diff --git a/packages/cli-common/src/paths.ts b/packages/cli-common/src/paths.ts
index 70761ad2d7..0db712e6cb 100644
--- a/packages/cli-common/src/paths.ts
+++ b/packages/cli-common/src/paths.ts
@@ -106,7 +106,10 @@ export function findOwnRootDir(ownDir: string) {
  */
 export function findPaths(searchDir: string): Paths {
   const ownDir = findOwnDir(searchDir);
-  const targetDir = fs.realpathSync(process.cwd());
+  // Drive letter can end up being lowercased here on Windows, bring back to uppercase for consistency
+  const targetDir = fs
+    .realpathSync(process.cwd())
+    .replace(/^[a-z]:/, str => str.toUpperCase());
 
   // Lazy load this as it will throw an error if we're not inside the Backstage repo.
   let ownRoot = '';