diff --git a/Makefile b/Makefile
index 5099431..327be34 100644
--- a/Makefile
+++ b/Makefile
@@ -69,9 +69,8 @@ check: install format  ## Run formaters, linters, and static analysis
 ifdef CI
 	git diff --exit-code
 endif
+	poetry run mypy $(PACKAGES) --config-file=.mypy.ini
 	poetry run pylint $(PACKAGES) --rcfile=.pylint.ini
-	# TODO: Enable mypy after dropping legacy Python support
-	# poetry run mypy $(PACKAGES) --config-file=.mypy.ini
 	poetry run pydocstyle $(PACKAGES) $(CONFIG)
 
 # TESTS #######################################################################
diff --git a/poetry.lock b/poetry.lock
index 24ba3ef..60479f5 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -276,6 +276,30 @@ optional = false
 python-versions = ">=3.4"
 version = "7.2.0"
 
+[[package]]
+category = "dev"
+description = "Optional static typing for Python"
+name = "mypy"
+optional = false
+python-versions = ">=3.5"
+version = "0.730"
+
+[package.dependencies]
+mypy-extensions = ">=0.4.0,<0.5.0"
+typed-ast = ">=1.4.0,<1.5.0"
+typing-extensions = ">=3.7.4"
+
+[package.extras]
+dmypy = ["psutil (>=4.0)"]
+
+[[package]]
+category = "dev"
+description = "Experimental type system extensions for programs checked with the mypy typechecker."
+name = "mypy-extensions"
+optional = false
+python-versions = "*"
+version = "0.4.2"
+
 [[package]]
 category = "dev"
 description = "nose extends unittest to make testing easier"
@@ -567,12 +591,30 @@ version = "6.0.3"
 [[package]]
 category = "dev"
 description = "a fork of Python 2 and 3 ast modules with type comment support"
-marker = "implementation_name == \"cpython\" and python_version < \"3.8\""
 name = "typed-ast"
 optional = false
 python-versions = "*"
 version = "1.4.0"
 
+[[package]]
+category = "dev"
+description = "Type Hints for Python"
+name = "typing"
+optional = false
+python-versions = "*"
+version = "3.7.4.1"
+
+[[package]]
+category = "dev"
+description = "Backported and Experimental Type Hints for Python 3.5+"
+name = "typing-extensions"
+optional = false
+python-versions = "*"
+version = "3.7.4"
+
+[package.dependencies]
+typing = ">=3.7.4"
+
 [[package]]
 category = "dev"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
@@ -619,7 +661,7 @@ docs = ["sphinx", "jaraco.packaging (>=3.2)", "rst.linker (>=1.9)"]
 testing = ["pathlib2", "contextlib2", "unittest2"]
 
 [metadata]
-content-hash = "eb8dda22ef05d4fc5eef4b038f7696024f51a97c16b3132acf760ef12fd58ad3"
+content-hash = "17d163b8cf97d4999aad7a7d21d42fa832fca113d27854df79e3c8b6798d50f8"
 python-versions = "^3.6"
 
