diff --git a/pex/bin/pex.py b/pex/bin/pex.py
index 1beaba8df..7343e4241 100755
--- a/pex/bin/pex.py
+++ b/pex/bin/pex.py
@@ -876,7 +876,11 @@ def do_main(
             compress=options.compress,
         )
         if options.seed != Seed.NONE:
-            seed_info = seed_cache(options, pex, verbose=options.seed == Seed.VERBOSE)
+            seed_info = seed_cache(
+                options,
+                PEX(pex_file, interpreter=interpreter),
+                verbose=options.seed == Seed.VERBOSE,
+            )
             print(seed_info)
     else:
         if not _compatible_with_current_platform(interpreter, targets.platforms):
diff --git a/pex/pex.py b/pex/pex.py
index e2fb6d996..eebab8458 100644
--- a/pex/pex.py
+++ b/pex/pex.py
@@ -18,6 +18,7 @@
 from pex.finders import get_entry_point_from_console_script, get_script_from_distributions
 from pex.inherit_path import InheritPath
 from pex.interpreter import PythonInterpreter
+from pex.layout import Layout
 from pex.orderedset import OrderedSet
 from pex.pex_info import PexInfo
 from pex.targets import LocalInterpreter
@@ -162,9 +163,17 @@ def __init__(
         self._vars = env
         self._envs = None  # type: Optional[Iterable[PEXEnvironment]]
         self._activated_dists = None  # type: Optional[Iterable[Distribution]]
+        self._layout = None  # type: Optional[Layout.Value]
         if verify_entry_point:
             self._do_entry_point_verification()
 
+    @property
+    def layout(self):
+        # type: () -> Layout.Value
+        if self._layout is None:
+            self._layout = Layout.identify(self._pex)
+        return self._layout
+
     def pex_info(self, include_env_overrides=True):
         # type: (bool) -> PexInfo
         pex_info = self._pex_info.copy()
diff --git a/pex/pex_bootstrapper.py b/pex/pex_bootstrapper.py
index 7f5337446..3e168cbde 100644
--- a/pex/pex_bootstrapper.py
+++ b/pex/pex_bootstrapper.py
@@ -17,6 +17,7 @@
     InterpreterConstraints,
     UnsatisfiableInterpreterConstraintsError,
 )
+from pex.layout import Layout
 from pex.orderedset import OrderedSet
 from pex.pex_info import PexInfo
 from pex.targets import LocalInterpreter
@@ -528,6 +529,13 @@ def ensure_venv(
                         continue
 
                     os.symlink(venv_dir, os.path.join(short_venv.work_dir, "venv"))
+
+                    # Loose PEXes don't need to unpack themselves to the PEX_ROOT before running;
+                    # so we'll not have a stable base there to symlink from. As such, always copy
+                    # for loose PEXes to ensure the PEX_ROOT venv is stable in the face of
+                    # modification of the source loose PEX.
+                    symlink = pex.layout != Layout.LOOSE and not pex_info.venv_site_packages_copies
+
                     shebang = populate_venv(
                         virtualenv,
                         pex,
@@ -536,7 +544,7 @@ def ensure_venv(
                             short_venv_dir, "venv", "bin", os.path.basename(pex.interpreter.binary)
                         ),
                         collisions_ok=collisions_ok,
-                        symlink=not pex_info.venv_site_packages_copies,
+                        symlink=symlink,
                     )
 
                     # There are popular Linux distributions with shebang length limits
diff --git a/tests/integration/test_issue_2023.py b/tests/integration/test_issue_2023.py
new file mode 100644
index 000000000..66e2dfcca
--- /dev/null
+++ b/tests/integration/test_issue_2023.py
@@ -0,0 +1,83 @@
+# Copyright 2023 Pants project contributors (see CONTRIBUTORS.md).
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+import os.path
+import shutil
+import subprocess
+import sys
+from textwrap import dedent
+
+import pytest
+from colors import colors
+
+from pex.layout import Layout
+from pex.testing import run_pex_command
+from pex.typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from typing import Any, List
+
+
+@pytest.mark.parametrize(
+    "layout", [pytest.param(layout, id=layout.value) for layout in Layout.values()]
+)
+@pytest.mark.parametrize(
+    "execution_mode_args",
+    [
+        pytest.param([], id="UNZIP"),
+        pytest.param(["--venv", "--venv-site-packages-copies"], id="VENV (copies)"),
+        pytest.param(["--venv", "--no-venv-site-packages-copies"], id="VENV (symlinks)"),
+    ],
+)
+def test_unpack_robustness(
+    tmpdir,  # type: Any
+    layout,  # type: Layout.Value
+    execution_mode_args,  # type: List[str]
+):
+    # type: (...) -> None
+    exe = os.path.join(str(tmpdir), "exe.py")
+    with open(exe, "w") as fp:
+        fp.write(
+            dedent(
+                """\
+                import colors
+
+                print(colors.cyan("Wowbagger hasn't gotten to me yet."))
+                """
+            )
+        )
+
+    pex = os.path.join(str(tmpdir), "pex")
+    pex_root = os.path.join(str(tmpdir), "pex_root")
+    run_pex_command(
+        args=[
+            "--runtime-pex-root",
+            pex_root,
+            "ansicolors==1.1.8",
+            "--exe",
+            exe,
+            "--layout",
+            layout.value,
+            "-o",
+            pex,
+        ]
+        + execution_mode_args
+    ).assert_success()
+
+    def assert_pex_works(pex_path):
+        # type: (str) -> None
+        assert (
+            colors.cyan("Wowbagger hasn't gotten to me yet.")
+            == subprocess.check_output(args=[sys.executable, pex_path]).decode("utf-8").strip()
+        )
+
+    assert_pex_works(pex)
+
+    elsewhere = os.path.join(str(tmpdir), "elsewhere")
+    os.mkdir(elsewhere)
+    dest = os.path.join(elsewhere, "other")
+    shutil.move(pex, dest)
+    assert_pex_works(dest)
+
+    shutil.rmtree(pex_root)
+    assert_pex_works(dest)