diff --git a/lib/python/qmk/cli/__init__.py b/lib/python/qmk/cli/__init__.py
index 5149a6215af6..eb524217cde2 100644
--- a/lib/python/qmk/cli/__init__.py
+++ b/lib/python/qmk/cli/__init__.py
@@ -2,6 +2,8 @@
 
 We list each subcommand here explicitly because all the reliable ways of searching for modules are slow and delay startup.
 """
+from milc import cli
+
 from . import cformat
 from . import compile
 from . import config
@@ -16,3 +18,6 @@
 from . import new
 from . import pyformat
 from . import pytest
+
+if not hasattr(cli, 'config_source'):
+    cli.log.warning("Your QMK CLI is out of date. Please upgrade with `pip3 install --upgrade qmk` or by using your package manager.")
diff --git a/lib/python/qmk/cli/compile.py b/lib/python/qmk/cli/compile.py
index 3068c97d81e8..6480d624b043 100755
--- a/lib/python/qmk/cli/compile.py
+++ b/lib/python/qmk/cli/compile.py
@@ -8,13 +8,17 @@
 from milc import cli
 
 import qmk.path
-from qmk.commands import compile_configurator_json, create_make_command, find_keyboard_keymap, parse_configurator_json
+from qmk.decorators import automagic_keyboard, automagic_keymap
+from qmk.commands import compile_configurator_json, create_make_command, parse_configurator_json
 
 
 @cli.argument('filename', nargs='?', arg_only=True, type=FileType('r'), help='The configurator export to compile')
 @cli.argument('-kb', '--keyboard', help='The keyboard to build a firmware for. Ignored when a configurator export is supplied.')
 @cli.argument('-km', '--keymap', help='The keymap to build a firmware for. Ignored when a configurator export is supplied.')
+@cli.argument('-n', '--dry-run', arg_only=True, action='store_true', help="Don't actually build, just show the make command to be run.")
 @cli.subcommand('Compile a QMK Firmware.')
+@automagic_keyboard
+@automagic_keymap
 def compile(cli):
     """Compile a QMK Firmware.
 
@@ -22,8 +26,10 @@ def compile(cli):
 
     If a keyboard and keymap are provided this command will build a firmware based on that.
     """
+    command = None
+
     if cli.args.filename:
-        # If a configurator JSON was provided skip straight to compiling it
+        # If a configurator JSON was provided generate a keymap and compile it
         # FIXME(skullydazed): add code to check and warn if the keymap already exists when compiling a json keymap.
         user_keymap = parse_configurator_json(cli.args.filename)
         keymap_path = qmk.path.keymap(user_keymap['keyboard'])
@@ -32,16 +38,23 @@ def compile(cli):
         cli.log.info('Wrote keymap to {fg_cyan}%s/%s/keymap.c', keymap_path, user_keymap['keymap'])
 
     else:
-        # Perform the action the user specified
-        user_keyboard, user_keymap = find_keyboard_keymap()
-        if user_keyboard and user_keymap:
+        if cli.config.compile.keyboard and cli.config.compile.keymap:
             # Generate the make command for a specific keyboard/keymap.
-            command = create_make_command(user_keyboard, user_keymap)
+            command = create_make_command(cli.config.compile.keyboard, cli.config.compile.keymap)
+
+        elif not cli.config.compile.keyboard:
+            cli.log.error('Could not determine keyboard!')
+        elif not cli.config.compile.keymap:
+            cli.log.error('Could not determine keymap!')
 
