diff --git a/deployment/docker_compose/docker-compose.dev.yml b/deployment/docker_compose/docker-compose.dev.yml
index dba1e972a..046725846 100644
--- a/deployment/docker_compose/docker-compose.dev.yml
+++ b/deployment/docker_compose/docker-compose.dev.yml
@@ -94,6 +94,8 @@ services:
   nginx:
     image: nginx:1.23.4-alpine
     restart: always
+    # nginx will immediately crash with `nginx: [emerg] host not found in upstream`
+    # if api_server / web_server are not up 
     depends_on:
       - api_server
       - web_server
diff --git a/deployment/docker_compose/docker-compose.prod.yml b/deployment/docker_compose/docker-compose.prod.yml
index 8e33fddd7..7fab3bd70 100644
--- a/deployment/docker_compose/docker-compose.prod.yml
+++ b/deployment/docker_compose/docker-compose.prod.yml
@@ -84,6 +84,11 @@ services:
   nginx:
     image: nginx:1.23.4-alpine
     restart: always
+    # nginx will immediately crash with `nginx: [emerg] host not found in upstream`
+    # if api_server / web_server are not up 
+    depends_on:
+      - api_server
+      - web_server
     ports:
       - "80:80"
       - "443:443"
diff --git a/deployment/docker_compose/init-letsencrypt.sh b/deployment/docker_compose/init-letsencrypt.sh
index 6db73122e..c58e1230f 100755
--- a/deployment/docker_compose/init-letsencrypt.sh
+++ b/deployment/docker_compose/init-letsencrypt.sh
@@ -36,7 +36,7 @@ fi
 echo "### Creating dummy certificate for $domains ..."
 path="/etc/letsencrypt/live/$domains"
 mkdir -p "$data_path/conf/live/$domains"
-docker compose -f docker-compose.prod.yml run --rm --entrypoint "\
+docker compose -f docker-compose.prod.yml run  --name danswer-stack --rm --entrypoint "\
   openssl req -x509 -nodes -newkey rsa:$rsa_key_size -days 1\
     -keyout '$path/privkey.pem' \
     -out '$path/fullchain.pem' \
@@ -45,11 +45,11 @@ echo
 
 
 echo "### Starting nginx ..."
-docker compose -f docker-compose.prod.yml up --force-recreate -d nginx
+docker compose -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx
 echo
 
 echo "### Deleting dummy certificate for $domains ..."
-docker compose -f docker-compose.prod.yml run --rm --entrypoint "\
+docker compose -f docker-compose.prod.yml run  --name danswer-stack --rm --entrypoint "\
   rm -Rf /etc/letsencrypt/live/$domains && \
   rm -Rf /etc/letsencrypt/archive/$domains && \
   rm -Rf /etc/letsencrypt/renewal/$domains.conf" certbot
@@ -72,7 +72,7 @@ esac
 # Enable staging mode if needed
 if [ $staging != "0" ]; then staging_arg="--staging"; fi
 
-docker compose -f docker-compose.prod.yml run --rm --entrypoint "\
+docker compose -f docker-compose.prod.yml run --name danswer-stack --rm --entrypoint "\
   certbot certonly --webroot -w /var/www/certbot \
     $staging_arg \
     $email_arg \
@@ -83,4 +83,4 @@ docker compose -f docker-compose.prod.yml run --rm --entrypoint "\
 echo
 
 echo "### Reloading nginx ..."
-docker compose -f docker-compose.prod.yml exec nginx nginx -s reload
+docker compose -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx