diff --git a/google/cloud/contact_center_insights_v1/types/resources.py b/google/cloud/contact_center_insights_v1/types/resources.py
index e2df252..2d64af3 100644
--- a/google/cloud/contact_center_insights_v1/types/resources.py
+++ b/google/cloud/contact_center_insights_v1/types/resources.py
@@ -157,6 +157,9 @@ class Transcript(proto.Message):
         class TranscriptSegment(proto.Message):
             r"""A segment of a full transcript.
             Attributes:
+                message_time (google.protobuf.timestamp_pb2.Timestamp):
+                    The time that the message occurred, if
+                    provided.
                 text (str):
                     The text of this segment.
                 confidence (float):
@@ -179,6 +182,11 @@ class TranscriptSegment(proto.Message):
                     indicates that the audio is mono.
                 segment_participant (google.cloud.contact_center_insights_v1.types.ConversationParticipant):
                     The participant of this segment.
+                dialogflow_segment_metadata (google.cloud.contact_center_insights_v1.types.Conversation.Transcript.TranscriptSegment.DialogflowSegmentMetadata):
+                    CCAI metadata relating to the current
+                    transcript segment.
+                sentiment (google.cloud.contact_center_insights_v1.types.SentimentData):
+                    The sentiment for this transcript segment.
             """
 
             class WordInfo(proto.Message):
@@ -209,6 +217,22 @@ class WordInfo(proto.Message):
                 word = proto.Field(proto.STRING, number=3,)
                 confidence = proto.Field(proto.FLOAT, number=4,)
 
+            class DialogflowSegmentMetadata(proto.Message):
+                r"""Metadata from Dialogflow relating to the current transcript
+                segment.
+
+                Attributes:
+                    smart_reply_allowlist_covered (bool):
+                        Whether the transcript segment was covered
+                        under the configured smart reply allowlist in
+                        Agent Assist.
+                """
+
+                smart_reply_allowlist_covered = proto.Field(proto.BOOL, number=1,)
+
+            message_time = proto.Field(
+                proto.MESSAGE, number=6, message=timestamp_pb2.Timestamp,
+            )
             text = proto.Field(proto.STRING, number=1,)
             confidence = proto.Field(proto.FLOAT, number=2,)
             words = proto.RepeatedField(
@@ -221,6 +245,12 @@ class WordInfo(proto.Message):
             segment_participant = proto.Field(
                 proto.MESSAGE, number=9, message="ConversationParticipant",
             )
+            dialogflow_segment_metadata = proto.Field(
+                proto.MESSAGE,
+                number=10,
+                message="Conversation.Transcript.TranscriptSegment.DialogflowSegmentMetadata",
+            )
+            sentiment = proto.Field(proto.MESSAGE, number=11, message="SentimentData",)
 
         transcript_segments = proto.RepeatedField(
             proto.MESSAGE,
@@ -1276,6 +1306,8 @@ class ConversationParticipant(proto.Message):
             Deprecated. Use ``dialogflow_participant_name`` instead. The
             name of the Dialogflow participant. Format:
             projects/{project}/locations/{location}/conversations/{conversation}/participants/{participant}
+        obfuscated_external_user_id (str):
+            Obfuscated user ID from Dialogflow.
         role (google.cloud.contact_center_insights_v1.types.ConversationParticipant.Role):
             The role of the participant.
     """
@@ -1293,6 +1325,7 @@ class Role(proto.Enum):
     )
     user_id = proto.Field(proto.STRING, number=6, oneof="participant",)
     dialogflow_participant = proto.Field(proto.STRING, number=1,)
+    obfuscated_external_user_id = proto.Field(proto.STRING, number=3,)
     role = proto.Field(proto.ENUM, number=2, enum=Role,)