diff --git a/pex/bin/pex.py b/pex/bin/pex.py
old mode 100755
new mode 100644
diff --git a/pex/cache/root.py b/pex/cache/root.py
index 8793b7e1e..c624de107 100644
--- a/pex/cache/root.py
+++ b/pex/cache/root.py
@@ -14,8 +14,10 @@
     from pex.third_party import appdirs
 
 
-_USER_DIR = os.path.expanduser("~")
-_CACHE_DIR = appdirs.user_cache_dir(appauthor="pex-tool.org", appname="pex")  # type: str
+_USER_DIR = os.path.realpath(os.path.expanduser("~"))
+_CACHE_DIR = os.path.realpath(
+    appdirs.user_cache_dir(appauthor="pex-tool.org", appname="pex")
+)  # type: str
 
 
 def path(expand_user=True):
diff --git a/pex/pex_info.py b/pex/pex_info.py
index dbc07bdd3..9a8024326 100644
--- a/pex/pex_info.py
+++ b/pex/pex_info.py
@@ -507,7 +507,7 @@ def raw_pex_root(self):
     @property
     def pex_root(self):
         # type: () -> str
-        pex_root = os.path.expanduser(self.raw_pex_root)
+        pex_root = os.path.realpath(os.path.expanduser(self.raw_pex_root))
         if not can_write_dir(pex_root):
             tmp_root = safe_mkdtemp()
             pex_warnings.warn(
diff --git a/pex/variables.py b/pex/variables.py
index 43ffdebfe..b22f041ad 100644
--- a/pex/variables.py
+++ b/pex/variables.py
@@ -167,7 +167,7 @@ def _default_pex_root():
     # third party import lifecycle events.
     from pex.cache import root as cache_root
 
-    return cache_root.path(expand_user=False)
+    return cache_root.path(expand_user=True)
 
 
 class Variables(object):
@@ -796,7 +796,7 @@ def __repr__(self):
 #  calculations: https://github.com/pex-tool/pex/issues/1154
 def _expand_pex_root(pex_root):
     # type: (str) -> str
-    fallback = os.path.expanduser(pex_root)
+    fallback = os.path.realpath(os.path.expanduser(pex_root))
     return os.path.expanduser(Variables.PEX_ROOT.value_or(ENV, fallback=fallback))