diff --git a/build-support/bin/check_header.py b/build-support/bin/check_header.py
index 7a51ae4b063..d8900ffd9ce 100755
--- a/build-support/bin/check_header.py
+++ b/build-support/bin/check_header.py
@@ -4,10 +4,10 @@
 
 import argparse
 import datetime
-import os
 import re
+from pathlib import Path
 from textwrap import dedent
-from typing import Iterable, List
+from typing import List, Sequence
 
 from common import die
 
@@ -20,8 +20,14 @@
 
 EXPECTED_NUM_LINES = 3
 
-_current_year = str(datetime.datetime.now().year)
-_current_century_regex = re.compile(r'20\d\d')
+CURRENT_YEAR = str(datetime.datetime.now().year)
+CURRENT_CENTURY_REGEX = re.compile(r'20\d\d')
+
+PY2_DIRECTORIES = {
+  Path("contrib/python/src/python/pants/contrib/python/checks/checker"),
+  Path("src/python/pants/backend/python/tasks/coverage"),
+  Path("src/python/pants/backend/python/tasks/pytest"),
+}
 
 
 class HeaderCheckFailure(Exception):
@@ -32,7 +38,8 @@ def main() -> None:
   args = create_parser().parse_args()
   header_parse_failures = []
   for directory in args.dirs:
-    header_parse_failures.extend(check_dir(directory, args.files_added))
+    directory_failures = check_dir(directory=directory, newly_created_files=args.files_added)
+    header_parse_failures.extend(directory_failures)
   if header_parse_failures:
     failures = '\n  '.join(str(failure) for failure in header_parse_failures)
     die(f"""\
@@ -47,79 +54,77 @@ def main() -> None:
 
 def create_parser() -> argparse.ArgumentParser:
   parser = argparse.ArgumentParser(
-    description="Check that all .py files start with the appropriate header."
+    description="Check that all .py files start with the appropriate header.",
   )
-  parser.add_argument("dirs", nargs="+",
-    help="The directories to check. Will recursively check subdirectories."
+  parser.add_argument("dirs", nargs="+", type=Path,
+    help="The directories to check. Will recursively check subdirectories.",
   )
-  parser.add_argument("-a", "--files-added", nargs="*", default=[],
+  parser.add_argument("-a", "--files-added", nargs="*", default=[], type=Path,
     help="Any passed files will be checked for a current copyright year."
   )
   return parser
 
 
-def check_header(filename: str, *, is_newly_created: bool = False) -> None:
+def check_dir(*, directory: Path, newly_created_files: Sequence[Path]) -> List[HeaderCheckFailure]:
+  header_parse_failures: List[HeaderCheckFailure] = []
+  for fp in directory.rglob("*.py"):
+    if fp.name == '__init__.py' or fp.parent in PY2_DIRECTORIES:
+      continue
+    try:
+      check_header(fp, is_newly_created=fp in newly_created_files)
+    except HeaderCheckFailure as e:
+      header_parse_failures.append(e)
+  return header_parse_failures
+
+
+def check_header(file_path: Path, *, is_newly_created: bool = False) -> None:
   """Raises `HeaderCheckFailure` if the header doesn't match."""
-  lines = get_header_lines(filename)
-  check_header_present(filename, lines)
+  lines = get_header_lines(file_path)
+  check_header_present(file_path, lines)
   check_copyright_year(
-    filename, copyright_line=lines[0], is_newly_created=is_newly_created
+    file_path, copyright_line=lines[0], is_newly_created=is_newly_created
   )
-  check_matches_header(filename, lines)
+  check_matches_header(file_path, lines)
 
 
-def get_header_lines(filename: str) -> List[str]:
+def get_header_lines(file_path: Path) -> List[str]:
   try:
-    with open(filename, 'r') as f:
+    with file_path.open() as f:
       # We grab an extra line in case there is a shebang.
       lines = [f.readline() for _ in range(0, EXPECTED_NUM_LINES + 1)]
-  except IOError as e:
-    raise HeaderCheckFailure(f"{filename}: error while reading input ({e})")
+  except OSError as e:
+    raise HeaderCheckFailure(f"{file_path}: error while reading input ({e})")
   # If a shebang line is included, remove it. Otherwise, we will have conservatively grabbed
   # one extra line at the end for the shebang case that is no longer necessary.
   lines.pop(0 if lines[0].startswith("#!") else - 1)
   return lines
 