-        else:
-            cli.log.error('You must supply a configurator export, both `--keyboard` and `--keymap`, or be in a directory for a keyboard or keymap.')
-            cli.echo('usage: qmk compile [-h] [-b] [-kb KEYBOARD] [-km KEYMAP] [filename]')
-            return False
+    # Compile the firmware, if we're able to
+    if command:
+        cli.log.info('Compiling keymap with {fg_cyan}%s', ' '.join(command))
+        if not cli.args.dry_run:
+            cli.echo('\n')
+            subprocess.run(command)
 
-    cli.log.info('Compiling keymap with {fg_cyan}%s\n\n', ' '.join(command))
-    subprocess.run(command)
+    else:
+        cli.log.error('You must supply a configurator export, both `--keyboard` and `--keymap`, or be in a directory for a keyboard or keymap.')
+        cli.echo('usage: qmk compile [-h] [-b] [-kb KEYBOARD] [-km KEYMAP] [filename]')
+        return False
diff --git a/lib/python/qmk/cli/flash.py b/lib/python/qmk/cli/flash.py
index f669c3cb7e74..f8497071efd5 100644
--- a/lib/python/qmk/cli/flash.py
+++ b/lib/python/qmk/cli/flash.py
@@ -6,9 +6,11 @@
 import subprocess
 from argparse import FileType
 
-import qmk.path
 from milc import cli
-from qmk.commands import compile_configurator_json, create_make_command, find_keyboard_keymap, parse_configurator_json
+
+import qmk.path
+from qmk.decorators import automagic_keyboard, automagic_keymap
+from qmk.commands import compile_configurator_json, create_make_command, parse_configurator_json
 
 
 def print_bootloader_help():
@@ -28,12 +30,15 @@ def print_bootloader_help():
     cli.echo('For more info, visit https://docs.qmk.fm/#/flashing')
 
 
-@cli.argument('-bl', '--bootloader', default='flash', help='The flash command, corresponding to qmk\'s make options of bootloaders.')
 @cli.argument('filename', nargs='?', arg_only=True, type=FileType('r'), help='The configurator export JSON to compile.')
+@cli.argument('-b', '--bootloaders', action='store_true', help='List the available bootloaders.')
+@cli.argument('-bl', '--bootloader', default='flash', help='The flash command, corresponding to qmk\'s make options of bootloaders.')
 @cli.argument('-km', '--keymap', help='The keymap to build a firmware for. Use this if you dont have a configurator file. Ignored when a configurator file is supplied.')
 @cli.argument('-kb', '--keyboard', help='The keyboard to build a firmware for. Use this if you dont have a configurator file. Ignored when a configurator file is supplied.')
-@cli.argument('-b', '--bootloaders', action='store_true', help='List the available bootloaders.')
+@cli.argument('-n', '--dry-run', arg_only=True, action='store_true', help="Don't actually build, just show the make command to be run.")
 @cli.subcommand('QMK Flash.')
+@automagic_keyboard
+@automagic_keymap
 def flash(cli):
     """Compile and or flash QMK Firmware or keyboard/layout
 
@@ -42,12 +47,13 @@ def flash(cli):
 
     If no file is supplied, keymap and keyboard are expected.
 
-    If bootloader is omitted, the one according to the rules.mk will be used.
-
+    If bootloader is omitted the make system will use the configured bootloader for that keyboard.
     """
+    command = ''
+
     if cli.args.bootloaders:
         # Provide usage and list bootloaders
-        cli.echo('usage: qmk flash [-h] [-b] [-kb KEYBOARD] [-km KEYMAP] [-bl BOOTLOADER] [filename]')
+        cli.echo('usage: qmk flash [-h] [-b] [-n] [-kb KEYBOARD] [-km KEYMAP] [-bl BOOTLOADER] [filename]')
         print_bootloader_help()
         return False
 
@@ -60,16 +66,23 @@ def flash(cli):
         cli.log.info('Wrote keymap to {fg_cyan}%s/%s/keymap.c', keymap_path, user_keymap['keymap'])
 
     else:
-        # Perform the action the user specified
-        user_keyboard, user_keymap = find_keyboard_keymap()
-        if user_keyboard and user_keymap:
+        if cli.config.flash.keyboard and cli.config.flash.keymap:
             # Generate the make command for a specific keyboard/keymap.
-            command = create_make_command(user_keyboard, user_keymap, cli.args.bootloader)
+            command = create_make_command(cli.config.flash.keyboard, cli.config.flash.keymap, cli.args.bootloader)
 
-        else:
-            cli.log.error('You must supply a configurator export or both `--keyboard` and `--keymap`.')
-            cli.echo('usage: qmk flash [-h] [-b] [-kb KEYBOARD] [-km KEYMAP] [-bl BOOTLOADER] [filename]')
-            return False
+        elif not cli.config.flash.keyboard:
+            cli.log.error('Could not determine keyboard!')
+        elif not cli.config.flash.keymap:
+            cli.log.error('Could not determine keymap!')
 
