diff --git a/testpath/commands.py b/testpath/commands.py
index c40c18e..21e2430 100644
--- a/testpath/commands.py
+++ b/testpath/commands.py
@@ -74,8 +74,12 @@ def __init__(self, name, content=None, python=''):
         self.command_dir = tempfile.mkdtemp()
 
         if content is None:
+            # Shebangs have a limited length, so symlink the Python executable
+            # to a short name that can't conflict with the real command.
+            tmp_python = os.path.join(self.command_dir, 'python-' + name)
+            os.symlink(sys.executable, tmp_python)
             content = _record_run.format(
-                python=sys.executable, recording_file=self.recording_file,
+                python=tmp_python, recording_file=self.recording_file,
                 extra_code=python,
             )
         elif python:
diff --git a/tests/test_commands.py b/tests/test_commands.py
index 63955fb..34675e1 100644
--- a/tests/test_commands.py
+++ b/tests/test_commands.py
@@ -1,6 +1,9 @@
 import os
 from subprocess import call, check_output
 import unittest
+import shutil
+import sys
+import tempfile
 
 from testpath.commands import *
 
@@ -35,6 +38,26 @@ def test_assert_calls_twice(self):
             with assert_calls('git'):
                 pass
 
+    def test_assert_calls_long_python_path(self):
+        current_python = sys.executable
+        tmp = tempfile.mkdtemp()
+        try:
+            tmp_python_dir = tmp
+            for _ in range(10):
+                tmp_python_dir = os.path.join(tmp_python_dir, 'looooooooooooooooooooooooooooooooooooooooooong_segment')
+            os.makedirs(tmp_python_dir)
+            tmp_python = os.path.join(tmp_python_dir, 'python')
+            os.symlink(sys.executable, tmp_python)
+            sys.executable = tmp_python
+
+            with assert_calls('i_dont_exist'):
+                call(['i_dont_exist'])
+            with assert_calls('git'):
+                call(['git'])
+        finally:
+            sys.executable = current_python
+            shutil.rmtree(tmp, ignore_errors=True)
+
 def test_fixed_output():
     t = 'Sat 24 Apr 17:11:58 BST 2021\n'
     with MockCommand.fixed_output('date', t) as mock_date: