diff --git a/bench/app.py b/bench/app.py
index bd69152cc..322afa54a 100755
--- a/bench/app.py
+++ b/bench/app.py
@@ -765,9 +765,9 @@ def pull_apps(apps=None, bench_path=".", reset=False):
 Here are your choices:
 
 1. Merge the {app} app manually with "git pull" / "git pull --rebase" and fix conflicts.
-1. Temporarily remove your changes with "git stash" or discard them completely
+2. Temporarily remove your changes with "git stash" or discard them completely
 	with "bench update --reset" or for individual repositries "git reset --hard"
-2. If your changes are helpful for others, send in a pull request via GitHub and
+3. If your changes are helpful for others, send in a pull request via GitHub and
 	wait for them to be merged in the core."""
 					)
 					sys.exit(1)
diff --git a/bench/commands/install.py b/bench/commands/install.py
index 31ad59b66..a0f1fd417 100644
--- a/bench/commands/install.py
+++ b/bench/commands/install.py
@@ -77,7 +77,7 @@ def install_nginx(user=None):
 		setup_sudoers(user)
 
 
-@click.command("virtualbox", help="Installs supervisor")
+@click.command("virtualbox", help="Installs virtualbox")
 def install_virtualbox():
 	run_playbook("vm_build.yml", tag="virtualbox")
 
diff --git a/bench/commands/setup.py b/bench/commands/setup.py
index 9b13c269a..e291f86ae 100755
--- a/bench/commands/setup.py
+++ b/bench/commands/setup.py
@@ -73,7 +73,9 @@ def setup_supervisor(user=None, yes=False, skip_redis=False, skip_supervisord=Fa
 		generate_supervisor_config,
 	)
 
-	which("supervisorctl", raise_err=True)
+	if which("supervisorctl") is None:
+		click.secho("Please install `supervisor` to proceed", fg="red")
+		sys.exit(1)
 
 	if not skip_supervisord and "Permission denied" in get_cmd_output(
 		"supervisorctl status"
diff --git a/bench/config/supervisor.py b/bench/config/supervisor.py
index 1055d3baa..0eb6a8485 100644
--- a/bench/config/supervisor.py
+++ b/bench/config/supervisor.py
@@ -59,6 +59,7 @@ def generate_supervisor_config(bench_path, user=None, yes=False, skip_redis=Fals
 			"skip_redis": skip_redis,
 			"workers": config.get("workers", {}),
 			"multi_queue_consumption": can_enable_multi_queue_consumption(bench_path),
+			"supervisor_startretries": 10,
 		}
 	)
 
diff --git a/bench/config/templates/nginx.conf b/bench/config/templates/nginx.conf
index 5cba57828..cd6a67014 100644
--- a/bench/config/templates/nginx.conf
+++ b/bench/config/templates/nginx.conf
@@ -58,6 +58,7 @@ server {
 
 	location /assets {
 		try_files $uri =404;
+		add_header Cache-Control "max-age=31536000";
 	}
 
 	location ~ ^/protected/(.*) {
diff --git a/bench/config/templates/supervisor.conf b/bench/config/templates/supervisor.conf
index 57fd85748..9303edb76 100644
--- a/bench/config/templates/supervisor.conf
+++ b/bench/config/templates/supervisor.conf
@@ -14,6 +14,7 @@ stopwaitsecs=40
 killasgroup=true
 user={{ user }}
 directory={{ sites_dir }}
+startretries={{ supervisor_startretries }}
 
 [program:{{ bench_name }}-frappe-schedule]
 command={{ bench_cmd }} schedule
@@ -24,6 +25,7 @@ stdout_logfile={{ bench_dir }}/logs/schedule.log
 stderr_logfile={{ bench_dir }}/logs/schedule.error.log
 user={{ user }}
 directory={{ bench_dir }}
+startretries={{ supervisor_startretries }}
 
 {% if not multi_queue_consumption %}
 [program:{{ bench_name }}-frappe-default-worker]
@@ -39,6 +41,7 @@ directory={{ bench_dir }}
 killasgroup=true
 numprocs={{ background_workers }}
 process_name=%(program_name)s-%(process_num)d
+startretries={{ supervisor_startretries }}
 {% endif %}
 
