fix: prevent zeroed data in local trace message and ensure cleanup on all paths

- Read execution start time non-destructively before _finalize_backend_batch
    consumes it, so the server receives the real duration and the local
    fallback message also shows the correct value
  - Pass pre-captured events_count, duration_ms, and batch_id to
    _show_local_trace_message instead of reading from batch_manager
    (buffer cleared by send, duration consumed by finalize)
  - Extract _reset_batch_state to reset all singleton state (current_batch,
    event_buffer, trace_batch_id, is_current_batch_ephemeral,
    backend_initialized, batch_owner_type/id) and call it in every exit
    path: success, init failure, send failure, and exception handler

lib/crewai/src/crewai/agent/core.py

@@ -75,7 +75,6 @@ from crewai.utilities.agent_utils import (
 )
 from crewai.utilities.constants import TRAINED_AGENTS_DATA_FILE, TRAINING_DATA_FILE
 from crewai.utilities.converter import Converter, ConverterError
-from crewai.utilities.env import get_env_context
 from crewai.utilities.guardrail import process_guardrail
 from crewai.utilities.guardrail_types import GuardrailType
 from crewai.utilities.llm_utils import create_llm
@@ -365,7 +364,6 @@ class Agent(BaseAgent):
             ValueError: If the max execution time is not a positive integer.
             RuntimeError: If the agent execution fails for other reasons.
         """
-        get_env_context()
         # Only call handle_reasoning for legacy CrewAgentExecutor
         # For AgentExecutor, planning is handled in AgentExecutor.generate_plan()
         if self.executor_class is not AgentExecutor:

lib/crewai/src/crewai/crew.py

@@ -98,7 +98,6 @@ from crewai.types.streaming import CrewStreamingOutput
 from crewai.types.usage_metrics import UsageMetrics
 from crewai.utilities.constants import NOT_SPECIFIED, TRAINING_DATA_FILE
 from crewai.utilities.crew.models import CrewContext
-from crewai.utilities.env import get_env_context
 from crewai.utilities.evaluators.crew_evaluator_handler import CrewEvaluator
 from crewai.utilities.evaluators.task_evaluator import TaskEvaluator
 from crewai.utilities.file_handler import FileHandler
@@ -680,7 +679,6 @@ class Crew(FlowTrackable, BaseModel):
         Returns:
             CrewOutput or CrewStreamingOutput if streaming is enabled.
         """
-        get_env_context()
         if self.stream:
             enable_agent_streaming(self.agents)
             ctx = StreamingContext()

lib/crewai/src/crewai/events/event_listener.py

@@ -34,12 +34,6 @@ from crewai.events.types.crew_events import (
     CrewTrainFailedEvent,
     CrewTrainStartedEvent,
 )
-from crewai.events.types.env_events import (
-    CCEnvEvent,
-    CodexEnvEvent,
-    CursorEnvEvent,
-    DefaultEnvEvent,
-)
 from crewai.events.types.flow_events import (
     FlowCreatedEvent,
     FlowFinishedEvent,
@@ -149,23 +143,6 @@ class EventListener(BaseEventListener):
     # ----------- CREW EVENTS -----------
 
     def setup_listeners(self, crewai_event_bus: CrewAIEventsBus) -> None:
-
-        @crewai_event_bus.on(CCEnvEvent)
-        def on_cc_env(_: Any, event: CCEnvEvent) -> None:
-            self._telemetry.env_context_span(event.type)
-
-        @crewai_event_bus.on(CodexEnvEvent)
-        def on_codex_env(_: Any, event: CodexEnvEvent) -> None:
-            self._telemetry.env_context_span(event.type)
-
-        @crewai_event_bus.on(CursorEnvEvent)
-        def on_cursor_env(_: Any, event: CursorEnvEvent) -> None:
-            self._telemetry.env_context_span(event.type)
-
-        @crewai_event_bus.on(DefaultEnvEvent)
-        def on_default_env(_: Any, event: DefaultEnvEvent) -> None:
-            self._telemetry.env_context_span(event.type)
-
         @crewai_event_bus.on(CrewKickoffStartedEvent)
         def on_crew_started(source: Any, event: CrewKickoffStartedEvent) -> None:
             self.formatter.handle_crew_started(event.crew_name or "Crew", source.id)

lib/crewai/src/crewai/events/listeners/tracing/first_time_trace_handler.py

@@ -1,6 +1,7 @@
 import logging
 import uuid
 import webbrowser
+from datetime import datetime, timezone
 
 from rich.console import Console
 from rich.panel import Panel
@@ -100,20 +101,48 @@ class FirstTimeTraceHandler:
                     user_context=user_context,
                     execution_metadata=execution_metadata,
                     use_ephemeral=True,
+                    skip_context_check=True,
                 )
+
+                if not self.batch_manager.trace_batch_id:
+                    self._gracefully_fail("Backend batch creation failed, cannot send events.")
+                    self._reset_batch_state()
+                    return
+
                 self.batch_manager.backend_initialized = True
 
