diff --git a/frappe/commands/__init__.py b/frappe/commands/__init__.py
index 0080ac22f0..9d9f61cdd4 100644
--- a/frappe/commands/__init__.py
+++ b/frappe/commands/__init__.py
@@ -27,13 +27,12 @@ def pass_context(f):
 
 		try:
 			ret = f(frappe._dict(ctx.obj), *args, **kwargs)
-		except frappe.exceptions.SiteNotSpecifiedError as e:
-			click.secho(str(e), fg="yellow")
-			sys.exit(1)
-		except frappe.exceptions.IncorrectSitePath:
-			site = ctx.obj.get("sites", "")[0]
-			click.secho(f"Site {site} does not exist!", fg="yellow")
-			sys.exit(1)
+		except (
+			frappe.exceptions.SiteNotSpecifiedError,
+			frappe.exceptions.IncorrectSitePath,
+			frappe.exceptions.CommandFailedError,
+		) as e:
+			raise click.UsageError(e, ctx) from e
 
 		if profile:
 			pr.disable()
diff --git a/frappe/tests/utils.py b/frappe/tests/utils.py
index 84189c8046..1786b5d23a 100644
--- a/frappe/tests/utils.py
+++ b/frappe/tests/utils.py
@@ -68,29 +68,20 @@ def debug_on(*exceptions):
 				return f(*args, **kwargs)
 			except exceptions as e:
 				exc_type, exc_value, exc_traceback = sys.exc_info()
+				# Pretty print the exception
+				print("\n\033[91m" + "=" * 60 + "\033[0m")  # Red line
+				print("\033[93m" + str(exc_type.__name__) + ": " + str(exc_value) + "\033[0m")
+				print("\033[91m" + "=" * 60 + "\033[0m")  # Red line
 
-				traceback.print_exception(exc_type, exc_value, exc_traceback)
+				# Print the formatted traceback
+				traceback_lines = traceback.format_exception(exc_type, exc_value, exc_traceback)
+				for line in traceback_lines:
+					print("\033[96m" + line.rstrip() + "\033[0m")  # Cyan color
 
-				# Find the most relevant traceback frame
-				apps_path = frappe.get_app_path("frappe", "..", "..")
-
-				tb = exc_traceback.tb_next
-				target_frame = None
-
-				while tb:
-					if tb.tb_frame.f_code.co_filename.startswith(apps_path):
-						target_frame = tb
-						break
-					tb = tb.tb_next
-
-				if target_frame:
-					print(f"Starting debugger in: {target_frame.tb_frame.f_code.co_filename}:{tb.tb_lineno}")
-					p = pdb.Pdb()
-					p.reset()
-					p.interaction(target_frame.tb_frame, None)
-				else:
-					print("Could not find a suitable traceback frame, using the last frame.")
-					pdb.post_mortem(exc_traceback)
+				print("\033[91m" + "=" * 60 + "\033[0m")  # Red line
+				print("\033[92mEntering post-mortem debugging\033[0m")
+				print("\033[91m" + "=" * 60 + "\033[0m")  # Red line
+				pdb.post_mortem()
 
 				raise e
 
diff --git a/frappe/utils/bench_helper.py b/frappe/utils/bench_helper.py
index 6de374a2a2..bbcdb00e5d 100644
--- a/frappe/utils/bench_helper.py
+++ b/frappe/utils/bench_helper.py
@@ -1,6 +1,8 @@
 import importlib
 import json
+import linecache
 import os
+import sys
 import traceback
 import warnings
 from textwrap import dedent
@@ -13,25 +15,85 @@ import frappe.utils
 click.disable_unicode_literals_warning = True
 
 
-class FrappeCommandGroup(click.Group):
-	def get_command(self, ctx, cmd_name):
-		rv = super().get_command(ctx, cmd_name)
-		if rv is not None:
-			return rv
+def FrappeClickWrapper(cls, handler):
+	class Cls(cls):
+		# only implemented on groups
+		def get_command(self, ctx, cmd_name):
+			rv = super().get_command(ctx, cmd_name)
+			if rv is not None:
+				return rv
 
-		all_commands = self.list_commands(ctx)
-		from difflib import get_close_matches
+			all_commands = self.list_commands(ctx)
+			from difflib import get_close_matches
 
-		possibilities = get_close_matches(cmd_name, all_commands)
-		raise click.NoSuchOption(
-			cmd_name, possibilities=possibilities, message=f"No such command: {cmd_name}."
-		)
+			possibilities = get_close_matches(cmd_name, all_commands)
+			raise click.NoSuchOption(
+				cmd_name, possibilities=possibilities, message=f"No such command: {cmd_name}."
+			)
+
+		def make_context(self, info_name, args, parent=None, **extra):
+			try:
+				return super().make_context(info_name, args, parent=parent, **extra)
+			except click.ClickException as e:
+				raise e
+			except Exception as exc:
+				# call the handler
+				handler(self, info_name, exc)
+				sys.exit(1)
+
+		def invoke(self, ctx):
+			try:
+				return super().invoke(ctx)
+			except click.ClickException as e:
+				raise e
+			except Exception as exc:
+				# call the handler
+				handler(self, ctx.info_name, exc)
+				sys.exit(1)
+
+	return Cls
+
+
+def handle_exception(cmd, info_name, exc):
+	tb = sys.exc_info()[2]
+	while tb.tb_next:
+		tb = tb.tb_next
+	frame = tb.tb_frame
+	filename = frame.f_code.co_filename
+	lineno = frame.f_lineno
+
+	(
+		click.secho("\n:: ", nl=False),
+		click.secho(f"{exc}", fg="red", bold=True, nl=False),
+		click.secho(" ::"),
+	)
+	click.secho("\nContext:", fg="yellow", bold=True)
+	click.secho(f" File '{filename}', line {lineno}\n")
+	context_lines = 5
+	start = max(1, lineno - context_lines)
+	end = lineno + context_lines + 1
+
+	for i in range(start, end):
+		line = linecache.getline(filename, i).rstrip()
+		if i == lineno:
+			click.secho(f"{i:4d}> {line}", fg="red")
+		else:
+			click.echo(f"{i:4d}: {line}")
+
+	show_exception = (not sys.stdout.isatty()) or click.confirm(
+		"\nDo you want to see the full traceback?", default=False
+	)
+	if show_exception:
+		click.secho("\nFull traceback:", fg="red")
+		click.echo(traceback.format_exc())
+
+		click.echo(exc)
 
 
 def main():
 	commands = get_app_groups()
 	commands.update({"get-frappe-commands": get_frappe_commands, "get-frappe-help": get_frappe_help})
-	FrappeCommandGroup(commands=commands)(prog_name="bench")
+	FrappeClickWrapper(click.Group, handle_exception)(commands=commands)(prog_name="bench")
 
 
 def get_app_groups() -> dict[str, click.Group]:
@@ -41,12 +103,18 @@ def get_app_groups() -> dict[str, click.Group]:
 	for app in get_apps():
 		if app_commands := get_app_commands(app):
 			commands |= app_commands
-	return dict(frappe=click.group(name="frappe", commands=commands, cls=FrappeCommandGroup)(app_group))
+	return dict(
+		frappe=click.group(
+			name="frappe", commands=commands, cls=FrappeClickWrapper(click.Group, handle_exception)
+		)(app_group)
+	)
 
 
 def get_app_group(app: str) -> click.Group:
 	if app_commands := get_app_commands(app):
-		return click.group(name=app, commands=app_commands)(app_group)
+		return click.group(
+			name=app, commands=app_commands, cls=FrappeClickWrapper(click.Group, handle_exception)
+		)(app_group)
 
 
 @click.option("--site")
diff --git a/pyproject.toml b/pyproject.toml
index ef4ce7f7d9..6125a9f412 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -109,6 +109,7 @@ watchdog = "~=3.0.0"
 hypothesis = "~=6.77.0"
 responses = "==0.23.1"
 freezegun = "~=1.2.2"
+pdbpp = "~=0.10.3"
 
 [tool.ruff]
 line-length = 110