diff --git a/{{cookiecutter.project_slug}}/compose/production/django/entrypoint b/{{cookiecutter.project_slug}}/compose/production/django/entrypoint
index 95ab8297a..2fbcad955 100644
--- a/{{cookiecutter.project_slug}}/compose/production/django/entrypoint
+++ b/{{cookiecutter.project_slug}}/compose/production/django/entrypoint
@@ -16,30 +16,34 @@ if [ -z "${POSTGRES_USER}" ]; then
 fi
 export DATABASE_URL="postgres://${POSTGRES_USER}:${POSTGRES_PASSWORD}@${POSTGRES_HOST}:${POSTGRES_PORT}/${POSTGRES_DB}"
 
-postgres_ready() {
 python << END
 import sys
+import time
 
 import psycopg2
 
-try:
-    psycopg2.connect(
-        dbname="${POSTGRES_DB}",
-        user="${POSTGRES_USER}",
-        password="${POSTGRES_PASSWORD}",
-        host="${POSTGRES_HOST}",
-        port="${POSTGRES_PORT}",
-    )
-except psycopg2.OperationalError:
-    sys.exit(-1)
-sys.exit(0)
+suggest_unrecoverable_after = 30
+start = time.time()
 
+while True:
+    try:
+        psycopg2.connect(
+            dbname="${POSTGRES_DB}",
+            user="${POSTGRES_USER}",
+            password="${POSTGRES_PASSWORD}",
+            host="${POSTGRES_HOST}",
+            port="${POSTGRES_PORT}",
+        )
+        break
+    except psycopg2.OperationalError as error:
+        sys.stderr.write("Waiting for PostgreSQL to become available...\n")
+
+        if time.time() - start > suggest_unrecoverable_after:
+            sys.stderr.write("  This is taking longer than expected. The following exception may be indicative of an unrecoverable error: '{}'\n".format(error))
+
+    time.sleep(1)
 END
-}
-until postgres_ready; do
-  >&2 echo 'Waiting for PostgreSQL to become available...'
-  sleep 1
-done
+
 >&2 echo 'PostgreSQL is available'
 
 exec "$@"