 [metadata.hashes]
@@ -649,6 +691,8 @@ markupsafe = ["00bc623926325b26bb9605ae9eae8a215691f33cae5df11ca5424f06f2d1f473"
 mccabe = ["ab8a6258860da4b6677da4bd2fe5dc2c659cff31b3ee4f7f5d64e79735b80d42", "dd8d182285a0fe56bace7f45b5e7d1a6ebcbf524e8f3bd87eb0f125271b8831f"]
 mkdocs = ["17d34329aad75d5de604b9ed4e31df3a4d235afefdc46ce7b1964fddb2e1e939", "8cc8b38325456b9e942c981a209eaeb1e9f3f77b493ad755bfef889b9c8d356a"]
 more-itertools = ["409cd48d4db7052af495b09dec721011634af3753ae1ef92d2b32f73a745f832", "92b8c4b06dac4f0611c0729b2f2ede52b2e1bac1ab48f089c7ddc12e26bb60c4"]
+mypy = ["1d98fd818ad3128a5408148c9e4a5edce6ed6b58cc314283e631dd5d9216527b", "22ee018e8fc212fe601aba65d3699689dd29a26410ef0d2cc1943de7bec7e3ac", "3a24f80776edc706ec8d05329e854d5b9e464cd332e25cde10c8da2da0a0db6c", "42a78944e80770f21609f504ca6c8173f7768043205b5ac51c9144e057dcf879", "4b2b20106973548975f0c0b1112eceb4d77ed0cafe0a231a1318f3b3a22fc795", "591a9625b4d285f3ba69f541c84c0ad9e7bffa7794da3fa0585ef13cf95cb021", "5b4b70da3d8bae73b908a90bb2c387b977e59d484d22c604a2131f6f4397c1a3", "84edda1ffeda0941b2ab38ecf49302326df79947fa33d98cdcfbf8ca9cf0bb23", "b2b83d29babd61b876ae375786960a5374bba0e4aba3c293328ca6ca5dc448dd", "cc4502f84c37223a1a5ab700649b5ab1b5e4d2bf2d426907161f20672a21930b", "e29e24dd6e7f39f200a5bb55dcaa645d38a397dd5a6674f6042ef02df5795046"]
+mypy-extensions = ["a161e3b917053de87dbe469987e173e49fb454eca10ef28b48b384538cc11458"]
 nose = ["9ff7c6cc443f8c51994b34a667bbcf45afd6d945be7477b52e97516fd17c53ac", "dadcddc0aefbf99eea214e0f1232b94f2fa9bd98fa8353711dacb112bfcbbb2a", "f1bffef9cbc82628f6e7d7b40d7e255aefaa1adb6a1b1d26c69a8b79e6208a98"]
 packaging = ["28b924174df7a2fa32c1953825ff29c61e2f5e082343165438812f00d3a7fc47", "d9551545c6d761f3def1677baf08ab2a3ca17c56879e70fecba2fc4dde4ed108"]
 pluggy = ["0db4b7601aae1d35b4a033282da476845aa19185c1e6964b25cf324b5e4ec3e6", "fa5fa1622fa6dd5c030e9cad086fa19ef6a0cf6d7a2d12318e10cb49d6d68f34"]
@@ -675,6 +719,8 @@ snowballstemmer = ["209f257d7533fdb3cb73bdbd24f436239ca3b2fa67d56f6ff88e86be08cc
 toml = ["229f81c57791a41d65e399fc06bf0848bab550a9dfd5ed66df18ce5f05e73d5c", "235682dd292d5899d361a811df37e04a8828a5b1da3115886b73cf81ebc9100e", "f1db651f9657708513243e61e6cc67d101a39bad662eaa9b5546f789338e07a3"]
 tornado = ["349884248c36801afa19e342a77cc4458caca694b0eda633f5878e458a44cb2c", "398e0d35e086ba38a0427c3b37f4337327231942e731edaa6e9fd1865bbd6f60", "4e73ef678b1a859f0cb29e1d895526a20ea64b5ffd510a2307b5998c7df24281", "559bce3d31484b665259f50cd94c5c28b961b09315ccd838f284687245f416e5", "abbe53a39734ef4aba061fca54e30c6b4639d3e1f59653f0da37a0003de148c7", "c845db36ba616912074c5b1ee897f8e0124df269468f25e4fe21fe72f6edd7a9", "c9399267c926a4e7c418baa5cbe91c7d1cf362d505a1ef898fde44a07c9dd8a5"]
 typed-ast = ["18511a0b3e7922276346bcb47e2ef9f38fb90fd31cb9223eed42c85d1312344e", "262c247a82d005e43b5b7f69aff746370538e176131c32dda9cb0f324d27141e", "2b907eb046d049bcd9892e3076c7a6456c93a25bebfe554e931620c90e6a25b0", "354c16e5babd09f5cb0ee000d54cfa38401d8b8891eefa878ac772f827181a3c", "4e0b70c6fc4d010f8107726af5fd37921b666f5b31d9331f0bd24ad9a088e631", "630968c5cdee51a11c05a30453f8cd65e0cc1d2ad0d9192819df9978984529f4", "66480f95b8167c9c5c5c87f32cf437d585937970f3fc24386f313a4c97b44e34", "71211d26ffd12d63a83e079ff258ac9d56a1376a25bc80b1cdcdf601b855b90b", "95bd11af7eafc16e829af2d3df510cecfd4387f6453355188342c3e79a2ec87a", "bc6c7d3fa1325a0c6613512a093bc2a2a15aeec350451cbdf9e1d4bffe3e3233", "cc34a6f5b426748a507dd5d1de4c1978f2eb5626d51326e43280941206c209e1", "d755f03c1e4a51e9b24d899561fec4ccaf51f210d52abdf8c07ee2849b212a36", "d7c45933b1bdfaf9f36c579671fec15d25b06c8398f113dab64c18ed1adda01d", "d896919306dd0aa22d0132f62a1b78d11aaf4c9fc5b3410d3c666b818191630a", "ffde2fbfad571af120fcbfbbc61c72469e72f550d676c3342492a9dfdefb8f12"]
+typing = ["91dfe6f3f706ee8cc32d38edbbf304e9b7583fb37108fef38229617f8b3eba23", "c8cabb5ab8945cd2f54917be357d134db9cc1eb039e59d1606dc1e60cb1d9d36", "f38d83c5a7a7086543a0f649564d661859c5146a85775ab90c0d2f93ffaa9714"]
+typing-extensions = ["2ed632b30bb54fc3941c382decfd0ee4148f5c591651c9272473fea2c6397d95", "b1edbbf0652660e32ae780ac9433f4231e7339c7f9a8057d0f042fcbcea49b87", "d8179012ec2c620d3791ca6fe2bf7979d979acdbef1fca0bc56b37411db682ed"]
 urllib3 = ["3de946ffbed6e6746608990594d08faac602528ac7015ac28d33cee6a45b7398", "9a107b99a5393caf59c7aa3c1249c16e6879447533d0887f4336dde834c7be86"]
 wcwidth = ["3df37372226d6e63e1b1e1eda15c594bca98a22d33a23832a90998faa96bc65e", "f4ebe71925af7b40a864553f761ed559b43544f8f71746c2d756c7fe788ade7c"]
 wrapt = ["565a021fd19419476b9362b05eeaa094178de64f8361e44468f9e9d7843901e1"]
diff --git a/pyproject.toml b/pyproject.toml
index 8145012..2494bbc 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -45,8 +45,7 @@ black = "=19.3b0"
 isort = "=4.3.21"
 
 # Linters
-# TODO: Enable mypy after dropping legacy Python support
-# mypy = "*"
+mypy = "*"
 pydocstyle = "^3"
 pylint = "^2"
 
diff --git a/verchew/script.py b/verchew/script.py
index 4b53973..1406a6d 100755
--- a/verchew/script.py
+++ b/verchew/script.py
@@ -38,6 +38,7 @@
 import warnings
 from collections import OrderedDict
 from subprocess import PIPE, STDOUT, Popen
+from typing import Any, Dict
 
 
 __version__ = '1.6.3'
@@ -179,7 +180,7 @@ def generate_config(root=None, filenames=None):
 
 
 def parse_config(path):
-    data = OrderedDict()
+    data: Dict[str, Any] = OrderedDict()
 
     log.info("Parsing config file: %s", path)
     config = configparser.ConfigParser()