-            if self.batch_manager.event_buffer:
-                self.batch_manager._send_events_to_backend()
+            # Capture values before send/finalize consume them
+            events_count = len(self.batch_manager.event_buffer)
+            batch_id = self.batch_manager.trace_batch_id
+            # Read duration non-destructively — _finalize_backend_batch will consume it
+            start_time = self.batch_manager.execution_start_times.get("execution")
+            duration_ms = (
+                int((datetime.now(timezone.utc) - start_time).total_seconds() * 1000)
+                if start_time
+                else 0
+            )
 
-            self.batch_manager.finalize_batch()
+            if self.batch_manager.event_buffer:
+                send_status = self.batch_manager._send_events_to_backend()
+                if send_status == 500 and self.batch_manager.trace_batch_id:
+                    self.batch_manager.plus_api.mark_trace_batch_as_failed(
+                        self.batch_manager.trace_batch_id,
+                        "Error sending events to backend",
+                    )
+                    self._reset_batch_state()
+                    return
+
+            self.batch_manager._finalize_backend_batch(events_count)
             self.ephemeral_url = self.batch_manager.ephemeral_trace_url
 
             if not self.ephemeral_url:
-                self._show_local_trace_message()
+                self._show_local_trace_message(events_count, duration_ms, batch_id)
+
+            self._reset_batch_state()
 
         except Exception as e:
             self._gracefully_fail(f"Backend initialization failed: {e}")
+            self._reset_batch_state()
 
     def _display_ephemeral_trace_link(self):
         """Display the ephemeral trace link to the user and automatically open browser."""
@@ -184,6 +213,19 @@ To enable tracing later, do any one of these:
         console.print(panel)
         console.print()
 
+    def _reset_batch_state(self):
+        """Reset batch manager state to allow future executions to re-initialize."""
+        if not self.batch_manager:
+            return
+        self.batch_manager.batch_owner_type = None
+        self.batch_manager.batch_owner_id = None
+        self.batch_manager.current_batch = None
+        self.batch_manager.event_buffer.clear()
+        self.batch_manager.trace_batch_id = None
+        self.batch_manager.is_current_batch_ephemeral = False
+        self.batch_manager.backend_initialized = False
+        self.batch_manager._cleanup_batch_data()
+
     def _gracefully_fail(self, error_message: str):
         """Handle errors gracefully without disrupting user experience."""
         console = Console()
@@ -191,7 +233,7 @@ To enable tracing later, do any one of these:
 
         logger.debug(f"First-time trace error: {error_message}")
 
-    def _show_local_trace_message(self):
+    def _show_local_trace_message(self, events_count: int = 0, duration_ms: int = 0, batch_id: str | None = None):
         """Show message when traces were collected locally but couldn't be uploaded."""
         console = Console()
 
@@ -199,9 +241,9 @@ To enable tracing later, do any one of these:
 📊 Your execution traces were collected locally!
 
 Unfortunately, we couldn't upload them to the server right now, but here's what we captured:
-• {len(self.batch_manager.event_buffer)} trace events
-• Execution duration: {self.batch_manager.calculate_duration("execution")}ms
-• Batch ID: {self.batch_manager.trace_batch_id}
+• {events_count} trace events
+• Execution duration: {duration_ms}ms
+• Batch ID: {batch_id}
 
 ✅ Tracing has been enabled for future runs!
 Your preference has been saved. Future Crew/Flow executions will automatically collect traces.

lib/crewai/src/crewai/events/listeners/tracing/trace_batch_manager.py

@@ -1,3 +1,4 @@
+import time
 from dataclasses import dataclass, field
 from datetime import datetime, timezone
 from logging import getLogger
@@ -108,10 +109,11 @@ class TraceBatchManager:
         user_context: dict[str, str],
         execution_metadata: dict[str, Any],
         use_ephemeral: bool = False,
+        skip_context_check: bool = False,
     ) -> None:
         """Send batch initialization to backend"""
 
