diff --git a/.generator/schemas/v2/openapi.yaml b/.generator/schemas/v2/openapi.yaml
index 2dc5dce2c0ac..dfe28385c5a7 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/services/llm_observability/src/v2/LLMObservabilityApi.ts b/services/llm_observability/src/v2/LLMObservabilityApi.ts
index 718936416671..f8b0ec270bf0 100644
--- a/services/llm_observability/src/v2/LLMObservabilityApi.ts
+++ b/services/llm_observability/src/v2/LLMObservabilityApi.ts
@@ -4775,7 +4775,7 @@ export class LLMObservabilityApi {
   }
 
   /**
-   * 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.
    * @param param The request object
    */
@@ -5075,7 +5075,7 @@ export class LLMObservabilityApi {
   }
 
   /**
-   * 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.
    * @param param The request object
    */
   public getLLMObsAnnotatedInteractions(
diff --git a/services/llm_observability/src/v2/models/LLMObsAnnotatedInteractionItem.ts b/services/llm_observability/src/v2/models/LLMObsAnnotatedInteractionItem.ts
index 093eb53d54b8..2a87e467dcfe 100644
--- a/services/llm_observability/src/v2/models/LLMObsAnnotatedInteractionItem.ts
+++ b/services/llm_observability/src/v2/models/LLMObsAnnotatedInteractionItem.ts
@@ -12,7 +12,7 @@ export class LLMObsAnnotatedInteractionItem {
    */
   "annotations": Array<LLMObsAnnotationItem>;
   /**
-   * Identifier of the content for this interaction.
+   * Identifier of the content (trace ID or session ID) for this interaction.
    */
   "contentId": string;
   /**
diff --git a/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionItem.ts b/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionItem.ts
index 69f8534c5fd0..7168dc04ae67 100644
--- a/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionItem.ts
+++ b/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionItem.ts
@@ -7,7 +7,7 @@ import { LLMObsInteractionType } from "./LLMObsInteractionType";
  */
 export class LLMObsAnnotationQueueInteractionItem {
   /**
-   * 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;
   /**
diff --git a/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionResponseItem.ts b/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionResponseItem.ts
index 5c56c37fa17a..5d0bfbdd3650 100644
--- a/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionResponseItem.ts
+++ b/services/llm_observability/src/v2/models/LLMObsAnnotationQueueInteractionResponseItem.ts
@@ -11,7 +11,7 @@ export class LLMObsAnnotationQueueInteractionResponseItem {
    */
   "alreadyExisted": boolean;
   /**
-   * Identifier of the content for this interaction.
+   * Identifier of the content (trace ID or session ID) for this interaction.
    */
   "contentId": string;
   /**
diff --git a/services/llm_observability/src/v2/models/LLMObsInteractionType.ts b/services/llm_observability/src/v2/models/LLMObsInteractionType.ts
index 9a5cb228e7ee..d495b4d8cc0d 100644
--- a/services/llm_observability/src/v2/models/LLMObsInteractionType.ts
+++ b/services/llm_observability/src/v2/models/LLMObsInteractionType.ts
@@ -6,6 +6,8 @@ import { UnparsedObject } from "@datadog/datadog-api-client";
 export type LLMObsInteractionType =
   | typeof TRACE
   | typeof EXPERIMENT_TRACE
+  | typeof SESSION
   | UnparsedObject;
 export const TRACE = "trace";
 export const EXPERIMENT_TRACE = "experiment_trace";
+export const SESSION = "session";
diff --git a/services/llm_observability/src/v2/models/TypingInfo.ts b/services/llm_observability/src/v2/models/TypingInfo.ts
index 4b37e187bacb..f78f044fe2be 100644
--- a/services/llm_observability/src/v2/models/TypingInfo.ts
+++ b/services/llm_observability/src/v2/models/TypingInfo.ts
@@ -141,7 +141,7 @@ export const TypingInfo: ModelTypingInfo = {
     LLMObsEventType: ["events"],
     LLMObsExperimentSpanStatus: ["ok", "error"],
     LLMObsExperimentType: ["experiments"],
-    LLMObsInteractionType: ["trace", "experiment_trace"],
+    LLMObsInteractionType: ["trace", "experiment_trace", "session"],
     LLMObsLabelSchemaType: ["score", "categorical", "boolean", "text"],
     LLMObsMetricAssessment: ["pass", "fail"],
     LLMObsMetricScoreType: ["score", "categorical", "boolean", "json"],