-    cli.log.info('Flashing keymap with {fg_cyan}%s\n\n', ' '.join(command))
-    subprocess.run(command)
+    # Compile the firmware, if we're able to
+    if command:
+        cli.log.info('Compiling keymap with {fg_cyan}%s', ' '.join(command))
+        if not cli.args.dry_run:
+            cli.echo('\n')
+            subprocess.run(command)
+
+    else:
+        cli.log.error('You must supply a configurator export, both `--keyboard` and `--keymap`, or be in a directory for a keyboard or keymap.')
+        cli.echo('usage: qmk flash [-h] [-b] [-n] [-kb KEYBOARD] [-km KEYMAP] [-bl BOOTLOADER] [filename]')
+        return False
diff --git a/lib/python/qmk/cli/list/keymaps.py b/lib/python/qmk/cli/list/keymaps.py
index d199d29bc3d4..cec9ca0224e9 100644
--- a/lib/python/qmk/cli/list/keymaps.py
+++ b/lib/python/qmk/cli/list/keymaps.py
@@ -1,12 +1,15 @@
 """List the keymaps for a specific keyboard
 """
 from milc import cli
+
 import qmk.keymap
+from qmk.decorators import automagic_keyboard
 from qmk.errors import NoSuchKeyboardError
 
 
 @cli.argument("-kb", "--keyboard", help="Specify keyboard name. Example: 1upkeyboards/1up60hse")
 @cli.subcommand("List the keymaps for a specific keyboard")
+@automagic_keyboard
 def list_keymaps(cli):
     """List the keymaps for a specific keyboard
     """
diff --git a/lib/python/qmk/cli/new/keymap.py b/lib/python/qmk/cli/new/keymap.py
index cbe50692ec0b..5ae262856594 100755
--- a/lib/python/qmk/cli/new/keymap.py
+++ b/lib/python/qmk/cli/new/keymap.py
@@ -4,12 +4,15 @@
 from pathlib import Path
 
 import qmk.path
+from qmk.decorators import automagic_keyboard, automagic_keymap
 from milc import cli
 
 
 @cli.argument('-kb', '--keyboard', help='Specify keyboard name. Example: 1upkeyboards/1up60hse')
 @cli.argument('-km', '--keymap', help='Specify the name for the new keymap directory')
 @cli.subcommand('Creates a new keymap for the keyboard of your choosing')
+@automagic_keyboard
+@automagic_keymap
 def new_keymap(cli):
     """Creates a new keymap for the keyboard of your choosing.
     """
diff --git a/lib/python/qmk/commands.py b/lib/python/qmk/commands.py
index cdb8ee037ad2..3d4ed1616364 100644
--- a/lib/python/qmk/commands.py
+++ b/lib/python/qmk/commands.py
@@ -1,12 +1,8 @@
 """Helper functions for commands.
 """
 import json
-from pathlib import Path
-
-from milc import cli
 
 import qmk.keymap
-from qmk.path import is_keyboard, is_keymap_dir, under_qmk_firmware
 
 
 def create_make_command(keyboard, keymap, target=None):
@@ -59,71 +55,6 @@ def compile_configurator_json(user_keymap, bootloader=None):
     return create_make_command(user_keymap['keyboard'], user_keymap['keymap'], bootloader)
 
