diff --git a/lib/python/qmk/cli/find.py b/lib/python/qmk/cli/find.py
index 8f3a29c90c..bfed91e22c 100644
--- a/lib/python/qmk/cli/find.py
+++ b/lib/python/qmk/cli/find.py
@@ -2,6 +2,7 @@
 """
 from milc import cli
 from qmk.search import filter_help, search_keymap_targets
+from qmk.util import maybe_exit_config
 
 
 @cli.argument(
@@ -19,6 +20,8 @@ from qmk.search import filter_help, search_keymap_targets
 def find(cli):
     """Search through all keyboards and keymaps for a given search criteria.
     """
+    maybe_exit_config(should_exit=False, should_reraise=True)
+
     targets = search_keymap_targets([('all', cli.config.find.keymap)], cli.args.filter)
     for target in sorted(targets, key=lambda t: (t.keyboard, t.keymap)):
         print(f'{target}')
diff --git a/lib/python/qmk/cli/generate/autocorrect_data.py b/lib/python/qmk/cli/generate/autocorrect_data.py
index b11c66d95d..01a29b46fe 100644
--- a/lib/python/qmk/cli/generate/autocorrect_data.py
+++ b/lib/python/qmk/cli/generate/autocorrect_data.py
@@ -27,7 +27,6 @@ Example:
 For full documentation, see QMK Docs
 """
 
-import sys
 import textwrap
 from typing import Any, Dict, Iterator, List, Tuple
 
@@ -38,6 +37,7 @@ from qmk.constants import GPL2_HEADER_C_LIKE, GENERATED_HEADER_C_LIKE
 from qmk.keyboard import keyboard_completer, keyboard_folder
 from qmk.keymap import keymap_completer, locate_keymap
 from qmk.path import normpath
+from qmk.util import maybe_exit
 
 KC_A = 4
 KC_SPC = 0x2c
@@ -88,16 +88,16 @@ def parse_file(file_name: str) -> List[Tuple[str, str]]:
         # Check that `typo` is valid.
         if not (all([c in TYPO_CHARS for c in typo])):
             cli.log.error('{fg_red}Error:%d:{fg_reset} Typo "{fg_cyan}%s{fg_reset}" has characters other than a-z, \' and :.', line_number, typo)
-            sys.exit(1)
+            maybe_exit(1)
         for other_typo in typos:
             if typo in other_typo or other_typo in typo:
                 cli.log.error('{fg_red}Error:%d:{fg_reset} Typos may not be substrings of one another, otherwise the longer typo would never trigger: "{fg_cyan}%s{fg_reset}" vs. "{fg_cyan}%s{fg_reset}".', line_number, typo, other_typo)
-                sys.exit(1)
+                maybe_exit(1)
         if len(typo) < 5:
             cli.log.warning('{fg_yellow}Warning:%d:{fg_reset} It is suggested that typos are at least 5 characters long to avoid false triggers: "{fg_cyan}%s{fg_reset}"', line_number, typo)
         if len(typo) > 127:
             cli.log.error('{fg_red}Error:%d:{fg_reset} Typo exceeds 127 chars: "{fg_cyan}%s{fg_reset}"', line_number, typo)
-            sys.exit(1)
+            maybe_exit(1)
 
         check_typo_against_dictionary(typo, line_number, correct_words)
 
@@ -136,7 +136,7 @@ def parse_file_lines(file_name: str) -> Iterator[Tuple[int, str, str]]:
             tokens = [token.strip() for token in line.split('->', 1)]
             if len(tokens) != 2 or not tokens[0]:
                 print(f'Error:{line_number}: Invalid syntax: "{line}"')
-                sys.exit(1)
+                maybe_exit(1)
 
             typo, correction = tokens
             typo = typo.lower()  # Force typos to lowercase.
@@ -237,7 +237,7 @@ def encode_link(link: Dict[str, Any]) -> List[int]:
     byte_offset = link['byte_offset']
     if not (0 <= byte_offset <= 0xffff):
         cli.log.error('{fg_red}Error:{fg_reset} The autocorrection table is too large, a node link exceeds 64KB limit. Try reducing the autocorrection dict to fewer entries.')
-        sys.exit(1)
+        maybe_exit(1)
     return [byte_offset & 255, byte_offset >> 8]
 
