pex 2.60.1__py2.py3-none-any.whl → 2.61.0__py2.py3-none-any.whl

pex/bin/pex.py

@@ -24,6 +24,7 @@ from pex.commands.command import (
     register_global_arguments,
 )
 from pex.common import CopyMode, die, is_pyc_dir, is_pyc_file
+from pex.compatibility import commonpath
 from pex.dependency_configuration import DependencyConfiguration
 from pex.dependency_manager import DependencyManager
 from pex.dist_metadata import Requirement
@@ -801,6 +802,16 @@ class PositionalArgumentFromFileParser(object):
 
 def configure_clp():
     # type: () -> PositionalArgumentFromFileParser
+
+    prog = sys.argv[0]
+    if os.path.isabs(prog):
+        entries = os.environ.get("PATH", os.defpath).split(os.pathsep)
+        entries.append(os.getcwd())
+        for entry in entries:
+            if os.path.isabs(entry) and entry == commonpath((entry, prog)):
+                prog = os.path.relpath(prog, entry)
+                break
+
     usage = (
         "%(prog)s [-o OUTPUT.PEX] [options] [-- arg1 arg2 ...]\n\n"
         "%(prog)s builds a PEX (Python Executable) file based on the given specifications: "
@@ -810,7 +821,7 @@ def configure_clp():
         "with an @ symbol. These files must contain one argument per line."
     )
 
-    parser = ArgumentParser(usage=usage, formatter_class=ArgumentDefaultsHelpFormatter)
+    parser = ArgumentParser(prog=prog, usage=usage, formatter_class=ArgumentDefaultsHelpFormatter)
     parser.add_argument("-V", "--version", action="version", version=__version__)
 
     configure_clp_pex_resolution(parser)

pex/cache/dirs.py

@@ -144,7 +144,7 @@ class CacheDir(Enum["CacheDir.Value"]):
 
     INSTALLED_WHEELS = Value(
         "installed_wheels",
-        version=1,
+        version=2,
         name="Pre-installed Wheels",
         description=(
             "Pre-installed wheel chroots used to both build PEXes and serve as runtime `sys.path` "
@@ -178,7 +178,7 @@ class CacheDir(Enum["CacheDir.Value"]):
 
     PIP = Value(
         "pip",
-        version=2,
+        version=3,
         name="Pip Versions",
         description="Isolated Pip caches and Pip PEXes Pex uses to resolve distributions.",
         dependencies=[INSTALLED_WHEELS],
@@ -236,7 +236,7 @@ class CacheDir(Enum["CacheDir.Value"]):
 
     UNZIPPED_PEXES = Value(
         "unzipped_pexes",
-        version=2,
+        version=3,
         name="Unzipped PEXes",
         description="The unzipped PEX files executed on this machine.",
         dependencies=[BOOTSTRAPS, USER_CODE, INSTALLED_WHEELS],
@@ -244,7 +244,7 @@ class CacheDir(Enum["CacheDir.Value"]):
 
     VENVS = Value(
         "venvs",
-        version=2,
+        version=3,
         name="Virtual Environments",
         description="Virtual environments generated at runtime for `--venv` mode PEXes.",
         dependencies=[INSTALLED_WHEELS],

pex/docs/html/_pagefind/pagefind-entry.json

@@ -1 +1 @@
-{"version":"1.3.0","languages":{"en":{"hash":"en_71c76562fd","wasm":"en","page_count":8}}}
+{"version":"1.3.0","languages":{"en":{"hash":"en_50edc69c3c","wasm":"en","page_count":8}}}

pex/docs/html/_static/documentation_options.js

@@ -1,5 +1,5 @@
 const DOCUMENTATION_OPTIONS = {
-    VERSION: '2.60.1',
+    VERSION: '2.61.0',
     LANGUAGE: 'en',
     COLLAPSE_INDEX: false,
     BUILDER: 'html',

pex/docs/html/api/vars.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="../_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="../_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>PEX runtime environment variables - Pex Docs (v2.60.1)</title>
+        <title>PEX runtime environment variables - Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="../_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="../_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="../_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="../index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="../index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -643,12 +643,12 @@
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -671,7 +671,7 @@
       
