diff --git a/.castiron.stats.yml b/.castiron.stats.yml
index 23b33efd22..3e48e35d8c 100644
--- a/.castiron.stats.yml
+++ b/.castiron.stats.yml
@@ -1,7 +1,7 @@
 schema_version: 1
-generation_id: 02a4f051-9120-487b-8954-9ea8b97df229
-openapi_spec_hash: 017866de8f67cefec8724f830463cbe2
-openapi_transformed_spec_hash: d7de2a7f65152a983cdba4c6b4a20d76
-config_hash: 3d64bda5a8bbef3ad0572848ae7e87f7
-codegen_sha: ab8360c6a37ccd1f94712f0aa9646349279084b1
-codegen_hash: cd27c533727eae2ee5d4350f07afd15d7de38e89fd3c4c2e35dbda61cd39f5d8
+generation_id: 27aedac3-d226-45f3-9b03-cdbc31e26c4a
+openapi_spec_hash: 6e0c0f870093ed93cda3b6c04057dff1
+openapi_transformed_spec_hash: 6dca3c69339704dc304046890bab23a2
+config_hash: 8a684aec06907ff8ced7809753e16225
+codegen_sha: a437bfc5da2d18f1d2cf8b2e0dabf33cbce30762
+codegen_hash: 7c728907f3820a04cdb65380930c806a947d51378d79412f730f857ec317f0bf
diff --git a/api_reference/openapi.transformed.yml b/api_reference/openapi.transformed.yml
index 2b783ff234..0851d765e6 100644
--- a/api_reference/openapi.transformed.yml
+++ b/api_reference/openapi.transformed.yml
@@ -52062,6 +52062,7 @@ components:
       - $ref: '#/components/schemas/LiveInputAudioMuteParam'
       - $ref: '#/components/schemas/LiveInputAudioUnmuteParam'
       - $ref: '#/components/schemas/LiveOutputAudioFixturePlayParam'
+      - $ref: '#/components/schemas/LiveTransportDTMFSendParam'
       - $ref: '#/components/schemas/LiveInstructionsAppendParam'
       - $ref: '#/components/schemas/LiveThinkingAppendParam'
       - $ref: '#/components/schemas/LiveCommentaryAppendParam'
@@ -52117,6 +52118,7 @@ components:
       - $ref: '#/components/schemas/LiveOutputAudioDelta'
       - $ref: '#/components/schemas/LiveTransportDTMFReceived'
       - $ref: '#/components/schemas/LiveTransportDTMFSend'
+      - $ref: '#/components/schemas/LiveTransportDTMFSent'
       - $ref: '#/components/schemas/LiveTransportRinging'
       - $ref: '#/components/schemas/LiveTransportAnswered'
       - $ref: '#/components/schemas/LiveTransportFailed'
@@ -79111,6 +79113,41 @@ components:
       - auto
       - none
       - required
+    LiveTransportDTMFSend:
+      description: Legacy SIP DTMF delivery notification retained for SDK compatibility and saved events. Current servers confirm delivery with transport.dtmf.sent; transport.dtmf.send is now the client command.
+      example:
+        type: transport.dtmf.send
+        event_id: event_dtmf_2
+        event: '#'
+      type: object
+      properties:
+        type:
+          default: transport.dtmf.send
+          x-stainless-const: true
+          type: string
+          enum:
+          - transport.dtmf.send
+        event_id:
+          type: string
+        event:
+          type: string
+          minLength: 1
+          maxLength: 1
+          pattern: ^[0-9A-D*#]$
+        client_event_id:
+          description: The event_id of the client command, when supplied.
+          type: string
+          x-stainless-skip:
+          - cli
+      required:
+      - type
+      - event_id
+      - event
+      x-oaiMeta:
+        example:
+          type: transport.dtmf.send
+          event_id: event_dtmf_2
+          event: '#'
     LegacyComputerAction:
       discriminator:
         propertyName: type
@@ -79124,42 +79161,6 @@ components:
       - $ref: '#/components/schemas/ScrollParam'
       - $ref: '#/components/schemas/TypeParam'
       - $ref: '#/components/schemas/WaitParam'
-    CodeInterpreterContainerAuto:
-      properties:
-        type:
-          type: string
-          enum:
-          - auto
-          description: Always `auto`.
-          default: auto
-          x-stainless-const: true
-        file_ids:
-          items:
-            type: string
-            example: file-123
-          type: array
-          maxItems: 50
-          description: An optional list of uploaded files to make available to your code.
-        memory_limit:
-          anyOf:
-          - $ref: '#/components/schemas/ContainerMemoryLimit'
-            description: The memory limit for the code interpreter container.
-          - type: 'null'
-        network_policy:
-          discriminator:
-            propertyName: type
-          description: Network access policy for the container.
-          anyOf:
-          - $ref: '#/components/schemas/ContainerNetworkPolicyDisabledParam'