 
diff --git a/lib/python/qmk/cli/mass_compile.py b/lib/python/qmk/cli/mass_compile.py
index 7db704d6c2..d13afc6143 100755
--- a/lib/python/qmk/cli/mass_compile.py
+++ b/lib/python/qmk/cli/mass_compile.py
@@ -12,6 +12,7 @@ from qmk.constants import QMK_FIRMWARE
 from qmk.commands import find_make, get_make_parallel_args, build_environment
 from qmk.search import search_keymap_targets, search_make_targets
 from qmk.build_targets import BuildTarget, JsonKeymapBuildTarget
+from qmk.util import maybe_exit_config
 
 
 def mass_compile_targets(targets: List[BuildTarget], clean: bool, dry_run: bool, no_temp: bool, parallel: int, **env):
@@ -100,6 +101,8 @@ all: {keyboard_safe}_{keymap_name}_binary
 def mass_compile(cli):
     """Compile QMK Firmware against all keyboards.
     """
+    maybe_exit_config(should_exit=False, should_reraise=True)
+
     if len(cli.args.builds) > 0:
         json_like_targets = list([Path(p) for p in filter(lambda e: Path(e).exists() and Path(e).suffix == '.json', cli.args.builds)])
         make_like_targets = list(filter(lambda e: Path(e) not in json_like_targets, cli.args.builds))
diff --git a/lib/python/qmk/cli/userspace/compile.py b/lib/python/qmk/cli/userspace/compile.py
index fb320a16f0..e8cdf6cd97 100644
--- a/lib/python/qmk/cli/userspace/compile.py
+++ b/lib/python/qmk/cli/userspace/compile.py
@@ -9,6 +9,7 @@ from qmk.userspace import UserspaceDefs
 from qmk.build_targets import JsonKeymapBuildTarget
 from qmk.search import search_keymap_targets
 from qmk.cli.mass_compile import mass_compile_targets
+from qmk.util import maybe_exit_config
 
 
 @cli.argument('-t', '--no-temp', arg_only=True, action='store_true', help="Remove temporary files during build.")
@@ -22,6 +23,8 @@ def userspace_compile(cli):
         cli.log.error('Could not determine QMK userspace location. Please run `qmk doctor` or `qmk userspace-doctor` to diagnose.')
         return False
 
+    maybe_exit_config(should_exit=False, should_reraise=True)
+
     userspace = UserspaceDefs(QMK_USERSPACE / 'qmk.json')
 
     build_targets = []
diff --git a/lib/python/qmk/cli/userspace/list.py b/lib/python/qmk/cli/userspace/list.py
index a63f669dd7..8689c80a76 100644
--- a/lib/python/qmk/cli/userspace/list.py
+++ b/lib/python/qmk/cli/userspace/list.py
@@ -10,6 +10,7 @@ from qmk.build_targets import BuildTarget
 from qmk.keyboard import is_all_keyboards, keyboard_folder
 from qmk.keymap import is_keymap_target
 from qmk.search import search_keymap_targets
+from qmk.util import maybe_exit_config
 
 
 @cli.argument('-e', '--expand', arg_only=True, action='store_true', help="Expands any use of `all` for either keyboard or keymap.")
@@ -19,6 +20,8 @@ def userspace_list(cli):
         cli.log.error('Could not determine QMK userspace location. Please run `qmk doctor` or `qmk userspace-doctor` to diagnose.')
         return False
 
+    maybe_exit_config(should_exit=False, should_reraise=True)
+
     userspace = UserspaceDefs(QMK_USERSPACE / 'qmk.json')
 
     if cli.args.expand:
diff --git a/lib/python/qmk/cli/via2json.py b/lib/python/qmk/cli/via2json.py
index 77823b5d9d..73c9a61b3d 100755
--- a/lib/python/qmk/cli/via2json.py
+++ b/lib/python/qmk/cli/via2json.py
@@ -69,7 +69,7 @@ def _via_to_keymap(via_backup, keyboard_data, keymap_layout):
     layout_data = keyboard_data['layouts'].get(keymap_layout)
     if not layout_data:
         cli.log.error(f'LAYOUT macro {keymap_layout} is not a valid one for keyboard {cli.args.keyboard}!')
-        exit(1)
+        return None
 
     layout_data = layout_data['layout']
     sorting_hat = list()
@@ -118,7 +118,7 @@ def via2json(cli):
     keymap_layout = cli.args.layout if cli.args.layout else _find_via_layout_macro(cli.args.keyboard)
     if not keymap_layout:
         cli.log.error(f"Couldn't find LAYOUT macro for keyboard {cli.args.keyboard}. Please specify it with the '-l' argument.")
-        exit(1)
+        return False
 
