diff --git a/lib/python/qmk/cli/doctor/__init__.py b/lib/python/qmk/cli/doctor/__init__.py
new file mode 100755
index 00000000000..75a7e7d1963
--- /dev/null
+++ b/lib/python/qmk/cli/doctor/__init__.py
@@ -0,0 +1,5 @@
+"""QMK Doctor
+
+Check out the user's QMK environment and make sure it's ready to compile.
+"""
+from .main import doctor
\ No newline at end of file
diff --git a/lib/python/qmk/os_helpers/__init__.py b/lib/python/qmk/cli/doctor/check.py
similarity index 91%
rename from lib/python/qmk/os_helpers/__init__.py
rename to lib/python/qmk/cli/doctor/check.py
index 3e98db3c32e..a0bbb281688 100644
--- a/lib/python/qmk/os_helpers/__init__.py
+++ b/lib/python/qmk/cli/doctor/check.py
@@ -1,4 +1,4 @@
-"""OS-agnostic helper functions
+"""Check for specific programs.
 """
 from enum import Enum
 import re
@@ -30,7 +30,7 @@ ESSENTIAL_BINARIES = {
 }
 
 
-def parse_gcc_version(version):
+def _parse_gcc_version(version):
     m = re.match(r"(\d+)(?:\.(\d+))?(?:\.(\d+))?", version)
 
     return {
@@ -40,7 +40,7 @@ def parse_gcc_version(version):
     }
 
 
-def check_arm_gcc_version():
+def _check_arm_gcc_version():
     """Returns True if the arm-none-eabi-gcc version is not known to cause problems.
     """
     if 'output' in ESSENTIAL_BINARIES['arm-none-eabi-gcc']:
@@ -50,7 +50,7 @@ def check_arm_gcc_version():
     return CheckStatus.OK  # Right now all known arm versions are ok
 
 
-def check_avr_gcc_version():
+def _check_avr_gcc_version():
     """Returns True if the avr-gcc version is not known to cause problems.
     """
     rc = CheckStatus.ERROR
@@ -60,7 +60,7 @@ def check_avr_gcc_version():
         cli.log.info('Found avr-gcc version %s', version_number)
         rc = CheckStatus.OK
 
-        parsed_version = parse_gcc_version(version_number)
+        parsed_version = _parse_gcc_version(version_number)
         if parsed_version['major'] > 8:
             cli.log.warning('{fg_yellow}We do not recommend avr-gcc newer than 8. Downgrading to 8.x is recommended.')
             rc = CheckStatus.WARNING
@@ -68,7 +68,7 @@ def check_avr_gcc_version():
     return rc
 
 
-def check_avrdude_version():
+def _check_avrdude_version():
     if 'output' in ESSENTIAL_BINARIES['avrdude']:
         last_line = ESSENTIAL_BINARIES['avrdude']['output'].split('\n')[-2]
         version_number = last_line.split()[2][:-1]
@@ -77,7 +77,7 @@ def check_avrdude_version():
     return CheckStatus.OK
 
 
-def check_dfu_util_version():
+def _check_dfu_util_version():
     if 'output' in ESSENTIAL_BINARIES['dfu-util']:
         first_line = ESSENTIAL_BINARIES['dfu-util']['output'].split('\n')[0]
         version_number = first_line.split()[1]
@@ -86,7 +86,7 @@ def check_dfu_util_version():
     return CheckStatus.OK
 
 
-def check_dfu_programmer_version():
+def _check_dfu_programmer_version():
     if 'output' in ESSENTIAL_BINARIES['dfu-programmer']:
         first_line = ESSENTIAL_BINARIES['dfu-programmer']['output'].split('\n')[0]
         version_number = first_line.split()[1]
@@ -111,7 +111,7 @@ def check_binary_versions():
     """Check the versions of ESSENTIAL_BINARIES
     """
     versions = []
-    for check in (check_arm_gcc_version, check_avr_gcc_version, check_avrdude_version, check_dfu_util_version, check_dfu_programmer_version):
+    for check in (_check_arm_gcc_version, _check_avr_gcc_version, _check_avrdude_version, _check_dfu_util_version, _check_dfu_programmer_version):
         versions.append(check())
     return versions
 
diff --git a/lib/python/qmk/os_helpers/linux/__init__.py b/lib/python/qmk/cli/doctor/linux.py
similarity index 89%
rename from lib/python/qmk/os_helpers/linux/__init__.py
rename to lib/python/qmk/cli/doctor/linux.py
index 008654ab0fc..c0b77216a19 100644
--- a/lib/python/qmk/os_helpers/linux/__init__.py
+++ b/lib/python/qmk/cli/doctor/linux.py
@@ -1,11 +1,13 @@
 """OS-specific functions for: Linux
 """
-from pathlib import Path
+import platform
 import shutil
+from pathlib import Path
 
 from milc import cli
+
 from qmk.constants import QMK_FIRMWARE
-from qmk.os_helpers import CheckStatus
+from .check import CheckStatus
 
