diff --git a/authentik/root/settings.py b/authentik/root/settings.py
index fc17f16aa..23d569a38 100644
--- a/authentik/root/settings.py
+++ b/authentik/root/settings.py
@@ -18,7 +18,7 @@ from hashlib import sha512
 from json import dumps
 from tempfile import gettempdir
 from time import time
-from urllib.parse import quote
+from urllib.parse import quote_plus
 
 import structlog
 from celery.schedules import crontab
@@ -220,7 +220,7 @@ if CONFIG.y_bool("redis.tls", False):
     REDIS_CELERY_TLS_REQUIREMENTS = f"?ssl_cert_reqs={CONFIG.y('redis.tls_reqs')}"
 _redis_url = (
     f"{REDIS_PROTOCOL_PREFIX}:"
-    f"{quote(CONFIG.y('redis.password'))}@{quote(CONFIG.y('redis.host'))}:"
+    f"{quote_plus(CONFIG.y('redis.password'))}@{quote_plus(CONFIG.y('redis.host'))}:"
     f"{int(CONFIG.y('redis.port'))}"
 )
 
diff --git a/lifecycle/wait_for_db.py b/lifecycle/wait_for_db.py
index 86e3cb80b..7088f070f 100755
--- a/lifecycle/wait_for_db.py
+++ b/lifecycle/wait_for_db.py
@@ -26,6 +26,8 @@ def j_print(event: str, log_level: str = "info", **kwargs):
     print(dumps(data), file=stderr)
 
 
+j_print("Starting authentik bootstrap")
+
 # Sanity check, ensure SECRET_KEY is set before we even check for database connectivity
 if CONFIG.y("secret_key") is None or len(CONFIG.y("secret_key")) == 0:
     j_print("----------------------------------------------------------------------")
@@ -47,7 +49,9 @@ while True:
         break
     except OperationalError as exc:
         sleep(1)
-        j_print(f"PostgreSQL Connection failed, retrying... ({exc})")
+        j_print(f"PostgreSQL connection failed, retrying... ({exc})")
+    finally:
+        j_print("PostgreSQL connection successful")
 
 REDIS_PROTOCOL_PREFIX = "redis://"
 if CONFIG.y_bool("redis.tls", False):
@@ -65,3 +69,7 @@ while True:
     except RedisError as exc:
         sleep(1)
         j_print(f"Redis Connection failed, retrying... ({exc})", redis_url=REDIS_URL)
+    finally:
+        j_print("Redis Connection successful")
+
+j_print("Finished authentik bootstrap")