diff --git a/CHANGES.md b/CHANGES.md
index c38392edc..6faa6a834 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,5 +1,15 @@
 # Release Notes
 
+## 2.30.0
+
+This release brings `--sh-boot` support to PEXes with
+`--layout {loose,packed}`. Previously, the `--sh-boot` option only took
+effect for traditional PEX zip files. Now all PEX output and runtime
+schemes, in any combination, can benefit from the reduced boot latency
+`--sh-boot` brings on all runs of a PEX after the first.
+
+* Support `--sh-boot` for `--layout {loose,packed}`. (#2645)
+
 ## 2.29.0
 
 This release brings 1st class support for newer Pip's
diff --git a/pex/bin/pex.py b/pex/bin/pex.py
index 8b3ace8d1..58e57532d 100644
--- a/pex/bin/pex.py
+++ b/pex/bin/pex.py
@@ -1349,6 +1349,7 @@ def do_main(
                     pex_name=pex_file,
                     targets=targets,
                     python_shebang=options.python_shebang,
+                    layout=options.layout,
                 )
 
         pex_builder.build(
diff --git a/pex/cache/dirs.py b/pex/cache/dirs.py
index bbfd043d4..d10753544 100644
--- a/pex/cache/dirs.py
+++ b/pex/cache/dirs.py
@@ -6,10 +6,11 @@
 import glob
 import os
 
-from pex.common import is_exe, safe_rmtree
+from pex.common import safe_rmtree
 from pex.compatibility import commonpath
 from pex.enum import Enum
 from pex.exceptions import production_assert
+from pex.executables import is_exe
 from pex.orderedset import OrderedSet
 from pex.typing import TYPE_CHECKING, cast
 from pex.variables import ENV, Variables
diff --git a/pex/cli/commands/lock.py b/pex/cli/commands/lock.py
index cb0970a36..d67360d3a 100644
--- a/pex/cli/commands/lock.py
+++ b/pex/cli/commands/lock.py
@@ -14,7 +14,7 @@
 from pex.argparse import HandleBoolAction
 from pex.cli.command import BuildTimeCommand
 from pex.commands.command import JsonMixin, OutputMixin
-from pex.common import is_exe, pluralize, safe_delete, safe_open
+from pex.common import pluralize, safe_delete, safe_open
 from pex.compatibility import commonpath, shlex_quote
 from pex.dependency_configuration import DependencyConfiguration
 from pex.dist_metadata import (
@@ -26,6 +26,7 @@
 )
 from pex.enum import Enum
 from pex.exceptions import production_assert
+from pex.executables import is_exe
 from pex.interpreter import PythonInterpreter
 from pex.orderedset import OrderedSet
 from pex.pep_376 import InstalledWheel, Record
diff --git a/pex/cli/commands/venv.py b/pex/cli/commands/venv.py
index cb95fc31e..9cc670599 100644
--- a/pex/cli/commands/venv.py
+++ b/pex/cli/commands/venv.py
@@ -11,9 +11,10 @@
 from pex import pex_warnings
 from pex.cli.command import BuildTimeCommand
 from pex.commands.command import JsonMixin, OutputMixin
-from pex.common import DETERMINISTIC_DATETIME, CopyMode, is_script, open_zip, pluralize
+from pex.common import DETERMINISTIC_DATETIME, CopyMode, open_zip, pluralize
 from pex.dist_metadata import Distribution
 from pex.enum import Enum
+from pex.executables import is_script
 from pex.executor import Executor
 from pex.pex import PEX
 from pex.pex_info import PexInfo
diff --git a/pex/common.py b/pex/common.py
index 056ce6fbf..0c239ecfa 100644
--- a/pex/common.py
+++ b/pex/common.py
@@ -23,6 +23,7 @@
 from zipfile import ZipFile, ZipInfo
 
 from pex.enum import Enum
+from pex.executables import chmod_plus_x
 from pex.typing import TYPE_CHECKING, cast
 
 if TYPE_CHECKING:
@@ -446,72 +447,6 @@ def safe_sleep(seconds):
             current_time = time.time()
 
