diff --git a/packages/@aws-cdk/aws-ec2/lib/cfn-init-elements.ts b/packages/@aws-cdk/aws-ec2/lib/cfn-init-elements.ts
index 73153cd1025a3..ed2aef6fb14ed 100644
--- a/packages/@aws-cdk/aws-ec2/lib/cfn-init-elements.ts
+++ b/packages/@aws-cdk/aws-ec2/lib/cfn-init-elements.ts
@@ -489,7 +489,9 @@ export abstract class InitFile extends InitElement {
       if (fileOptions.group || fileOptions.owner || fileOptions.mode) {
         throw new Error('Owner, group, and mode options not supported for Windows.');
       }
-      return {};
+      return {
+        [this.fileName]: { ...contentVars },
+      };
     }
 
     return {
diff --git a/packages/@aws-cdk/aws-ec2/test/cfn-init-element.test.ts b/packages/@aws-cdk/aws-ec2/test/cfn-init-element.test.ts
index 1fc7399f63c60..2f81ff04acbbe 100644
--- a/packages/@aws-cdk/aws-ec2/test/cfn-init-element.test.ts
+++ b/packages/@aws-cdk/aws-ec2/test/cfn-init-element.test.ts
@@ -177,6 +177,22 @@ describe('InitFile', () => {
     }).toThrow('Owner, group, and mode options not supported for Windows.');
   });
 
+  test('file renders properly on Windows', () => {
+    // GIVEN
+    const file = ec2.InitFile.fromString('/tmp/foo', 'My content');
+
+    // WHEN
+    const rendered = getElementConfig(file, InitPlatform.WINDOWS);
+
+    // THEN
+    expect(rendered).toEqual({
+      '/tmp/foo': {
+        content: 'My content',
+        encoding: 'plain',
+      },
+    });
+  });
+
   test('symlink throws an error if mode is set incorrectly', () => {
     expect(() => {
       ec2.InitFile.symlink('/tmp/foo', '/tmp/bar', {