 
-def find_keyboard_keymap():
-    """Returns `(keyboard_name, keymap_name)` based on the user's current environment.
-
-    This determines the keyboard and keymap name using the following precedence order:
-
-        * Command line flags (--keyboard and --keymap)
-        * Current working directory
-            * `keyboards/<keyboard_name>`
-            * `keyboards/<keyboard_name>/keymaps/<keymap_name>`
-            * `layouts/**/<keymap_name>`
-            * `users/<keymap_name>`
-        * Configuration
-            * cli.config.<subcommand>.keyboard
-            * cli.config.<subcommand>.keymap
-    """
-    # Check to make sure their copy of MILC supports config_source
-    if not hasattr(cli, 'config_source'):
-        cli.log.error("Your QMK CLI is out of date. Please upgrade using pip3 or your package manager.")
-        exit(1)
-
-    # State variables
-    relative_cwd = under_qmk_firmware()
-    keyboard_name = ""
-    keymap_name = ""
-
-    # If the keyboard or keymap are passed as arguments use that in preference to anything else
-    if cli.config_source[cli._entrypoint.__name__]['keyboard'] == 'argument':
-        keyboard_name = cli.config[cli._entrypoint.__name__]['keyboard']
-    if cli.config_source[cli._entrypoint.__name__]['keymap'] == 'argument':
-        keymap_name = cli.config[cli._entrypoint.__name__]['keymap']
-
-    if not keyboard_name or not keymap_name:
-        # If we don't have a keyboard_name and keymap_name from arguments try to derive one or both
-        if relative_cwd and relative_cwd.parts and relative_cwd.parts[0] == 'keyboards':
-            # Try to determine the keyboard and/or keymap name
-            current_path = Path('/'.join(relative_cwd.parts[1:]))
-
-            if current_path.parts[-2] == 'keymaps':
-                if not keymap_name:
-                    keymap_name = current_path.parts[-1]
-                if not keyboard_name:
-                    keyboard_name = '/'.join(current_path.parts[:-2])
-            elif not keyboard_name and is_keyboard(current_path):
-                keyboard_name = str(current_path)
-
-        elif relative_cwd and relative_cwd.parts and relative_cwd.parts[0] == 'layouts':
-            # Try to determine the keymap name from the community layout
-            if is_keymap_dir(relative_cwd) and not keymap_name:
-                keymap_name = relative_cwd.name
-
-        elif relative_cwd and relative_cwd.parts and relative_cwd.parts[0] == 'users':
-            # Try to determine the keymap name based on which userspace they're in
-            if not keymap_name and len(relative_cwd.parts) > 1:
-                keymap_name = relative_cwd.parts[1]
-
-    # If we still don't have a keyboard and keymap check the config
-    if not keyboard_name and cli.config[cli._entrypoint.__name__]['keyboard']:
-        keyboard_name = cli.config[cli._entrypoint.__name__]['keyboard']
-
-    if not keymap_name and cli.config[cli._entrypoint.__name__]['keymap']:
-        keymap_name = cli.config[cli._entrypoint.__name__]['keymap']
-
-    return (keyboard_name, keymap_name)
-
-
 def parse_configurator_json(configurator_file):
     """Open and parse a configurator json export
     """
diff --git a/lib/python/qmk/decorators.py b/lib/python/qmk/decorators.py
new file mode 100644
index 000000000000..94e14bf375a0
--- /dev/null
+++ b/lib/python/qmk/decorators.py
@@ -0,0 +1,85 @@
+"""Helpful decorators that subcommands can use.
+"""
+import functools
+from pathlib import Path
+
+from milc import cli
+
+from qmk.path import is_keyboard, is_keymap_dir, under_qmk_firmware
+
+
+def automagic_keyboard(func):
+    """Sets `cli.config.<subcommand>.keyboard` based on environment.
+
+    This will rewrite cli.config.<subcommand>.keyboard if the user did not pass `--keyboard` and the directory they are currently in is a keyboard or keymap directory.
+    """
+    @functools.wraps(func)
+    def wrapper(*args, **kwargs):
+        # Check to make sure their copy of MILC supports config_source
+        if not hasattr(cli, 'config_source'):