     </aside>
   </div>
-</div><script src="../_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="../_static/documentation_options.js?v=6a15f429"></script>
     <script src="../_static/doctools.js?v=9bcbadda"></script>
     <script src="../_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="../_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/buildingpex.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>Building .pex files - Pex Docs (v2.60.1)</title>
+        <title>Building .pex files - Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -681,12 +681,12 @@ scary like <code class="docutils literal notranslate"><span class="pre">sudo</sp
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -709,7 +709,7 @@ scary like <code class="docutils literal notranslate"><span class="pre">sudo</sp
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/genindex.html

@@ -6,7 +6,7 @@
         <link rel="prefetch" href="_static/pex-logo-light.png" as="image">
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
-    <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 --><title>Index - Pex Docs (v2.60.1)</title>
+    <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 --><title>Index - Pex Docs (v2.61.0)</title>
 <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -161,7 +161,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -260,12 +260,12 @@
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -288,7 +288,7 @@
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/index.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>Pex Docs (v2.60.1)</title>
+        <title>Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="#"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="#"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -341,12 +341,12 @@ To go straight to building pex files, see <a class="reference internal" href="bu
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -389,7 +389,7 @@ To go straight to building pex files, see <a class="reference internal" href="bu
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/recipes.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>PEX Recipes and Notes - Pex Docs (v2.60.1)</title>
+        <title>PEX Recipes and Notes - Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -430,12 +430,12 @@ $<span class="w"> </span><span class="nb">export</span><span class="w"> </span><
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -482,7 +482,7 @@ $<span class="w"> </span><span class="nb">export</span><span class="w"> </span><
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/scie.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>PEX with included Python interpreter - Pex Docs (v2.60.1)</title>
+        <title>PEX with included Python interpreter - Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -623,12 +623,12 @@ uuid
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -672,7 +672,7 @@ uuid
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/search.html

@@ -6,7 +6,7 @@
         <link rel="prefetch" href="_static/pex-logo-light.png" as="image">
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
-    <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 --><title>Search - Pex Docs (v2.60.1)</title><link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
+    <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 --><title>Search - Pex Docs (v2.61.0)</title><link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
     
@@ -176,7 +176,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -273,12 +273,12 @@
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -301,7 +301,7 @@
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/docs/html/whatispex.html

@@ -8,7 +8,7 @@
         <link rel="prefetch" href="_static/pex-logo-dark.png" as="image">
 
     <link rel="shortcut icon" href="_static/pex-icon.png"><!-- Generated with Sphinx 8.2.3 and Furo 2025.09.25 -->
-        <title>What are .pex files? - Pex Docs (v2.60.1)</title>
+        <title>What are .pex files? - Pex Docs (v2.61.0)</title>
       <link rel="stylesheet" type="text/css" href="_static/pygments.css?v=d111a655" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo.css?v=580074bf" />
     <link rel="stylesheet" type="text/css" href="_static/styles/furo-extensions.css?v=8dab3a3b" />
@@ -163,7 +163,7 @@
       </label>
     </div>
     <div class="header-center">
-      <a href="index.html"><div class="brand">Pex Docs (v2.60.1)</div></a>
+      <a href="index.html"><div class="brand">Pex Docs (v2.61.0)</div></a>
     </div>
     <div class="header-right">
       <div class="theme-toggle-container theme-toggle-header">
@@ -322,12 +322,12 @@ build executable .pex files.  This is described more thoroughly in
           </div>
           <div class="right-details">
             <div class="icons">
-              <a class="muted-link " href="https://pypi.org/project/pex/2.60.1/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://pypi.org/project/pex/2.61.0/" aria-label="PyPI"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 448 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M439.8 200.5c-7.7-30.9-22.3-54.2-53.4-54.2h-40.1v47.4c0 36.8-31.2 67.8-66.8 67.8H172.7c-29.2 0-53.4 25-53.4 54.3v101.8c0 29 25.2 46 53.4 54.3 33.8 9.9 66.3 11.7 106.8 0 26.9-7.8 53.4-23.5 53.4-54.3v-40.7H226.2v-13.6h160.2c31.1 0 42.6-21.7 53.4-54.2 11.2-33.5 10.7-65.7 0-108.6zM286.2 404c11.1 0 20.1 9.1 20.1 20.3 0 11.3-9 20.4-20.1 20.4-11 0-20.1-9.2-20.1-20.4.1-11.3 9.1-20.3 20.1-20.3zM167.8 248.1h106.8c29.7 0 53.4-24.5 53.4-54.3V91.9c0-29-24.4-50.7-53.4-55.6-35.8-5.9-74.7-5.6-106.8.1-45.2 8-53.4 24.7-53.4 55.6v40.7h106.9v13.6h-147c-31.1 0-58.3 18.7-66.8 54.2-9.8 40.7-10.2 66.1 0 108.6 7.6 31.6 25.7 54.2 56.8 54.2H101v-48.8c0-35.3 30.5-66.4 66.8-66.4zm-6.7-142.6c-11.1 0-20.1-9.1-20.1-20.3.1-11.3 9-20.4 20.1-20.4 11 0 20.1 9.2 20.1 20.4s-9 20.3-20.1 20.3z">
     </path>
 </svg>
 </a>
-              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.60.1/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
+              <a class="muted-link " href="https://github.com/pex-tool/pex/releases/download/v2.61.0/pex" aria-label="Download"><svg stroke="currentColor" fill="currentColor" stroke-width="0" viewBox="0 0 640 512" height="1em" width="1em" xmlns="http://www.w3.org/2000/svg">
     <path d="M537.6 226.6c4.1-10.7 6.4-22.4 6.4-34.6 0-53-43-96-96-96-19.7 0-38.1 6-53.3 16.2C367 64.2 315.3 32 256 32c-88.4 0-160 71.6-160 160 0 2.7.1 5.4.2 8.1C40.2 219.8 0 273.2 0 336c0 79.5 64.5 144 144 144h368c70.7 0 128-57.3 128-128 0-61.9-44-113.6-102.4-125.4zm-132.9 88.7L299.3 420.7c-6.2 6.2-16.4 6.2-22.6 0L171.3 315.3c-10.1-10.1-2.9-27.3 11.3-27.3H248V176c0-8.8 7.2-16 16-16h48c8.8 0 16 7.2 16 16v112h65.4c14.2 0 21.4 17.2 11.3 27.3z">
     </path>
 </svg>
@@ -371,7 +371,7 @@ build executable .pex files.  This is described more thoroughly in
       
     </aside>
   </div>
-</div><script src="_static/documentation_options.js?v=bfb83a69"></script>
+</div><script src="_static/documentation_options.js?v=6a15f429"></script>
     <script src="_static/doctools.js?v=9bcbadda"></script>
     <script src="_static/sphinx_highlight.js?v=dc90522c"></script>
     <script src="_static/scripts/furo.js?v=46bd48cc"></script>

pex/environment.py

@@ -15,6 +15,7 @@ from pex.dependency_configuration import DependencyConfiguration
 from pex.dist_metadata import Distribution, Requirement, is_wheel
 from pex.fingerprinted_distribution import FingerprintedDistribution
 from pex.inherit_path import InheritPath
+from pex.installed_wheel import InstalledWheel
 from pex.interpreter import PythonInterpreter
 from pex.layout import ensure_installed, identify_layout
 from pex.orderedset import OrderedSet
@@ -820,22 +821,25 @@ class PEXEnvironment(object):
             if dist.location in sys.path:
                 continue
             with TRACER.timed("Activating %s" % dist, V=2):
-                if self._pex_info.inherit_path == InheritPath.FALLBACK:
-                    # Prepend location to sys.path.
-                    #
-                    # This ensures that bundled versions of libraries will be used before system-installed
-                    # versions, in case something is installed in both, helping to favor hermeticity in
-                    # the case of non-hermetic PEX files (i.e. those with inherit_path=True).
-                    #
-                    # If the path is not already in sys.path, site.addsitedir will append (not prepend)
-                    # the path to sys.path. But if the path is already in sys.path, site.addsitedir will
-                    # leave sys.path unmodified, but will do everything else it would do. This is not part
-                    # of its advertised contract (which is very vague), but has been verified to be the
-                    # case by inspecting its source for both cpython 2.7 and cpython 3.7.
-                    sys.path.insert(0, dist.location)
-                else:
-                    sys.path.append(dist.location)
-
-                with TRACER.timed("Adding sitedir", V=2):
-                    site.addsitedir(dist.location)
+                for entry in InstalledWheel.load(dist.location).iter_sys_path_entries():
+                    if self._pex_info.inherit_path == InheritPath.FALLBACK:
+                        # Prepend location to sys.path.
+                        #
+                        # This ensures that bundled versions of libraries will be used before
+                        # system-installed versions, in case something is installed in both, helping
+                        # to favor hermeticity in the case of non-hermetic PEX files (i.e. those
+                        # with inherit_path=True).
+                        #
+                        # If the path is not already in sys.path, site.addsitedir will append (not
+                        # prepend) the path to sys.path. But if the path is already in sys.path,
+                        # site.addsitedir will leave sys.path unmodified, but will do everything
+                        # else it would do. This is not part of its advertised contract (which is
+                        # very vague), but has been verified to be the case by inspecting its source
+                        # for both cpython 2.7 and cpython 3.7.
+                        sys.path.insert(0, entry)
+                    else:
+                        sys.path.append(entry)
+
+                    with TRACER.timed("Adding sitedir", V=2):
+                        site.addsitedir(entry)
         return resolved