-          - $ref: '#/components/schemas/ContainerNetworkPolicyAllowlistParam'
-      type: object
-      required:
-      - type
-      title: CodeInterpreterToolAuto
-      description: Configuration for a code interpreter container. Optionally specify the IDs of the files to run the code on.
-      x-stainless-naming:
-        go:
-          type_name: ToolCodeInterpreterContainerCodeInterpreterContainerAuto
     LiveSpecificFileSearchParam:
       type: object
       properties:
@@ -97649,41 +97650,6 @@ components:
           type: transport.dtmf.received
           event_id: event_dtmf_1
           event: '5'
-    LiveTransportDTMFSend:
-      description: A SIP DTMF keypress successfully sent to the SIP trunk. Delivered only to sideband observers; this is not a client command.
-      example:
-        type: transport.dtmf.send
-        event_id: event_dtmf_2
-        event: '#'
-      type: object
-      properties:
-        type:
-          default: transport.dtmf.send
-          x-stainless-const: true
-          type: string
-          enum:
-          - transport.dtmf.send
-        event_id:
-          type: string
-        event:
-          type: string
-          minLength: 1
-          maxLength: 1
-          pattern: ^[0-9A-D*#]$
-        client_event_id:
-          description: The event_id of the client command, when supplied.
-          type: string
-          x-stainless-skip:
-          - cli
-      required:
-      - type
-      - event_id
-      - event
-      x-oaiMeta:
-        example:
-          type: transport.dtmf.send
-          event_id: event_dtmf_2
-          event: '#'
     LiveTransportRinging:
       description: The outbound SIP provider leg is ringing or providing early media. Delivered only to sideband observers.
       example:
@@ -97831,6 +97797,7 @@ components:
       - $ref: '#/components/schemas/LiveInfoEvent'
       - $ref: '#/components/schemas/LiveTransportDTMFReceived'
       - $ref: '#/components/schemas/LiveTransportDTMFSend'
+      - $ref: '#/components/schemas/LiveTransportDTMFSent'
       - $ref: '#/components/schemas/LiveTransportRinging'
       - $ref: '#/components/schemas/LiveTransportAnswered'
       - $ref: '#/components/schemas/LiveTransportFailed'
@@ -111027,6 +110994,73 @@ components:
       type: object
       required:
       - status
+    LiveTransportDTMFSendParam:
+      description: Send one DTMF keypress to the SIP trunk through a Live sideband connection. This command is supported only for SIP calls. A successful send emits `transport.dtmf.sent` on sideband. If you provide `event_id`, the success notification includes it as `client_event_id`; a failure includes it as `error.client_event_id`. Send separate events for multiple keypresses.
+      example:
+        type: transport.dtmf.send
+        event_id: evt_dtmf_001
+        event: '#'
+      type: object
+      properties:
+        event_id:
+          anyOf:
+          - description: Optional client identifier for correlating this command with a server event's client_event_id or error.client_event_id.
+            type: string
+            maxLength: 512
+          - type: 'null'
+        type:
+          default: transport.dtmf.send
+          x-stainless-const: true
+          type: string
+          enum:
+          - transport.dtmf.send
+        event:
+          description: 'The DTMF key to send: one of `0`–`9`, `A`–`D`, `*`, or `#`.'
+          type: string
+          minLength: 1
+          maxLength: 1
+          pattern: ^[0-9A-D*#]$
+      required:
+      - type
+      - event
+      x-oaiMeta:
+        example:
+          type: transport.dtmf.send
+          event_id: evt_dtmf_001
+          event: '#'
+    LiveTransportDTMFSent:
+      description: A SIP DTMF keypress successfully sent to the SIP trunk. Delivered only to sideband observers; this is not a client command.
+      example:
+        type: transport.dtmf.sent
+        event_id: event_dtmf_2
+        event: '#'
+      type: object
+      properties:
+        type:
+          default: transport.dtmf.sent
+          x-stainless-const: true
+          type: string
+          enum:
+          - transport.dtmf.sent
+        event_id:
+          type: string
+        event:
+          type: string
+          minLength: 1
+          maxLength: 1
+          pattern: ^[0-9A-D*#]$
+        client_event_id:
+          description: The event_id of the client command, when supplied.
+          type: string
+      required:
+      - type
+      - event_id
+      - event
+      x-oaiMeta:
+        example:
+          type: transport.dtmf.sent
+          event_id: event_dtmf_2
+          event: '#'
     SessionSpendControlResource:
       type: object
       properties:
@@ -111813,6 +111847,42 @@ components:
       - completed
       - incomplete
       - expired
+    CodeInterpreterContainerAuto:
+      properties:
+        type:
+          type: string
+          enum:
+          - auto
+          description: Always `auto`.
+          default: auto
+          x-stainless-const: true
+        file_ids:
+          items:
+            type: string
+            example: file-123
+          type: array
+          maxItems: 50
+          description: An optional list of uploaded files to make available to your code.
+        memory_limit:
+          anyOf:
+          - $ref: '#/components/schemas/ContainerMemoryLimit'
+            description: The memory limit for the code interpreter container.
+          - type: 'null'
+        network_policy:
+          discriminator:
+            propertyName: type
+          description: Network access policy for the container.
+          anyOf:
+          - $ref: '#/components/schemas/ContainerNetworkPolicyDisabledParam'
+          - $ref: '#/components/schemas/ContainerNetworkPolicyAllowlistParam'
+      type: object
+      required:
+      - type
+      title: CodeInterpreterToolAuto
+      description: Configuration for a code interpreter container. Optionally specify the IDs of the files to run the code on.
+      x-stainless-naming:
+        go:
+          type_name: ToolCodeInterpreterContainerCodeInterpreterContainerAuto
     LiveFunctionToolChoiceParam:
       type: object
       properties:
diff --git a/scripts/castiron/generated-files.json b/scripts/castiron/generated-files.json
index bbc7b41e27..605ae3081d 100644
--- a/scripts/castiron/generated-files.json
+++ b/scripts/castiron/generated-files.json
@@ -571,7 +571,7 @@
     },
     "src/openai/resources/live/sideband.py": {
       "mode": "100644",
-      "sha256": "4ed10b89fadd3aff1e3226cd7e0db9e1463ef834ce3d2c1e437618c7292cbd20"
+      "sha256": "9f780c2c96066d0f2a70f48b5c7f4f610900a1d07371c7b19fd0a7b787e79120"
     },
     "src/openai/resources/models.py": {
       "mode": "100644",
@@ -4635,15 +4635,15 @@
     },
     "src/openai/types/live/connect_client_event.py": {
       "mode": "100644",
-      "sha256": "bc941c81d969470e47b82605313ca6beff3d40bf152eabe7ba0b6e6649cf2afa"
+      "sha256": "3dafdbb32c5765eaa39a1473d56f1b5113b2af596feac4fb4332b5632c5332fc"
     },
     "src/openai/types/live/connect_client_event_param.py": {
       "mode": "100644",
-      "sha256": "b8f84462deda4beb537beb4f8dcf18a1be3bc842bc1679adb9d4fc66e1b8b18b"
+      "sha256": "348e243ff821cf55dd0c1a5f04aa5c83ee12221b033913314c7c25ffb47101da"
     },
     "src/openai/types/live/connect_server_event.py": {
       "mode": "100644",
-      "sha256": "f1762b5ae9f57faaf5bc12d24497b6736a454d9c9b0a92bea8556ec5e191c948"
+      "sha256": "0ea5b662cd3893671b1ed1f89cc49852a8db23a4591ef6694a5a789e8aa253ed"
     },
     "src/openai/types/live/custom_voice.py": {
       "mode": "100644",
@@ -4823,7 +4823,7 @@
     },
     "src/openai/types/live/fork_server_event.py": {
       "mode": "100644",
-      "sha256": "a908fc4ff11c69feb00f2e5bdd57ec4af95fd5c7bbdf02a8dbf8b566257ae837"
+      "sha256": "e7b6e1523075c44d6a39125cbec89984be35a60c3b314f521768bca68f92caae"
     },
     "src/openai/types/live/fork_session_config.py": {
       "mode": "100644",
@@ -4987,7 +4987,7 @@
     },
     "src/openai/types/live/server_event.py": {
       "mode": "100644",
-      "sha256": "ab64c366facea5dd4ba3e487fc09227bb806401fee45d0512156507695f20feb"
+      "sha256": "6b7bbf4ebd0cafdccda1532cf059e9c6a4be2ea3c4fde83c2c3c3d30ab37ae2b"
     },
     "src/openai/types/live/server_event_selector.py": {
       "mode": "100644",
diff --git a/src/openai/resources/live/sideband.py b/src/openai/resources/live/sideband.py
index c916ecfcd4..fca3846e44 100644
--- a/src/openai/resources/live/sideband.py
+++ b/src/openai/resources/live/sideband.py
@@ -115,6 +115,7 @@ class AsyncSidebandConnection(AsyncWebSocketConnectionBase):
     """Represents a live WebSocket connection to the Sideband API"""
 