-        if not is_tracing_enabled_in_context():
+        if not skip_context_check and not is_tracing_enabled_in_context():
             return
 
         if not self.plus_api or not self.current_batch:
@@ -142,19 +144,62 @@ class TraceBatchManager:
                 payload["ephemeral_trace_id"] = self.current_batch.batch_id
                 payload["user_identifier"] = get_user_id()
 
-            response = (
-                self.plus_api.initialize_ephemeral_trace_batch(payload)
-                if use_ephemeral
-                else self.plus_api.initialize_trace_batch(payload)
-            )
+            max_retries = 2
+            response = None
+            last_exception = None
+
+            for attempt in range(max_retries + 1):
+                try:
+                    response = (
+                        self.plus_api.initialize_ephemeral_trace_batch(payload)
+                        if use_ephemeral
+                        else self.plus_api.initialize_trace_batch(payload)
+                    )
+                    if response is not None and response.status_code < 500:
+                        break
+                    if attempt < max_retries:
+                        logger.debug(
+                            f"Trace batch init attempt {attempt + 1} failed "
+                            f"(status={response.status_code if response else 'None'}), retrying..."
+                        )
+                        time.sleep(0.2)
+                except Exception as e:
+                    last_exception = e
+                    if attempt < max_retries:
+                        logger.debug(
+                            f"Trace batch init attempt {attempt + 1} raised {type(e).__name__}, retrying..."
+                        )
+                        time.sleep(0.2)
+
+            if last_exception and response is None:
+                logger.warning(
+                    f"Error initializing trace batch: {last_exception}. Continuing without tracing."
+                )
+                self.trace_batch_id = None
+                return
 
             if response is None:
                 logger.warning(
                     "Trace batch initialization failed gracefully. Continuing without tracing."
                 )
+                self.trace_batch_id = None
                 return
 
+            # Fall back to ephemeral on auth failure (expired/revoked token)
+            if response.status_code in [401, 403] and not use_ephemeral:
+                logger.warning(
+                    "Auth rejected by server, falling back to ephemeral tracing."
+                )
+                self.is_current_batch_ephemeral = True
+                return self._initialize_backend_batch(
+                    user_context,
+                    execution_metadata,
+                    use_ephemeral=True,
+                    skip_context_check=skip_context_check,
+                )
+
             if response.status_code in [201, 200]:
+                self.is_current_batch_ephemeral = use_ephemeral
                 response_data = response.json()
                 self.trace_batch_id = (
                     response_data["trace_id"]
@@ -165,11 +210,13 @@ class TraceBatchManager:
                 logger.warning(
                     f"Trace batch initialization returned status {response.status_code}. Continuing without tracing."
                 )
+                self.trace_batch_id = None
 
         except Exception as e:
             logger.warning(
                 f"Error initializing trace batch: {e}. Continuing without tracing."
             )
+            self.trace_batch_id = None
 
     def begin_event_processing(self) -> None:
         """Mark that an event handler started processing (for synchronization)."""

lib/crewai/src/crewai/events/listeners/tracing/trace_listener.py

@@ -58,12 +58,6 @@ from crewai.events.types.crew_events import (
     CrewKickoffFailedEvent,
     CrewKickoffStartedEvent,
 )
-from crewai.events.types.env_events import (
-    CCEnvEvent,
-    CodexEnvEvent,
-    CursorEnvEvent,
-    DefaultEnvEvent,
-)
 from crewai.events.types.flow_events import (
     FlowCreatedEvent,
     FlowFinishedEvent,
@@ -198,7 +192,6 @@ class TraceCollectionListener(BaseEventListener):
         if self._listeners_setup:
             return
 