 
-def chmod_plus_x(path):
-    # type: (Text) -> None
-    """Equivalent of unix `chmod a+x path`"""
-    path_mode = os.stat(path).st_mode
-    path_mode &= int("777", 8)
-    if path_mode & stat.S_IRUSR:
-        path_mode |= stat.S_IXUSR
-    if path_mode & stat.S_IRGRP:
-        path_mode |= stat.S_IXGRP
-    if path_mode & stat.S_IROTH:
-        path_mode |= stat.S_IXOTH
-    os.chmod(path, path_mode)
-
-
-def chmod_plus_w(path):
-    # type: (str) -> None
-    """Equivalent of unix `chmod +w path`"""
-    path_mode = os.stat(path).st_mode
-    path_mode &= int("777", 8)
-    path_mode |= stat.S_IWRITE
-    os.chmod(path, path_mode)
-
-
-def is_exe(path):
-    # type: (str) -> bool
-    """Determines if the given path is a file executable by the current user.
-
-    :param path: The path to check.
-    :return: `True if the given path is a file executable by the current user.
-    """
-    return os.path.isfile(path) and os.access(path, os.R_OK | os.X_OK)
-
-
-def is_script(
-    path,  # type: str
-    pattern=None,  # type: Optional[str]
-    check_executable=True,  # type: bool
-):
-    # type: (...) -> bool
-    """Determines if the given path is a script.
-
-    A script is a file that starts with a shebang (#!...) line.
-
-    :param path: The path to check.
-    :param pattern: An optional pattern to match against the shebang (excluding the leading #!).
-    :param check_executable: Check that the script is executable by the current user.
-    :return: True if the given path is a script.
-    """
-    if check_executable and not is_exe(path):
-        return False
-    with open(path, "rb") as fp:
-        if b"#!" != fp.read(2):
-            return False
-        if not pattern:
-            return True
-        return bool(re.match(pattern, fp.readline().decode("utf-8")))
-
-
-def is_python_script(
-    path,  # type: str
-    check_executable=True,  # type: bool
-):
-    # type: (...) -> bool
-    return is_script(path, pattern=r"(?i)^.*(?:python|pypy)", check_executable=check_executable)
-
-
 def can_write_dir(path):
     # type: (str) -> bool
     """Determines if the directory at path can be written to by the current process.
diff --git a/pex/executables.py b/pex/executables.py
new file mode 100644
index 000000000..34a28172f
--- /dev/null
+++ b/pex/executables.py
@@ -0,0 +1,147 @@
+# Copyright 2025 Pants project contributors (see CONTRIBUTORS.md).
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from __future__ import absolute_import
+
+import os
+import re
+import stat
+from textwrap import dedent
+
+from pex.typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from typing import BinaryIO, Callable, Optional, Text, Tuple
+
+
+def chmod_plus_x(path):
+    # type: (Text) -> None
+    """Equivalent of unix `chmod a+x path`"""
+    path_mode = os.stat(path).st_mode
+    path_mode &= int("777", 8)
+    if path_mode & stat.S_IRUSR:
+        path_mode |= stat.S_IXUSR
+    if path_mode & stat.S_IRGRP:
+        path_mode |= stat.S_IXGRP
+    if path_mode & stat.S_IROTH:
+        path_mode |= stat.S_IXOTH
+    os.chmod(path, path_mode)
+
+
+def is_exe(path):
+    # type: (Text) -> bool
+    """Determines if the given path is a file executable by the current user.
+
+    :param path: The path to check.
+    :return: True if the given path is a file executable by the current user.
+    """
+    return os.path.isfile(path) and os.access(path, os.R_OK | os.X_OK)
+
+
+def is_script(
+    path,  # type: Text
+    pattern=None,  # type: Optional[bytes]
+    check_executable=True,  # type: bool
+    extra_check=None,  # type: Optional[Callable[[bytes, BinaryIO], bool]]
+):
+    # type: (...) -> bool
+    """Determines if the given path is a script.
+
+    A script is a file that starts with a shebang (#!...) line.
+
+    :param path: The path to check.
+    :param pattern: Optional pattern to match against the shebang line (excluding the leading #!
+                    and trailing \n).
+    :param check_executable: Check that the script is executable by the current user.
+    :param extra_check: Optional callable accepting the shebang line (excluding the leading #! and
+                        trailing \n) and a file opened for binary read pointing just after that
+                        line.
+    :return: True if the given path is a script.
+    """
+    if check_executable and not is_exe(path):
+        return False
+    with open(path, "rb") as fp:
+        if b"#!" != fp.read(2):
+            return False
+        if not pattern:
+            return True
+        shebang_suffix = fp.readline().rstrip()
+        if bool(re.match(pattern, shebang_suffix)):
+            return True
+        if extra_check:
+            return extra_check(shebang_suffix, fp)
+        return False
+
+
+def create_sh_python_redirector_shebang(sh_script_content):
+    # type: (str) -> Tuple[str, str]
+    """Create a shebang block for a Python file that uses /bin/sh to find an appropriate Python.
+
+    The script should be POSIX compliant sh and terminate on all execution paths with an
+    explicit exit or exec.
+
+    The returned shebang block will include the leading `#!` but will not include a trailing new
+    line character.
+
+    :param sh_script_content: A POSIX compliant sh script that always explicitly terminates.
+    :return: A shebang line and trailing block of text that can be combined for use as a shebang
+             header for a Python file.
+    """
+    # This trick relies on /bin/sh being ubiquitous and the concordance of:
+    #
+    # 1. Python: Has triple quoted strings plus allowance for free-floating string values in
+    #    python files.
+    # 2. sh: Any number of pairs of `'` evaluating away when followed immediately by a
+    #    command string (`''command` -> `command`).
+    # 3. sh: The `:` noop command which accepts and discards arbitrary args.
+    #    See: https://pubs.opengroup.org/onlinepubs/009604599/utilities/colon.html
+    # 4. sh: Lazy parsing allowing for invalid sh content immediately following an exit or exec
+    #        line.
+    #
+    # The end result is a file that is both a valid sh script with a short shebang and a valid
+    # Python program.
+    return "#!/bin/sh", (
+        dedent(
+            """\
+            '''': pshprs
+            {sh_script_content}
+            '''
+            """
+        )
+        .format(sh_script_content=sh_script_content.rstrip())
+        .strip()
+    )
+
+
+def is_python_script(
+    path,  # type: Text
+    check_executable=True,  # type: bool
+):
+    # type: (...) -> bool
+    return is_script(
+        path,
+        pattern=br"""(?ix)
+        # The aim is to admit the common shebang forms:
+        # + python
+        # + /usr/bin/env (<args>)? <python bin name> (<args>)?
+        # + /absolute/path/to/<python bin name> (<args>)?
+        # The 1st corresponds to the special placeholder shebang #!python specified here:
+        # + https://peps.python.org/pep-0427
+        # + https://packaging.python.org/specifications/binary-distribution-format
+        (?:^|.*\W)
+
+        # Python executable names Pex supports (see PythonIdentity).
+        (?:
+              python
+            | pypy
+        )
+
+        # Optional Python version
+        (?:\d+(?:\.\d+)*)?
+
+        # Support a shebang with an argument to the interpreter at the end.
+        (?:\s[^\s]|$)
+        """,
+        check_executable=check_executable,
+        extra_check=lambda shebang, fp: shebang == b"/bin/sh" and fp.read(13) == b"'''': pshprs\n",
+    )
diff --git a/pex/finders.py b/pex/finders.py
index 747e325ab..fb80c5227 100644
--- a/pex/finders.py
+++ b/pex/finders.py
@@ -6,7 +6,7 @@
 import ast
 import os
 
