diff --git a/src/AWS.Deploy.ServerMode.Client/ServerModeSession.cs b/src/AWS.Deploy.ServerMode.Client/ServerModeSession.cs
index e9ce6c337..2c6b60c3b 100644
--- a/src/AWS.Deploy.ServerMode.Client/ServerModeSession.cs
+++ b/src/AWS.Deploy.ServerMode.Client/ServerModeSession.cs
@@ -6,6 +6,7 @@
 using System.IO;
 using System.Linq;
 using System.Net.Http;
+using System.Net.NetworkInformation;
 using System.Runtime.InteropServices;
 using System.Security.Cryptography;
 using System.Text;
@@ -126,6 +127,14 @@ public async Task Start(CancellationToken cancellationToken)
 
             for (var port = _startPort; port <= _endPort; port++)
             {
+                // This ensures that deploy tool CLI doesn't try on the in-use port
+                // because server availability task will return success response for
+                // an in-use port
+                if (IsPortInUse(port))
+                {
+                    continue;
+                }
+
                 _aes = Aes.Create();
                 _aes.GenerateKey();
 
@@ -216,6 +225,14 @@ private Task<bool> IsServerAvailable(CancellationToken cancellationToken)
                 cancellationToken);
         }
 
+        private static bool IsPortInUse(int port)
+        {
+            var ipGlobalProperties = IPGlobalProperties.GetIPGlobalProperties();
+            var listeners = ipGlobalProperties.GetActiveTcpListeners();
+
+            return listeners.Any(x => x.Port == port);
+        }
+
         #endregion
 
         #region Disposable
diff --git a/version.json b/version.json
index a9b9390fb..bc8aec0c6 100644
--- a/version.json
+++ b/version.json
@@ -1,6 +1,6 @@
 {
   "$schema": "https://raw.githubusercontent.com/dotnet/Nerdbank.GitVersioning/master/src/NerdBank.GitVersioning/version.schema.json",
-  "version": "0.24",
+  "version": "0.25",
   "publicReleaseRefSpec": [
     ".*"
   ],