diff --git a/.generator/schemas/v2/openapi.yaml b/.generator/schemas/v2/openapi.yaml
index 2dc5dce2c0a..dfe28385c5a 100644
--- a/.generator/schemas/v2/openapi.yaml
+++ b/.generator/schemas/v2/openapi.yaml
@@ -38202,7 +38202,7 @@ components:
             $ref: "#/components/schemas/LLMObsAnnotationItem"
           type: array
         content_id:
-          description: Identifier of the content for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         id:
@@ -38405,7 +38405,7 @@ components:
       description: A single interaction to add to an annotation queue.
       properties:
         content_id:
-          description: Identifier of the content (such as trace ID) for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         type:
@@ -38422,7 +38422,7 @@ components:
           example: false
           type: boolean
         content_id:
-          description: Identifier of the content for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         id:
@@ -39941,11 +39941,13 @@ components:
       enum:
         - trace
         - experiment_trace
+        - session
       example: trace
       type: string
       x-enum-varnames:
         - TRACE
         - EXPERIMENT_TRACE
+        - SESSION
     LLMObsLabelSchema:
       description: Schema definition for a single label in an annotation queue.
       properties:
@@ -109649,7 +109651,7 @@ paths:
         If you have any feedback, contact [Datadog support](https://docs.datadoghq.com/help/).
   /api/v2/llm-obs/v1/annotation-queues/{queue_id}/annotated-interactions:
     get:
-      description: Retrieve all interactions and their annotations for a given annotation queue.
+      description: Retrieve all interactions (traces and sessions) and their annotations for a given annotation queue.
       operationId: GetLLMObsAnnotatedInteractions
       parameters:
         - $ref: "#/components/parameters/LLMObsAnnotationQueueIDPathParameter"
@@ -109710,7 +109712,7 @@ paths:
   /api/v2/llm-obs/v1/annotation-queues/{queue_id}/interactions:
     post:
       description: |-
-        Add one or more interactions (traces) to an annotation queue.
+        Add one or more interactions (traces or sessions) to an annotation queue.
         At least one interaction must be provided.
       operationId: CreateLLMObsAnnotationQueueInteractions
       parameters:
diff --git a/api/datadogV2/api_llm_observability.go b/api/datadogV2/api_llm_observability.go
index eba358361d9..5c554a6e5bf 100644
--- a/api/datadogV2/api_llm_observability.go
+++ b/api/datadogV2/api_llm_observability.go
@@ -120,7 +120,7 @@ func (a *LLMObservabilityApi) CreateLLMObsAnnotationQueue(ctx _context.Context,
 }
 
 // CreateLLMObsAnnotationQueueInteractions Add annotation queue interactions.
-// Add one or more interactions (traces) to an annotation queue.
+// Add one or more interactions (traces or sessions) to an annotation queue.
 // At least one interaction must be provided.
 func (a *LLMObservabilityApi) CreateLLMObsAnnotationQueueInteractions(ctx _context.Context, queueId string, body LLMObsAnnotationQueueInteractionsRequest) (LLMObsAnnotationQueueInteractionsResponse, *_nethttp.Response, error) {
 	var (
@@ -1320,7 +1320,7 @@ func (a *LLMObservabilityApi) DeleteLLMObsProjects(ctx _context.Context, body LL
 }
 
 // GetLLMObsAnnotatedInteractions Get annotated queue interactions.
-// Retrieve all interactions and their annotations for a given annotation queue.
+// Retrieve all interactions (traces and sessions) and their annotations for a given annotation queue.
 func (a *LLMObservabilityApi) GetLLMObsAnnotatedInteractions(ctx _context.Context, queueId string) (LLMObsAnnotatedInteractionsResponse, *_nethttp.Response, error) {
 	var (
 		localVarHTTPMethod  = _nethttp.MethodGet
diff --git a/api/datadogV2/model_llm_obs_annotated_interaction_item.go b/api/datadogV2/model_llm_obs_annotated_interaction_item.go
index a42466c291f..116be59d97e 100644
--- a/api/datadogV2/model_llm_obs_annotated_interaction_item.go
+++ b/api/datadogV2/model_llm_obs_annotated_interaction_item.go
@@ -14,7 +14,7 @@ import (
 type LLMObsAnnotatedInteractionItem struct {
 	// List of annotations for this interaction.
 	Annotations []LLMObsAnnotationItem `json:"annotations"`
-	// Identifier of the content for this interaction.
+	// Identifier of the content (trace ID or session ID) for this interaction.
 	ContentId string `json:"content_id"`
 	// Unique identifier of the interaction.
 	Id string `json:"id"`
diff --git a/api/datadogV2/model_llm_obs_annotation_queue_interaction_item.go b/api/datadogV2/model_llm_obs_annotation_queue_interaction_item.go
index 8c767c23004..50cf6436a56 100644
--- a/api/datadogV2/model_llm_obs_annotation_queue_interaction_item.go
+++ b/api/datadogV2/model_llm_obs_annotation_queue_interaction_item.go
@@ -12,7 +12,7 @@ import (
 
 // LLMObsAnnotationQueueInteractionItem A single interaction to add to an annotation queue.
 type LLMObsAnnotationQueueInteractionItem struct {
-	// Identifier of the content (such as trace ID) for this interaction.
+	// Identifier of the content (trace ID or session ID) for this interaction.
 	ContentId string `json:"content_id"`
 	// Type of interaction in an annotation queue.
 	Type LLMObsInteractionType `json:"type"`
diff --git a/api/datadogV2/model_llm_obs_annotation_queue_interaction_response_item.go b/api/datadogV2/model_llm_obs_annotation_queue_interaction_response_item.go
index 5b6787f4bb3..8df925d300a 100644
--- a/api/datadogV2/model_llm_obs_annotation_queue_interaction_response_item.go
+++ b/api/datadogV2/model_llm_obs_annotation_queue_interaction_response_item.go
@@ -14,7 +14,7 @@ import (
 type LLMObsAnnotationQueueInteractionResponseItem struct {
 	// Whether this interaction already existed in the queue.
 	AlreadyExisted bool `json:"already_existed"`
-	// Identifier of the content for this interaction.
+	// Identifier of the content (trace ID or session ID) for this interaction.
 	ContentId string `json:"content_id"`
 	// Unique identifier of the interaction.
 	Id string `json:"id"`
diff --git a/api/datadogV2/model_llm_obs_interaction_type.go b/api/datadogV2/model_llm_obs_interaction_type.go
index 7e38b4f8339..f547a346727 100644
--- a/api/datadogV2/model_llm_obs_interaction_type.go
+++ b/api/datadogV2/model_llm_obs_interaction_type.go
@@ -17,11 +17,13 @@ type LLMObsInteractionType string
 const (
 	LLMOBSINTERACTIONTYPE_TRACE            LLMObsInteractionType = "trace"
 	LLMOBSINTERACTIONTYPE_EXPERIMENT_TRACE LLMObsInteractionType = "experiment_trace"
+	LLMOBSINTERACTIONTYPE_SESSION          LLMObsInteractionType = "session"
 )
 
 var allowedLLMObsInteractionTypeEnumValues = []LLMObsInteractionType{
 	LLMOBSINTERACTIONTYPE_TRACE,
 	LLMOBSINTERACTIONTYPE_EXPERIMENT_TRACE,
+	LLMOBSINTERACTIONTYPE_SESSION,
 }
 
 // GetAllowedValues reeturns the list of possible values.