diff --git a/authentik/root/settings.py b/authentik/root/settings.py
index 99d0b0f6f..df2e0dc33 100644
--- a/authentik/root/settings.py
+++ b/authentik/root/settings.py
@@ -265,6 +265,8 @@ DATABASES = {
         "USER": CONFIG.y("postgresql.user"),
         "PASSWORD": CONFIG.y("postgresql.password"),
         "PORT": int(CONFIG.y("postgresql.port")),
+        "CONN_MAX_AGE": 300,
+        "ATOMIC_REQUESTS": True,
     }
 }
 
diff --git a/tests/e2e/test_provider_proxy.py b/tests/e2e/test_provider_proxy.py
index 6a8ad3651..3f00ee88e 100644
--- a/tests/e2e/test_provider_proxy.py
+++ b/tests/e2e/test_provider_proxy.py
@@ -32,6 +32,7 @@ class TestProviderProxy(SeleniumTestCase):
 
     def tearDown(self) -> None:
         super().tearDown()
+        self.output_container_logs(self.proxy_container)
         self.proxy_container.kill()
 
     def get_container_specs(self) -> Optional[dict[str, Any]]:
@@ -88,6 +89,16 @@ class TestProviderProxy(SeleniumTestCase):
 
         self.proxy_container = self.start_proxy(outpost)
 
+        # Wait until outpost healthcheck succeeds
+        healthcheck_retries = 0
+        while healthcheck_retries < 50:
+            if len(outpost.state) > 0:
+                state = outpost.state[0]
+                if state.last_seen:
+                    break
+            healthcheck_retries += 1
+            sleep(0.5)
+
         self.driver.get("http://localhost:4180")
         self.login()
         sleep(1)
diff --git a/tests/e2e/utils.py b/tests/e2e/utils.py
index 735dc4fde..20193d464 100644
--- a/tests/e2e/utils.py
+++ b/tests/e2e/utils.py
@@ -71,6 +71,14 @@ class SeleniumTestCase(StaticLiveServerTestCase):
             self.logger.info("Container failed healthcheck")
             sleep(1)
 
+    def output_container_logs(self, container: Optional[Container] = None):
+        """Output the container logs to our STDOUT"""
+        ct = container or self.container
+        self.logger.debug("--------container logs", container=ct.image.tags[0])
+        for log in ct.logs().decode().split("\n"):
+            self.logger.debug(log, container=ct.image.tags[0])
+        self.logger.debug("--------end container logs", container=ct.image.tags[0])
+
     def get_container_specs(self) -> Optional[dict[str, Any]]:
         """Optionally get container specs which will launched on setup, wait for the container to
         be healthy, and deleted again on tearDown"""
@@ -97,6 +105,7 @@ class SeleniumTestCase(StaticLiveServerTestCase):
             )
         self.logger.debug("--------end browser logs")
         if self.container:
+            self.output_container_logs()
             self.container.kill()
         self.driver.quit()
         super().tearDown()