     session: AsyncSidebandSessionResource
+    transport: AsyncSidebandTransportResource
     decision: AsyncSidebandDecisionResource
     response: AsyncSidebandResponseResource
 
@@ -148,6 +149,7 @@ def __init__(
         self._event_handler_registry = EventHandlerRegistry(use_lock=False)
 
         self.session = AsyncSidebandSessionResource(self)
+        self.transport = AsyncSidebandTransportResource(self)
         self.decision = AsyncSidebandDecisionResource(self)
         self.response = AsyncSidebandResponseResource(self)
 
@@ -544,6 +546,7 @@ class SidebandConnection(WebSocketConnectionBase):
     """Represents a live WebSocket connection to the Sideband API"""
 
     session: SidebandSessionResource
+    transport: SidebandTransportResource
     decision: SidebandDecisionResource
     response: SidebandResponseResource
 
@@ -577,6 +580,7 @@ def __init__(
         self._event_handler_registry = EventHandlerRegistry(use_lock=True)
 
         self.session = SidebandSessionResource(self)
+        self.transport = SidebandTransportResource(self)
         self.decision = SidebandDecisionResource(self)
         self.response = SidebandResponseResource(self)
 
@@ -1122,6 +1126,26 @@ def play(self, *, audio: str, event_id: Optional[str] | Omit = omit) -> None:
         )
 
