diff --git a/chatkit/agents.py b/chatkit/agents.py
index 82c08e7..c061846 100644
--- a/chatkit/agents.py
+++ b/chatkit/agents.py
@@ -66,6 +66,7 @@
     GeneratedImageUpdated,
     HiddenContextItem,
     SDKHiddenContextItem,
+    StructuredInputItem,
     Task,
     TaskItem,
     ThoughtTask,
@@ -552,14 +553,19 @@ def end_workflow(item: WorkflowItem):
 
             if event.type == "run_item_stream_event":
                 event = event.item
-                if (
-                    event.type == "tool_call_item"
-                    and event.raw_item.type == "function_call"
-                ):
-                    current_tool_call = event.raw_item.call_id
-                    current_item_id = event.raw_item.id
-                    assert current_item_id
-                    produced_items.add(current_item_id)
+                if event.type == "tool_call_item":
+                    raw_item = event.raw_item
+                    if isinstance(raw_item, dict):
+                        if raw_item.get("type") == "function_call":
+                            current_tool_call = event.call_id
+                            current_item_id = raw_item.get("id")
+                            assert current_item_id
+                            produced_items.add(current_item_id)
+                    elif raw_item.type == "function_call":
+                        current_tool_call = event.call_id
+                        current_item_id = raw_item.id
+                        assert current_item_id
+                        produced_items.add(current_item_id)
                 continue
 
             if event.type != "raw_response_event":
@@ -964,6 +970,39 @@ async def task_to_input(
             role="user",
         )
 
+    async def structured_input_to_input(
+        self, item: StructuredInputItem
+    ) -> TResponseInputItem | list[TResponseInputItem] | None:
+        """
+        Convert a StructuredInputItem into input item(s) to send to the model.
+        """
+        lines = []
+        for question in item.inputs:
+            answer = question.answer
+            if answer is None:
+                lines.append(f"- {question.question}: unanswered")
+            elif answer.skipped:
+                lines.append(f"- {question.question}: skipped")
+            else:
+                lines.append(f"- {question.question}: {', '.join(answer.values)}")
+
+        text = (
+            "A structured input request was displayed to the user with the following "
+            f"status: {item.status}\n<StructuredInput>\n"
+            + "\n".join(lines)
+            + "\n</StructuredInput>"
+        )
+        return Message(
+            type="message",
+            content=[
+                ResponseInputTextParam(
+                    type="input_text",
+                    text=text,
+                ),
+            ],
+            role="user",
+        )
+
     async def workflow_to_input(
         self, item: WorkflowItem
     ) -> TResponseInputItem | list[TResponseInputItem] | None:
@@ -1172,6 +1211,9 @@ async def _thread_item_to_input_item(
             case TaskItem():
                 out = await self.task_to_input(item) or []
                 return out if isinstance(out, list) else [out]
+            case StructuredInputItem():
+                out = await self.structured_input_to_input(item) or []
+                return out if isinstance(out, list) else [out]
             case HiddenContextItem():
                 out = await self.hidden_context_to_input(item) or []
                 return out if isinstance(out, list) else [out]
diff --git a/chatkit/server.py b/chatkit/server.py
index 267769e..865135f 100644
--- a/chatkit/server.py
+++ b/chatkit/server.py
@@ -52,6 +52,10 @@
     StreamingReq,
     StreamOptions,
     StreamOptionsEvent,
+    StructuredInputAnswer,
+    StructuredInputItem,
+    StructuredInputMultipleChoice,
+    StructuredInputSubmission,
     SyncCustomActionResponse,
     Thread,
     ThreadCreatedEvent,
@@ -63,6 +67,7 @@
     ThreadItemUpdatedEvent,
     ThreadMetadata,
     ThreadsAddClientToolOutputReq,
+    ThreadsAddStructuredInputReq,
     ThreadsAddUserMessageReq,
     ThreadsCreateReq,
     ThreadsCustomActionReq,
@@ -616,6 +621,41 @@ async def _process_streaming_impl(
                 ):
                     yield event
 
+            case ThreadsAddStructuredInputReq():
+                thread = await self.store.load_thread(
+                    request.params.thread_id, context=context
+                )
+                item = await self.store.load_item(
+                    request.params.thread_id,
+                    request.params.item_id,
+                    context=context,
+                )
+                if not isinstance(item, StructuredInputItem):
+                    raise ValueError(
+                        f"Item {request.params.item_id} is not a StructuredInputItem"
+                    )
+
+                updated_item = await self._apply_structured_input_submission(
+                    item,
+                    request.params.input,
+                )
+
+                async def stream_structured_input_response() -> AsyncIterator[
+                    ThreadStreamEvent
+                ]:
+                    # Keep this replacement inside _process_events so it is persisted
+                    # through the same event pipeline as other thread item replacements.
+                    yield ThreadItemReplacedEvent(item=updated_item)
+                    async for event in self.respond(thread, None, context):
+                        yield event
+
+                async for event in self._process_events(
+                    thread,
+                    context,
+                    stream_structured_input_response,
+                ):
+                    yield event
+
             case ThreadsRetryAfterItemReq():
                 thread_metadata = await self.store.load_thread(
                     request.params.thread_id, context=context
@@ -715,6 +755,48 @@ async def _process_sync_custom_action(
             )
         )
 