pex/installed_wheel.py

@@ -12,7 +12,7 @@ from pex.util import CacheHelper
 from pex.wheel import WHEEL, Wheel, WheelMetadataLoadError
 
 if TYPE_CHECKING:
-    from typing import Optional, Text
+    from typing import Iterator, Optional, Text, Tuple
 
     import attr  # vendor:skip
 else:
@@ -38,6 +38,7 @@ class InstalledWheel(object):
         stash_dir,  # type: str
         record_relpath,  # type: Text
         root_is_purelib,  # type: bool
+        sys_path_entries,  # type: Tuple[str, ...]
     ):
         # type: (...) -> InstalledWheel
 
@@ -50,6 +51,7 @@ class InstalledWheel(object):
             "record_relpath": record_relpath,
             "fingerprint": fingerprint,
             "root_is_purelib": root_is_purelib,
+            "sys_path_entries": sys_path_entries,
         }
         with open(cls.layout_file(prefix_dir), "w") as fp:
             json.dump(layout, fp, sort_keys=True, separators=(",", ":"))
@@ -59,6 +61,7 @@ class InstalledWheel(object):
             record_relpath=record_relpath,
             fingerprint=fingerprint,
             root_is_purelib=root_is_purelib,
+            sys_path_entries=sys_path_entries,
         )
 
     @classmethod
@@ -104,12 +107,17 @@ class InstalledWheel(object):
                 )
             root_is_purelib = wheel.root_is_purelib
 
+        # N.B.: Older versions of Pex installed wheel chroots did not have this field since the
+        # `sys.path` entry was always just the prefix_dir for those.
+        sys_path_entries = layout.get("sys_path_entries", [""])
+
         return cls(
             prefix_dir=prefix_dir,
             stash_dir=cast(str, stash_dir),
             record_relpath=cast(str, record_relpath),
             fingerprint=cast("Optional[str]", fingerprint),
             root_is_purelib=root_is_purelib,
+            sys_path_entries=tuple(sys_path_entries),
         )
 
     prefix_dir = attr.ib()  # type: str
@@ -117,6 +125,7 @@ class InstalledWheel(object):
     record_relpath = attr.ib()  # type: Text
     fingerprint = attr.ib()  # type: Optional[str]
     root_is_purelib = attr.ib()  # type: bool
+    sys_path_entries = attr.ib()  # type: Tuple[str, ...]
 
     def wheel_file_name(self):
         # type: () -> str
@@ -125,3 +134,8 @@ class InstalledWheel(object):
     def stashed_path(self, *components):
         # type: (*str) -> str
         return os.path.join(self.prefix_dir, self.stash_dir, *components)
+
+    def iter_sys_path_entries(self):
+        # type: () -> Iterator[str]
+        for sys_path_entry in self.sys_path_entries:
+            yield os.path.normpath(os.path.join(self.prefix_dir, sys_path_entry))

pex/interpreter_constraints.py

@@ -379,7 +379,7 @@ COMPATIBLE_PYTHON_VERSIONS = (
     PythonVersion(Lifecycle.STABLE, 3, 10, 19),
     PythonVersion(Lifecycle.STABLE, 3, 11, 14),
     PythonVersion(Lifecycle.STABLE, 3, 12, 12),
-    PythonVersion(Lifecycle.STABLE, 3, 13, 8),
+    PythonVersion(Lifecycle.STABLE, 3, 13, 9),
     PythonVersion(Lifecycle.STABLE, 3, 14, 0),
     PythonVersion(Lifecycle.DEV, 3, 15, 0),
 )