diff --git a/src/crewai/cli/plus_api.py b/src/crewai/cli/plus_api.py
index 2758c662a..c4d4422d2 100644
--- a/src/crewai/cli/plus_api.py
+++ b/src/crewai/cli/plus_api.py
@@ -119,12 +119,17 @@ class PlusAPI:
 
     def initialize_trace_batch(self, payload) -> requests.Response:
         return self._make_request(
-            "POST", f"{self.TRACING_RESOURCE}/batches", json=payload
+            "POST",
+            f"{self.TRACING_RESOURCE}/batches",
+            json=payload,
+            timeout=30,
         )
 
     def initialize_ephemeral_trace_batch(self, payload) -> requests.Response:
         return self._make_request(
-            "POST", f"{self.EPHEMERAL_TRACING_RESOURCE}/batches", json=payload
+            "POST",
+            f"{self.EPHEMERAL_TRACING_RESOURCE}/batches",
+            json=payload,
         )
 
     def send_trace_events(self, trace_batch_id: str, payload) -> requests.Response:
@@ -150,6 +155,7 @@ class PlusAPI:
             "PATCH",
             f"{self.TRACING_RESOURCE}/batches/{trace_batch_id}/finalize",
             json=payload,
+            timeout=30,
         )
 
     def finalize_ephemeral_trace_batch(
@@ -159,4 +165,5 @@ class PlusAPI:
             "PATCH",
             f"{self.EPHEMERAL_TRACING_RESOURCE}/batches/{trace_batch_id}/finalize",
             json=payload,
+            timeout=30,
         )
diff --git a/src/crewai/cli/shared/token_manager.py b/src/crewai/cli/shared/token_manager.py
index 7f00ee61f..c0e69dc43 100644
--- a/src/crewai/cli/shared/token_manager.py
+++ b/src/crewai/cli/shared/token_manager.py
@@ -56,6 +56,8 @@ class TokenManager:
         :return: The access token if valid and not expired, otherwise None.
         """
         encrypted_data = self.read_secure_file(self.file_path)
+        if encrypted_data is None:
+            return None
 
         decrypted_data = self.fernet.decrypt(encrypted_data)  # type: ignore
         data = json.loads(decrypted_data)
diff --git a/src/crewai/utilities/events/listeners/tracing/trace_batch_manager.py b/src/crewai/utilities/events/listeners/tracing/trace_batch_manager.py
index b51784f4a..3fa38e84e 100644
--- a/src/crewai/utilities/events/listeners/tracing/trace_batch_manager.py
+++ b/src/crewai/utilities/events/listeners/tracing/trace_batch_manager.py
@@ -50,7 +50,9 @@ class TraceBatchManager:
 
     def __init__(self):
         try:
-            self.plus_api = PlusAPI(api_key=get_auth_token())
+            self.plus_api = PlusAPI(
+                api_key=get_auth_token(),
+            )
         except AuthError:
             self.plus_api = PlusAPI(api_key="")
 
@@ -114,7 +116,13 @@ class TraceBatchManager:
                 else self.plus_api.initialize_trace_batch(payload)
             )
 
-            if response.status_code == 201 or response.status_code == 200:
+            if response is None:
+                logger.warning(
+                    "Trace batch initialization failed gracefully. Continuing without tracing."
+                )
+                return
+
+            if response.status_code in [201, 200]:
                 response_data = response.json()
                 self.trace_batch_id = (
                     response_data["trace_id"]
@@ -129,19 +137,21 @@ class TraceBatchManager:
                 )
                 console.print(panel)
             else:
-                logger.error(
-                    f"❌ Failed to initialize trace batch: {response.status_code} - {response.text}"
+                logger.warning(
+                    f"Trace batch initialization returned status {response.status_code}. Continuing without tracing."
                 )
 
         except Exception as e:
-            logger.error(f"❌ Error initializing trace batch: {str(e)}")
+            logger.warning(
+                f"Error initializing trace batch: {str(e)}. Continuing without tracing."
+            )
 
     def add_event(self, trace_event: TraceEvent):
         """Add event to buffer"""
         self.event_buffer.append(trace_event)
 
     def _send_events_to_backend(self):
-        """Send buffered events to backend"""
+        """Send buffered events to backend with graceful failure handling"""
         if not self.plus_api or not self.trace_batch_id or not self.event_buffer:
             return
 
@@ -155,24 +165,27 @@ class TraceBatchManager:
                 },
             }
 
-            if not self.trace_batch_id:
-                raise Exception("❌ Trace batch ID not found")
-
             response = (
                 self.plus_api.send_ephemeral_trace_events(self.trace_batch_id, payload)
                 if self.is_current_batch_ephemeral
                 else self.plus_api.send_trace_events(self.trace_batch_id, payload)
             )
 
-            if response.status_code == 200 or response.status_code == 201:
+            if response is None:
+                logger.warning("Failed to send trace events. Events will be lost.")
+                return
+
+            if response.status_code in [200, 201]:
                 self.event_buffer.clear()
             else:
-                logger.error(
-                    f"❌ Failed to send events: {response.status_code} - {response.text}"
+                logger.warning(
+                    f"Failed to send events: {response.status_code}. Events will be lost."
                 )
 
         except Exception as e:
-            logger.error(f"❌ Error sending events to backend: {str(e)}")
+            logger.warning(
+                f"Error sending events to backend: {str(e)}. Events will be lost."
+            )
 
     def finalize_batch(self) -> Optional[TraceBatch]:
         """Finalize batch and return it for sending"""