diff --git a/src/pip/_vendor/distlib/scripts.py b/src/pip/_vendor/distlib/scripts.py
index e16292b8330..0982e6b726e 100644
--- a/src/pip/_vendor/distlib/scripts.py
+++ b/src/pip/_vendor/distlib/scripts.py
@@ -164,6 +164,12 @@ def _build_shebang(self, executable, post_interp):
         """
         if os.name != 'posix':
             simple_shebang = True
+        elif getattr(sys, "cross_compiling", False):
+            # In a cross-compiling environment, the shebang will likely be a
+            # script; this *must* be invoked with the "safe" version of the
+            # shebang, or else using os.exec() to run the entry script will
+            # fail, raising "OSError 8 [Errno 8] Exec format error".
+            simple_shebang = False
         else:
             # Add 3 for '#!' prefix and newline suffix.
             shebang_length = len(executable) + len(post_interp) + 3
diff --git a/tools/vendoring/patches/distlib.patch b/tools/vendoring/patches/distlib.patch
index de2834710a3..f8a066bf699 100644
--- a/tools/vendoring/patches/distlib.patch
+++ b/tools/vendoring/patches/distlib.patch
@@ -5,7 +5,7 @@ index cfa45d2af..e16292b83 100644
 @@ -49,6 +49,24 @@ if __name__ == '__main__':
      sys.exit(%(func)s())
  '''
- 
+
 +# Pre-fetch the contents of all executable wrapper stubs.
 +# This is to address https://github.com/pypa/pip/issues/12666.
 +# When updating pip, we rename the old pip in place before installing the
@@ -24,9 +24,22 @@ index cfa45d2af..e16292b83 100644
 +    if r.name.endswith(".exe")
 +}
 +
- 
+
  def enquote_executable(executable):
      if ' ' in executable:
+@@ -164,6 +164,12 @@ class ScriptMaker(object):
+         """
+         if os.name != 'posix':
+             simple_shebang = True
++        elif getattr(sys, "cross_compiling", False):
++            # In a cross-compiling environment, the shebang will likely be a
++            # script; this *must* be invoked with the "safe" version of the
++            # shebang, or else using os.exec() to run the entry script will
++            # fail, raising "OSError 8 [Errno 8] Exec format error".
++            simple_shebang = False
+         else:
+             # Add 3 for '#!' prefix and newline suffix.
+             shebang_length = len(executable) + len(post_interp) + 3
 @@ -409,15 +427,11 @@ class ScriptMaker(object):
                  bits = '32'
              platform_suffix = '-arm' if get_platform() == 'win-arm64' else ''
@@ -42,6 +55,6 @@ index cfa45d2af..e16292b83 100644
                  raise ValueError(msg)
 -            return resource.bytes
 +            return WRAPPERS[name]
- 
+
      # Public API follows
- 
+