-        self._register_env_event_handlers(crewai_event_bus)
         self._register_flow_event_handlers(crewai_event_bus)
         self._register_context_event_handlers(crewai_event_bus)
         self._register_action_event_handlers(crewai_event_bus)
@@ -207,25 +200,6 @@ class TraceCollectionListener(BaseEventListener):
 
         self._listeners_setup = True
 
-    def _register_env_event_handlers(self, event_bus: CrewAIEventsBus) -> None:
-        """Register handlers for environment context events."""
-
-        @event_bus.on(CCEnvEvent)
-        def on_cc_env(source: Any, event: CCEnvEvent) -> None:
-            self._handle_action_event("cc_env", source, event)
-
-        @event_bus.on(CodexEnvEvent)
-        def on_codex_env(source: Any, event: CodexEnvEvent) -> None:
-            self._handle_action_event("codex_env", source, event)
-
-        @event_bus.on(CursorEnvEvent)
-        def on_cursor_env(source: Any, event: CursorEnvEvent) -> None:
-            self._handle_action_event("cursor_env", source, event)
-
-        @event_bus.on(DefaultEnvEvent)
-        def on_default_env(source: Any, event: DefaultEnvEvent) -> None:
-            self._handle_action_event("default_env", source, event)
-
     def _register_flow_event_handlers(self, event_bus: CrewAIEventsBus) -> None:
         """Register handlers for flow events."""
 

lib/crewai/src/crewai/events/types/env_events.py

@@ -1,36 +0,0 @@
-from typing import Annotated, Literal
-
-from pydantic import Field, TypeAdapter
-
-from crewai.events.base_events import BaseEvent
-
-
-class CCEnvEvent(BaseEvent):
-    type: Literal["cc_env"] = "cc_env"
-
-
-class CodexEnvEvent(BaseEvent):
-    type: Literal["codex_env"] = "codex_env"
-
-
-class CursorEnvEvent(BaseEvent):
-    type: Literal["cursor_env"] = "cursor_env"
-
-
-class DefaultEnvEvent(BaseEvent):
-    type: Literal["default_env"] = "default_env"
-
-
-EnvContextEvent = Annotated[
-    CCEnvEvent | CodexEnvEvent | CursorEnvEvent | DefaultEnvEvent,
-    Field(discriminator="type"),
-]
-
-env_context_event_adapter: TypeAdapter[EnvContextEvent] = TypeAdapter(EnvContextEvent)
-
-ENV_CONTEXT_EVENT_TYPES: tuple[type[BaseEvent], ...] = (
-    CCEnvEvent,
-    CodexEnvEvent,
-    CursorEnvEvent,
-    DefaultEnvEvent,
-)

lib/crewai/src/crewai/flow/flow.py

@@ -110,7 +110,6 @@ if TYPE_CHECKING:
 
 from crewai.flow.visualization import build_flow_structure, render_interactive
 from crewai.types.streaming import CrewStreamingOutput, FlowStreamingOutput
-from crewai.utilities.env import get_env_context
 from crewai.utilities.streaming import (
     TaskInfo,
     create_async_chunk_generator,
@@ -1771,7 +1770,6 @@ class Flow(Generic[T], metaclass=FlowMeta):
         Returns:
             The final output from the flow or FlowStreamingOutput if streaming.
         """
-        get_env_context()
         if self.stream:
             result_holder: list[Any] = []
             current_task_info: TaskInfo = {

lib/crewai/src/crewai/telemetry/telemetry.py

@@ -986,22 +986,6 @@ class Telemetry:
 
         self._safe_telemetry_operation(_operation)
 
-    def env_context_span(self, tool: str) -> None:
-        """Records the coding tool environment context."""
-
-        def _operation() -> None:
-            tracer = trace.get_tracer("crewai.telemetry")
-            span = tracer.start_span("Environment Context")
-            self._add_attribute(
-                span,
-                "crewai_version",
-                version("crewai"),
-            )
-            self._add_attribute(span, "tool", tool)
-            close_span(span)
-
-        self._safe_telemetry_operation(_operation)
-
     def human_feedback_span(
         self,
         event_type: str,

lib/crewai/src/crewai/utilities/constants.py

@@ -8,21 +8,6 @@ TRAINED_AGENTS_DATA_FILE: Final[str] = "trained_agents_data.pkl"
 KNOWLEDGE_DIRECTORY: Final[str] = "knowledge"
 MAX_FILE_NAME_LENGTH: Final[int] = 255
 EMITTER_COLOR: Final[PrinterColor] = "bold_blue"
-CC_ENV_VAR: Final[str] = "CLAUDECODE"
-CODEX_ENV_VARS: Final[tuple[str, ...]] = (
-    "CODEX_CI",
-    "CODEX_MANAGED_BY_NPM",
-    "CODEX_SANDBOX",
-    "CODEX_SANDBOX_NETWORK_DISABLED",
-    "CODEX_THREAD_ID",
-)
-CURSOR_ENV_VARS: Final[tuple[str, ...]] = (
-    "CURSOR_AGENT",
-    "CURSOR_EXTENSION_HOST_ROLE",
-    "CURSOR_SANDBOX",
-    "CURSOR_TRACE_ID",
-    "CURSOR_WORKSPACE_LABEL",
-)
 
