diff --git a/src/client/debugger/Common/Contracts.ts b/src/client/debugger/Common/Contracts.ts
index cd32d1304dfd..989568fa731a 100644
--- a/src/client/debugger/Common/Contracts.ts
+++ b/src/client/debugger/Common/Contracts.ts
@@ -39,7 +39,8 @@ export enum DebugOptions {
     BreakOnSystemExitZero = 'BreakOnSystemExitZero',
     Sudo = 'Sudo',
     Pyramid = 'Pyramid',
-    FixFilePathCase = 'FixFilePathCase'
+    FixFilePathCase = 'FixFilePathCase',
+    WindowsClient = 'WindowsClient'
 }
 
 export interface ExceptionHandling {
diff --git a/src/client/debugger/configProviders/pythonV2Provider.ts b/src/client/debugger/configProviders/pythonV2Provider.ts
index 4c6b74d7faac..47e587daabc7 100644
--- a/src/client/debugger/configProviders/pythonV2Provider.ts
+++ b/src/client/debugger/configProviders/pythonV2Provider.ts
@@ -41,6 +41,9 @@ export class PythonV2DebugConfigurationProvider extends BaseConfigurationProvide
         if (this.serviceContainer.get<IPlatformService>(IPlatformService).isWindows && isLocalHost) {
             debugConfiguration.debugOptions.push(DebugOptions.FixFilePathCase);
         }
+        if (this.serviceContainer.get<IPlatformService>(IPlatformService).isWindows) {
+            debugConfiguration.debugOptions.push(DebugOptions.WindowsClient);
+        }
 
         if (!debugConfiguration.pathMappings) {
             debugConfiguration.pathMappings = [];
diff --git a/src/test/debugger/configProvider/provider.attach.test.ts b/src/test/debugger/configProvider/provider.attach.test.ts
index 596cc907c7dc..30d1a4192800 100644
--- a/src/test/debugger/configProvider/provider.attach.test.ts
+++ b/src/test/debugger/configProvider/provider.attach.test.ts
@@ -35,6 +35,7 @@ enum OS {
             const debugOptionsAvailable = [DebugOptions.RedirectOutput];
             if (os.value === OS.Windows && provider.debugType === 'pythonExperimental') {
                 debugOptionsAvailable.push(DebugOptions.FixFilePathCase);
+                debugOptionsAvailable.push(DebugOptions.WindowsClient);
             }
             setup(() => {
                 serviceContainer = TypeMoq.Mock.ofType<IServiceContainer>();