c);
+      });
+      c.keepConnecting = true;
+      var port = ConnectionManager.getFreeTCPPort();
+      ok(parseInt(port), "Free TCP port looks like a port number");
+      c.port = port;
+      c.host = "locahost";
+      c.connect();
+    }
+
     function finish() {
       is(events.join(" "), eventsRef, "Events received in the right order");
       DebuggerServer.destroy();