+            cli.log.error("This subcommand requires a newer version of the QMK CLI. Please upgrade using `pip3 install --upgrade qmk` or your package manager.")
+            exit(1)
+
+        # Ensure that `--keyboard` was not passed and CWD is under `qmk_firmware/keyboards`
+        if cli.config_source[cli._entrypoint.__name__]['keyboard'] != 'argument':
+            relative_cwd = under_qmk_firmware()
+
+            if relative_cwd and len(relative_cwd.parts) > 1 and relative_cwd.parts[0] == 'keyboards':
+                # Attempt to extract the keyboard name from the current directory
+                current_path = Path('/'.join(relative_cwd.parts[1:]))
+
+                if 'keymaps' in current_path.parts:
+                    # Strip current_path of anything after `keymaps`
+                    keymap_index = len(current_path.parts) - current_path.parts.index('keymaps') - 1
+                    current_path = current_path.parents[keymap_index]
+
+                if is_keyboard(current_path):
+                    cli.config[cli._entrypoint.__name__]['keyboard'] = str(current_path)
+                    cli.config_source[cli._entrypoint.__name__]['keyboard'] = 'keyboard_directory'
+
+        return func(*args, **kwargs)
+
+    return wrapper
+
+
+def automagic_keymap(func):
+    """Sets `cli.config.<subcommand>.keymap` based on environment.
+
+    This will rewrite cli.config.<subcommand>.keymap if the user did not pass `--keymap` and the directory they are currently in is a keymap, layout, or user directory.
+    """
+    @functools.wraps(func)
+    def wrapper(*args, **kwargs):
+        # Check to make sure their copy of MILC supports config_source
+        if not hasattr(cli, 'config_source'):
+            cli.log.error("This subcommand requires a newer version of the QMK CLI. Please upgrade using `pip3 install --upgrade qmk` or your package manager.")
+            exit(1)
+
+        # Ensure that `--keymap` was not passed and that we're under `qmk_firmware`
+        if cli.config_source[cli._entrypoint.__name__]['keymap'] != 'argument':
+            relative_cwd = under_qmk_firmware()
+
+            if relative_cwd and len(relative_cwd.parts) > 1:
+                # If we're in `qmk_firmware/keyboards` and `keymaps` is in our path, try to find the keyboard name.
+                if relative_cwd.parts[0] == 'keyboards' and 'keymaps' in relative_cwd.parts:
+                    current_path = Path('/'.join(relative_cwd.parts[1:]))  # Strip 'keyboards' from the front
+
+                    if 'keymaps' in current_path.parts and current_path.name != 'keymaps':
+                        while current_path.parent.name != 'keymaps':
+                            current_path = current_path.parent
+                        cli.config[cli._entrypoint.__name__]['keymap'] = current_path.name
+                        cli.config_source[cli._entrypoint.__name__]['keyboard'] = 'keymap_directory'
+
+                # If we're in `qmk_firmware/layouts` guess the name from the community keymap they're in
+                elif relative_cwd.parts[0] == 'layouts' and is_keymap_dir(relative_cwd):
+                    cli.config[cli._entrypoint.__name__]['keymap'] = relative_cwd.name
+                    cli.config_source[cli._entrypoint.__name__]['keyboard'] = 'layouts_directory'
+
+                # If we're in `qmk_firmware/users` guess the name from the userspace they're in
+                elif relative_cwd.parts[0] == 'users':
+                    # Guess the keymap name based on which userspace they're in
+                    cli.config[cli._entrypoint.__name__]['keymap'] = relative_cwd.parts[1]
+                    cli.config_source[cli._entrypoint.__name__]['keyboard'] = 'users_directory'
+
+        return func(*args, **kwargs)
+
+    return wrapper
diff --git a/lib/python/qmk/path.py b/lib/python/qmk/path.py
index bfaa439249d3..7306c433b86e 100644
--- a/lib/python/qmk/path.py
+++ b/lib/python/qmk/path.py
@@ -65,7 +65,7 @@ def normpath(path):
     path = Path(path)
 
     if path.is_absolute():
-        return Path(path)
+        return path
 
     return Path(os.environ['ORIG_CWD']) / path