 [program:{{ bench_name }}-frappe-short-worker]
@@ -54,6 +57,7 @@ directory={{ bench_dir }}
 killasgroup=true
 numprocs={{ background_workers }}
 process_name=%(program_name)s-%(process_num)d
+startretries={{ supervisor_startretries }}
 
 [program:{{ bench_name }}-frappe-long-worker]
 command={{ bench_cmd }} worker --queue long{{',default,short' if multi_queue_consumption else ''}}
@@ -68,6 +72,7 @@ directory={{ bench_dir }}
 killasgroup=true
 numprocs={{ background_workers }}
 process_name=%(program_name)s-%(process_num)d
+startretries={{ supervisor_startretries }}
 
 {% for worker_name, worker_details in workers.items() %}
 [program:{{ bench_name }}-frappe-{{ worker_name }}-worker]
@@ -83,6 +88,7 @@ directory={{ bench_dir }}
 killasgroup=true
 numprocs={{ worker_details["background_workers"] or background_workers }}
 process_name=%(program_name)s-%(process_num)d
+startretries={{ supervisor_startretries }}
 {% endfor %}
 
 
@@ -96,6 +102,7 @@ stdout_logfile={{ bench_dir }}/logs/redis-cache.log
 stderr_logfile={{ bench_dir }}/logs/redis-cache.error.log
 user={{ user }}
 directory={{ sites_dir }}
+startretries={{ supervisor_startretries }}
 
 [program:{{ bench_name }}-redis-queue]
 command={{ redis_server }} {{ redis_queue_config }}
@@ -106,6 +113,7 @@ stdout_logfile={{ bench_dir }}/logs/redis-queue.log
 stderr_logfile={{ bench_dir }}/logs/redis-queue.error.log
 user={{ user }}
 directory={{ sites_dir }}
+startretries={{ supervisor_startretries }}
 {% endif %}
 
 {% if node %}
@@ -118,6 +126,7 @@ stdout_logfile={{ bench_dir }}/logs/node-socketio.log
 stderr_logfile={{ bench_dir }}/logs/node-socketio.error.log
 user={{ user }}
 directory={{ bench_dir }}
+startretries={{ supervisor_startretries }}
 {% endif %}
 
 [group:{{ bench_name }}-web]
diff --git a/bench/utils/bench.py b/bench/utils/bench.py
index 9f1daded7..c0b9a4308 100644
--- a/bench/utils/bench.py
+++ b/bench/utils/bench.py
@@ -313,22 +313,23 @@ def restart_supervisor_processes(bench_path=".", web_workers=False, _raise=False
 			supervisor_status = get_cmd_output("sudo supervisorctl status", cwd=bench_path)
 
 		if web_workers and f"{bench_name}-web:" in supervisor_status:
-			group = f"{bench_name}-web:\t"
+			groups = [f"{bench_name}-web:\t"]
 
 		elif f"{bench_name}-workers:" in supervisor_status:
-			group = f"{bench_name}-workers: {bench_name}-web:"
+			groups = [f"{bench_name}-web:", f"{bench_name}-workers:"]
 
 		# backward compatibility
 		elif f"{bench_name}-processes:" in supervisor_status:
-			group = f"{bench_name}-processes:"
+			groups = [f"{bench_name}-processes:"]
 
 		# backward compatibility
 		else:
-			group = "frappe:"
+			groups = ["frappe:"]
 
-		failure = bench.run(f"{sudo}supervisorctl restart {group}", _raise=_raise)
-		if failure:
-			log("restarting supervisor failed. Use `bench restart` to retry.", level=3)
+		for group in groups:
+			failure = bench.run(f"{sudo}supervisorctl restart {group}", _raise=_raise)
+			if failure:
+				log(f"restarting supervisor group `{group}` failed. Use `bench restart` to retry.", level=3)
 
 
 def restart_systemd_processes(bench_path=".", web_workers=False, _raise=True):