diff --git a/lib/python/qmk/cli/doctor/check.py b/lib/python/qmk/cli/doctor/check.py
index 426876e98a..cd69cdd11c 100644
--- a/lib/python/qmk/cli/doctor/check.py
+++ b/lib/python/qmk/cli/doctor/check.py
@@ -158,3 +158,21 @@ def is_executable(command):
 
     cli.log.error("{fg_red}Can't run `%s %s`", command, version_arg)
     return False
+
+
+def release_info(file='/etc/os-release'):
+    """Parse release info to dict
+    """
+    ret = {}
+    try:
+        with open(file) as f:
+            for line in f:
+                if '=' in line:
+                    key, value = map(str.strip, line.split('=', 1))
+                    if value.startswith('"') and value.endswith('"'):
+                        value = value[1:-1]
+                    ret[key] = value
+    except (PermissionError, FileNotFoundError):
+        pass
+
+    return ret
diff --git a/lib/python/qmk/cli/doctor/linux.py b/lib/python/qmk/cli/doctor/linux.py
index 95bafe8c64..f0850d4e64 100644
--- a/lib/python/qmk/cli/doctor/linux.py
+++ b/lib/python/qmk/cli/doctor/linux.py
@@ -7,7 +7,11 @@ from pathlib import Path
 from milc import cli
 
 from qmk.constants import QMK_FIRMWARE, BOOTLOADER_VIDS_PIDS
-from .check import CheckStatus
+from .check import CheckStatus, release_info
+
+
+def _is_wsl():
+    return 'microsoft' in platform.uname().release.lower()
 
 
 def _udev_rule(vid, pid=None, *args):
@@ -130,17 +134,22 @@ def check_modem_manager():
 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}.")
+    info = release_info()
+    release_id = info.get('PRETTY_NAME', info.get('ID', 'Unknown'))
+    plat = 'WSL, ' if _is_wsl() else ''
 
+    cli.log.info(f"Detected {{fg_cyan}}Linux ({plat}{release_id}){{fg_reset}}.")
+
+    # Don't bother with udev on WSL, for now
+    if _is_wsl():
         # 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}.")
+        rc = check_udev_rules()
+        if rc != CheckStatus.OK:
+            return rc
 
-        return check_udev_rules()
+    return CheckStatus.OK
diff --git a/lib/python/qmk/cli/doctor/windows.py b/lib/python/qmk/cli/doctor/windows.py
index 381ab36fde..26bb65374b 100644
--- a/lib/python/qmk/cli/doctor/windows.py
+++ b/lib/python/qmk/cli/doctor/windows.py
@@ -2,7 +2,7 @@ import platform
 
 from milc import cli
 
-from .check import CheckStatus
+from .check import CheckStatus, release_info
 
 
 def os_test_windows():
@@ -11,4 +11,10 @@ def os_test_windows():
     win32_ver = platform.win32_ver()
     cli.log.info("Detected {fg_cyan}Windows %s (%s){fg_reset}.", win32_ver[0], win32_ver[1])
 
+    # MSYS really does not like "/" files - resolve manually
+    file = cli.run(['cygpath', '-m', '/etc/qmk-release']).stdout.strip()
+    qmk_distro_version = release_info(file).get('VERSION', None)
+    if qmk_distro_version:
+        cli.log.info('QMK MSYS version: %s', qmk_distro_version)
+
     return CheckStatus.OK