diff --git a/src/client/pythonEnvironments/discovery/locators/services/virtualenvwrapperLocator.ts b/src/client/pythonEnvironments/discovery/locators/services/virtualenvwrapperLocator.ts
index a1ad3fa7ed26..8e89c7ad7e46 100644
--- a/src/client/pythonEnvironments/discovery/locators/services/virtualenvwrapperLocator.ts
+++ b/src/client/pythonEnvironments/discovery/locators/services/virtualenvwrapperLocator.ts
@@ -20,10 +20,12 @@ export async function isVirtualenvwrapperEnvironment(interpreterPath:string): Pr
     const environmentName = path.basename(path.dirname(path.dirname(interpreterPath)));
 
     let environmentDir = path.join(workonHomeDir, environmentName);
+    let pathToCheck = interpreterPath;
 
     if (getOSType() === OSType.Windows) {
         environmentDir = environmentDir.toUpperCase();
+        pathToCheck = interpreterPath.toUpperCase();
     }
 
-    return await pathExists(environmentDir) && interpreterPath.startsWith(`${environmentDir}${path.sep}`);
+    return await pathExists(environmentDir) && pathToCheck.startsWith(`${environmentDir}${path.sep}`);
 }
diff --git a/src/test/pythonEnvironments/discovery/locators/virtualenvwrapperLocator.unit.test.ts b/src/test/pythonEnvironments/discovery/locators/virtualenvwrapperLocator.unit.test.ts
index 05d73758e2a4..2221e109a1ae 100644
--- a/src/test/pythonEnvironments/discovery/locators/virtualenvwrapperLocator.unit.test.ts
+++ b/src/test/pythonEnvironments/discovery/locators/virtualenvwrapperLocator.unit.test.ts
@@ -22,8 +22,7 @@ suite('Virtualenvwrapper Locator Tests', () => {
         pathExistsStub = sinon.stub(fileUtils, 'pathExists');
         getDefaultDirStub = sinon.stub(virtualenvwrapperUtils, 'getDefaultVirtualenvwrapperDir');
 
-        pathExistsStub.withArgs(path.join(homeDir, envDirectory)).resolves(true);
-        pathExistsStub.resolves(false);
+        pathExistsStub.resolves(true);
     });
 
     teardown(() => {
@@ -32,7 +31,7 @@ suite('Virtualenvwrapper Locator Tests', () => {
         getDefaultDirStub.restore();
     });
 
-    test('WORKON_HOME is not set, and the interpreter is is in a subfolder', async () => {
+    test('WORKON_HOME is not set, and the interpreter is in a subfolder of virtualenvwrapper', async () => {
         const interpreter = path.join(homeDir, envDirectory, 'bin', 'python');
 
         getEnvVariableStub.withArgs('WORKON_HOME').returns(undefined);
@@ -56,7 +55,6 @@ suite('Virtualenvwrapper Locator Tests', () => {
         const interpreter = path.join('some', 'path', envDirectory, 'bin', 'python');
 
         getEnvVariableStub.withArgs('WORKON_HOME').returns(workonHomeDirectory);
-        pathExistsStub.withArgs(path.join(workonHomeDirectory, envDirectory)).resolves(false);
 
         assert.deepStrictEqual(await isVirtualenvwrapperEnvironment(interpreter), false);
     });