 
+class SidebandTransportResource(BaseSidebandConnectionResource):
+    @cached_property
+    def dtmf(self) -> SidebandTransportDtmfResource:
+        return SidebandTransportDtmfResource(self._connection)
+
+
+class SidebandTransportDtmfResource(BaseSidebandConnectionResource):
+    def send(self, *, event: str, event_id: Optional[str] | Omit = omit) -> None:
+        """Send one DTMF keypress to the SIP trunk through a Live sideband connection.
+
+        This command is supported only for SIP calls. A successful send emits `transport.dtmf.sent` on sideband. If you provide `event_id`, the success notification includes it as `client_event_id`; a failure includes it as `error.client_event_id`. Send separate events for multiple keypresses.
+        """
+        self._connection.send(
+            cast(
+                ConnectClientEventParam,
+                strip_not_given({"type": "transport.dtmf.send", "event": event, "event_id": event_id}),
+            )
+        )
+
+
 class SidebandDecisionResource(BaseSidebandConnectionResource):
     @cached_property
     def item(self) -> SidebandDecisionItemResource:
@@ -1357,6 +1381,26 @@ async def play(self, *, audio: str, event_id: Optional[str] | Omit = omit) -> No
         )
 
 
+class AsyncSidebandTransportResource(BaseAsyncSidebandConnectionResource):
+    @cached_property
+    def dtmf(self) -> AsyncSidebandTransportDtmfResource:
+        return AsyncSidebandTransportDtmfResource(self._connection)
+
+
+class AsyncSidebandTransportDtmfResource(BaseAsyncSidebandConnectionResource):
+    async def send(self, *, event: str, event_id: Optional[str] | Omit = omit) -> None:
+        """Send one DTMF keypress to the SIP trunk through a Live sideband connection.
+
+        This command is supported only for SIP calls. A successful send emits `transport.dtmf.sent` on sideband. If you provide `event_id`, the success notification includes it as `client_event_id`; a failure includes it as `error.client_event_id`. Send separate events for multiple keypresses.
+        """
+        await self._connection.send(
+            cast(
+                ConnectClientEventParam,
+                strip_not_given({"type": "transport.dtmf.send", "event": event, "event_id": event_id}),
+            )
+        )
+
+
 class AsyncSidebandDecisionResource(BaseAsyncSidebandConnectionResource):
     @cached_property
     def item(self) -> AsyncSidebandDecisionItemResource:
diff --git a/src/openai/types/live/connect_client_event.py b/src/openai/types/live/connect_client_event.py
index 0d46cf6ef5..430e87cb8b 100644
--- a/src/openai/types/live/connect_client_event.py
+++ b/src/openai/types/live/connect_client_event.py
@@ -1,9 +1,10 @@
 # File generated from our OpenAPI spec by Castiron. See CONTRIBUTING.md for details.
 
-from typing import Union
-from typing_extensions import Annotated, TypeAlias
+from typing import Union, Optional
+from typing_extensions import Literal, Annotated, TypeAlias
 
 from ..._utils import PropertyInfo
+from ..._models import BaseModel
 from .session_close_event import SessionCloseEvent
 from .session_update_event import SessionUpdateEvent
 from .decision_create_event import DecisionCreateEvent
@@ -18,7 +19,26 @@
 from .response_item_create_event import ResponseItemCreateEvent
 from .output_audio_fixture_play_event import OutputAudioFixturePlayEvent
 
-__all__ = ["ConnectClientEvent"]
+__all__ = ["ConnectClientEvent", "TransportDtmfSend"]
+
+
+class TransportDtmfSend(BaseModel):
+    """Send one DTMF keypress to the SIP trunk through a Live sideband connection.
+
+    This command is supported only for SIP calls. A successful send emits `transport.dtmf.sent` on sideband. If you provide `event_id`, the success notification includes it as `client_event_id`; a failure includes it as `error.client_event_id`. Send separate events for multiple keypresses.
+    """
+
+    event: str
+    """The DTMF key to send: one of `0`–`9`, `A`–`D`, `*`, or `#`."""
+
+    type: Literal["transport.dtmf.send"]
+
+    event_id: Optional[str] = None
+    """
+    Optional client identifier for correlating this command with a server event's
+    client_event_id or error.client_event_id.
+    """
+
 
