diff --git a/python/tests/test_boot.py b/python/tests/test_boot.py
index c5fb3d1..bbc23db 100644
--- a/python/tests/test_boot.py
+++ b/python/tests/test_boot.py
@@ -16,9 +16,10 @@
     from testing.compare import ProcessResult  # noqa: F401
 
 
-def test_basic(tmpdir):
-    # type: (Any) -> None
-
+def create_cowsay_pex(
+    tmpdir,  # type: Any
+    *pex_args,  # type: str
+):
     pex = os.path.join(str(tmpdir), "cowsay.pex")
     pex_root = os.path.join(str(tmpdir), "pex-root")
     subprocess.check_call(
@@ -32,19 +33,54 @@ def test_basic(tmpdir):
             "--runtime-pex-root",
             pex_root,
         ]
+        + list(pex_args)
     )
+    return pex
+
+
+def assert_result(
+    result,  # type: ProcessResult
+    _is_traditional_pex,  # type: bool
+):
+    # type: (...) -> None
+    result.assert_success()
+    assert "| Moo! |" in result.stdout
+
+
+def read_shebang(pex):
+    # type: (str) -> Text
+
+    with open(pex, "rb") as fp:
+        return fp.readline().decode("utf-8")
+
+
+def test_basic(tmpdir):
+    # type: (Any) -> None
+
+    pex = create_cowsay_pex(tmpdir)
+    expected_shebang = read_shebang(pex)
+    assert expected_shebang.startswith("#!/usr/bin/env ")
+
+    injected_pex = compare(
+        pex,
+        args=["Moo!"],
+        env=dict(PEXRC_ROOT=os.path.join(str(tmpdir), "pexrc-root")),
+        test_result=assert_result,
+    )
+    assert expected_shebang == read_shebang(injected_pex)
+
+
+def test_sh_boot(tmpdir):
+    # type: (Any) -> None
 
-    def test_result(
-        result,  # type: ProcessResult
-        _is_traditional_pex,  # type: bool
-    ):
-        # type: (...) -> None
-        result.assert_success()
-        assert "| Moo! |" in result.stdout
+    pex = create_cowsay_pex(tmpdir, "--sh-boot")
+    expected_shebang = read_shebang(pex)
+    assert expected_shebang == "#!/bin/sh\n"
 
-    compare(
+    injected_pex = compare(
         pex,
         args=["Moo!"],
         env=dict(PEXRC_ROOT=os.path.join(str(tmpdir), "pexrc-root")),
-        test_result=test_result,
+        test_result=assert_result,
     )
+    assert expected_shebang == read_shebang(injected_pex)
diff --git a/python/tests/test_python_args.py b/python/tests/test_python_args.py
index 64ed46d..251f5e8 100644
--- a/python/tests/test_python_args.py
+++ b/python/tests/test_python_args.py
@@ -1,7 +1,7 @@
 # Copyright 2026 Pex project contributors.
 # SPDX-License-Identifier: Apache-2.0
 
-from __future__ import absolute_import, print_function
+from __future__ import absolute_import
 
 import os.path
 import subprocess
@@ -29,13 +29,15 @@ def test_python_args_forwarded(tmpdir):
         fp.write(
             dedent(
                 """\
+                from __future__ import print_function
+
                 import sys
 
                 import colors
 
 
                 assert False, colors.red("Failed")
-                print(colors.green("Worked: {}".format(" ".join(sys.argv[1:]))))
+                print(colors.green("Worked: {}".format(" ".join(sys.argv[1:]))), end="")
                 """
             )
         )
@@ -59,7 +61,7 @@ def test_result(
     ):
         # type: (...) -> None
         result.assert_success()
-        assert colors.green("Worked: Slartibartfast Ford") == result.stdout.strip()
+        assert colors.green("Worked: Slartibartfast Ford") == result.stdout
 
     injected_pex = compare(
         pex,