-from pex.common import is_python_script, open_zip, safe_mkdtemp
+from pex.common import open_zip, safe_mkdtemp
 from pex.dist_metadata import (
     CallableEntryPoint,
     Distribution,
@@ -14,6 +14,7 @@
     ModuleEntryPoint,
     NamedEntryPoint,
 )
+from pex.executables import is_python_script
 from pex.pep_376 import InstalledWheel
 from pex.pep_503 import ProjectName
 from pex.typing import TYPE_CHECKING, cast
diff --git a/pex/interpreter.py b/pex/interpreter.py
index 761d38619..7323fbc3d 100644
--- a/pex/interpreter.py
+++ b/pex/interpreter.py
@@ -17,7 +17,8 @@
 
 from pex import third_party
 from pex.cache.dirs import InterpreterDir
-from pex.common import is_exe, safe_mkdtemp, safe_rmtree
+from pex.common import safe_mkdtemp, safe_rmtree
+from pex.executables import is_exe
 from pex.executor import Executor
 from pex.jobs import Job, Retain, SpawnedJob, execute_parallel
 from pex.orderedset import OrderedSet
diff --git a/pex/layout.py b/pex/layout.py
index e38425bb9..5f5699fef 100644
--- a/pex/layout.py
+++ b/pex/layout.py
@@ -11,8 +11,9 @@
 from pex.atomic_directory import atomic_directory
 from pex.cache import access as cache_access
 from pex.cache.dirs import BootstrapDir, InstalledWheelDir, UserCodeDir
-from pex.common import ZipFileEx, is_script, open_zip, safe_copy, safe_mkdir, safe_mkdtemp
+from pex.common import ZipFileEx, open_zip, safe_copy, safe_mkdir, safe_mkdtemp
 from pex.enum import Enum
+from pex.executables import is_script
 from pex.tracer import TRACER
 from pex.typing import TYPE_CHECKING
 from pex.variables import ENV, unzip_dir
@@ -559,7 +560,9 @@ def extract_code(self, dest_dir):
             if root == self._path:
                 dirs[:] = [d for d in dirs if d not in ("__pex__", DEPS_DIR)]
                 files[:] = [
-                    f for f in files if f not in ("__main__.py", PEX_INFO_PATH, BOOTSTRAP_DIR)
+                    f
+                    for f in files
+                    if f not in ("__main__.py", "pex", PEX_INFO_PATH, BOOTSTRAP_DIR)
                 ]
             for d in dirs:
                 safe_mkdir(os.path.join(dest_dir, rel_root, d))
@@ -635,7 +638,7 @@ def extract_code(self, dest_dir):
             rel_root = os.path.relpath(root, self._path)
             if root == self._path:
                 dirs[:] = [d for d in dirs if d not in ("__pex__", DEPS_DIR, BOOTSTRAP_DIR)]
-                files[:] = [f for f in files if f not in ("__main__.py", PEX_INFO_PATH)]
+                files[:] = [f for f in files if f not in ("__main__.py", "pex", PEX_INFO_PATH)]
             for d in dirs:
                 safe_mkdir(os.path.join(dest_dir, rel_root, d))
             for f in files:
diff --git a/pex/pep_427.py b/pex/pep_427.py
index 046725c4e..291598476 100644
--- a/pex/pep_427.py
+++ b/pex/pep_427.py
@@ -14,10 +14,11 @@
 from textwrap import dedent
 
 from pex import pex_warnings
-from pex.common import chmod_plus_x, is_pyc_file, iter_copytree, open_zip, safe_open, touch
+from pex.common import is_pyc_file, iter_copytree, open_zip, safe_open, touch
 from pex.compatibility import commonpath, get_stdout_bytes_buffer
 from pex.dist_metadata import CallableEntryPoint, Distribution, ProjectNameAndVersion
 from pex.enum import Enum
+from pex.executables import chmod_plus_x
 from pex.interpreter import PythonInterpreter
 from pex.pep_376 import InstalledFile, InstalledWheel, Record
 from pex.pep_503 import ProjectName
diff --git a/pex/pex.py b/pex/pex.py
index 4da401d4d..2ce7c478a 100644
--- a/pex/pex.py
+++ b/pex/pex.py
@@ -542,6 +542,7 @@ def execute(self):
 
         This function makes assumptions that it is the last function called by the interpreter.
         """
+        pex_file = self._vars.PEX
         if self._vars.PEX_TOOLS:
             if not self._pex_info.includes_tools:
                 die(
@@ -551,11 +552,10 @@ def execute(self):
 
             from pex.tools import main as tools
 
-            sys.exit(tools.main(pex=PEX(sys.argv[0])))
+            sys.exit(tools.main(pex=PEX(pex_file or sys.argv[0])))
 
         self.activate()
 
-        pex_file = self._vars.PEX
         if pex_file:
             try:
                 from setproctitle import setproctitle  # type: ignore[import]
diff --git a/pex/pex_boot.py b/pex/pex_boot.py
index a936a79fe..fa7d5755e 100644
--- a/pex/pex_boot.py
+++ b/pex/pex_boot.py
@@ -115,7 +115,7 @@ def __maybe_run_venv__(
 ):
     # type: (...) -> Optional[str]
 
-    from pex.common import is_exe
+    from pex.executables import is_exe
     from pex.tracer import TRACER
     from pex.variables import venv_dir
 
