diff --git a/build-support/bin/ci.py b/build-support/bin/ci.py
index cd8c72d0798..6929e0adaf2 100755
--- a/build-support/bin/ci.py
+++ b/build-support/bin/ci.py
@@ -262,6 +262,7 @@ def get_listed_targets(filename: str) -> TargetSet:
         f"--tag={'-' if test_type == TestType.unit else '+'}integration",
         "filter",
         "--type=python_tests",
+        "build-support::",
         "src/python::",
         "tests/python::",
         "contrib::",
diff --git a/build-support/migration-support/fix_deprecated_globs_usage.py b/build-support/migration-support/fix_deprecated_globs_usage.py
index 52451476fd0..61c1dfe6458 100755
--- a/build-support/migration-support/fix_deprecated_globs_usage.py
+++ b/build-support/migration-support/fix_deprecated_globs_usage.py
@@ -45,7 +45,7 @@ def create_parser() -> argparse.ArgumentParser:
     description='Modernize BUILD files to no longer use globs, rglobs, and zglobs.',
   )
   parser.add_argument(
-    'folders', type=Path, nargs='*',
+    'folders', type=Path, nargs='+',
     help="Folders to recursively search for `BUILD` files",
   )
   parser.add_argument(
diff --git a/build-support/migration-support/migrate_to_toml_config.py b/build-support/migration-support/migrate_to_toml_config.py
new file mode 100755
index 00000000000..e74d5c0135d
--- /dev/null
+++ b/build-support/migration-support/migrate_to_toml_config.py
@@ -0,0 +1,127 @@
+#!/usr/bin/env python3
+# Copyright 2020 Pants project contributors (see CONTRIBUTORS.md).
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+"""A script to automatically convert an INI Pants config file to TOML. There will still likely be
+some issues remaining which require manual fixes, but this script will automate most of the tedium.
+
+Run `python3 migrate_to_toml_config.py --help`.
+"""
+
+import argparse
+import logging
+import re
+from pathlib import Path
+from typing import Dict, List
+
+
+def main() -> None:
+  args = create_parser().parse_args()
+  updates: Dict[Path, List[str]] = {}
+  for config in args.files:
+    if config.suffix not in [".ini", ".cfg"]:
+      logging.warning(f"This script may only be run on INI files. Skipping {config}.")
+      continue
+    new_path = Path(config.parent, f"{config.stem}.toml")
+    if new_path.exists():
+      logging.warning(f"{new_path} already exists. Skipping conversion of {config}.")
+      continue
+    new_config_content = generate_new_config(config)
+    updates[new_path] = new_config_content
+  for new_path, new_content in updates.items():
+    joined_new_content = '\n'.join(new_content) + "\n"
+    if args.preview:
+      print(f"Would create {new_path} with the following content:\n\n{joined_new_content}")
+    else:
+      logging.info(
+        f"Created {new_path}. There are likely some remaining issues that need manual "
+        "attention. Please copy the file into https://www.toml-lint.com or open with your editor "
+        "to fix any remaining issues."