 
 class _NotSpecified:

lib/crewai/src/crewai/utilities/env.py

@@ -1,39 +0,0 @@
-import contextvars
-import os
-
-from crewai.events.event_bus import crewai_event_bus
-from crewai.events.types.env_events import (
-    CCEnvEvent,
-    CodexEnvEvent,
-    CursorEnvEvent,
-    DefaultEnvEvent,
-)
-from crewai.utilities.constants import CC_ENV_VAR, CODEX_ENV_VARS, CURSOR_ENV_VARS
-
-
-_env_context_emitted: contextvars.ContextVar[bool] = contextvars.ContextVar(
-    "_env_context_emitted", default=False
-)
-
-
-def _is_codex_env() -> bool:
-    return any(os.environ.get(var) for var in CODEX_ENV_VARS)
-
-
-def _is_cursor_env() -> bool:
-    return any(os.environ.get(var) for var in CURSOR_ENV_VARS)
-
-
-def get_env_context() -> None:
-    if _env_context_emitted.get():
-        return
-    _env_context_emitted.set(True)
-
-    if os.environ.get(CC_ENV_VAR):
-        crewai_event_bus.emit(None, CCEnvEvent())
-    elif _is_codex_env():
-        crewai_event_bus.emit(None, CodexEnvEvent())
-    elif _is_cursor_env():
-        crewai_event_bus.emit(None, CursorEnvEvent())
-    else:
-        crewai_event_bus.emit(None, DefaultEnvEvent())

lib/crewai/tests/tracing/test_tracing.py

@@ -7,6 +7,7 @@ from crewai.events.listeners.tracing.first_time_trace_handler import (
     FirstTimeTraceHandler,
 )
 from crewai.events.listeners.tracing.trace_batch_manager import (
+    TraceBatch,
     TraceBatchManager,
 )
 from crewai.events.listeners.tracing.trace_listener import (
@@ -657,6 +658,16 @@ class TestTraceListenerSetup:
 
