diff --git a/src/fortifyroot/_vendor/VENDOR_DEPENDENCIES.json b/src/fortifyroot/_vendor/VENDOR_DEPENDENCIES.json
index b9c0927..9654231 100644
--- a/src/fortifyroot/_vendor/VENDOR_DEPENDENCIES.json
+++ b/src/fortifyroot/_vendor/VENDOR_DEPENDENCIES.json
@@ -52,7 +52,7 @@
   },
   "test": {
     "anthropic": ">=0.25.2,<0.83.0",
-    "boto3": ">=1.35.49,<2",
+    "boto3": ">=1.34.120,<2",
     "chromadb": ">=0.5.23,<0.6.0",
     "google-genai": ">=1.58.0,<1.59.0",
     "langchain": ">=1.0.0,<2.0.0",
@@ -83,7 +83,7 @@
     "pytest": ">=8.2.2,<9",
     "pytest-asyncio": ">=0.23.7,<1.4.0",
     "pytest-recording": ">=0.13.1,<0.14.0",
-    "pytest-sugar": "==1.1.1",
+    "pytest-sugar": "==1.0.0",
     "requests": ">=2.31.0,<3",
     "sqlalchemy": ">=2.0.31,<3",
     "vcrpy": ">=8.0.0,<9"
diff --git a/src/fortifyroot/_vendor/VENDOR_MANIFEST.json b/src/fortifyroot/_vendor/VENDOR_MANIFEST.json
index 7f9cb46..47dba2a 100644
--- a/src/fortifyroot/_vendor/VENDOR_MANIFEST.json
+++ b/src/fortifyroot/_vendor/VENDOR_MANIFEST.json
@@ -1,9 +1,9 @@
 {
-  "vendored_at": "2026-06-19T15:31:31.520765",
+  "vendored_at": "2026-06-19T16:42:00.072255",
   "openllmetry_version": "0.52.6",
-  "git_commit": "c011bcf0077e",
+  "git_commit": "c42896177f36",
   "git_branch": "HEAD",
-  "git_tag": "fr-v0.52.6.26",
+  "git_tag": "fr-v0.52.6.27",
   "instrumentation_package_policy": {
     "opentelemetry-instrumentation-agno": false,
     "opentelemetry-instrumentation-alephalpha": false,
diff --git a/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/callback_handler.py b/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/callback_handler.py
index 11dc812..45e6eb9 100644
--- a/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/callback_handler.py
+++ b/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/callback_handler.py
@@ -74,6 +74,11 @@
 from opentelemetry.trace.status import Status, StatusCode
 from opentelemetry.semconv.attributes.error_attributes import ERROR_TYPE
 
+FR_STREAMING_TIME_TO_FIRST_TOKEN_MS = (
+    "fortifyroot.llm.streaming.time_to_first_token_ms"
+)
+FR_STREAMING_TIME_TO_GENERATE_MS = "fortifyroot.llm.streaming.time_to_generate_ms"
+
 
 def _extract_class_name_from_serialized(serialized: Optional[dict[str, Any]]) -> str:
     """
@@ -596,6 +601,38 @@ def on_llm_start(
         else:
             set_llm_request(span, serialized, prompts, kwargs, self.spans[run_id])
 
+    @dont_throw
+    def on_llm_new_token(
+        self,
+        token: str,
+        *,
+        run_id: UUID,
+        parent_run_id: Union[UUID, None] = None,
+        chunk: Union[GenerationChunk, ChatGenerationChunk, None] = None,
+        **kwargs: Any,
+    ) -> Any:
+        """Run when a streaming LLM emits a new token."""
+        if context_api.get_value(_SUPPRESS_INSTRUMENTATION_KEY):
+            return
+        if not token and chunk is None:
+            return
+        if run_id not in self.spans:
+            return
+
+        span_holder = self.spans[run_id]
+        if span_holder.streaming_first_token_time is not None:
+            return
+
+        first_token_time = time.time()
+        span_holder.streaming_first_token_time = first_token_time
+        span = span_holder.span
+        if span.is_recording():
+            _set_span_attribute(
+                span,
+                FR_STREAMING_TIME_TO_FIRST_TOKEN_MS,
+                round((first_token_time - span_holder.start_time) * 1000),
+            )
+
     @dont_throw
     def on_llm_end(
         self,
@@ -698,7 +735,15 @@ def on_llm_end(
             set_chat_response(span, response)
 
         # Record duration before ending span
-        duration = time.time() - self.spans[run_id].start_time
+        end_time = time.time()
+        streaming_first_token_time = self.spans[run_id].streaming_first_token_time
+        if streaming_first_token_time is not None and span.is_recording():
+            _set_span_attribute(
+                span,
+                FR_STREAMING_TIME_TO_GENERATE_MS,
+                round((end_time - streaming_first_token_time) * 1000),
+            )
+        duration = end_time - self.spans[run_id].start_time
         vendor = span.attributes.get(GenAIAttributes.GEN_AI_SYSTEM, "Langchain")
         self.duration_histogram.record(
             duration,
diff --git a/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/span_utils.py b/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/span_utils.py
index a308368..d05c95a 100644
--- a/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/span_utils.py
+++ b/src/fortifyroot/_vendor/opentelemetry/instrumentation/langchain/span_utils.py
@@ -40,6 +40,7 @@ class SpanHolder:
     entity_path: str
     start_time: float = field(default_factory=time.time)
     request_model: Optional[str] = None
+    streaming_first_token_time: Optional[float] = None
     # ST-10 review-round-2 fix (2026-05-11): every context_api.attach()
     # performed for this span — span-context, suppression, metadata
     # association_properties — appended here in attach order. ``_end_span``