+      )
+      new_path.write_text(joined_new_content)
+
+
+def create_parser() -> argparse.ArgumentParser:
+  parser = argparse.ArgumentParser(
+    description='Convert INI config files to TOML config files.',
+  )
+  parser.add_argument(
+    'files', type=Path, nargs='*',
+    help="Config files to convert.",
+  )
+  parser.add_argument(
+    '-p', '--preview', action='store_true',
+    help="Output to stdout rather than creating the new TOML config file(s).",
+  )
+  return parser
+
+
+def update_primitive_value(original: str) -> str:
+  if original in ["true", "True"]:
+    return "true"
+  if original in ["false", "False"]:
+    return "false"
+
+  try:
+    return str(int(original))
+  except ValueError:
+    pass
+
+  try:
+    return str(float(original))
+  except ValueError:
+    pass
+
+  return f'"{original}"'
+
+
+def generate_new_config(config: Path) -> List[str]:
+  original_text = config.read_text()
+  original_text_lines = original_text.splitlines()
+  updated_text_lines = original_text_lines.copy()
+
+  for i, line in enumerate(original_text_lines):
+    option_regex = r"(?P<option>[a-zA-Z0-9_]+)"
+    before_value_regex = rf"\s*{option_regex}\s*[:=]\s*"
+    valid_value_characters = r"a-zA-Z0-9_.@!%\=\>\<\-\(\)\/"
+    value_regex = rf"(?P<value>[{valid_value_characters}]+)"
+    parsed_line = re.match(
+      rf"{before_value_regex}{value_regex}\s*$", line,
+    )
+
+    if parsed_line:
+      option, value = parsed_line.groups()
+      updated_text_lines[i] = f"{option} = {update_primitive_value(value)}"
+      continue
+
+    # Check if it's a one-line list value
+    list_value_regex = rf"(?P<list>[\+\-]?\[[{valid_value_characters},\s\'\"]*\])"
+    parsed_list_line = re.match(rf"{before_value_regex}{list_value_regex}\s*$", line)
+    if parsed_list_line:
+      option, value = parsed_list_line.groups()
+      if value.startswith("+"):
+        updated_line = f"{option}.add = {value[1:]}"
+      elif value.startswith("-"):
+        updated_line = f"{option}.remove = {value[1:]}"
+      else:
+        updated_line = f"{option} = {value}"
+      updated_text_lines[i] = updated_line
+      continue
+
+    # Check if it's a one-line dict value
+    dict_value_regex = rf"(?P<dict>{{[{valid_value_characters},:\s\'\"]*}})"
+    parsed_dict_line = re.match(rf"{before_value_regex}{dict_value_regex}\s*$", line)
+    if parsed_dict_line:
+      option, value = parsed_dict_line.groups()
+      updated_text_lines[i] = f'{option} = """{value}"""'
+      continue
+
+  return updated_text_lines
+
+
+if __name__ == '__main__':
+  logging.basicConfig(format="[%(levelname)s]: %(message)s", level=logging.INFO)
+  try:
+    main()
+  except KeyboardInterrupt:
+    pass
diff --git a/build-support/migration-support/migrate_to_toml_config_test.py b/build-support/migration-support/migrate_to_toml_config_test.py
new file mode 100644
index 00000000000..198b91134b6
--- /dev/null
+++ b/build-support/migration-support/migrate_to_toml_config_test.py
@@ -0,0 +1,228 @@
+# Copyright 2020 Pants project contributors (see CONTRIBUTORS.md).
+# Licensed under the Apache License, Version 2.0 (see LICENSE).
+
+from pathlib import Path
+from textwrap import dedent
+
+from migrate_to_toml_config import generate_new_config
+
+from pants.util.contextutil import temporary_dir
+
+
+def assert_rewrite(*, original: str, expected: str) -> None:
+  with temporary_dir() as tmpdir:
+    build = Path(tmpdir, "pants.ini")
+    build.write_text(original)
+    result = generate_new_config(build)
+  assert result == expected.splitlines()
+
+
+def test_fully_automatable_config() -> None:
+  """We should be able to safely convert all of this config without any issues."""
+  assert_rewrite(
+    original=dedent(
+      """\
+      [GLOBAL]
+      bool_opt1: false
+      bool_opt2: True
+      int_opt: 10
+      float_opt: 5.0
+      
+      [str_values]
+      normal: .isort.cfg
+      version: isort>=4.8
+      path: /usr/bin/test.txt
+      fromfile: @build-support/example.txt
+      interpolation: %(foo)s/example
+      """
+    ),
+    expected=dedent(
+      """\
+      [GLOBAL]
+      bool_opt1 = false
+      bool_opt2 = true
+      int_opt = 10
+      float_opt = 5.0
+      
+      [str_values]
+      normal = ".isort.cfg"
+      version = "isort>=4.8"
+      path = "/usr/bin/test.txt"
+      fromfile = "@build-support/example.txt"
+      interpolation = "%(foo)s/example"
+      """
+    )
+  )
+
+
+def test_different_key_value_symbols() -> None:
+  """You can use both `:` or `=` in INI for key-value pairs."""