             trace_listener.first_time_handler.collected_events = True
 
+            mock_batch_response = MagicMock()
+            mock_batch_response.status_code = 201
+            mock_batch_response.json.return_value = {
+                "trace_id": "mock-trace-id",
+                "ephemeral_trace_id": "mock-ephemeral-trace-id",
+                "access_code": "TRACE-mock",
+            }
+            mock_events_response = MagicMock()
+            mock_events_response.status_code = 200
+
             with (
                 patch.object(
                     trace_listener.first_time_handler,
@@ -666,6 +677,40 @@ class TestTraceListenerSetup:
                 patch.object(
                     trace_listener.first_time_handler, "_display_ephemeral_trace_link"
                 ) as mock_display_link,
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "initialize_trace_batch",
+                    return_value=mock_batch_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "initialize_ephemeral_trace_batch",
+                    return_value=mock_batch_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "send_trace_events",
+                    return_value=mock_events_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "send_ephemeral_trace_events",
+                    return_value=mock_events_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "finalize_trace_batch",
+                    return_value=mock_events_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager.plus_api,
+                    "finalize_ephemeral_trace_batch",
+                    return_value=mock_events_response,
+                ),
+                patch.object(
+                    trace_listener.batch_manager,
+                    "_cleanup_batch_data",
+                ),
             ):
                 crew.kickoff()
                 wait_for_event_handlers()
@@ -918,3 +963,576 @@ class TestTraceListenerSetup:
                 mock_init.assert_called_once()
                 payload = mock_init.call_args[0][0]
                 assert "user_identifier" not in payload
+
+
+class TestTraceBatchIdClearedOnFailure:
+    """Tests: trace_batch_id is cleared when _initialize_backend_batch fails."""
+
+    def _make_batch_manager(self):
+        """Create a TraceBatchManager with a pre-set trace_batch_id (simulating first-time user)."""
+        with patch(
+            "crewai.events.listeners.tracing.trace_batch_manager.get_auth_token",
+            return_value="mock_token",
+        ):
+            bm = TraceBatchManager()
+        bm.current_batch = TraceBatch(
+            user_context={"privacy_level": "standard"},
+            execution_metadata={"execution_type": "crew", "crew_name": "test"},
+        )
+        bm.trace_batch_id = bm.current_batch.batch_id  # simulate line 96
+        bm.is_current_batch_ephemeral = True
+        return bm
+
+    def test_trace_batch_id_cleared_on_exception(self):
+        """trace_batch_id must be None when the API call raises an exception."""
+        bm = self._make_batch_manager()
+        assert bm.trace_batch_id is not None
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                side_effect=ConnectionError("network down"),
+            ),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id is None
+
+    def test_trace_batch_id_set_on_success(self):
+        """trace_batch_id must be set from the server response on success."""
+        bm = self._make_batch_manager()
+        server_id = "server-ephemeral-trace-id-999"
+
+        mock_response = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=mock_response,
+            ),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id == server_id
+
+    def test_send_events_skipped_when_trace_batch_id_none(self):
+        """_send_events_to_backend must return early when trace_batch_id is None."""
+        bm = self._make_batch_manager()
+        bm.trace_batch_id = None
+        bm.event_buffer = [MagicMock()]  # has events
+
+        with patch.object(
+            bm.plus_api, "send_ephemeral_trace_events"
+        ) as mock_send:
+            result = bm._send_events_to_backend()
+
+        assert result == 500
+        mock_send.assert_not_called()
+
+
+class TestInitializeBackendBatchRetry:
+    """Tests for retry logic in _initialize_backend_batch."""
+
+    def _make_batch_manager(self):
+        """Create a TraceBatchManager with a pre-set trace_batch_id."""
+        with patch(
+            "crewai.events.listeners.tracing.trace_batch_manager.get_auth_token",
+            return_value="mock_token",
+        ):
+            bm = TraceBatchManager()
+        bm.current_batch = TraceBatch(
+            user_context={"privacy_level": "standard"},
+            execution_metadata={"execution_type": "crew", "crew_name": "test"},
+        )
+        bm.trace_batch_id = bm.current_batch.batch_id
+        bm.is_current_batch_ephemeral = True
+        return bm
+
+    def test_retries_on_none_response_then_succeeds(self):
+        """Retries when API returns None, succeeds on second attempt."""
+        bm = self._make_batch_manager()
+        server_id = "server-id-after-retry"
+
+        success_response = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                side_effect=[None, success_response],
+            ) as mock_init,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep") as mock_sleep,
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id == server_id
+        assert mock_init.call_count == 2
+        mock_sleep.assert_called_once_with(0.2)
+
+    def test_retries_on_5xx_then_succeeds(self):
+        """Retries on 500 server error, succeeds on second attempt."""
+        bm = self._make_batch_manager()
+        server_id = "server-id-after-5xx"
+
+        error_response = MagicMock(status_code=500, text="Internal Server Error")
