diff --git a/frappe/__init__.py b/frappe/__init__.py
index 02b8d71e40..9b208f7c2d 100644
--- a/frappe/__init__.py
+++ b/frappe/__init__.py
@@ -10,9 +10,16 @@ be used to build database driven apps.
 
 Read the documentation: https://frappeframework.com/docs
 """
+import os, warnings
+
+_dev_server = os.environ.get('DEV_SERVER', False)
+
+if _dev_server:
+	warnings.simplefilter('always', DeprecationWarning)
+	warnings.simplefilter('always', PendingDeprecationWarning)
 
 from werkzeug.local import Local, release_local
-import os, sys, importlib, inspect, json, warnings
+import sys, importlib, inspect, json
 import typing
 from past.builtins import cmp
 import click
@@ -31,8 +38,6 @@ __title__ = "Frappe Framework"
 
 local = Local()
 controllers = {}
-warnings.simplefilter('always', DeprecationWarning)
-warnings.simplefilter('always', PendingDeprecationWarning)
 
 class _dict(dict):
 	"""dict like object that exposes keys as attributes"""
@@ -197,7 +202,7 @@ def init(site, sites_path=None, new_site=False):
 	local.meta_cache = {}
 	local.form_dict = _dict()
 	local.session = _dict()
-	local.dev_server = os.environ.get('DEV_SERVER', False)
+	local.dev_server = _dev_server
 
 	setup_module_map()
 
diff --git a/frappe/build.py b/frappe/build.py
index d710cd04f6..c970ae3a28 100644
--- a/frappe/build.py
+++ b/frappe/build.py
@@ -317,13 +317,20 @@ def clear_broken_symlinks():
 
 
 
-def unstrip(message):
+def unstrip(message: str) -> str:
+	"""Pads input string on the right side until the last available column in the terminal
+	"""
+	_len = len(message)
 	try:
 		max_str = os.get_terminal_size().columns
 	except Exception:
 		max_str = 80
-	_len = len(message)
-	_rem = max_str - _len
+
+	if _len < max_str:
+		_rem = max_str - _len
+	else:
+		_rem = max_str % _len
+
 	return f"{message}{' ' * _rem}"
 
 
@@ -336,6 +343,7 @@ def make_asset_dirs(hard_link=False):
 		start_message = unstrip(f"{'Copying assets from' if hard_link else 'Linking'} {source} to {target}")
 		fail_message = unstrip(f"Cannot {'copy' if hard_link else 'link'} {source} to {target}")
 
+		# Used '\r' instead of '\x1b[1K\r' to print entire lines in smaller terminal sizes
 		try:
 			print(start_message, end="\r")
 			link_assets_dir(source, target, hard_link=hard_link)
diff --git a/frappe/commands/utils.py b/frappe/commands/utils.py
index 2fff120852..4da0f6bb78 100644
--- a/frappe/commands/utils.py
+++ b/frappe/commands/utils.py
@@ -507,8 +507,6 @@ frappe.db.connect()
 @pass_context
 def console(context):
 	"Start ipython console for a site"
-	import warnings
-
 	site = get_site(context)
 	frappe.init(site=site)
 	frappe.connect()
@@ -529,7 +527,6 @@ def console(context):
 	if failed_to_import:
 		print("\nFailed to import:\n{}".format(", ".join(failed_to_import)))
 
-	warnings.simplefilter('ignore')
 	IPython.embed(display_banner="", header="", colors="neutral")
 
 
diff --git a/frappe/utils/bench_helper.py b/frappe/utils/bench_helper.py
index 633d867306..2fb0bda058 100644
--- a/frappe/utils/bench_helper.py
+++ b/frappe/utils/bench_helper.py
@@ -6,6 +6,7 @@ import json
 import importlib
 import frappe.utils
 import traceback
+import warnings
 
 click.disable_unicode_literals_warning = True
 
@@ -98,5 +99,6 @@ def get_apps():
 	return frappe.get_all_apps(with_internal_apps=False, sites_path='.')
 
 if __name__ == "__main__":
+	if not frappe._dev_server:
+		warnings.simplefilter('ignore')
 	main()
-
diff --git a/frappe/utils/safe_exec.py b/frappe/utils/safe_exec.py
index 6c1fa21685..643812b226 100644
--- a/frappe/utils/safe_exec.py
+++ b/frappe/utils/safe_exec.py
@@ -119,7 +119,7 @@ def get_safe_globals():
 		scrub=scrub,
 		guess_mimetype=mimetypes.guess_type,
 		html2text=html2text,
-		dev_server=1 if os.environ.get('DEV_SERVER', False) else 0,
+		dev_server=1 if frappe._dev_server else 0,
 		run_script=run_script
 	)