+    async def _apply_structured_input_submission(
+        self,
+        item: StructuredInputItem,
+        submission: StructuredInputSubmission,
+    ) -> StructuredInputItem:
+        if item.status != "pending":
+            raise ValueError(f"Structured input item {item.id} is not pending")
+
+        updated_item = item.model_copy(deep=True)
+        questions_by_id = {
+            question.id: question for question in updated_item.inputs
+        }
+        submitted_question_ids = set(submission.answers)
+        unknown_question_ids = submitted_question_ids.difference(questions_by_id)
+        if unknown_question_ids:
+            unknown = ", ".join(sorted(unknown_question_ids))
+            logger.warning(
+                f"Structured input item {item.id} received unknown question id(s), ignoring: {unknown}"
+            )
+
+        for question in updated_item.inputs:
+            answer = submission.answers.get(question.id)
+
+            if (
+                submission.status == "skipped" or
+                answer is None or
+                answer.skipped or
+                not answer.values
+            ):
+                question.answer = StructuredInputAnswer(skipped=True)
+                continue
+
+            values = answer.values
+            if isinstance(question, StructuredInputMultipleChoice):
+                if not question.multiple:
+                    values = values[:1]
+
+            question.answer = StructuredInputAnswer(values=values)
+
+        updated_item.status = submission.status
+        return updated_item
+
     async def _cleanup_pending_client_tool_call(
         self, thread: ThreadMetadata, context: TContext
     ) -> None:
diff --git a/chatkit/types.py b/chatkit/types.py
index f9da6a0..4163758 100644
--- a/chatkit/types.py
+++ b/chatkit/types.py
@@ -108,6 +108,39 @@ class ThreadAddClientToolOutputParams(BaseModel):
     result: Any
 
 
+class StructuredInputAnswerSubmission(BaseModel):
+    """Client-submitted answer for a structured input."""
+
+    values: list[str] = Field(default_factory=list)
+    """Text answer values submitted for the structured input."""
+    skipped: bool = False
+    """Whether this structured input answer was skipped."""
+
+
+class StructuredInputSubmission(BaseModel):
+    """Client-submitted answers for a pending structured input item."""
+
+    status: Literal["answered", "skipped"] = "answered"
+    """Overall status for the structured input submission."""
+    answers: dict[str, StructuredInputAnswerSubmission] = Field(default_factory=dict)
+    """Answers keyed by structured input id."""
+
+
+class ThreadsAddStructuredInputReq(BaseReq):
+    """Request to submit answers for a pending structured input item."""
+
+    type: Literal["threads.add_structured_input"] = "threads.add_structured_input"
+    params: ThreadAddStructuredInputParams
+
+
+class ThreadAddStructuredInputParams(BaseModel):
+    """Parameters for adding structured input to a thread."""
+
+    thread_id: str
+    item_id: str
+    input: StructuredInputSubmission
+
+
 class ThreadsCustomActionReq(BaseReq):
     """Request to execute a custom action within a thread."""
 
@@ -272,6 +305,7 @@ class ThreadDeleteParams(BaseModel):
     ThreadsCreateReq
     | ThreadsAddUserMessageReq
     | ThreadsAddClientToolOutputReq
+    | ThreadsAddStructuredInputReq
     | ThreadsRetryAfterItemReq
     | ThreadsCustomActionReq
 )
@@ -308,6 +342,7 @@ def is_streaming_req(request: ChatKitReq) -> TypeIs[StreamingReq]:
             ThreadsAddUserMessageReq,
             ThreadsRetryAfterItemReq,
             ThreadsAddClientToolOutputReq,
+            ThreadsAddStructuredInputReq,
             ThreadsCustomActionReq,
         ),
     )
@@ -660,6 +695,66 @@ class GeneratedImageItem(ThreadItemBase):
     image: GeneratedImage | None = None
 
 
+class StructuredInputAnswer(BaseModel):
+    """Answer recorded for a structured input."""
+
+    values: list[str] = Field(default_factory=list)
+    """Text answer values recorded for the structured input."""
+    skipped: bool = False
+    """Whether this structured input answer was skipped."""
+
+
+class StructuredInputBase(BaseModel):
+    """Base fields shared by structured inputs."""
+
+    id: str
+    """Stable id for this structured input."""
+    question: str
+    """Question shown to the user."""
+    answer: StructuredInputAnswer | None = None
+    """Answer recorded for this structured input, if available."""
+
+
+class StructuredInputMultipleChoiceOption(BaseModel):
+    """Option shown for a multiple-choice structured input."""
+
+    value: str
+    """Text value submitted when this option is selected."""
+
+
+class StructuredInputMultipleChoice(StructuredInputBase):
+    """Structured input answered by choosing one or more options."""
+
+    type: Literal["multiple_choice"] = "multiple_choice"
+    options: list[StructuredInputMultipleChoiceOption]
+    """Suggested choices to display before the freeform custom answer affordance."""
+    multiple: bool = False
+    """Whether the user may submit more than one text value."""
+
+
+class StructuredInputFreeform(StructuredInputBase):
+    """Structured input answered with freeform text."""
+
+    type: Literal["freeform"] = "freeform"
+    description: str | None = None
+    """Supporting text shown with this input."""
+
+
+StructuredInput = Annotated[
+    StructuredInputMultipleChoice | StructuredInputFreeform,
+    Field(discriminator="type"),
+]
+"""Structured input variants supported by a structured input item."""
+
+
+class StructuredInputItem(ThreadItemBase):
+    """Thread item requesting structured input from the user."""
+
+    type: Literal["structured_input"] = "structured_input"
+    status: Literal["pending", "answered", "skipped"] = "pending"
+    inputs: list[StructuredInput]
+
+
 class TaskItem(ThreadItemBase):
     """Thread item containing a task."""
 
@@ -706,6 +801,7 @@ class SDKHiddenContextItem(ThreadItemBase):
     | ClientToolCallItem
     | WidgetItem
     | GeneratedImageItem
+    | StructuredInputItem
     | WorkflowItem
     | TaskItem
     | HiddenContextItem
diff --git a/docs/guides/accept-rich-user-input.md b/docs/guides/accept-rich-user-input.md
index 0849103..6a1cea1 100644
--- a/docs/guides/accept-rich-user-input.md
+++ b/docs/guides/accept-rich-user-input.md
@@ -1,10 +1,11 @@
 # Accept rich user input
 
-This guide explains how a ChatKit server accepts user input beyond plain text—such as attachments and @-mentions—and makes it available to your inference pipeline.
+This guide explains how a ChatKit server accepts user input beyond plain text, such as attachments, structured follow-up answers, and @-mentions, and makes it available to your inference pipeline.
 
 At a high level:
 
 - Attachments let users upload files that your model can read.
+- Structured input lets the assistant ask for specific follow-up answers.
 - @-mentions let users tag entities so the model does not have to guess from free text.
 
 ## Attachments: let users upload files
@@ -228,6 +229,64 @@ async def transcribe(self, audio_input: AudioInput, context: RequestContext) ->
 
 Return a `TranscriptionResult` that includes the final `text` that should appear in the composer.
 
+## Structured input: ask for specific answers
+
+Structured input lets your assistant ask the user for small, typed follow-up answers as part of the conversation. The prompt takes over the composer with focused controls, plus a skip option. Use structured input when the next step depends on specific choices or short fields, and free-text back-and-forth would be slower or easier to misread.
+
+The server streams a [`StructuredInputItem`](../api/chatkit/types.md#chatkit.types.StructuredInputItem) during `respond`. ChatKit renders the questions in the composer area instead of the normal free-text input, then records the result on the same thread item when the user answers or skips.
+
+### Stream a structured input item
+
+Yield a `StructuredInputItem` from `respond` when you need the user to answer before continuing.
+
+```python
+from datetime import datetime
+
+from chatkit.types import (
+    StructuredInputFreeform,
+    StructuredInputItem,
+    StructuredInputMultipleChoice,
+    StructuredInputMultipleChoiceOption,
+    ThreadItemDoneEvent,
+)
+
+
+yield ThreadItemDoneEvent(
+    item=StructuredInputItem(
+        id=self.store.generate_item_id("message", thread, context),
+        thread_id=thread.id,
+        created_at=datetime.now(),
+        inputs=[
+            StructuredInputMultipleChoice(
+                id="priority",
+                question="What priority should I use?",
+                options=[
+                    StructuredInputMultipleChoiceOption(value="Low"),
+                    StructuredInputMultipleChoiceOption(value="Medium"),
+                    StructuredInputMultipleChoiceOption(value="High"),
+                ],
+            ),
+            StructuredInputFreeform(
+                id="notes",
+                question="Any extra context?",
+                description="Optional details to include.",
+            ),
+        ],
+    )
+)
+return
+```
+
+Use [`StructuredInputMultipleChoice`](../api/chatkit/types.md#chatkit.types.StructuredInputMultipleChoice) for choice prompts and [`StructuredInputFreeform`](../api/chatkit/types.md#chatkit.types.StructuredInputFreeform) for short text answers. Set `multiple=True` on multiple-choice input when the user may submit more than one value.
+
+After the user submits or skips, ChatKit records the result on the structured input item.
+
+### Convert structured input submissions into model input
+
+The default [`ThreadItemConverter`](../api/chatkit/agents.md#chatkit.agents.ThreadItemConverter) includes structured input items in model input. It describes the prompt status and each answer as answered, skipped, or unanswered.
+
+If your model needs a different format, override `ThreadItemConverter.structured_input_to_input` before calling `Runner.run_streamed`.
+
 ## @-mentions: tag entities in user messages
 