+        success_response = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                side_effect=[error_response, success_response],
+            ) as mock_init,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id == server_id
+        assert mock_init.call_count == 2
+
+    def test_retries_on_exception_then_succeeds(self):
+        """Retries on ConnectionError, succeeds on second attempt."""
+        bm = self._make_batch_manager()
+        server_id = "server-id-after-exception"
+
+        success_response = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                side_effect=[ConnectionError("network down"), success_response],
+            ) as mock_init,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id == server_id
+        assert mock_init.call_count == 2
+
+    def test_no_retry_on_4xx(self):
+        """Does NOT retry on 422 — client error is not transient."""
+        bm = self._make_batch_manager()
+
+        error_response = MagicMock(status_code=422, text="Unprocessable Entity")
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=error_response,
+            ) as mock_init,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep") as mock_sleep,
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id is None
+        assert mock_init.call_count == 1
+        mock_sleep.assert_not_called()
+
+    def test_exhausts_retries_then_clears_batch_id(self):
+        """After all retries fail, trace_batch_id is None."""
+        bm = self._make_batch_manager()
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=None,
+            ) as mock_init,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id is None
+        assert mock_init.call_count == 3  # initial + 2 retries
+
+
+class TestFirstTimeHandlerBackendInitGuard:
+    """Tests: backend_initialized gated on actual batch creation success."""
+
+    def _make_handler_with_manager(self):
+        """Create a FirstTimeTraceHandler wired to a TraceBatchManager."""
+        with patch(
+            "crewai.events.listeners.tracing.trace_batch_manager.get_auth_token",
+            return_value="mock_token",
+        ):
+            bm = TraceBatchManager()
+        bm.current_batch = TraceBatch(
+            user_context={"privacy_level": "standard"},
+            execution_metadata={"execution_type": "crew", "crew_name": "test"},
+        )
+        bm.trace_batch_id = bm.current_batch.batch_id
+        bm.is_current_batch_ephemeral = True
+
+        handler = FirstTimeTraceHandler()
+        handler.is_first_time = True
+        handler.collected_events = True
+        handler.batch_manager = bm
+        return handler, bm
+
+    def test_backend_initialized_true_on_success(self):
+        """Events are sent when batch creation succeeds, then state is cleaned up."""
+        handler, bm = self._make_handler_with_manager()
+        server_id = "server-id-abc"
+
+        mock_init_response = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+        mock_send_response = MagicMock(status_code=200)
+
+        trace_batch_id_during_send = None
+
+        def capture_send(*args, **kwargs):
+            nonlocal trace_batch_id_during_send
+            trace_batch_id_during_send = bm.trace_batch_id
+            return mock_send_response
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=mock_init_response,
+            ),
+            patch.object(
+                bm.plus_api,
+                "send_ephemeral_trace_events",
+                side_effect=capture_send,
+            ),
+            patch.object(bm, "_finalize_backend_batch"),
+        ):
+            bm.event_buffer = [MagicMock(to_dict=MagicMock(return_value={}))]
+            handler._initialize_backend_and_send_events()
+
+        # trace_batch_id was set correctly during send
+        assert trace_batch_id_during_send == server_id
+        # State cleaned up after completion (singleton reuse)
+        assert bm.backend_initialized is False
+        assert bm.trace_batch_id is None
+        assert bm.current_batch is None
+
+    def test_backend_initialized_false_on_failure(self):
+        """backend_initialized stays False and events are NOT sent when batch creation fails."""
+        handler, bm = self._make_handler_with_manager()
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=None,  # server call fails
+            ),
+            patch.object(bm, "_send_events_to_backend") as mock_send,
+            patch.object(bm, "_finalize_backend_batch") as mock_finalize,
+            patch.object(handler, "_gracefully_fail") as mock_fail,
+        ):
+            bm.event_buffer = [MagicMock()]
+            handler._initialize_backend_and_send_events()
+
+        assert bm.backend_initialized is False
+        assert bm.trace_batch_id is None
+        mock_send.assert_not_called()
+        mock_finalize.assert_not_called()
+        mock_fail.assert_called_once()
+
+    def test_backend_initialized_false_on_non_2xx(self):
+        """backend_initialized stays False when server returns non-2xx."""
+        handler, bm = self._make_handler_with_manager()
+
+        mock_response = MagicMock(status_code=500, text="Internal Server Error")
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=mock_response,
+            ),
+            patch.object(bm, "_send_events_to_backend") as mock_send,
+            patch.object(bm, "_finalize_backend_batch") as mock_finalize,
+            patch.object(handler, "_gracefully_fail") as mock_fail,
+        ):
+            bm.event_buffer = [MagicMock()]
+            handler._initialize_backend_and_send_events()
+
+        assert bm.backend_initialized is False
+        assert bm.trace_batch_id is None
+        mock_send.assert_not_called()
+        mock_finalize.assert_not_called()
