diff --git a/lib/python/qmk/cli/mass_compile.py b/lib/python/qmk/cli/mass_compile.py
index 9dad5420e9d..b978a1ef7ce 100755
--- a/lib/python/qmk/cli/mass_compile.py
+++ b/lib/python/qmk/cli/mass_compile.py
@@ -7,7 +7,7 @@ from pathlib import Path
 from subprocess import DEVNULL
 from milc import cli
 
-from qmk.constants import QMK_FIRMWARE, QMK_USERSPACE
+from qmk.constants import QMK_FIRMWARE, QMK_USERSPACE, HAS_QMK_USERSPACE
 from qmk.commands import _find_make, get_make_parallel_args
 from qmk.keyboard import resolve_keyboard
 from qmk.search import search_keymap_targets
@@ -51,7 +51,7 @@ def mass_compile(cli):
     with open(makefile, "w") as f:
 
         userspace_suffix = ''
-        if Path(QMK_FIRMWARE).resolve() != Path(QMK_USERSPACE).resolve():
+        if HAS_QMK_USERSPACE:
             userspace_suffix = f'QMK_USERSPACE={Path(QMK_USERSPACE).resolve()}'
 
         for target in sorted(targets):
diff --git a/lib/python/qmk/cli/new/keymap.py b/lib/python/qmk/cli/new/keymap.py
index 9b0ac221a4a..f7ffcab0e99 100755
--- a/lib/python/qmk/cli/new/keymap.py
+++ b/lib/python/qmk/cli/new/keymap.py
@@ -1,10 +1,12 @@
 """This script automates the copying of the default keymap into your own keymap.
 """
 import shutil
+from pathlib import Path
 
 from milc import cli
 from milc.questions import question
 
+from qmk.constants import HAS_QMK_USERSPACE, QMK_USERSPACE, QMK_FIRMWARE
 from qmk.path import is_keyboard, keymaps, keymap
 from qmk.git import git_get_username
 from qmk.decorators import automagic_keyboard, automagic_keymap
@@ -54,6 +56,9 @@ def new_keymap(cli):
     keymap_path_default = keymap(kb_name, 'default')
     keymap_path_new = keymaps_dirs[0] / user_name
 
+    if HAS_QMK_USERSPACE:
+        keymap_path_new = Path(QMK_USERSPACE) / keymaps_dirs[0].relative_to(QMK_FIRMWARE) / user_name
+
     if not keymap_path_default.exists():
         cli.log.error(f'Default keymap {{fg_cyan}}{keymap_path_default}{{fg_reset}} does not exist!')
         return False
diff --git a/lib/python/qmk/commands.py b/lib/python/qmk/commands.py
index 4b1fea6bbb8..ad73fc58d16 100644
--- a/lib/python/qmk/commands.py
+++ b/lib/python/qmk/commands.py
@@ -9,7 +9,7 @@ from pathlib import Path
 from milc import cli
 import jsonschema
 
-from qmk.constants import INTERMEDIATE_OUTPUT_PREFIX, QMK_FIRMWARE, QMK_USERSPACE
+from qmk.constants import INTERMEDIATE_OUTPUT_PREFIX, QMK_USERSPACE, HAS_QMK_USERSPACE
 from qmk.json_schema import json_load, validate
 
 
@@ -51,7 +51,7 @@ def create_make_target(target, dry_run=False, parallel=1, **env_vars):
     for key, value in env_vars.items():
         env.append(f'{key}={value}')
 
-    if Path(QMK_FIRMWARE).resolve() != Path(QMK_USERSPACE).resolve():
+    if HAS_QMK_USERSPACE:
         env.append(f'QMK_USERSPACE={Path(QMK_USERSPACE).resolve()}')
 
     if cli.config.general.verbose:
diff --git a/lib/python/qmk/constants.py b/lib/python/qmk/constants.py
index 58d00faa528..b9555948e9f 100644
--- a/lib/python/qmk/constants.py
+++ b/lib/python/qmk/constants.py
@@ -25,6 +25,9 @@ def _detect_qmk_userspace():
 # The detected userspace tree
 QMK_USERSPACE = _detect_qmk_userspace()
 
+# Whether or not we have a separate userspace directory
+HAS_QMK_USERSPACE = True if Path(QMK_USERSPACE).resolve() != Path(QMK_FIRMWARE).resolve() else False
+
 # Upstream repo url
 QMK_FIRMWARE_UPSTREAM = 'qmk/qmk_firmware'
 
diff --git a/lib/python/qmk/keymap.py b/lib/python/qmk/keymap.py
index bac919a773f..f3c620ed8ef 100644
--- a/lib/python/qmk/keymap.py
+++ b/lib/python/qmk/keymap.py
@@ -12,7 +12,7 @@ from pygments.token import Token
 from pygments import lex
 
 import qmk.path
-from qmk.constants import QMK_FIRMWARE, QMK_USERSPACE
+from qmk.constants import QMK_FIRMWARE, QMK_USERSPACE, HAS_QMK_USERSPACE
 from qmk.keyboard import find_keyboard_from_dir, keyboard_folder
 from qmk.errors import CppError
 from qmk.info import info_json
@@ -218,7 +218,7 @@ def find_keymap_from_dir():
                 return relative_cwd.parts[1], 'users_directory'
         return None, None
 
-    if Path(QMK_FIRMWARE).resolve() != Path(QMK_USERSPACE).resolve():
+    if HAS_QMK_USERSPACE:
         name, source = _impl_find_keymap_from_dir(qmk.path.under_qmk_userspace())
         if name and source:
             return name, source
@@ -430,7 +430,7 @@ def locate_keymap(keyboard, keymap):
     # Check the keyboard folder first, last match wins
     keymap_path = ''
 
-    for search_dir in [QMK_FIRMWARE, QMK_USERSPACE]:
+    for search_dir in [QMK_FIRMWARE, QMK_USERSPACE] if HAS_QMK_USERSPACE else [QMK_FIRMWARE]:
         checked_dirs = ''
         for dir in keyboard_folder(keyboard).split('/'):
             if checked_dirs:
@@ -452,7 +452,7 @@ def locate_keymap(keyboard, keymap):
     info = info_json(keyboard)
 
     community_parents = list(Path('layouts').glob('*/'))
-    if Path(QMK_FIRMWARE).resolve() != Path(QMK_USERSPACE).resolve() and (Path(QMK_USERSPACE) / "layouts").exists():
+    if HAS_QMK_USERSPACE and (Path(QMK_USERSPACE) / "layouts").exists():
         community_parents.append(Path(QMK_USERSPACE) / "layouts")
 
     for community_parent in community_parents:
@@ -509,7 +509,7 @@ def list_keymaps(keyboard, c=True, json=True, additional_files=None, fullpath=Fa
     info = info_json(keyboard)
 
     community_parents = list(Path('layouts').glob('*/'))
-    if Path(QMK_FIRMWARE).resolve() != Path(QMK_USERSPACE).resolve() and (Path(QMK_USERSPACE) / "layouts").exists():
+    if HAS_QMK_USERSPACE and (Path(QMK_USERSPACE) / "layouts").exists():
         community_parents.append(Path(QMK_USERSPACE) / "layouts")
 
     for community_parent in community_parents: