diff --git a/deployment/docker_compose/init-letsencrypt.sh b/deployment/docker_compose/init-letsencrypt.sh
index c58e1230f88..d821f28c071 100755
--- a/deployment/docker_compose/init-letsencrypt.sh
+++ b/deployment/docker_compose/init-letsencrypt.sh
@@ -6,10 +6,20 @@ set -o allexport
 source .env.nginx
 set +o allexport
 
-if ! docker compose --version >/dev/null 2>&1; then
-  echo 'Error: docker compose is not installed.' >&2
-  exit 1
-fi
+# Function to determine correct docker compose command
+docker_compose_cmd() {
+  if command -v docker-compose >/dev/null 2>&1; then
+    echo "docker-compose"
+  elif command -v docker compose >/dev/null 2>&1; then
+    echo "docker compose"
+  else
+    echo 'Error: docker-compose or docker compose is not installed.' >&2
+    exit 1
+  fi
+}
+
+# Assign appropriate Docker Compose command
+COMPOSE_CMD=$(docker_compose_cmd)
 
 domains=("$DOMAIN" "www.$DOMAIN")
 rsa_key_size=4096
@@ -36,7 +46,7 @@ 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  --name danswer-stack --rm --entrypoint "\
+$COMPOSE_CMD -f docker-compose.prod.yml run  --name danswer-stack --rm --entrypoint "\
   openssl req -x509 -nodes -newkey rsa:$rsa_key_size -days 1\
     -keyout '$path/privkey.pem' \
     -out '$path/fullchain.pem' \
@@ -45,11 +55,25 @@ echo
 
 
 echo "### Starting nginx ..."
-docker compose -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx
+$COMPOSE_CMD -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx
 echo
 
+echo "Waiting for nginx to be ready, this may take a minute..."
+while true; do
+  # Use curl to send a request and capture the HTTP status code
+  status_code=$(curl -o /dev/null -s -w "%{http_code}\n" "http://localhost/api/health")
+  
+  # Check if the status code is 200
+  if [ "$status_code" -eq 200 ]; then
+    break  # Exit the loop
+  else
+    echo "Nginx is not ready yet, retrying in 5 seconds..."
+    sleep 5  # Sleep for 5 seconds before retrying
+  fi
+done
+
 echo "### Deleting dummy certificate for $domains ..."
-docker compose -f docker-compose.prod.yml run  --name danswer-stack --rm --entrypoint "\
+$COMPOSE_CMD -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 +96,7 @@ esac
 # Enable staging mode if needed
 if [ $staging != "0" ]; then staging_arg="--staging"; fi
 
-docker compose -f docker-compose.prod.yml run --name danswer-stack --rm --entrypoint "\
+$COMPOSE_CMD -f docker-compose.prod.yml run --name danswer-stack --rm --entrypoint "\
   certbot certonly --webroot -w /var/www/certbot \
     $staging_arg \
     $email_arg \
@@ -83,4 +107,4 @@ docker compose -f docker-compose.prod.yml run --name danswer-stack --rm --entryp
 echo
 
 echo "### Reloading nginx ..."
-docker compose -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx
+$COMPOSE_CMD -f docker-compose.prod.yml -p danswer-stack up --force-recreate -d nginx