 Enable @-mentions so users can tag entities (like documents, tickets, or users) instead of pasting raw identifiers. Mentions travel through ChatKit as structured tags so the model can resolve entities instead of guessing from free text.
@@ -361,4 +420,3 @@ Clicks and hover previews apply to the tagged entities shown in past user messag
 
 - `entities.onClick` fires when a user clicks a tag in the transcript. Handle navigation or open a detail view. See the [onClick option](https://openai.github.io/chatkit-js/api/openai/chatkit/type-aliases/entitiesoption/#onclick).
 - `entities.onRequestPreview` runs when the user hovers or taps a tag that has `interactive: true`. Return a `BasicRoot` widget; you can build one with `WidgetTemplate.build_basic(...)` if you are building the preview widgets server-side. See the [onRequestPreview option](https://openai.github.io/chatkit-js/api/openai/chatkit/type-aliases/entitiesoption/#onrequestpreview).
-
diff --git a/pyproject.toml b/pyproject.toml
index 04ad045..9f24fee 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "openai-chatkit"
-version = "1.6.3"
+version = "1.6.4"
 description = "A ChatKit backend SDK."
 readme = "README.md"
 requires-python = ">=3.10"
@@ -8,9 +8,10 @@ dependencies = ["pydantic", "uvicorn", "openai", "openai-agents>=0.3.2", "jinja2
 
 [dependency-groups]
 dev = [
+  "griffe==1.14.0",
   "pytest", "pytest-asyncio", "debugpy", "fastapi", "python-multipart", "psycopg2-binary", "flask", "pyright",
   "mypy", "ruff==0.9.2",
-  "mkdocs", "mkdocs-material", "mkdocstrings[python]", "mkdocs-gen-files"
+  "mkdocs", "mkdocs-material", "mkdocstrings==0.30.1", "mkdocstrings-python==1.18.2", "mkdocs-gen-files"
 ]
 lint = [
   "ruff"
diff --git a/tests/test_agents.py b/tests/test_agents.py
index 1dfe81d..5a97d07 100644
--- a/tests/test_agents.py
+++ b/tests/test_agents.py
@@ -2,6 +2,7 @@
 import json
 from collections.abc import AsyncIterator
 from datetime import datetime
+from importlib import import_module
 from typing import cast
 from unittest.mock import AsyncMock, Mock
 
@@ -23,7 +24,6 @@
     StreamEvent,
     ToolCallItem,
 )
-from agents._run_impl import QueueCompleteSentinel
 from openai.types.responses import (
     EasyInputMessageParam,
     ResponseFileSearchToolCall,
@@ -85,6 +85,11 @@
     HiddenContextItem,
     InferenceOptions,
     Page,
+    StructuredInputAnswer,
+    StructuredInputFreeform,
+    StructuredInputItem,
+    StructuredInputMultipleChoice,
+    StructuredInputMultipleChoiceOption,
     TaskItem,
     ThoughtTask,
     Thread,
@@ -112,13 +117,31 @@
 mock_store.add_thread_item = AsyncMock()
 
 
+def make_queue_complete_sentinel():
+    for module_name in (
+        "agents.result",
+        "agents.run_internal.run_steps",
+        "agents._run_impl",
+    ):
+        try:
+            module = import_module(module_name)
+        except ImportError:
+            continue
+
+        sentinel = getattr(module, "QueueCompleteSentinel", None)
+        if sentinel is not None:
+            return sentinel()
+
+    raise ImportError("QueueCompleteSentinel not found in installed agents package")
+
+
 class RunResult(RunResultStreaming):
     def add_event(self, event: StreamEvent):
         self._event_queue.put_nowait(event)
 
     def done(self):
         self.is_complete = True
-        self._event_queue.put_nowait(QueueCompleteSentinel())
+        self._event_queue.put_nowait(make_queue_complete_sentinel())
 
     def throw_input_guardrails(self):
         self._stored_exception = InputGuardrailTripwireTriggered(
@@ -131,7 +154,7 @@ def throw_input_guardrails(self):
             )
         )
         self.is_complete = True
-        self._event_queue.put_nowait(QueueCompleteSentinel())
+        self._event_queue.put_nowait(make_queue_complete_sentinel())
 
     def throw_output_guardrails(self):
         self._stored_exception = OutputGuardrailTripwireTriggered(
@@ -146,7 +169,7 @@ def throw_output_guardrails(self):
             )
         )
         self.is_complete = True
-        self._event_queue.put_nowait(QueueCompleteSentinel())
+        self._event_queue.put_nowait(make_queue_complete_sentinel())
 
 
 def make_result() -> RunResult:
@@ -725,6 +748,46 @@ async def test_input_item_converter_with_client_tool_call():
     }
 
