diff --git a/src/canopy/knowledge_base/record_encoder/openai.py b/src/canopy/knowledge_base/record_encoder/openai.py
index 3a1ec728..ce18a3f8 100644
--- a/src/canopy/knowledge_base/record_encoder/openai.py
+++ b/src/canopy/knowledge_base/record_encoder/openai.py
@@ -23,6 +23,7 @@ def __init__(self,
         super().__init__(dense_encoder=encoder, batch_size=batch_size, **kwargs)
 
     @retry(
+        reraise=True,
         wait=wait_random_exponential(min=1, max=10),
         stop=stop_after_attempt(3),
         retry=retry_if_exception_type(OPEN_AI_TRANSIENT_EXCEPTIONS),
diff --git a/src/canopy/llm/openai.py b/src/canopy/llm/openai.py
index 812fc5e0..4cb3d43f 100644
--- a/src/canopy/llm/openai.py
+++ b/src/canopy/llm/openai.py
@@ -30,6 +30,7 @@ def available_models(self):
         return [k["id"] for k in openai.Model.list().data]
 
     @retry(
+        reraise=True,
         wait=wait_random_exponential(min=1, max=10),
         stop=stop_after_attempt(3),
         retry=retry_if_exception_type(OPEN_AI_TRANSIENT_EXCEPTIONS),
@@ -66,6 +67,7 @@ def streaming_iterator(response):
         return ChatResponse(**response)
 
     @retry(
+        reraise=True,
         wait=wait_random_exponential(min=1, max=10),
         stop=stop_after_attempt(3),
         retry=retry_if_exception_type(
diff --git a/src/canopy_cli/cli.py b/src/canopy_cli/cli.py
index b3ba714d..7fcf8757 100644
--- a/src/canopy_cli/cli.py
+++ b/src/canopy_cli/cli.py
@@ -64,7 +64,7 @@ def check_service_health(url: str):
         raise CLIError(msg)
 
 
-@retry(wait=wait_fixed(5), stop=stop_after_attempt(6))
+@retry(reraise=True, wait=wait_fixed(5), stop=stop_after_attempt(6))
 def wait_for_service(chat_service_url: str):
     check_service_health(chat_service_url)
 
@@ -193,7 +193,7 @@ def new(index_name: str, config: Optional[str]):
     help=(
         """
         \b
-        Upload local data files containing documents to the Canopy service.
+        Upload local data files to the Canopy service.
 
         Load all the documents from data file or a directory containing multiple data files.
         The allowed formats are .jsonl and .parquet.
@@ -297,6 +297,7 @@ def upsert(index_name: str,
                 raise CLIError(msg)
 
         pbar.update(len(batch))
+    pbar.close()
 
     if failed_docs:
         msg = (