 ConnectClientEvent: TypeAlias = Annotated[
     Union[
@@ -26,6 +46,7 @@
         InputAudioMuteEvent,
         InputAudioUnmuteEvent,
         OutputAudioFixturePlayEvent,
+        TransportDtmfSend,
         InstructionsAppendEvent,
         ThinkingAppendEvent,
         CommentaryAppendEvent,
diff --git a/src/openai/types/live/connect_client_event_param.py b/src/openai/types/live/connect_client_event_param.py
index d4309ae7bb..71690d037f 100644
--- a/src/openai/types/live/connect_client_event_param.py
+++ b/src/openai/types/live/connect_client_event_param.py
@@ -2,8 +2,8 @@
 
 from __future__ import annotations
 
-from typing import Union
-from typing_extensions import TypeAlias
+from typing import Union, Optional
+from typing_extensions import Literal, Required, TypeAlias, TypedDict
 
 from .session_close_event_param import SessionCloseEventParam
 from .session_update_event_param import SessionUpdateEventParam
@@ -19,13 +19,33 @@
 from .response_item_create_event_param import ResponseItemCreateEventParam
 from .output_audio_fixture_play_event_param import OutputAudioFixturePlayEventParam
 
-__all__ = ["ConnectClientEventParam"]
+__all__ = ["ConnectClientEventParam", "TransportDtmfSend"]
+
+
+class TransportDtmfSend(TypedDict, total=False):
+    """Send one DTMF keypress to the SIP trunk through a Live sideband connection.
+
+    This command is supported only for SIP calls. A successful send emits `transport.dtmf.sent` on sideband. If you provide `event_id`, the success notification includes it as `client_event_id`; a failure includes it as `error.client_event_id`. Send separate events for multiple keypresses.
+    """
+
+    event: Required[str]
+    """The DTMF key to send: one of `0`–`9`, `A`–`D`, `*`, or `#`."""
+
+    type: Required[Literal["transport.dtmf.send"]]
+
+    event_id: Optional[str]
+    """
+    Optional client identifier for correlating this command with a server event's
+    client_event_id or error.client_event_id.
+    """
+
 
 ConnectClientEventParam: TypeAlias = Union[
     SessionUpdateEventParam,
     InputAudioMuteEventParam,
     InputAudioUnmuteEventParam,
     OutputAudioFixturePlayEventParam,
+    TransportDtmfSend,
     InstructionsAppendEventParam,
     ThinkingAppendEventParam,
     CommentaryAppendEventParam,
diff --git a/src/openai/types/live/connect_server_event.py b/src/openai/types/live/connect_server_event.py
index 928f95aeae..217325632e 100644
--- a/src/openai/types/live/connect_server_event.py
+++ b/src/openai/types/live/connect_server_event.py
@@ -32,6 +32,7 @@
     "SessionInputAudioAppend",
     "TransportDtmfReceived",
     "TransportDtmfSend",
+    "TransportDtmfSent",
     "TransportRinging",
     "TransportAnswered",
     "TransportFailed",
@@ -69,6 +70,21 @@ class TransportDtmfReceived(BaseModel):
 
 
 class TransportDtmfSend(BaseModel):
+    """
+    Legacy SIP DTMF delivery notification retained for SDK compatibility and saved events. Current servers confirm delivery with transport.dtmf.sent; transport.dtmf.send is now the client command.
+    """
+
+    event: str
+
+    event_id: str
+
+    type: Literal["transport.dtmf.send"]
+
+    client_event_id: Optional[str] = None
+    """The event_id of the client command, when supplied."""
+
+
+class TransportDtmfSent(BaseModel):
     """A SIP DTMF keypress successfully sent to the SIP trunk.
 
