diff --git a/src/AWS.Deploy.Constants/CDK.cs b/src/AWS.Deploy.Constants/CDK.cs
index 2d8fe7c4d..a2c5c1563 100644
--- a/src/AWS.Deploy.Constants/CDK.cs
+++ b/src/AWS.Deploy.Constants/CDK.cs
@@ -11,7 +11,15 @@ internal static class CDK
         /// <summary>
         /// Deployment tool workspace directory to create CDK app during the deployment.
         /// </summary>
-        public static readonly string DeployToolWorkspaceDirectoryRoot = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.UserProfile), ".aws-dotnet-deploy");
+        public static string DeployToolWorkspaceDirectoryRoot {
+            get
+            {
+                var deployToolWorkspace = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.UserProfile), ".aws-dotnet-deploy");
+                if (!Directory.Exists(deployToolWorkspace))
+                    Directory.CreateDirectory(deployToolWorkspace);
+                return deployToolWorkspace;
+            }
+        }
 
         /// <summary>
         /// Directory that contains CDK projects
diff --git a/src/AWS.Deploy.Orchestration/CDK/CDKManager.cs b/src/AWS.Deploy.Orchestration/CDK/CDKManager.cs
index d2ae5d15c..8946acb15 100644
--- a/src/AWS.Deploy.Orchestration/CDK/CDKManager.cs
+++ b/src/AWS.Deploy.Orchestration/CDK/CDKManager.cs
@@ -45,17 +45,22 @@ public CDKManager(ICDKInstaller cdkInstaller, INPMPackageInitializer npmPackageI
             _interactiveService = interactiveService;
         }
 
+        private async Task CreateCDKBootstrapTemplate()
+        {
+            // The CDK bootstrap template can be generated by running 'cdk bootstrap --show-template'.
+            // We need to keep the template up to date while making sure that the 'Staging Bucket' retention policies are set to 'Delete'.
+            var cdkBootstrapTemplate = typeof(CdkProjectHandler).Assembly.ReadEmbeddedFile(TemplateIdentifier);
+            await using var cdkBootstrapTemplateFile = new StreamWriter(Constants.CDK.CDKBootstrapTemplatePath);
+            await cdkBootstrapTemplateFile.WriteAsync(cdkBootstrapTemplate);
+        }
+
         public async Task EnsureCompatibleCDKExists(string workingDirectory, Version cdkVersion)
         {
             await s_cdkManagerSemaphoreSlim.WaitAsync();
 
             try
             {
-                // The CDK bootstrap template can be generated by running 'cdk bootstrap --show-template'.
-                // We need to keep the template up to date while making sure that the 'Staging Bucket' retention policies are set to 'Delete'.
-                var cdkBootstrapTemplate = typeof(CdkProjectHandler).Assembly.ReadEmbeddedFile(TemplateIdentifier);
-                await using var cdkBootstrapTemplateFile = new StreamWriter(Constants.CDK.CDKBootstrapTemplatePath);
-                await cdkBootstrapTemplateFile.WriteAsync(cdkBootstrapTemplate);
+                await CreateCDKBootstrapTemplate();
 
                 var installedCdkVersion = await _cdkInstaller.GetVersion(workingDirectory);
                 if (installedCdkVersion.Success && installedCdkVersion.Result?.CompareTo(cdkVersion) >= 0)