diff --git a/pex/variables.py b/pex/variables.py
index e14b7351a..dd536abf4 100644
--- a/pex/variables.py
+++ b/pex/variables.py
@@ -660,7 +660,7 @@ def PEX_ROOT(self):
 
     @PEX_ROOT.validator
     def _ensure_writeable_pex_root(self, raw_pex_root):
-        pex_root = os.path.expanduser(raw_pex_root)
+        pex_root = os.path.realpath(os.path.expanduser(raw_pex_root))
         if not can_write_dir(pex_root):
             tmp_root = os.path.realpath(safe_mkdtemp())
             pex_warnings.warn(