 
+async def test_input_item_converter_with_structured_input():
+    items = [
+        StructuredInputItem(
+            id="si_123",
+            thread_id=thread.id,
+            created_at=datetime.now(),
+            status="answered",
+            inputs=[
+                StructuredInputMultipleChoice(
+                    id="subject",
+                    question="Which subject is this lesson for?",
+                    options=[
+                        StructuredInputMultipleChoiceOption(value="Math"),
+                        StructuredInputMultipleChoiceOption(value="Science"),
+                    ],
+                    answer=StructuredInputAnswer(values=["Math"]),
+                ),
+                StructuredInputFreeform(
+                    id="details",
+                    question="Anything else to know?",
+                    answer=StructuredInputAnswer(skipped=True),
+                ),
+            ],
+        )
+    ]
+
+    input_items = await simple_to_agent_input(items)
+    assert len(input_items) == 1
+    assert input_items[0] == {
+        "content": [
+            {
+                "text": "A structured input request was displayed to the user with the following status: answered\n<StructuredInput>\n- Which subject is this lesson for?: Math\n- Anything else to know?: skipped\n</StructuredInput>",
+                "type": "input_text",
+            },
+        ],
+        "role": "user",
+        "type": "message",
+    }
+
+
 async def test_stream_agent_response_yields_context_events_without_streaming_events():
     context = AgentContext(
         previous_response_id=None, thread=thread, store=mock_store, request_context=None
diff --git a/tests/test_chatkit_server.py b/tests/test_chatkit_server.py
index ec30b51..ae045d2 100644
--- a/tests/test_chatkit_server.py
+++ b/tests/test_chatkit_server.py
@@ -50,9 +50,16 @@
     LockedStatus,
     Page,
     ProgressUpdateEvent,
+    StructuredInputAnswerSubmission,
+    StructuredInputFreeform,
+    StructuredInputItem,
+    StructuredInputMultipleChoice,
+    StructuredInputMultipleChoiceOption,
+    StructuredInputSubmission,
     SyncCustomActionResponse,
     Thread,
     ThreadAddClientToolOutputParams,
+    ThreadAddStructuredInputParams,
     ThreadAddUserMessageParams,
     ThreadCreatedEvent,
     ThreadCreateParams,
@@ -69,6 +76,7 @@
     ThreadMetadata,
     ThreadRetryAfterItemParams,
     ThreadsAddClientToolOutputReq,
+    ThreadsAddStructuredInputReq,
     ThreadsAddUserMessageReq,
     ThreadsCreateReq,
     ThreadsCustomActionReq,
@@ -1070,6 +1078,322 @@ async def action(
         assert events[1].update.widget == Card(children=[Text(value="Email sent!")])
 