     Delivered only to sideband observers; this is not a client command.
@@ -78,7 +94,7 @@ class TransportDtmfSend(BaseModel):
 
     event_id: str
 
-    type: Literal["transport.dtmf.send"]
+    type: Literal["transport.dtmf.sent"]
 
     client_event_id: Optional[str] = None
     """The event_id of the client command, when supplied."""
@@ -166,6 +182,7 @@ class TransportFailed(BaseModel):
         OutputAudioDeltaEvent,
         TransportDtmfReceived,
         TransportDtmfSend,
+        TransportDtmfSent,
         TransportRinging,
         TransportAnswered,
         TransportFailed,
diff --git a/src/openai/types/live/fork_server_event.py b/src/openai/types/live/fork_server_event.py
index 88a006ab51..30ea40b5b2 100644
--- a/src/openai/types/live/fork_server_event.py
+++ b/src/openai/types/live/fork_server_event.py
@@ -32,6 +32,7 @@
     "SessionInputAudioAppend",
     "TransportDtmfReceived",
     "TransportDtmfSend",
+    "TransportDtmfSent",
     "TransportRinging",
     "TransportAnswered",
     "TransportFailed",
@@ -69,6 +70,21 @@ class TransportDtmfReceived(BaseModel):
 
 
 class TransportDtmfSend(BaseModel):
+    """
+    Legacy SIP DTMF delivery notification retained for SDK compatibility and saved events. Current servers confirm delivery with transport.dtmf.sent; transport.dtmf.send is now the client command.
+    """
+
+    event: str
+
+    event_id: str
+
+    type: Literal["transport.dtmf.send"]
+
+    client_event_id: Optional[str] = None
+    """The event_id of the client command, when supplied."""
+
+
+class TransportDtmfSent(BaseModel):
     """A SIP DTMF keypress successfully sent to the SIP trunk.
 
     Delivered only to sideband observers; this is not a client command.
@@ -78,7 +94,7 @@ class TransportDtmfSend(BaseModel):
 
     event_id: str
 
-    type: Literal["transport.dtmf.send"]
+    type: Literal["transport.dtmf.sent"]
 
     client_event_id: Optional[str] = None
     """The event_id of the client command, when supplied."""
@@ -166,6 +182,7 @@ class TransportFailed(BaseModel):
         InfoEvent,
         TransportDtmfReceived,
         TransportDtmfSend,
+        TransportDtmfSent,
         TransportRinging,
         TransportAnswered,
         TransportFailed,
diff --git a/src/openai/types/live/server_event.py b/src/openai/types/live/server_event.py
index 26dc6a3604..0c9d2b3b6c 100644
--- a/src/openai/types/live/server_event.py
+++ b/src/openai/types/live/server_event.py
@@ -32,6 +32,7 @@
     "SessionInputAudioAppend",
     "TransportDtmfReceived",
     "TransportDtmfSend",
+    "TransportDtmfSent",
     "TransportRinging",
     "TransportAnswered",
     "TransportFailed",
@@ -69,6 +70,21 @@ class TransportDtmfReceived(BaseModel):
 
 
 class TransportDtmfSend(BaseModel):
+    """
+    Legacy SIP DTMF delivery notification retained for SDK compatibility and saved events. Current servers confirm delivery with transport.dtmf.sent; transport.dtmf.send is now the client command.
+    """
+
+    event: str
+
+    event_id: str
+
+    type: Literal["transport.dtmf.send"]
+
+    client_event_id: Optional[str] = None
+    """The event_id of the client command, when supplied."""
+
+
+class TransportDtmfSent(BaseModel):
     """A SIP DTMF keypress successfully sent to the SIP trunk.
 
     Delivered only to sideband observers; this is not a client command.
@@ -78,7 +94,7 @@ class TransportDtmfSend(BaseModel):
 
     event_id: str
 
-    type: Literal["transport.dtmf.send"]
+    type: Literal["transport.dtmf.sent"]
 
     client_event_id: Optional[str] = None
     """The event_id of the client command, when supplied."""
@@ -166,6 +182,7 @@ class TransportFailed(BaseModel):
         InfoEvent,
         TransportDtmfReceived,
         TransportDtmfSend,
+        TransportDtmfSent,
         TransportRinging,
         TransportAnswered,
         TransportFailed,