+  assert_rewrite(
+    original=dedent(
+      """\
+      [GLOBAL]
+      o1: a
+      o2:  a
+      o3 : a
+      o4  :  a
+      o5 :a
+      o6  :a
+      o7= a
+      o8=  a
+      o9 = a
+      o10  =  a
+      o11 =a
+      o12  =a
+      """
+    ),
+    expected=dedent(
+      """\
+      [GLOBAL]
+      o1 = "a"
+      o2 = "a"
+      o3 = "a"
+      o4 = "a"
+      o5 = "a"
+      o6 = "a"
+      o7 = "a"
+      o8 = "a"
+      o9 = "a"
+      o10 = "a"
+      o11 = "a"
+      o12 = "a"
+      """
+    )
+  )
+
+
+def test_comments() -> None:
+  """We don't mess with comments."""
+  assert_rewrite(
+    original=dedent(
+      """\
+      [GLOBAL]
+      bool_opt1: False  # Good riddance!
+      bool_opt2: True
+      int_opt: 10  ; semicolons matter too
+      # commented_out: 10
+      ; commented_out: 10
+      
+      # Comments on new lines should be preserved
+      ; Semicolon comments should also be preserved
+      [isort]  # comments on section headers shouldn't matter because we don't convert sections
+      config: .isort.cfg
+      """
+    ),
+    expected=dedent(
+      """\
+      [GLOBAL]
+      bool_opt1: False  # Good riddance!
+      bool_opt2 = true
+      int_opt: 10  ; semicolons matter too
+      # commented_out: 10
+      ; commented_out: 10
+      
+      # Comments on new lines should be preserved
+      ; Semicolon comments should also be preserved
+      [isort]  # comments on section headers shouldn't matter because we don't convert sections
+      config = ".isort.cfg"
+      """
+    )
+  )
+
+
+def test_list_options() -> None:
+  """We can safely update one-line lists.
+
+  The list members will already be correctly quoted for us. All that we need to update is the
+  option->key symbol and simple `+` adds and `-` removes.
+  """
+  assert_rewrite(
+    original=dedent(
+      """\
+      [GLOBAL]
+      l1: []
+      l2: [0, 1]
+      l3: ["a", "b"]
+      l4: ['a', 'b']
+      l5: [ "a", 'b' ]
+      l6: +["a", "b"]
+      l7: -["x", "y"]
+      l8: +["a", "b"],-["x", "y"]
+      l9: [[0], [1]]
+      l10: [0, 1]  # comment
+      l11: [0, 1]  ; comment
+      """
+    ),
+    expected=dedent(
+      """\
+      [GLOBAL]
+      l1 = []
+      l2 = [0, 1]
+      l3 = ["a", "b"]
+      l4 = ['a', 'b']
+      l5 = [ "a", 'b' ]
+      l6.add = ["a", "b"]
+      l7.remove = ["x", "y"]
+      l8: +["a", "b"],-["x", "y"]
+      l9: [[0], [1]]
+      l10: [0, 1]  # comment
+      l11: [0, 1]  ; comment
+      """
+    )
+  )
+
+
+def test_dict_options() -> None:
+  """We can safely preserve one-line dict values, which only need to be wrapped in quotes to work
+  properly.
+  """
+  assert_rewrite(
+    original=dedent(
+      """\
+      [GLOBAL]
+      d1: {}
+      d2: {"a": 0}
+      d3: {'a': 0}
+      d4: { "a": 0, "b: 0" }
+      d5: {"a": {"nested": 0}}
+      d6: {"a": 0}  # comment
+      d7: {"a": 0}  ; comment
+      """
+    ),
+    expected=dedent(
+      """\
+      [GLOBAL]
+      d1 = \"""{}\"""
+      d2 = \"""{"a": 0}\"""
+      d3 = \"""{'a': 0}\"""
+      d4 = \"""{ "a": 0, "b: 0" }\"""
+      d5: {"a": {"nested": 0}}
+      d6: {"a": 0}  # comment
+      d7: {"a": 0}  ; comment
+      """
+    )
+  )
+
+
+def test_multiline_options_ignored() -> None:
+  """Don't mess with multiline options, which are too difficult to get right."""
+  original = dedent(
+    """\
+    [GLOBAL]
+    multiline_string: in a galaxy far,
+       far, away...
+
+    l1: [
+        'foo',
+      ]
+
+    l2: ['foo',
+         'bar']
+  
+    d: {
+        'a': 0,
+      }
+    """
+  )
+  assert_rewrite(original=original, expected=original)