 
+async def test_add_structured_input_replaces_item_with_custom_answer_and_resumes_response():
+    async def responder(
+        thread: ThreadMetadata,
+        input: UserMessageItem | None,
+        context: Any,
+    ) -> AsyncIterator[ThreadStreamEvent]:
+        if input is not None:
+            yield ThreadItemDoneEvent(
+                item=StructuredInputItem(
+                    id="si_1",
+                    thread_id=thread.id,
+                    created_at=datetime.now(),
+                    inputs=[
+                        StructuredInputMultipleChoice(
+                            id="subject",
+                            question="Which subject is this lesson for?",
+                            options=[
+                                StructuredInputMultipleChoiceOption(value="Math"),
+                                StructuredInputMultipleChoiceOption(value="Science"),
+                            ],
+                        ),
+                        StructuredInputFreeform(
+                            id="details",
+                            question="Anything else to know?",
+                        ),
+                    ],
+                )
+            )
+            return
+
+        yield ThreadItemDoneEvent(
+            item=AssistantMessageItem(
+                id="msg_after_structured_input",
+                content=[AssistantMessageContent(text="Thanks, continuing now.")],
+                created_at=datetime.now(),
+                thread_id=thread.id,
+            )
+        )
+
+    with make_server(responder) as server:
+        events = await server.process_streaming(
+            ThreadsCreateReq(
+                params=ThreadCreateParams(
+                    input=UserMessageInput(
+                        content=[UserMessageTextContent(text="Plan a lesson")],
+                        attachments=[],
+                        inference_options=InferenceOptions(),
+                    )
+                )
+            )
+        )
+        thread = next(
+            event.thread for event in events if isinstance(event, ThreadCreatedEvent)
+        )
+
+        events = await server.process_streaming(
+            ThreadsAddStructuredInputReq(
+                params=ThreadAddStructuredInputParams(
+                    thread_id=thread.id,
+                    item_id="si_1",
+                    input=StructuredInputSubmission(
+                        status="answered",
+                        answers={
+                            "subject": StructuredInputAnswerSubmission(
+                                values=["Private class"]
+                            ),
+                            "details": StructuredInputAnswerSubmission(
+                                values=["Please include group work."]
+                            ),
+                        },
+                    ),
+                )
+            )
+        )
+
+        replaced_event = next(
+            event for event in events if isinstance(event, ThreadItemReplacedEvent)
+        )
+        assert isinstance(replaced_event.item, StructuredInputItem)
+        assert replaced_event.item.status == "answered"
+        assert replaced_event.item.inputs[0].answer is not None
+        assert replaced_event.item.inputs[0].answer.values == ["Private class"]
+        assert replaced_event.item.inputs[1].answer is not None
+        assert replaced_event.item.inputs[1].answer.values == [
+            "Please include group work."
+        ]
+
+        persisted_item = await server.store.load_item(
+            thread.id,
+            "si_1",
+            DEFAULT_CONTEXT,
+        )
+        assert persisted_item == replaced_event.item
+        assert any(
+            isinstance(event, ThreadItemDoneEvent)
+            and isinstance(event.item, AssistantMessageItem)
+            and event.item.id == "msg_after_structured_input"
+            for event in events
+        )
+
+
+async def test_add_structured_input_treats_omitted_answers_as_skipped():
+    async def responder(
+        thread: ThreadMetadata,
+        input: UserMessageItem | None,
+        context: Any,
+    ) -> AsyncIterator[ThreadStreamEvent]:
+        if input is not None:
+            yield ThreadItemDoneEvent(
+                item=StructuredInputItem(
+                    id="si_1",
+                    thread_id=thread.id,
+                    created_at=datetime.now(),
+                    inputs=[
+                        StructuredInputMultipleChoice(
+                            id="subject",
+                            question="Which subject is this lesson for?",
+                            options=[
+                                StructuredInputMultipleChoiceOption(value="Math"),
+                                StructuredInputMultipleChoiceOption(value="Science"),
+                            ],
+                        ),
+                        StructuredInputFreeform(
+                            id="details",
+                            question="Anything else to know?",
+                        ),
+                    ],
+                )
+            )
+
+    with make_server(responder) as server:
+        events = await server.process_streaming(
+            ThreadsCreateReq(
+                params=ThreadCreateParams(
+                    input=UserMessageInput(
+                        content=[UserMessageTextContent(text="Plan a lesson")],
+                        attachments=[],
+                        inference_options=InferenceOptions(),
+                    )
+                )
+            )
+        )
+        thread = next(
+            event.thread for event in events if isinstance(event, ThreadCreatedEvent)
+        )
+
+        events = await server.process_streaming(
+            ThreadsAddStructuredInputReq(
+                params=ThreadAddStructuredInputParams(
+                    thread_id=thread.id,
+                    item_id="si_1",
+                    input=StructuredInputSubmission(
+                        status="answered",
