diff --git a/bin/colcon b/bin/colcon
index 28ea5fd9..8e228042 100755
--- a/bin/colcon
+++ b/bin/colcon
@@ -41,6 +41,8 @@ from colcon_core.command import LOG_LEVEL_ENVIRONMENT_VARIABLE  # noqa: E402
 from colcon_core.entry_point \
     import EXTENSION_BLOCKLIST_ENVIRONMENT_VARIABLE  # noqa: E402
 from colcon_core.environment.path import PathEnvironment  # noqa: E402
+from colcon_core.environment.path \
+    import PythonScriptsPathEnvironment  # noqa: E402
 from colcon_core.environment.pythonpath \
     import PythonPathEnvironment  # noqa: E402
 from colcon_core.event_handler.console_direct \
@@ -79,6 +81,7 @@ custom_entry_points.update({
     'colcon_core.argument_parser': {},
     'colcon_core.environment': {
         'path': PathEnvironment,
+        'pythonscriptspath': PythonScriptsPathEnvironment,
         'pythonpath': PythonPathEnvironment,
     },
     'colcon_core.environment_variable': {
diff --git a/colcon_core/environment/path.py b/colcon_core/environment/path.py
index 6dbef3c7..9795108b 100644
--- a/colcon_core/environment/path.py
+++ b/colcon_core/environment/path.py
@@ -1,13 +1,23 @@
 # Copyright 2016-2018 Dirk Thomas
 # Licensed under the Apache License, Version 2.0
 
-import os
-import sys
-
 from colcon_core import shell
 from colcon_core.environment import EnvironmentExtensionPoint
 from colcon_core.environment import logger
 from colcon_core.plugin_system import satisfies_version
+from colcon_core.python_install_path import get_python_install_path
+
+
+def _has_file(path):
+    logger.log(1, "checking '%s'" % path)
+
+    if not path.is_dir():
+        return False
+
+    for child in path.iterdir():
+        if child.is_file():
+            return True
+    return False
 
 
 class PathEnvironment(EnvironmentExtensionPoint):
@@ -19,29 +29,34 @@ def __init__(self):  # noqa: D107
             EnvironmentExtensionPoint.EXTENSION_POINT_VERSION, '^1.0')
 
     def create_environment_hooks(self, prefix_path, pkg_name):  # noqa: D102
-        hooks = self._create_environment_hooks(prefix_path, pkg_name, 'bin')
-        if sys.platform == 'win32':
-            hooks += self._create_environment_hooks(
-                prefix_path, pkg_name, 'Scripts', '-scripts')
+        subdirectory = 'bin'
+        hooks = []
+        bin_path = prefix_path / subdirectory
+
+        if _has_file(bin_path):
+            hooks += shell.create_environment_hook(
+                'path', prefix_path, pkg_name, 'PATH', subdirectory,
+                mode='prepend')
+
         return hooks
 
-    def _create_environment_hooks(
-        self, prefix_path, pkg_name, subdirectory, suffix=''
-    ):
+
+class PythonScriptsPathEnvironment(EnvironmentExtensionPoint):
+    """Extend the `PATH` variable to find python scripts."""
+
+    def __init__(self):  # noqa: D107
+        super().__init__()
+        satisfies_version(
+            EnvironmentExtensionPoint.EXTENSION_POINT_VERSION, '^1.0')
+
+    def create_environment_hooks(self, prefix_path, pkg_name):  # noqa: D102
         hooks = []
-        bin_path = prefix_path / subdirectory
-        logger.log(1, "checking '%s'" % bin_path)
-        try:
-            names = os.listdir(str(bin_path))
-        except FileNotFoundError:
-            pass
-        else:
-            for name in names:
-                if not (bin_path / name).is_file():
-                    continue
-                hooks += shell.create_environment_hook(
-                    'path' + suffix, prefix_path, pkg_name, 'PATH',
-                    subdirectory, mode='prepend')
-                break
+        bin_path = get_python_install_path('scripts', {'base': prefix_path})
+
+        if _has_file(bin_path):
+            rel_bin_path = bin_path.relative_to(prefix_path)
+            hooks += shell.create_environment_hook(
+                'pythonscriptspath', prefix_path, pkg_name, 'PATH',
+                str(rel_bin_path), mode='prepend')
 
         return hooks
diff --git a/colcon_core/environment/pythonpath.py b/colcon_core/environment/pythonpath.py
index 6b557e4b..9d65e289 100644
--- a/colcon_core/environment/pythonpath.py
+++ b/colcon_core/environment/pythonpath.py
@@ -1,13 +1,11 @@
 # Copyright 2016-2018 Dirk Thomas
 # Licensed under the Apache License, Version 2.0
 
-from pathlib import Path
-import sysconfig
-
 from colcon_core import shell
 from colcon_core.environment import EnvironmentExtensionPoint
 from colcon_core.environment import logger
 from colcon_core.plugin_system import satisfies_version
+from colcon_core.python_install_path import get_python_install_path
 
 
 class PythonPathEnvironment(EnvironmentExtensionPoint):
@@ -21,8 +19,7 @@ def __init__(self):  # noqa: D107
     def create_environment_hooks(self, prefix_path, pkg_name):  # noqa: D102
         hooks = []
 
-        python_path = Path(
-            sysconfig.get_path('purelib', vars={'base': prefix_path}))
+        python_path = get_python_install_path('purelib', {'base': prefix_path})
         logger.log(1, "checking '%s'" % python_path)
         if python_path.exists():
             rel_python_path = python_path.relative_to(prefix_path)
diff --git a/colcon_core/python_install_path.py b/colcon_core/python_install_path.py
new file mode 100644
index 00000000..d5f26d15
--- /dev/null
+++ b/colcon_core/python_install_path.py
@@ -0,0 +1,24 @@
+# Copyright 2022 Open Source Robotics Foundation, Inc.
+# Licensed under the Apache License, Version 2.0
+
+from pathlib import Path
+import sysconfig
+
+
+def get_python_install_path(name, vars_=()):
+    """
+    Get Python install paths matching Colcon's preferred scheme.
+
+    See sysconfig.get_path for more info about the arguments.
+
+    :param name: Name of the path type
+    :param vars_: A dictionary of variables updating the values of
+        sysconfig.get_config_vars()
+    :rtype: Pathlib.Path
+    """
+    kwargs = {}
+    kwargs['vars'] = dict(vars_)
+    if 'deb_system' in sysconfig.get_scheme_names():
+        kwargs['scheme'] = 'deb_system'
+
+    return Path(sysconfig.get_path(name, **kwargs))
diff --git a/colcon_core/task/python/build.py b/colcon_core/task/python/build.py
index ff7956c0..bc5d73de 100644
--- a/colcon_core/task/python/build.py
+++ b/colcon_core/task/python/build.py
@@ -8,12 +8,12 @@
 import shutil
 import sys
 from sys import executable
-import sysconfig
 
 from colcon_core.environment import create_environment_hooks
 from colcon_core.environment import create_environment_scripts
 from colcon_core.logging import colcon_logger
 from colcon_core.plugin_system import satisfies_version
+from colcon_core.python_install_path import get_python_install_path
 from colcon_core.shell import create_environment_hook
 from colcon_core.shell import get_command_environment
 from colcon_core.subprocess import check_output
@@ -296,7 +296,7 @@ def _symlinks_in_build(self, args, setup_py_data):
         return temp_symlinks
 
     def _get_python_lib(self, args):
-        path = sysconfig.get_path('purelib', vars={'base': args.install_base})
+        path = get_python_install_path('purelib', {'base': args.install_base})
         return os.path.relpath(path, start=args.install_base)
 
     def _append_install_layout(self, args, cmd):
diff --git a/setup.cfg b/setup.cfg
index b4f1b54d..bdcb900d 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -81,6 +81,7 @@ colcon_core.argument_parser =
 colcon_core.environment =
     path = colcon_core.environment.path:PathEnvironment
     pythonpath = colcon_core.environment.pythonpath:PythonPathEnvironment
+    pythonscriptspath = colcon_core.environment.path:PythonScriptsPathEnvironment
 colcon_core.environment_variable =
     all_shells = colcon_core.shell:ALL_SHELLS_ENVIRONMENT_VARIABLE
     default_executor = colcon_core.executor:DEFAULT_EXECUTOR_ENVIRONMENT_VARIABLE
diff --git a/test/spell_check.words b/test/spell_check.words
index 9ac1863d..8ee496aa 100644
--- a/test/spell_check.words
+++ b/test/spell_check.words
@@ -74,6 +74,7 @@ pydocstyle
 pytest
 pytests
 pythonpath
+pythonscriptspath
 pythonwarnings
 readouterr
 readthedocs
diff --git a/test/test_environment_pythonpath.py b/test/test_environment_pythonpath.py
index 842e3319..00aacb36 100644
--- a/test/test_environment_pythonpath.py
+++ b/test/test_environment_pythonpath.py
@@ -2,11 +2,11 @@
 # Licensed under the Apache License, Version 2.0
 
 from pathlib import Path
-import sysconfig
 from tempfile import TemporaryDirectory
 from unittest.mock import patch
 
 from colcon_core.environment.pythonpath import PythonPathEnvironment
+from colcon_core.python_install_path import get_python_install_path
 
 
 def test_pythonpath():
@@ -23,8 +23,8 @@ def test_pythonpath():
             assert len(hooks) == 0
 
             # Python path exists
-            python_path = Path(
-                sysconfig.get_path('purelib', vars={'base': prefix_path}))
+            python_path = get_python_install_path(
+                'purelib', {'base': prefix_path})
             python_path.mkdir(parents=True)
             hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
             assert len(hooks) == 2
diff --git a/test/test_environment_pythonscriptspath.py b/test/test_environment_pythonscriptspath.py
new file mode 100644
index 00000000..74c70120
--- /dev/null
+++ b/test/test_environment_pythonscriptspath.py
@@ -0,0 +1,45 @@
+# Copyright 2016-2018 Dirk Thomas
+# Licensed under the Apache License, Version 2.0
+
+from pathlib import Path
+from tempfile import TemporaryDirectory
+from unittest.mock import patch
+
+from colcon_core.environment.path import PythonScriptsPathEnvironment
+from colcon_core.python_install_path import get_python_install_path
+
+
+def test_path():
+    extension = PythonScriptsPathEnvironment()
+
+    with TemporaryDirectory(prefix='test_colcon_') as prefix_path:
+        prefix_path = Path(prefix_path)
+        scripts_path = get_python_install_path(
+            'scripts', {'base': prefix_path})
+        with patch(
+            'colcon_core.shell.create_environment_hook',
+            return_value=['/some/hook', '/other/hook']
+        ):
+            # bin directory does not exist
+            hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
+            assert len(hooks) == 0
+
+            # bin directory exists, but empty
+            scripts_path.mkdir()
+            hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
+            assert len(hooks) == 0
+
+            # bin directory exists, but only subdirectories
+            (scripts_path / 'subdir').mkdir()
+            hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
+            assert len(hooks) == 0
+
+            # bin directory exists, with file
+            (scripts_path / 'hook').write_text('')
+            hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
+            assert len(hooks) == 2
+
+            # bin directory exists, with files
+            (scripts_path / 'hook2').write_text('')
+            hooks = extension.create_environment_hooks(prefix_path, 'pkg_name')
+            assert len(hooks) == 2