@@ -180,7 +180,13 @@ def boot(
                 break
 
     installed_from = os.environ.pop(__INSTALLED_FROM__, None)
-    sys.argv[0] = installed_from or sys.argv[0]
+    if installed_from:
+        if os.path.isfile(installed_from):
+            sys.argv[0] = installed_from
+        else:
+            pex_exe = os.path.join(installed_from, "pex")
+            if os.path.isfile(pex_exe):
+                sys.argv[0] = pex_exe
 
     sys.path[0] = os.path.abspath(sys.path[0])
     sys.path.insert(0, os.path.abspath(os.path.join(entry_point, bootstrap_dir)))
diff --git a/pex/pex_builder.py b/pex/pex_builder.py
index 82bca4fd8..a3a205afd 100644
--- a/pex/pex_builder.py
+++ b/pex/pex_builder.py
@@ -17,7 +17,6 @@
 from pex.common import (
     Chroot,
     CopyMode,
-    chmod_plus_x,
     deterministic_walk,
     is_pyc_file,
     is_pyc_temporary_file,
@@ -31,6 +30,7 @@
 from pex.compiler import Compiler
 from pex.dist_metadata import Distribution, DistributionType, MetadataError
 from pex.enum import Enum
+from pex.executables import chmod_plus_x, create_sh_python_redirector_shebang
 from pex.finders import get_entry_point_from_console_script, get_script_from_distributions
 from pex.interpreter import PythonInterpreter
 from pex.layout import Layout
@@ -660,6 +660,19 @@ def build(
                 compress=compress,
                 bytecode_compile=bytecode_compile,
             )
+        if layout in (Layout.LOOSE, Layout.PACKED):
+            pex_script = os.path.join(tmp_pex, "pex")
+            if self._header:
+                main_py = os.path.join(tmp_pex, "__main__.py")
+                with open(pex_script, "w") as script_fp:
+                    print(self._shebang, file=script_fp)
+                    print(self._header, file=script_fp)
+                    with open(main_py) as main_fp:
+                        main_fp.readline()  # Throw away shebang line.
+                        shutil.copyfileobj(main_fp, script_fp)
+                chmod_plus_x(pex_script)
+                os.rename(pex_script, main_py)
+            os.symlink("__main__.py", pex_script)
 
         if os.path.isdir(path):
             shutil.rmtree(path, True)
@@ -673,19 +686,26 @@ def set_sh_boot_script(
         pex_name,  # type: str
         targets,  # type: Targets
         python_shebang,  # type: Optional[str]
+        layout=Layout.ZIPAPP,  # type: Layout.Value
     ):
         if not self._frozen:
             raise Exception("Generating a sh_boot script requires the pex to be frozen.")
 
-        self.set_shebang("/bin/sh")
         script = create_sh_boot_script(
             pex_name=pex_name,
             pex_info=self._pex_info,
             targets=targets,
             interpreter=self.interpreter,
             python_shebang=python_shebang,
+            layout=layout,
         )
-        self.set_header(script)
+        if layout is Layout.ZIPAPP:
+            self.set_shebang("/bin/sh")
+            self.set_header(script)
+        else:
+            shebang, header = create_sh_python_redirector_shebang(script)
+            self.set_shebang(shebang)
+            self.set_header(header)
 
     def _build_packedapp(
         self,
diff --git a/pex/pyenv.py b/pex/pyenv.py
index ba36ab59a..38988fe00 100644
--- a/pex/pyenv.py
+++ b/pex/pyenv.py
@@ -7,7 +7,7 @@
 import re
 import subprocess
 
-from pex.common import is_exe
+from pex.executables import is_exe
 from pex.tracer import TRACER
 from pex.typing import TYPE_CHECKING
 
diff --git a/pex/repl/pex_repl.py b/pex/repl/pex_repl.py
index 0d4d7aa5f..042d7e9ce 100644
--- a/pex/repl/pex_repl.py
+++ b/pex/repl/pex_repl.py
@@ -11,9 +11,10 @@
 from zipfile import is_zipfile
 
 from pex.cli_util import prog_path
-from pex.common import is_exe, pluralize
+from pex.common import pluralize
 from pex.compatibility import commonpath
 from pex.dist_metadata import Distribution
+from pex.executables import is_exe
 from pex.layout import Layout
 from pex.pex_info import PexInfo
 from pex.repl import custom
diff --git a/pex/scie/science.py b/pex/scie/science.py
index e42d275c9..af04e5f16 100644
--- a/pex/scie/science.py
+++ b/pex/scie/science.py
@@ -13,10 +13,11 @@
 from pex import toml
 from pex.atomic_directory import atomic_directory
 from pex.cache.dirs import CacheDir, UnzipDir
-from pex.common import chmod_plus_x, is_exe, pluralize, safe_mkdtemp, safe_open
+from pex.common import pluralize, safe_mkdtemp, safe_open
 from pex.compatibility import shlex_quote
 from pex.dist_metadata import NamedEntryPoint, parse_entry_point
 from pex.exceptions import production_assert
+from pex.executables import chmod_plus_x, is_exe
 from pex.fetcher import URLFetcher
 from pex.hashing import Sha256
 from pex.layout import Layout
diff --git a/pex/sh_boot.py b/pex/sh_boot.py
index f932da7dd..98b01a51d 100644
--- a/pex/sh_boot.py
+++ b/pex/sh_boot.py
@@ -13,6 +13,7 @@
 from pex.dist_metadata import Distribution
 from pex.interpreter import PythonInterpreter, calculate_binary_name
 from pex.interpreter_constraints import InterpreterConstraints, iter_compatible_versions
+from pex.layout import Layout
 from pex.orderedset import OrderedSet
 from pex.pep_440 import Version
 from pex.pex_info import PexInfo
@@ -123,6 +124,7 @@ def create_sh_boot_script(
     targets,  # type: Targets
     interpreter,  # type: PythonInterpreter
     python_shebang=None,  # type: Optional[str]
+    layout=Layout.ZIPAPP,  # type: Layout.Value
 ):
     # type: (...) -> str
     """Creates the body of a POSIX `sh` compatible script that executes a PEX ZIPAPP appended to it.
@@ -199,7 +201,7 @@ def create_sh_boot_script(
             # We're a --venv execution mode PEX installed under the PEX_ROOT and the venv
             # interpreter to use is embedded in the shebang of our venv pex script; so just
             # execute that script directly.
-            export PEX="$0"
+            export PEX="{pex}"
             exec "${{INSTALLED_PEX}}/bin/python" ${{VENV_PYTHON_ARGS}} "${{INSTALLED_PEX}}" \\
                 "$@"
         fi
@@ -227,7 +229,7 @@ def create_sh_boot_script(
                 # We're a --zipapp execution mode PEX installed under the PEX_ROOT with a
                 # __main__.py in our top-level directory; so execute Python against that
                 # directory.
-                export __PEX_EXE__="$0"
+                export __PEX_EXE__="{pex}"
                 exec "${{python_exe}}" ${{PYTHON_ARGS}} "${{INSTALLED_PEX}}" "$@"
             else
                 # The slow path: this PEX zipapp is not installed yet. Run the PEX zipapp so it
@@ -261,4 +263,5 @@ def create_sh_boot_script(
         venv_python_args=" ".join(
             shlex_quote(venv_python_arg) for venv_python_arg in venv_python_args
         ),
+        pex="$0" if layout is Layout.ZIPAPP else '$(dirname "$0")',
     )
diff --git a/pex/venv/installer.py b/pex/venv/installer.py
index cd78f72cf..f30e56fd6 100644
--- a/pex/venv/installer.py
+++ b/pex/venv/installer.py
@@ -11,10 +11,11 @@
 
 from pex import layout, pex_warnings, repl
 from pex.cache import access as cache_access
-from pex.common import CopyMode, chmod_plus_x, iter_copytree, pluralize
+from pex.common import CopyMode, iter_copytree, pluralize
 from pex.compatibility import is_valid_python_identifier
 from pex.dist_metadata import Distribution
 from pex.environment import PEXEnvironment
+from pex.executables import chmod_plus_x
 from pex.orderedset import OrderedSet
 from pex.pep_376 import InstalledWheel
 from pex.pep_440 import Version
@@ -535,6 +536,7 @@ def mount(cls, pex):
                 "__main__.py",
                 "__pex__",
                 "__pycache__",
+                "pex",
                 cache_access.LAST_ACCESS_FILE,
                 layout.BOOTSTRAP_DIR,
                 layout.DEPS_DIR,
diff --git a/pex/venv/venv_pex.py b/pex/venv/venv_pex.py
index daed27e8e..613494eb6 100644
--- a/pex/venv/venv_pex.py
+++ b/pex/venv/venv_pex.py
@@ -5,11 +5,11 @@
 
 import os
 import sys
-from types import CodeType
 
 TYPE_CHECKING = False
 
 if TYPE_CHECKING:
+    from types import CodeType
     from typing import Any, Dict, Iterable, List, Optional, Tuple
 
 _PY2_EXEC_FUNCTION = """
@@ -101,7 +101,12 @@ def maybe_log(*message):
     pex_file = os.environ.get("PEX", None)
     if pex_file:
         pex_file_path = os.path.realpath(pex_file)
-        sys.argv[0] = pex_file_path
+        if os.path.isfile(pex_file_path):
+            sys.argv[0] = pex_file_path
+        else:
+            pex_exe = os.path.join(pex_file_path, "pex")
+            if os.path.isfile(pex_exe):
+                sys.argv[0] = pex_exe
         os.environ["PEX"] = pex_file_path
         try:
             from setproctitle import setproctitle  # type: ignore[import]
diff --git a/pex/venv/virtualenv.py b/pex/venv/virtualenv.py
index 413df644d..de7d1f7da 100644
--- a/pex/venv/virtualenv.py
+++ b/pex/venv/virtualenv.py
@@ -15,10 +15,11 @@
 from textwrap import dedent
 
 from pex.atomic_directory import AtomicDirectory, atomic_directory
-from pex.common import is_exe, safe_mkdir, safe_open
+from pex.common import safe_mkdir, safe_open
 from pex.compatibility import commonpath, get_stdout_bytes_buffer
 from pex.dist_metadata import Distribution, find_distributions
 from pex.enum import Enum
+from pex.executables import is_exe
 from pex.executor import Executor
 from pex.fetcher import URLFetcher
 from pex.interpreter import (
diff --git a/pex/version.py b/pex/version.py
index 39be95acf..2842169b6 100644
--- a/pex/version.py
+++ b/pex/version.py
@@ -1,4 +1,4 @@
 # Copyright 2015 Pex project contributors.
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
-__version__ = "2.29.0"
+__version__ = "2.30.0"
diff --git a/testing/__init__.py b/testing/__init__.py
index fb0538b2b..f7e3b1efe 100644
--- a/testing/__init__.py
+++ b/testing/__init__.py
@@ -423,7 +423,7 @@ def create_pex_command(
     # type: (...) -> List[str]
     cmd = [python or sys.executable, "-mpex"]
     if not quiet:
-        cmd.append("-vvvvv")
+        cmd.append("-v")
     if args:
         cmd.extend(args)
     return cmd
diff --git a/testing/docker.py b/testing/docker.py
index 1b401ad7e..e9aaeacf8 100644
--- a/testing/docker.py
+++ b/testing/docker.py
@@ -9,7 +9,8 @@
 
 import pytest
 
-from pex.common import chmod_plus_x, is_exe, safe_mkdtemp
+from pex.common import safe_mkdtemp
+from pex.executables import chmod_plus_x, is_exe
 from pex.typing import TYPE_CHECKING
 from testing import pex_project_dir
 