+                        answers={
+                            "subject": StructuredInputAnswerSubmission(
+                                values=["Math"]
+                            ),
+                        },
+                    ),
+                )
+            )
+        )
+
+        replaced_event = next(
+            event for event in events if isinstance(event, ThreadItemReplacedEvent)
+        )
+        assert isinstance(replaced_event.item, StructuredInputItem)
+        subject_answer = replaced_event.item.inputs[0].answer
+        assert subject_answer is not None
+        assert subject_answer.values == ["Math"]
+        details_answer = replaced_event.item.inputs[1].answer
+        assert details_answer is not None
+        assert details_answer.skipped
+
+
+async def test_add_structured_input_ignores_unknown_answer_ids():
+    async def responder(
+        thread: ThreadMetadata,
+        input: UserMessageItem | None,
+        context: Any,
+    ) -> AsyncIterator[ThreadStreamEvent]:
+        if input is not None:
+            yield ThreadItemDoneEvent(
+                item=StructuredInputItem(
+                    id="si_1",
+                    thread_id=thread.id,
+                    created_at=datetime.now(),
+                    inputs=[
+                        StructuredInputFreeform(
+                            id="details",
+                            question="Anything else to know?",
+                        ),
+                    ],
+                )
+            )
+
+    with make_server(responder) as server:
+        events = await server.process_streaming(
+            ThreadsCreateReq(
+                params=ThreadCreateParams(
+                    input=UserMessageInput(
+                        content=[UserMessageTextContent(text="Plan a lesson")],
+                        attachments=[],
+                        inference_options=InferenceOptions(),
+                    )
+                )
+            )
+        )
+        thread = next(
+            event.thread for event in events if isinstance(event, ThreadCreatedEvent)
+        )
+
+        events = await server.process_streaming(
+            ThreadsAddStructuredInputReq(
+                params=ThreadAddStructuredInputParams(
+                    thread_id=thread.id,
+                    item_id="si_1",
+                    input=StructuredInputSubmission(
+                        status="answered",
+                        answers={
+                            "details": StructuredInputAnswerSubmission(
+                                values=["Please include group work."]
+                            ),
+                            "unknown": StructuredInputAnswerSubmission(
+                                values=["ignored"]
+                            ),
+                        },
+                    ),
+                )
+            )
+        )
+
+        replaced_event = next(
+            event for event in events if isinstance(event, ThreadItemReplacedEvent)
+        )
+        assert isinstance(replaced_event.item, StructuredInputItem)
+        answer = replaced_event.item.inputs[0].answer
+        assert answer is not None
+        assert answer.values == ["Please include group work."]
+
+
+async def test_add_structured_input_truncates_extra_single_choice_values():
+    async def responder(
+        thread: ThreadMetadata,
+        input: UserMessageItem | None,
+        context: Any,
+    ) -> AsyncIterator[ThreadStreamEvent]:
+        yield ThreadItemDoneEvent(
+            item=StructuredInputItem(
+                id="si_1",
+                thread_id=thread.id,
+                created_at=datetime.now(),
+                inputs=[
+                    StructuredInputMultipleChoice(
+                        id="subject",
+                        question="Which subject is this lesson for?",
+                        options=[
+                            StructuredInputMultipleChoiceOption(value="Math"),
+                            StructuredInputMultipleChoiceOption(value="Science"),
+                        ],
+                    ),
+                ],
+            )
+        )
+
+    with make_server(responder) as server:
+        events = await server.process_streaming(
+            ThreadsCreateReq(
+                params=ThreadCreateParams(
+                    input=UserMessageInput(
+                        content=[UserMessageTextContent(text="Plan a lesson")],
+                        attachments=[],
+                        inference_options=InferenceOptions(),
+                    )
+                )
+            )
+        )
+        thread = next(
+            event.thread for event in events if isinstance(event, ThreadCreatedEvent)
+        )
+
+        events = await server.process_streaming(
+            ThreadsAddStructuredInputReq(
+                params=ThreadAddStructuredInputParams(
+                    thread_id=thread.id,
+                    item_id="si_1",
+                    input=StructuredInputSubmission(
+                        status="answered",
+                        answers={
+                            "subject": StructuredInputAnswerSubmission(
+                                values=["Math", "Science"],
+                            ),
+                        },
+                    ),
+                )
+            )
+        )
+
+        replaced_event = next(
+            event for event in events if isinstance(event, ThreadItemReplacedEvent)
+        )
+        assert isinstance(replaced_event.item, StructuredInputItem)
+        answer = replaced_event.item.inputs[0].answer
+        assert answer is not None
+        assert answer.values == ["Math"]
+
+        persisted_item = await server.store.load_item(
+            thread.id,
+            "si_1",
+            DEFAULT_CONTEXT,
+        )
+        assert isinstance(persisted_item, StructuredInputItem)
+        assert persisted_item.status == "answered"
+        assert persisted_item.inputs[0].answer == answer
+
+
 async def test_calls_action_sync():
     sync_actions = []
 