+        mock_fail.assert_called_once()
+
+
+class TestFirstTimeHandlerAlwaysEphemeral:
+    """Tests that first-time handler always uses ephemeral with skip_context_check."""
+
+    def _make_handler_with_manager(self):
+        with patch(
+            "crewai.events.listeners.tracing.trace_batch_manager.get_auth_token",
+            return_value="mock_token",
+        ):
+            bm = TraceBatchManager()
+        bm.current_batch = TraceBatch(
+            user_context={"privacy_level": "standard"},
+            execution_metadata={"execution_type": "crew", "crew_name": "test"},
+        )
+        bm.trace_batch_id = bm.current_batch.batch_id
+        bm.is_current_batch_ephemeral = True
+
+        handler = FirstTimeTraceHandler()
+        handler.is_first_time = True
+        handler.collected_events = True
+        handler.batch_manager = bm
+        return handler, bm
+
+    def test_deferred_init_uses_ephemeral_and_skip_context_check(self):
+        """Deferred backend init always uses ephemeral=True and skip_context_check=True."""
+        handler, bm = self._make_handler_with_manager()
+
+        with (
+            patch.object(bm, "_initialize_backend_batch") as mock_init,
+            patch.object(bm, "_send_events_to_backend"),
+            patch.object(bm, "_finalize_backend_batch"),
+        ):
+            mock_init.side_effect = lambda **kwargs: None
+            bm.event_buffer = [MagicMock()]
+            handler._initialize_backend_and_send_events()
+
+            mock_init.assert_called_once()
+            assert mock_init.call_args.kwargs["use_ephemeral"] is True
+            assert mock_init.call_args.kwargs["skip_context_check"] is True
+
+
+class TestAuthFailbackToEphemeral:
+    """Tests for ephemeral fallback when server rejects auth (401/403)."""
+
+    def _make_batch_manager(self):
+        """Create a TraceBatchManager with a pre-set trace_batch_id."""
+        with patch(
+            "crewai.events.listeners.tracing.trace_batch_manager.get_auth_token",
+            return_value="mock_token",
+        ):
+            bm = TraceBatchManager()
+        bm.current_batch = TraceBatch(
+            user_context={"privacy_level": "standard"},
+            execution_metadata={"execution_type": "crew", "crew_name": "test"},
+        )
+        bm.trace_batch_id = bm.current_batch.batch_id
+        bm.is_current_batch_ephemeral = False  # authenticated path
+        return bm
+
+    def test_401_non_ephemeral_falls_back_to_ephemeral(self):
+        """A 401 on the non-ephemeral endpoint should retry as ephemeral."""
+        bm = self._make_batch_manager()
+        server_id = "ephemeral-fallback-id"
+
+        auth_rejected = MagicMock(status_code=401, text="Bad credentials")
+        ephemeral_success = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_trace_batch",
+                return_value=auth_rejected,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=ephemeral_success,
+            ) as mock_ephemeral,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=False,
+            )
+
+        assert bm.trace_batch_id == server_id
+        assert bm.is_current_batch_ephemeral is True
+        mock_ephemeral.assert_called_once()
+
+    def test_403_non_ephemeral_falls_back_to_ephemeral(self):
+        """A 403 on the non-ephemeral endpoint should also fall back."""
+        bm = self._make_batch_manager()
+        server_id = "ephemeral-fallback-403"
+
+        forbidden = MagicMock(status_code=403, text="Forbidden")
+        ephemeral_success = MagicMock(
+            status_code=201,
+            json=MagicMock(return_value={"ephemeral_trace_id": server_id}),
+        )
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_trace_batch",
+                return_value=forbidden,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=ephemeral_success,
+            ),
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=False,
+            )
+
+        assert bm.trace_batch_id == server_id
+        assert bm.is_current_batch_ephemeral is True
+
+    def test_401_on_ephemeral_does_not_recurse(self):
+        """A 401 on the ephemeral endpoint should NOT try to fall back again."""
+        bm = self._make_batch_manager()
+        bm.is_current_batch_ephemeral = True
+
+        auth_rejected = MagicMock(status_code=401, text="Bad credentials")
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=auth_rejected,
+            ) as mock_ephemeral,
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=True,
+            )
+
+        assert bm.trace_batch_id is None
+        # Called only once — no recursive fallback
+        mock_ephemeral.assert_called()
+
+    def test_401_fallback_ephemeral_also_fails(self):
+        """If ephemeral fallback also fails, trace_batch_id is cleared."""
+        bm = self._make_batch_manager()
+
+        auth_rejected = MagicMock(status_code=401, text="Bad credentials")
+        ephemeral_fail = MagicMock(status_code=422, text="Validation failed")
+
+        with (
+            patch(
+                "crewai.events.listeners.tracing.trace_batch_manager.is_tracing_enabled_in_context",
+                return_value=True,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_trace_batch",
+                return_value=auth_rejected,
+            ),
+            patch.object(
+                bm.plus_api,
+                "initialize_ephemeral_trace_batch",
+                return_value=ephemeral_fail,
+            ),
+            patch("crewai.events.listeners.tracing.trace_batch_manager.time.sleep"),
+        ):
+            bm._initialize_backend_batch(
+                user_context={"privacy_level": "standard"},
+                execution_metadata={"execution_type": "crew"},
+                use_ephemeral=False,
+            )
+
+        assert bm.trace_batch_id is None