diff --git a/tests/integration/scie/test_pex_scie.py b/tests/integration/scie/test_pex_scie.py
index e15ac1d1a..fda8c7503 100644
--- a/tests/integration/scie/test_pex_scie.py
+++ b/tests/integration/scie/test_pex_scie.py
@@ -16,7 +16,8 @@
 import pytest
 
 from pex.cache.dirs import CacheDir
-from pex.common import chmod_plus_x, is_exe, safe_open
+from pex.common import safe_open
+from pex.executables import chmod_plus_x, is_exe
 from pex.fetcher import URLFetcher
 from pex.layout import Layout
 from pex.orderedset import OrderedSet
diff --git a/tests/integration/test_integration.py b/tests/integration/test_integration.py
index 164763655..62819e2b3 100644
--- a/tests/integration/test_integration.py
+++ b/tests/integration/test_integration.py
@@ -19,17 +19,10 @@
 
 from pex import targets
 from pex.cache.dirs import CacheDir, InterpreterDir
-from pex.common import (
-    environment_as,
-    is_exe,
-    safe_mkdir,
-    safe_open,
-    safe_rmtree,
-    temporary_dir,
-    touch,
-)
+from pex.common import environment_as, safe_mkdir, safe_open, safe_rmtree, temporary_dir, touch
 from pex.compatibility import WINDOWS, commonpath
 from pex.dist_metadata import Distribution, Requirement, is_wheel
+from pex.executables import is_exe
 from pex.fetcher import URLFetcher
 from pex.interpreter import PythonInterpreter
 from pex.layout import Layout
diff --git a/tests/integration/test_issue_2017.py b/tests/integration/test_issue_2017.py
index 67d2fc2bf..2c8d69b31 100644
--- a/tests/integration/test_issue_2017.py
+++ b/tests/integration/test_issue_2017.py
@@ -12,8 +12,9 @@
 import pytest
 
 from pex.atomic_directory import atomic_directory
-from pex.common import is_exe, safe_open
+from pex.common import safe_open
 from pex.compatibility import urlparse
+from pex.executables import is_exe
 from pex.fetcher import URLFetcher
 from pex.pip.version import PipVersion, PipVersionValue
 from pex.typing import TYPE_CHECKING
diff --git a/tests/integration/test_issue_2413.py b/tests/integration/test_issue_2413.py
index 9c3129055..01e9fbb80 100644
--- a/tests/integration/test_issue_2413.py
+++ b/tests/integration/test_issue_2413.py
@@ -10,7 +10,8 @@
 
 import pytest
 
-from pex.common import is_exe, safe_open
+from pex.common import safe_open
+from pex.executables import is_exe
 from pex.pep_503 import ProjectName
 from pex.typing import TYPE_CHECKING
 from pex.venv.virtualenv import InstallationChoice, Virtualenv
diff --git a/tests/integration/test_pep_427.py b/tests/integration/test_pep_427.py
index b984717a0..9e5383597 100644
--- a/tests/integration/test_pep_427.py
+++ b/tests/integration/test_pep_427.py
@@ -7,7 +7,8 @@
 from glob import glob
 from textwrap import dedent
 
-from pex.common import is_exe, safe_open
+from pex.common import safe_open
+from pex.executables import is_exe
 from pex.pep_427 import install_wheel_interpreter
 from pex.pip.installation import get_pip
 from pex.resolve.configured_resolver import ConfiguredResolver
diff --git a/tests/integration/test_sh_boot.py b/tests/integration/test_sh_boot.py
index be04d9055..8929115a7 100644
--- a/tests/integration/test_sh_boot.py
+++ b/tests/integration/test_sh_boot.py
@@ -11,6 +11,7 @@
 import pytest
 
 from pex.common import safe_open
+from pex.layout import Layout
 from pex.typing import TYPE_CHECKING
 from testing import all_pythons, make_env, run_pex_command
 from testing.pytest.tmp import Tempdir
@@ -174,23 +175,33 @@ def test_python_shebang_respected(tmpdir):
     assert output.startswith(version), output
 
 
-EXECUTION_MODE_ARGS_PERMUTATIONS = [
-    pytest.param([], id="ZIPAPP"),
-    pytest.param(["--venv"], id="VENV"),
-    pytest.param(["--sh-boot"], id="ZIPAPP (--sh-boot)"),
-    pytest.param(["--venv", "--sh-boot"], id="VENV (--sh-boot)"),
-]
+execution_mode = pytest.mark.parametrize(
+    "execution_mode_args",
+    [
+        pytest.param([], id="ZIPAPP"),
+        pytest.param(["--venv"], id="VENV"),
+        pytest.param(["--sh-boot"], id="ZIPAPP (--sh-boot)"),
+        pytest.param(["--venv", "--sh-boot"], id="VENV (--sh-boot)"),
+    ],
+)
+layouts = pytest.mark.parametrize(
+    "layout", [pytest.param(layout, id=layout.value) for layout in Layout.values()]
+)
 
 
-@pytest.mark.parametrize("execution_mode_args", EXECUTION_MODE_ARGS_PERMUTATIONS)
+@execution_mode
+@layouts
 def test_issue_1782(
     tmpdir,  # type: Tempdir
     pex_project_dir,  # type: str
     execution_mode_args,  # type: List[str]
+    layout,  # type: Layout.Value
 ):
     # type: (...) -> None
 
     pex = os.path.realpath(tmpdir.join("pex.sh"))
+    pex_exe = pex if layout is Layout.ZIPAPP else os.path.join(pex, "pex")
+
     pex_root = os.path.realpath(tmpdir.join("pex_root"))
     python = "python{major}.{minor}".format(major=sys.version_info[0], minor=sys.version_info[1])
     run_pex_command(
@@ -206,18 +217,20 @@ def test_issue_1782(
             pex,
             "--python-shebang",
             "/usr/bin/env {python}".format(python=python),
+            "--layout",
+            str(layout),
         ]
         + execution_mode_args
     ).assert_success()
 