diff --git a/uv.lock b/uv.lock
index 7e68417..cba19bc 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1,6 +1,22 @@
 version = 1
 revision = 3
 requires-python = ">=3.10"
+resolution-markers = [
+    "python_full_version >= '3.15'",
+    "python_full_version < '3.15'",
+]
+
+[options]
+exclude-newer = "2026-05-06T15:30:24Z"
+
+[[package]]
+name = "annotated-doc"
+version = "0.0.4"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/57/ba/046ceea27344560984e26a590f90bc7f4a75b06701f653222458922b558c/annotated_doc-0.0.4.tar.gz", hash = "sha256:fbcda96e87e9c92ad167c2e53839e57503ecfda18804ea28102353485033faa4", size = 7288, upload-time = "2025-11-10T22:07:42.062Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/1e/d3/26bf1008eb3d2daa8ef4cacc7f3bfdc11818d111f7e2d0201bc6e3b49d45/annotated_doc-0.0.4-py3-none-any.whl", hash = "sha256:571ac1dc6991c450b25a9c2d84a3705e2ae7a53467b5d111c24fa8baabbed320", size = 5303, upload-time = "2025-11-10T22:07:40.673Z" },
+]
 
 [[package]]
 name = "annotated-types"
@@ -13,35 +29,34 @@ wheels = [
 
 [[package]]
 name = "anyio"
-version = "4.11.0"
+version = "4.13.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "exceptiongroup", marker = "python_full_version < '3.11'" },
     { name = "idna" },
-    { name = "sniffio" },
     { name = "typing-extensions", marker = "python_full_version < '3.13'" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/c6/78/7d432127c41b50bccba979505f272c16cbcadcc33645d5fa3a738110ae75/anyio-4.11.0.tar.gz", hash = "sha256:82a8d0b81e318cc5ce71a5f1f8b5c4e63619620b63141ef8c995fa0db95a57c4", size = 219094, upload-time = "2025-09-23T09:19:12.58Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/19/14/2c5dd9f512b66549ae92767a9c7b330ae88e1932ca57876909410251fe13/anyio-4.13.0.tar.gz", hash = "sha256:334b70e641fd2221c1505b3890c69882fe4a2df910cba14d97019b90b24439dc", size = 231622, upload-time = "2026-03-24T12:59:09.671Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/15/b3/9b1a8074496371342ec1e796a96f99c82c945a339cd81a8e73de28b4cf9e/anyio-4.11.0-py3-none-any.whl", hash = "sha256:0287e96f4d26d4149305414d4e3bc32f0dcd0862365a4bddea19d7a1ec38c4fc", size = 109097, upload-time = "2025-09-23T09:19:10.601Z" },
+    { url = "https://files.pythonhosted.org/packages/da/42/e921fccf5015463e32a3cf6ee7f980a6ed0f395ceeaa45060b61d86486c2/anyio-4.13.0-py3-none-any.whl", hash = "sha256:08b310f9e24a9594186fd75b4f73f4a4152069e3853f1ed8bfbf58369f4ad708", size = 114353, upload-time = "2026-03-24T12:59:08.246Z" },
 ]
 
 [[package]]
 name = "attrs"
-version = "25.4.0"
+version = "26.1.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/6b/5c/685e6633917e101e5dcb62b9dd76946cbb57c26e133bae9e0cd36033c0a9/attrs-25.4.0.tar.gz", hash = "sha256:16d5969b87f0859ef33a48b35d55ac1be6e42ae49d5e853b597db70c35c57e11", size = 934251, upload-time = "2025-10-06T13:54:44.725Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/9a/8e/82a0fe20a541c03148528be8cac2408564a6c9a0cc7e9171802bc1d26985/attrs-26.1.0.tar.gz", hash = "sha256:d03ceb89cb322a8fd706d4fb91940737b6642aa36998fe130a9bc96c985eff32", size = 952055, upload-time = "2026-03-19T14:22:25.026Z" }
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+    { url = "https://files.pythonhosted.org/packages/64/b4/17d4b0b2a2dc85a6df63d1157e028ed19f90d4cd97c36717afef2bc2f395/attrs-26.1.0-py3-none-any.whl", hash = "sha256:c647aa4a12dfbad9333ca4e71fe62ddc36f4e63b2d260a37a8b83d2f043ac309", size = 67548, upload-time = "2026-03-19T14:22:23.645Z" },
 ]
 
 [[package]]
 name = "babel"
-version = "2.17.0"
+version = "2.18.0"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/7d/6b/d52e42361e1aa00709585ecc30b3f9684b3ab62530771402248b1b1d6240/babel-2.17.0.tar.gz", hash = "sha256:0c54cffb19f690cdcc52a3b50bcbf71e07a808d1c80d549f2459b9d2cf0afb9d", size = 9951852, upload-time = "2025-02-01T15:17:41.026Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/7d/b2/51899539b6ceeeb420d40ed3cd4b7a40519404f9baf3d4ac99dc413a834b/babel-2.18.0.tar.gz", hash = "sha256:b80b99a14bd085fcacfa15c9165f651fbb3406e66cc603abf11c5750937c992d", size = 9959554, upload-time = "2026-02-01T12:30:56.078Z" }
 wheels = [
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+    { url = "https://files.pythonhosted.org/packages/77/f5/21d2de20e8b8b0408f0681956ca2c69f1320a3848ac50e6e7f39c6159675/babel-2.18.0-py3-none-any.whl", hash = "sha256:e2b422b277c2b9a9630c1d7903c2a00d0830c409c59ac8cae9081c92f1aeba35", size = 10196845, upload-time = "2026-02-01T12:30:53.445Z" },
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 [[package]]
@@ -55,16 +70,15 @@ wheels = [
 
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 name = "backrefs"
-version = "5.9"
+version = "7.0"
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-sdist = { url = "https://files.pythonhosted.org/packages/eb/a7/312f673df6a79003279e1f55619abbe7daebbb87c17c976ddc0345c04c7b/backrefs-5.9.tar.gz", hash = "sha256:808548cb708d66b82ee231f962cb36faaf4f2baab032f2fbb783e9c2fdddaa59", size = 5765857, upload-time = "2025-06-22T19:34:13.97Z" }
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 [[package]]
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+[[package]]
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