 
 def _udev_rule(vid, pid=None, *args):
@@ -138,3 +140,23 @@ def check_modem_manager():
         """(TODO): Add check for non-systemd systems
         """
     return False
+
+
+def os_test_linux():
+    """Run the Linux specific tests.
+    """
+    # Don't bother with udev on WSL, for now
+    if 'microsoft' in platform.uname().release.lower():
+        cli.log.info("Detected {fg_cyan}Linux (WSL){fg_reset}.")
+
+        # https://github.com/microsoft/WSL/issues/4197
+        if QMK_FIRMWARE.as_posix().startswith("/mnt"):
+            cli.log.warning("I/O performance on /mnt may be extremely slow.")
+            return CheckStatus.WARNING
+
+        return CheckStatus.OK
+    else:
+        cli.log.info("Detected {fg_cyan}Linux{fg_reset}.")
+        from .linux import check_udev_rules
+
+        return check_udev_rules()
diff --git a/lib/python/qmk/cli/doctor/macos.py b/lib/python/qmk/cli/doctor/macos.py
new file mode 100644
index 00000000000..00fb272858b
--- /dev/null
+++ b/lib/python/qmk/cli/doctor/macos.py
@@ -0,0 +1,13 @@
+import platform
+
+from milc import cli
+
+from .check import CheckStatus
+
+
+def os_test_macos():
+    """Run the Mac specific tests.
+    """
+    cli.log.info("Detected {fg_cyan}macOS %s{fg_reset}.", platform.mac_ver()[0])
+
+    return CheckStatus.OK
diff --git a/lib/python/qmk/cli/doctor.py b/lib/python/qmk/cli/doctor/main.py
similarity index 74%
rename from lib/python/qmk/cli/doctor.py
rename to lib/python/qmk/cli/doctor/main.py
index 9e105706207..45b0203b6e8 100755
--- a/lib/python/qmk/cli/doctor.py
+++ b/lib/python/qmk/cli/doctor/main.py
@@ -7,9 +7,10 @@ from subprocess import DEVNULL
 
 from milc import cli
 from milc.questions import yesno
+
 from qmk import submodules
 from qmk.constants import QMK_FIRMWARE
-from qmk.os_helpers import CheckStatus, check_binaries, check_binary_versions, check_submodules, check_git_repo
+from .check import CheckStatus, check_binaries, check_binary_versions, check_submodules, check_git_repo
 
 
 def os_tests():
@@ -18,53 +19,19 @@ def os_tests():
     platform_id = platform.platform().lower()
 
     if 'darwin' in platform_id or 'macos' in platform_id:
+        from .macos import os_test_macos
         return os_test_macos()
     elif 'linux' in platform_id:
+        from .linux import os_test_linux
         return os_test_linux()
     elif 'windows' in platform_id:
+        from .windows import os_test_windows
         return os_test_windows()
     else:
         cli.log.warning('Unsupported OS detected: %s', platform_id)
         return CheckStatus.WARNING
 
 
-def os_test_linux():
-    """Run the Linux specific tests.
-    """
-    # Don't bother with udev on WSL, for now
-    if 'microsoft' in platform.uname().release.lower():
-        cli.log.info("Detected {fg_cyan}Linux (WSL){fg_reset}.")
-
-        # https://github.com/microsoft/WSL/issues/4197
-        if QMK_FIRMWARE.as_posix().startswith("/mnt"):
-            cli.log.warning("I/O performance on /mnt may be extremely slow.")
-            return CheckStatus.WARNING
-
-        return CheckStatus.OK
-    else:
-        cli.log.info("Detected {fg_cyan}Linux{fg_reset}.")
-        from qmk.os_helpers.linux import check_udev_rules
-
-        return check_udev_rules()
-
-
-def os_test_macos():
-    """Run the Mac specific tests.
-    """
-    cli.log.info("Detected {fg_cyan}macOS %s{fg_reset}.", platform.mac_ver()[0])
-
-    return CheckStatus.OK
-
-
-def os_test_windows():
-    """Run the Windows specific tests.
-    """
-    win32_ver = platform.win32_ver()
-    cli.log.info("Detected {fg_cyan}Windows %s (%s){fg_reset}.", win32_ver[0], win32_ver[1])
-
-    return CheckStatus.OK
-
-
 @cli.argument('-y', '--yes', action='store_true', arg_only=True, help='Answer yes to all questions.')
 @cli.argument('-n', '--no', action='store_true', arg_only=True, help='Answer no to all questions.')
 @cli.subcommand('Basic QMK environment checks')
diff --git a/lib/python/qmk/cli/doctor/windows.py b/lib/python/qmk/cli/doctor/windows.py
new file mode 100644
index 00000000000..381ab36fde9
--- /dev/null
+++ b/lib/python/qmk/cli/doctor/windows.py
@@ -0,0 +1,14 @@
+import platform
+
+from milc import cli
+
+from .check import CheckStatus
+
+
+def os_test_windows():
+    """Run the Windows specific tests.
+    """
+    win32_ver = platform.win32_ver()
+    cli.log.info("Detected {fg_cyan}Windows %s (%s){fg_reset}.", win32_ver[0], win32_ver[1])
+
+    return CheckStatus.OK