diff --git a/deployment/data/nginx/run-nginx.sh b/deployment/data/nginx/run-nginx.sh
new file mode 100755
index 000000000..12f64127c
--- /dev/null
+++ b/deployment/data/nginx/run-nginx.sh
@@ -0,0 +1,20 @@
+# fill in the template
+envsubst '$DOMAIN $SSL_CERT_FILE_NAME $SSL_CERT_KEY_FILE_NAME' < "/etc/nginx/conf.d/$1" > /etc/nginx/conf.d/app.conf
+
+# wait for the api_server to be ready
+while true; do
+  # Use curl to send a request and capture the HTTP status code
+  status_code=$(curl -o /dev/null -s -w "%{http_code}\n" "http://api_server:8080/health")
+  
+  # Check if the status code is 200
+  if [ "$status_code" -eq 200 ]; then
+    echo "API server responded with 200, starting nginx..."
+    break  # Exit the loop
+  else
+    echo "API server responded with $status_code, retrying in 5 seconds..."
+    sleep 5  # Sleep for 5 seconds before retrying
+  fi
+done
+
+# Start nginx and reload every 6 hours
+while :; do sleep 6h & wait; nginx -s reload; done & nginx -g "daemon off;"
diff --git a/deployment/docker_compose/docker-compose.dev.yml b/deployment/docker_compose/docker-compose.dev.yml
index c533b1246..5e3bf1e04 100644
--- a/deployment/docker_compose/docker-compose.dev.yml
+++ b/deployment/docker_compose/docker-compose.dev.yml
@@ -219,13 +219,10 @@ services:
       options:
         max-size: "50m"
         max-file: "6"
-    # sleep a little bit to allow the web_server / api_server to start up. 
+    # the specified script waits for the api_server to start up. 
     # Without this we've seen issues where nginx shows no error logs but 
     # does not recieve any traffic
-    command: > 
-      /bin/sh -c "sleep 10 &&
-        envsubst '$$\{DOMAIN\}' < /etc/nginx/conf.d/app.conf.template.dev > /etc/nginx/conf.d/app.conf &&
-        while :; do sleep 6h & wait $${!}; nginx -s reload; done & nginx -g \"daemon off;\""
+    command: "/bin/sh -c \"/etc/nginx/conf.d/run-nginx.sh app.conf.template.dev\""
   # Run with --profile model-server to bring up the danswer-model-server container
   # Be sure to change MODEL_SERVER_HOST (see above) as well
   # ie. MODEL_SERVER_HOST="model_server" docker compose -f docker-compose.dev.yml -p danswer-stack --profile model-server up -d --build
diff --git a/deployment/docker_compose/docker-compose.prod-no-letsencrypt.yml b/deployment/docker_compose/docker-compose.prod-no-letsencrypt.yml
index c98eed433..2dfdac889 100644
--- a/deployment/docker_compose/docker-compose.prod-no-letsencrypt.yml
+++ b/deployment/docker_compose/docker-compose.prod-no-letsencrypt.yml
@@ -117,18 +117,15 @@ services:
     volumes:
       - ../data/nginx:/etc/nginx/conf.d
       - ../data/sslcerts:/etc/nginx/sslcerts
-    # sleep a little bit to allow the web_server / api_server to start up. 
-    # Without this we've seen issues where nginx shows no error logs but 
-    # does not recieve any traffic
     logging:
       driver: json-file
       options:
         max-size: "50m"
         max-file: "6"
-    command: > 
-      /bin/sh -c "sleep 10 && 
-        envsubst '$$\{DOMAIN\} $$\{SSL_CERT_FILE_NAME\} $$\{SSL_CERT_KEY_FILE_NAME\}' < /etc/nginx/conf.d/app.conf.template.no-letsencrypt > /etc/nginx/conf.d/app.conf &&
-        while :; do sleep 6h & wait $${!}; nginx -s reload; done & nginx -g \"daemon off;\""
+    # the specified script waits for the api_server to start up. 
+    # Without this we've seen issues where nginx shows no error logs but 
+    # does not recieve any traffic
+    command: "/bin/sh -c \"/etc/nginx/conf.d/run-nginx.sh app.conf.template.no-letsencrypt\""
     env_file:
       - .env.nginx
   # Run with --profile model-server to bring up the danswer-model-server container
diff --git a/deployment/docker_compose/docker-compose.prod.yml b/deployment/docker_compose/docker-compose.prod.yml
index 2d9f3a099..0891c968c 100644
--- a/deployment/docker_compose/docker-compose.prod.yml
+++ b/deployment/docker_compose/docker-compose.prod.yml
@@ -126,10 +126,10 @@ services:
       options:
         max-size: "50m"
         max-file: "6"
-    command: > 
-      /bin/sh -c "sleep 10 &&
-        envsubst '$$\{DOMAIN\}' < /etc/nginx/conf.d/app.conf.template > /etc/nginx/conf.d/app.conf &&
-        while :; do sleep 6h & wait $${!}; nginx -s reload; done & nginx -g \"daemon off;\""
+    # the specified script waits for the api_server to start up. 
+    # Without this we've seen issues where nginx shows no error logs but 
+    # does not recieve any traffic  
+    command: "/bin/sh -c \"/etc/nginx/conf.d/run-nginx.sh app.conf.template\""
     env_file:
       - .env.nginx
   # follows https://pentacent.medium.com/nginx-and-lets-encrypt-with-docker-in-less-than-5-minutes-b4b8a60d3a71