diff --git a/colcon_core/command.py b/colcon_core/command.py
index 10668edc..887b30cd 100644
--- a/colcon_core/command.py
+++ b/colcon_core/command.py
@@ -271,9 +271,28 @@ def get_prog_name():
     if basename == '__main__.py':
         # use the module name in case the script was invoked with python -m ...
         prog = os.path.basename(os.path.dirname(prog))
-    elif shutil.which(basename) == prog:
-        # use basename only if it is on the PATH
-        prog = basename
+    else:
+        default_prog = shutil.which(basename) or ''
+        default_ext = os.path.splitext(default_prog)[1]
+        real_prog = prog
+        if (
+            sys.platform == 'win32' and
+            os.path.splitext(real_prog)[1] != default_ext
+        ):
+            # On Windows, setuptools entry points drop the file extension from
+            # argv[0], but shutil.which does not. If the two don't end in the
+            # same extension, try appending the shutil extension for a better
+            # chance at matching.
+            real_prog += default_ext
+        try:
+            # The os.path.samefile requires that both files exist on disk, but
+            # has the advantage of working around symlinks, UNC-style paths,
+            # DOS 8.3 path atoms, and path normalization.
+            if os.path.samefile(default_prog, real_prog):
+                # use basename only if it is on the PATH
+                prog = basename
+        except (FileNotFoundError, NotADirectoryError):
+            pass
     return prog
 
 
diff --git a/test/spell_check.words b/test/spell_check.words
index 07ac1117..dab9ce0f 100644
--- a/test/spell_check.words
+++ b/test/spell_check.words
@@ -113,6 +113,7 @@ setuptools
 shlex
 sigint
 sitecustomize
+skipif
 sloretz
 stacklevel
 staticmethod
diff --git a/test/test_command.py b/test/test_command.py
index d2aca2d2..c8c6b6e9 100644
--- a/test/test_command.py
+++ b/test/test_command.py
@@ -1,15 +1,18 @@
 # Copyright 2016-2018 Dirk Thomas
 # Licensed under the Apache License, Version 2.0
 
+import os
 import shutil
 import signal
 import sys
 from tempfile import mkdtemp
+from tempfile import TemporaryDirectory
 from unittest.mock import Mock
 from unittest.mock import patch
 
 from colcon_core.command import CommandContext
 from colcon_core.command import create_parser
+from colcon_core.command import get_prog_name
 from colcon_core.command import main
 from colcon_core.command import verb_main
 from colcon_core.environment_variable import EnvironmentVariable
@@ -151,3 +154,86 @@ def test_verb_main():
     assert logger.error.call_args[0][0].startswith(
         'command_name verb_name: custom error message\n')
     assert 'Exception: custom error message' in logger.error.call_args[0][0]
+
+
+def test_prog_name_module():
+    argv = [os.path.join('foo', 'bar', '__main__.py')]
+    with patch('colcon_core.command.sys.argv', argv):
+        # prog should be the module containing __main__.py
+        assert get_prog_name() == 'bar'
+
+
+def test_prog_name_on_path():
+    # use __file__ since we know it exists
+    argv = [__file__]
+    with patch('colcon_core.command.sys.argv', argv):
+        with patch(
+            'colcon_core.command.shutil.which',
+            return_value=__file__
+        ):
+            # prog should be shortened to the basename
+            assert get_prog_name() == 'test_command.py'
+
+
+def test_prog_name_not_on_path():
+    # use __file__ since we know it exists
+    argv = [__file__]
+    with patch('colcon_core.command.sys.argv', argv):
+        with patch('colcon_core.command.shutil.which', return_value=None):
+            # prog should remain unchanged
+            assert get_prog_name() == __file__
+
+
+def test_prog_name_different_on_path():
+    # use __file__ since we know it exists
+    argv = [__file__]
+    with patch('colcon_core.command.sys.argv', argv):
+        with patch(
+            'colcon_core.command.shutil.which',
+            return_value=sys.executable
+        ):
+            # prog should remain unchanged
+            assert get_prog_name() == __file__
+
+
+def test_prog_name_not_a_file():
+    # pick some file that doesn't actually exist on disk
+    no_such_file = os.path.join(__file__, 'foobar')
+    argv = [no_such_file]
+    with patch('colcon_core.command.sys.argv', argv):
+        with patch(
+            'colcon_core.command.shutil.which',
+            return_value=no_such_file
+        ):
+            # prog should remain unchanged
+            assert get_prog_name() == no_such_file
+
+
+@pytest.mark.skipif(sys.platform == 'win32', reason='Symlinks not supported.')
+def test_prog_name_symlink():
+    # use __file__ since we know it exists
+    with TemporaryDirectory(prefix='test_colcon_') as temp_dir:
+        linked_file = os.path.join(temp_dir, 'test_command.py')
+        os.symlink(__file__, linked_file)
+
+        argv = [linked_file]
+        with patch('colcon_core.command.sys.argv', argv):
+            with patch(
+                'colcon_core.command.shutil.which',
+                return_value=__file__
+            ):
+                # prog should be shortened to the basename
+                assert get_prog_name() == 'test_command.py'
+
+
+@pytest.mark.skipif(sys.platform != 'win32', reason='Only valid on Windows.')
+def test_prog_name_easy_install():
+    # use __file__ since we know it exists
+    argv = [__file__[:-3]]
+    with patch('colcon_core.command.sys.argv', argv):
+        with patch(
+            'colcon_core.command.shutil.which',
+            return_value=__file__
+        ):
+            # prog should be shortened to the basename
+            assert get_prog_name() == 'test_command'