diff --git a/lib/ttb-util.js b/lib/ttb-util.js
index 24b1cee..6476a52 100644
--- a/lib/ttb-util.js
+++ b/lib/ttb-util.js
@@ -60,7 +60,10 @@ function ensurePathExists(resolvedPath) {
 function joinAndCreatePath(pathList) {
     var outPath;
     pathList.forEach(function (relPath) {
-        if (relPath === '') relPath = path.sep;
+        // Make sure to reappend the root if we need to
+        if (relPath === '') relPath = path.sep; // *NIX root
+        if (relPath.indexOf(':') >= 0) relPath += path.sep; // Windows root
+
         if (!outPath) {
             outPath = relPath;
         } else {