     # Load the VIA backup json
     with cli.args.filename.open('r') as fd:
@@ -126,9 +126,15 @@ def via2json(cli):
 
     # Generate keyboard metadata
     keyboard_data = info_json(cli.args.keyboard)
+    if not keyboard_data:
+        cli.log.error(f'LAYOUT macro {keymap_layout} is not a valid one for keyboard {cli.args.keyboard}!')
+        return False
 
     # Get keycode array
     keymap_data = _via_to_keymap(via_backup, keyboard_data, keymap_layout)
+    if not keymap_data:
+        cli.log.error(f'Could not extract valid keycode data from VIA backup matching keyboard {cli.args.keyboard}!')
+        return False
 
     # Convert macros
     macro_data = list()
diff --git a/lib/python/qmk/commands.py b/lib/python/qmk/commands.py
index d95ff5f923..3db8353bfd 100644
--- a/lib/python/qmk/commands.py
+++ b/lib/python/qmk/commands.py
@@ -11,6 +11,7 @@ import jsonschema
 from qmk.constants import QMK_USERSPACE, HAS_QMK_USERSPACE
 from qmk.json_schema import json_load, validate
 from qmk.keyboard import keyboard_alias_definitions
+from qmk.util import maybe_exit
 
 
 def find_make():
@@ -52,7 +53,7 @@ def parse_configurator_json(configurator_file):
 
     except jsonschema.ValidationError as e:
         cli.log.error(f'Invalid JSON keymap: {configurator_file} : {e.message}')
-        exit(1)
+        maybe_exit(1)
 
     keyboard = user_keymap['keyboard']
     aliases = keyboard_alias_definitions()
diff --git a/lib/python/qmk/info.py b/lib/python/qmk/info.py
index ffc9d57d68..833271c09c 100644
--- a/lib/python/qmk/info.py
+++ b/lib/python/qmk/info.py
@@ -14,6 +14,7 @@ from qmk.keyboard import config_h, rules_mk
 from qmk.commands import parse_configurator_json
 from qmk.makefile import parse_rules_mk_file
 from qmk.math import compute
+from qmk.util import maybe_exit
 
 true_values = ['1', 'on', 'yes']
 false_values = ['0', 'off', 'no']
@@ -208,7 +209,7 @@ def _validate(keyboard, info_data):
     except jsonschema.ValidationError as e:
         json_path = '.'.join([str(p) for p in e.absolute_path])
         cli.log.error('Invalid API data: %s: %s: %s', keyboard, json_path, e.message)
-        exit(1)
+        maybe_exit(1)
 
 
 def info_json(keyboard):
diff --git a/lib/python/qmk/json_schema.py b/lib/python/qmk/json_schema.py
index 1d5f863807..b11a0ed7ea 100644
--- a/lib/python/qmk/json_schema.py
+++ b/lib/python/qmk/json_schema.py
@@ -11,6 +11,8 @@ from copy import deepcopy
 
 from milc import cli
 
+from qmk.util import maybe_exit
+
 
 def _dict_raise_on_duplicates(ordered_pairs):
     """Reject duplicate keys."""
@@ -38,10 +40,10 @@ def _json_load_impl(json_file, strict=True):
 
     except (json.decoder.JSONDecodeError, hjson.HjsonDecodeError) as e:
         cli.log.error('Invalid JSON encountered attempting to load {fg_cyan}%s{fg_reset}:\n\t{fg_red}%s', json_file, e)
-        exit(1)
+        maybe_exit(1)
     except Exception as e:
         cli.log.error('Unknown error attempting to load {fg_cyan}%s{fg_reset}:\n\t{fg_red}%s', json_file, e)
-        exit(1)
+        maybe_exit(1)
 
 
 def json_load(json_file, strict=True):
diff --git a/lib/python/qmk/util.py b/lib/python/qmk/util.py
index db7debd578..0145ab1354 100644
--- a/lib/python/qmk/util.py
+++ b/lib/python/qmk/util.py
@@ -2,9 +2,30 @@
 """
 import contextlib
 import multiprocessing
+import sys
 
 from milc import cli
 
+maybe_exit_should_exit = True
+maybe_exit_reraise = False
+
+
+# Controls whether or not early `exit()` calls should be made
+def maybe_exit(rc):
+    if maybe_exit_should_exit:
+        sys.exit(rc)
+    if maybe_exit_reraise:
+        e = sys.exception()
+        if e:
+            raise e
+
+
+def maybe_exit_config(should_exit: bool = True, should_reraise: bool = False):
+    global maybe_exit_should_exit
+    global maybe_exit_reraise
+    maybe_exit_should_exit = should_exit
+    maybe_exit_reraise = should_reraise
+
 
 @contextlib.contextmanager
 def parallelize():