 
-def check_header_present(filename: str, lines: List[str]) -> None:
+def check_header_present(file_path: Path, lines: List[str]) -> None:
   num_nonempty_lines = len([line for line in lines if line])
   if num_nonempty_lines < EXPECTED_NUM_LINES:
-    raise HeaderCheckFailure(f"{filename}: missing the expected header")
+    raise HeaderCheckFailure(f"{file_path}: missing the expected header")
 
 
-def check_copyright_year(filename: str, *, copyright_line: str, is_newly_created: bool) -> None:
+def check_copyright_year(file_path: Path, *, copyright_line: str, is_newly_created: bool) -> None:
   """Check that copyright is current year if for a new file, else that it's within
   the current century."""
   year = copyright_line[12:16]
-  if is_newly_created and year != _current_year:
-    raise HeaderCheckFailure(f'{filename}: copyright year must be {_current_year} (was {year})')
-  elif not _current_century_regex.match(year):
+  if is_newly_created and year != CURRENT_YEAR:
+    raise HeaderCheckFailure(f'{file_path}: copyright year must be {CURRENT_YEAR} (was {year})')
+  elif not CURRENT_CENTURY_REGEX.match(year):
     raise HeaderCheckFailure(
-      f"{filename}: copyright year must match '{_current_century_regex.pattern}' (was {year}): " +
-      f"current year is {_current_year}"
+      f"{file_path}: copyright year must match '{CURRENT_CENTURY_REGEX.pattern}' (was {year}): " +
+      f"current year is {CURRENT_YEAR}"
     )
 
 
-def check_matches_header(filename: str, lines: List[str]) -> None:
+def check_matches_header(file_path: Path, lines: List[str]) -> None:
   copyright_line = lines[0]
   sanitized_lines = lines.copy()
   sanitized_lines[0] = "# Copyright YYYY" + copyright_line[16:]
   if "".join(sanitized_lines) != EXPECTED_HEADER:
-    raise HeaderCheckFailure(f"{filename}: header does not match the expected header")
-
-
-def check_dir(directory: str, newly_created_files: Iterable[str]) -> List[HeaderCheckFailure]:
-  header_parse_failures: List[HeaderCheckFailure] = []
-  for root, dirs, files in os.walk(directory):
-    for f in files:
-      if not f.endswith('.py') or os.path.basename(f) == '__init__.py' or root.endswith('contrib/python/checks/checker'):
-        continue
-      filename = os.path.join(root, f)
-      try:
-        check_header(filename, is_newly_created=filename in newly_created_files)
-      except HeaderCheckFailure as e:
-        header_parse_failures.append(e)
-  return header_parse_failures
+    raise HeaderCheckFailure(f"{file_path}: header does not match the expected header")
 
 
 if __name__ == '__main__':
diff --git a/src/python/pants/backend/python/tasks/coverage/plugin.py b/src/python/pants/backend/python/tasks/coverage/plugin.py
index c87d970d5f8..ed3e821dd07 100644
--- a/src/python/pants/backend/python/tasks/coverage/plugin.py
+++ b/src/python/pants/backend/python/tasks/coverage/plugin.py
@@ -1,6 +1,11 @@
+# coding=utf-8
 # Copyright 2018 Pants project contributors (see CONTRIBUTORS.md).
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
+from __future__ import absolute_import, division, print_function, unicode_literals
+
+# NB: This file must keep Python 2 support because it is a resource that may be run with Python 2.
+
 import json
 import os
 
diff --git a/src/python/pants/backend/python/tasks/pytest/plugin.py b/src/python/pants/backend/python/tasks/pytest/plugin.py
index 554b19e4dcd..0dcd03132a3 100644
--- a/src/python/pants/backend/python/tasks/pytest/plugin.py
+++ b/src/python/pants/backend/python/tasks/pytest/plugin.py
@@ -1,6 +1,11 @@
+# coding=utf-8
 # Copyright 2019 Pants project contributors (see CONTRIBUTORS.md).
 # Licensed under the Apache License, Version 2.0 (see LICENSE).
 
+from __future__ import absolute_import, division, print_function, unicode_literals
+
+# NB: This file must keep Python 2 support because it is a resource that may be run with Python 2.
+
 import json
 import os