diff --git a/analytics/management/commands/update_analytics_counts.py b/analytics/management/commands/update_analytics_counts.py
index 541ebf07b5..01efeac32e 100644
--- a/analytics/management/commands/update_analytics_counts.py
+++ b/analytics/management/commands/update_analytics_counts.py
@@ -95,4 +95,4 @@ class Command(ZulipBaseCommand):
             logger.info("Sleeping %d seconds before reporting...", delay)
             time.sleep(delay)
 
-            send_server_data_to_push_bouncer(consider_usage_statistics=True)
+            send_server_data_to_push_bouncer(consider_usage_statistics=True, raise_on_error=True)
diff --git a/zerver/lib/remote_server.py b/zerver/lib/remote_server.py
index 7b5b4d62b7..e2a224e7fa 100644
--- a/zerver/lib/remote_server.py
+++ b/zerver/lib/remote_server.py
@@ -387,13 +387,17 @@ def should_send_analytics_data() -> bool:  # nocoverage
     return settings.ANALYTICS_DATA_UPLOAD_LEVEL > AnalyticsDataUploadLevel.NONE
 
 
-def send_server_data_to_push_bouncer(consider_usage_statistics: bool = True) -> None:
+def send_server_data_to_push_bouncer(
+    consider_usage_statistics: bool = True, raise_on_error: bool = False
+) -> None:
     logger = logging.getLogger("zulip.analytics")
     # first, check what's latest
     try:
         result = send_to_push_bouncer("GET", "server/analytics/status", {})
     except (JsonableError, orjson.JSONDecodeError) as e:
         maybe_mark_pushes_disabled(e, logger)
+        if raise_on_error:  # nocoverage
+            raise
         return
 
     # Gather only entries with IDs greater than the last ID received by the push bouncer.
@@ -452,6 +456,8 @@ def send_server_data_to_push_bouncer(consider_usage_statistics: bool = True) ->
             "POST", "server/analytics", request.model_dump(round_trip=True)
         )
     except (JsonableError, orjson.JSONDecodeError) as e:
+        if raise_on_error:  # nocoverage
+            raise
         maybe_mark_pushes_disabled(e, logger)
         return
 
diff --git a/zerver/management/commands/register_server.py b/zerver/management/commands/register_server.py
index 6d93868b27..5822c07a4d 100644
--- a/zerver/management/commands/register_server.py
+++ b/zerver/management/commands/register_server.py
@@ -134,7 +134,7 @@ that registration and saving the updated secret in
             "/api/v1/remotes/server/register", request
         )
 
-        send_server_data_to_push_bouncer(consider_usage_statistics=False)
+        send_server_data_to_push_bouncer(consider_usage_statistics=False, raise_on_error=True)
 
         if response.json()["created"]:
             print(