diff --git a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Controller.cs b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Controller.cs
index 9a0ef98a..1936f006 100644
--- a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Controller.cs
+++ b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Controller.cs
@@ -59,7 +59,7 @@ internal set
 
         public bool IsIdle()
         {
-            return (DateTime.UtcNow - _lastActivity).TotalMilliseconds > 100;
+            return (DateTime.UtcNow - _lastActivity).TotalMilliseconds > 50;
         }
 
         public bool Send(MessageRaw raw)
diff --git a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Engine.cs b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Engine.cs
index 1ec8e913..356700e8 100644
--- a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Engine.cs
+++ b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/Engine.cs
@@ -453,10 +453,7 @@ public bool UpdateDebugFlags()
                     stateFlagsToSet |= Commands.DebuggingExecutionChangeConditions.State.DebuggerQuiet;
                 }
 
-                SetExecutionMode(stateFlagsToSet, 0);
-
-                // done here
-                return true;
+                return SetExecutionMode(stateFlagsToSet, 0);
             }
 
             // device isn't connected
diff --git a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/WireProtocolRequest.cs b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/WireProtocolRequest.cs
index ac967b1b..8e289f0f 100644
--- a/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/WireProtocolRequest.cs
+++ b/nanoFramework.Tools.DebugLibrary.Shared/WireProtocol/WireProtocolRequest.cs
@@ -40,10 +40,23 @@ public WireProtocolRequest(OutgoingMessage outgoingMessage, int millisecondsTime
 
         internal bool PerformRequest(IController controller)
         {
+            const int sleepTimeMs = 10;
+            int attemptsCount = 10000 / sleepTimeMs;
+
             // wait for controller to be idle
-            while(!controller.IsIdle())
+            while (
+                !controller.IsIdle() &&
+                attemptsCount > 0)
             {
                 Thread.Sleep(10);
+
+                attemptsCount--;
+            }
+
+            if(attemptsCount == 0)
+            {
+                // timeout waiting for idle controller
+                return false;
             }
 
             Debug.WriteLine($"Performing request");
@@ -67,6 +80,9 @@ internal bool PerformRequest(IController controller)
                 return true;
             }
 
+            // store start time
+            RequestTimestamp = DateTime.Now;
+
             return false;
         }