     if sys.version_info[:2] >= (3, 14) and "--venv" not in execution_mode_args:
-        argv0 = r"python(?:3(?:\.\d{{2,}})?)? {pex}".format(pex=re.escape(pex))
+        argv0 = r"python(?:3(?:\.\d{{2,}})?)? {pex}".format(pex=re.escape(pex_exe))
     else:
-        argv0 = re.escape(os.path.basename(pex))
+        argv0 = re.escape(os.path.basename(pex_exe))
     usage_line_re = re.compile(r"^usage: {argv0}".format(argv0=argv0))
     help_line1 = (
         subprocess.check_output(
-            args=[pex, "-h"], env=make_env(COLUMNS=max(80, len(usage_line_re.pattern) + 10))
+            args=[pex_exe, "-h"], env=make_env(COLUMNS=max(80, len(usage_line_re.pattern) + 10))
         )
         .decode("utf-8")
         .splitlines()[0]
@@ -231,21 +244,26 @@ def test_issue_1782(
     assert (
         pex
         == subprocess.check_output(
-            args=[pex, "-c", "import os; print(os.environ['PEX'])"], env=make_env(PEX_INTERPRETER=1)
+            args=[pex_exe, "-c", "import os; print(os.environ['PEX'])"],
+            env=make_env(PEX_INTERPRETER=1),
         )
         .decode("utf-8")
         .strip()
     )
 
 
-@pytest.mark.parametrize("execution_mode_args", EXECUTION_MODE_ARGS_PERMUTATIONS)
+@execution_mode
+@layouts
 def test_argv0(
     tmpdir,  # type: Any
     execution_mode_args,  # type: List[str]
+    layout,  # type: Layout.Value
 ):
     # type: (...) -> None
 
     pex = os.path.realpath(os.path.join(str(tmpdir), "pex.sh"))
+    pex_exe = pex if layout is Layout.ZIPAPP else os.path.join(pex, "pex")
+
     src = os.path.join(str(tmpdir), "src")
     with safe_open(os.path.join(src, "app.py"), "w") as fp:
         fp.write(
@@ -267,12 +285,14 @@ def main():
         )
 
     run_pex_command(
-        args=["-D", src, "-e", "app:main", "-o", pex] + execution_mode_args
+        args=["-D", src, "-e", "app:main", "-o", pex, "--layout", str(layout)] + execution_mode_args
     ).assert_success()
-    assert {"PEX": pex, "argv0": pex} == json.loads(subprocess.check_output(args=[pex]))
+    assert {"PEX": pex, "argv0": pex_exe} == json.loads(subprocess.check_output(args=[pex_exe]))
 
-    run_pex_command(args=["-D", src, "-m", "app", "-o", pex] + execution_mode_args).assert_success()
-    data = json.loads(subprocess.check_output(args=[pex]))
+    run_pex_command(
+        args=["-D", src, "-m", "app", "-o", pex, "--layout", str(layout)] + execution_mode_args
+    ).assert_success()
+    data = json.loads(subprocess.check_output(args=[pex_exe]))
     assert pex == data.pop("PEX")
     assert "app.py" == os.path.basename(data.pop("argv0")), (
         "When executing modules we expect runpy.run_module to `alter_sys` in order to support "
diff --git a/tests/integration/test_shebang_length_limit.py b/tests/integration/test_shebang_length_limit.py
index 40ed1eea1..e701f93ec 100644
--- a/tests/integration/test_shebang_length_limit.py
+++ b/tests/integration/test_shebang_length_limit.py
@@ -15,7 +15,8 @@
 
 from pex.atomic_directory import atomic_directory
 from pex.cache.dirs import CacheDir
-from pex.common import chmod_plus_x, safe_open, touch
+from pex.common import safe_open, touch
+from pex.executables import chmod_plus_x
 from pex.typing import TYPE_CHECKING
 from testing import IS_PYPY, make_project, run_pex_command
 from testing.cli import run_pex3
diff --git a/tests/pip/test_log_analyzer.py b/tests/pip/test_log_analyzer.py
index afaae43a1..09810295e 100644
--- a/tests/pip/test_log_analyzer.py
+++ b/tests/pip/test_log_analyzer.py
@@ -9,7 +9,7 @@
 
 import pytest
 
-from pex.common import chmod_plus_x
+from pex.executables import chmod_plus_x
 from pex.jobs import Job
 from pex.pip.log_analyzer import ErrorAnalyzer, ErrorMessage, LogAnalyzer, LogScrapeJob
 from pex.typing import TYPE_CHECKING
diff --git a/tests/test_common.py b/tests/test_common.py
index e1fabeb25..d3c4eb191 100644
--- a/tests/test_common.py
+++ b/tests/test_common.py
@@ -11,15 +11,13 @@
     Chroot,
     ZipFileEx,
     can_write_dir,
-    chmod_plus_x,
     deterministic_walk,
-    is_exe,
-    is_script,
     open_zip,
     safe_open,
     temporary_dir,
     touch,
 )
+from pex.executables import chmod_plus_x
 from pex.typing import TYPE_CHECKING
 from testing import NonDeterministicWalk
 
