diff --git a/lib/path.js b/lib/path.js
index f7a8612933a..e278c891482 100644
--- a/lib/path.js
+++ b/lib/path.js
@@ -518,11 +518,11 @@ const win32 = {
           lastCommonSep = 3;
         }
       }
+      if (lastCommonSep === -1)
+        lastCommonSep = 0;
     }
 
     let out = '';
-    if (lastCommonSep === -1)
-      lastCommonSep = 0;
     // Generate the relative path based on the path difference between `to` and
     // `from`
     for (i = fromStart + lastCommonSep + 1; i <= fromEnd; ++i) {