@@ -29,7 +27,7 @@
     import mock  # type: ignore[no-redef,import]
 
 if TYPE_CHECKING:
-    from typing import Any, Iterator, Tuple
+    from typing import Iterator, Tuple
 
 
 def extract_perms(path):
@@ -308,54 +306,3 @@ def test_safe_open_relative(temporary_working_dir):
     abs_path = os.path.join(temporary_working_dir, rel_path)
     with open(abs_path) as fp:
         assert "contents" == fp.read()
-
-
-def test_is_exe(tmpdir):
-    # type: (Any) -> None
-    all_exe = os.path.join(str(tmpdir), "all_exe")
-    touch(all_exe)
-    chmod_plus_x(all_exe)
-    assert is_exe(all_exe)
-
-    other_exe = os.path.join(str(tmpdir), "other_exe")
-    touch(other_exe)
-    os.chmod(other_exe, 0o665)
-    assert not is_exe(other_exe)
-
-    not_exe = os.path.join(str(tmpdir), "not_exe")
-    touch(not_exe)
-    assert not is_exe(not_exe)
-
-    exe_dir = os.path.join(str(tmpdir), "exe_dir")
-    os.mkdir(exe_dir)
-    chmod_plus_x(exe_dir)
-    assert not is_exe(exe_dir)
-
-
-def test_is_script(tmpdir):
-    # type: (Any) -> None
-    exe = os.path.join(str(tmpdir), "exe")
-
-    touch(exe)
-    assert not is_exe(exe)
-    assert not is_script(exe)
-
-    chmod_plus_x(exe)
-    assert is_exe(exe)
-    assert not is_script(exe)
-
-    with open(exe, "wb") as fp:
-        fp.write(bytearray([0xCA, 0xFE, 0xBA, 0xBE]))
-    assert not is_script(fp.name)
-
-    with open(exe, "wb") as fp:
-        fp.write(b"#!/mystery\n")
-        fp.write(bytearray([0xCA, 0xFE, 0xBA, 0xBE]))
-    assert is_script(exe)
-    assert is_script(exe, pattern=r"^/mystery")
-    assert not is_script(exe, pattern=r"^python")
-
-    os.chmod(exe, 0o665)
-    assert is_script(exe, check_executable=False)
-    assert not is_script(exe)
-    assert not is_exe(exe)
diff --git a/tests/test_executables.py b/tests/test_executables.py
new file mode 100644
index 000000000..4e3e0eccf
--- /dev/null
+++ b/tests/test_executables.py
@@ -0,0 +1,115 @@
+# Copyright 2025 Pex project contributors.
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from __future__ import absolute_import
+
+import os
+
+from pex.common import touch
+from pex.executables import chmod_plus_x, is_exe, is_python_script, is_script
+from testing.pytest.tmp import Tempdir
+
+
+def test_is_exe(tmpdir):
+    # type: (Tempdir) -> None
+
+    all_exe = tmpdir.join("all_exe")
+    touch(all_exe)
+    chmod_plus_x(all_exe)
+    assert is_exe(all_exe)
+
+    other_exe = tmpdir.join("other_exe")
+    touch(other_exe)
+    os.chmod(other_exe, 0o665)
+    assert not is_exe(other_exe)
+
+    not_exe = tmpdir.join("not_exe")
+    touch(not_exe)
+    assert not is_exe(not_exe)
+
+    exe_dir = tmpdir.join("exe_dir")
+    os.mkdir(exe_dir)
+    chmod_plus_x(exe_dir)
+    assert not is_exe(exe_dir)
+
+
+def test_is_script(tmpdir):
+    # type: (Tempdir) -> None
+
+    exe = tmpdir.join("exe")
+
+    touch(exe)
+    assert not is_exe(exe)
+    assert not is_script(exe, pattern=None, check_executable=True)
+
+    chmod_plus_x(exe)
+    assert is_exe(exe)
+    assert not is_script(exe, pattern=None, check_executable=True)
+
+    with open(exe, "wb") as fp:
+        fp.write(bytearray([0xCA, 0xFE, 0xBA, 0xBE]))
+    assert not is_script(fp.name, pattern=None, check_executable=True)
+
+    with open(exe, "wb") as fp:
+        fp.write(b"#!/mystery\n")
+        fp.write(bytearray([0xCA, 0xFE, 0xBA, 0xBE]))
+    assert is_script(exe, pattern=None, check_executable=True)
+    assert is_script(exe, pattern=br"^/mystery", check_executable=True)
+    assert not is_script(exe, pattern=br"^python", check_executable=True)
+
+    os.chmod(exe, 0o665)
+    assert is_script(exe, pattern=None, check_executable=False)
+    assert not is_script(exe, pattern=None, check_executable=True)
+    assert not is_exe(exe)
+
+
+def test_is_python_script(tmpdir):
+    # type: (Tempdir) -> None
+
+    exe = tmpdir.join("exe")
+
+    touch(exe)
+    assert not is_python_script(exe, check_executable=False)
+    assert not is_python_script(exe, check_executable=True)
+
+    def write_shebang(shebang):
+        # type: (str) -> None
+        with open(exe, "w") as fp:
+            fp.write(shebang)
+
+    write_shebang("#!python")
+    assert is_python_script(exe, check_executable=False)
+    assert not is_python_script(exe, check_executable=True)
+
+    chmod_plus_x(exe)
+    assert is_python_script(exe, check_executable=True)
+
+    write_shebang("#!/usr/bin/python")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/python3")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/python3.13")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/python -sE")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env python")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env python2.7")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env python -sE")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env -S python")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env -S python3")
+    assert is_python_script(exe)
+
+    write_shebang("#!/usr/bin/env -S python -sE")
+    assert is_python_script(exe)
diff --git a/tests/test_interpreter.py b/tests/test_interpreter.py
index de95e0661..e76f709ac 100644
--- a/tests/test_interpreter.py
+++ b/tests/test_interpreter.py
@@ -14,7 +14,8 @@
 import pytest
 
 from pex.cache.dirs import InterpreterDir
-from pex.common import chmod_plus_x, environment_as, safe_mkdir, safe_mkdtemp, temporary_dir, touch
+from pex.common import environment_as, safe_mkdir, safe_mkdtemp, temporary_dir, touch
+from pex.executables import chmod_plus_x
 from pex.executor import Executor
 from pex.interpreter import PythonInterpreter, create_shebang
 from pex.jobs import Job