diff --git a/codex-rs/core/src/tools/handlers/mod.rs b/codex-rs/core/src/tools/handlers/mod.rs
index 25a2ae1508..4ce3be4a24 100644
--- a/codex-rs/core/src/tools/handlers/mod.rs
+++ b/codex-rs/core/src/tools/handlers/mod.rs
@@ -24,6 +24,7 @@ pub(crate) mod request_plugin_install_spec;
 mod request_user_input;
 mod request_user_input_async;
 pub(crate) mod request_user_input_spec;
+mod send_message_to_user_async;
 pub(crate) mod shell_spec;
 mod sleep;
 mod test_sync;
@@ -70,6 +71,7 @@ pub use request_permissions::RequestPermissionsHandler;
 pub use request_plugin_install::RequestPluginInstallHandler;
 pub use request_user_input::RequestUserInputHandler;
 pub use request_user_input_async::RequestUserInputAsyncHandler;
+pub use send_message_to_user_async::SendMessageToUserAsyncHandler;
 pub use sleep::SleepHandler;
 pub use test_sync::TestSyncHandler;
 pub(crate) use tool_search::ToolSearchHandlerCache;
diff --git a/codex-rs/core/src/tools/handlers/send_message_to_user_async.rs b/codex-rs/core/src/tools/handlers/send_message_to_user_async.rs
new file mode 100644
index 0000000000..2dcc61ee93
--- /dev/null
+++ b/codex-rs/core/src/tools/handlers/send_message_to_user_async.rs
@@ -0,0 +1,109 @@
+use crate::function_tool::FunctionCallError;
+use crate::tools::context::FunctionToolOutput;
+use crate::tools::context::ToolInvocation;
+use crate::tools::context::ToolPayload;
+use crate::tools::context::boxed_tool_output;
+use crate::tools::handlers::parse_arguments;
+use crate::tools::registry::CoreToolRuntime;
+use crate::tools::registry::ToolExecutor;
+use codex_protocol::items::AgentMessageContent;
+use codex_protocol::items::AgentMessageDelivery;
+use codex_protocol::items::AgentMessageItem;
+use codex_protocol::items::TurnItem;
+use codex_protocol::models::MessagePhase;
+use codex_tools::JsonSchema;
+use codex_tools::ResponsesApiTool;
+use codex_tools::ToolName;
+use codex_tools::ToolSpec;
+use serde::Deserialize;
+use std::collections::BTreeMap;
+
+const TOOL_NAME: &str = "send_message_to_user_async";
+
+pub struct SendMessageToUserAsyncHandler;
+
+#[derive(Debug, Deserialize)]
+#[serde(deny_unknown_fields)]
+struct SendMessageToUserAsyncArgs {
+    message: String,
+}
+
+impl ToolExecutor<ToolInvocation> for SendMessageToUserAsyncHandler {
+    fn tool_name(&self) -> ToolName {
+        ToolName::plain(TOOL_NAME)
+    }
+
+    fn spec(&self) -> ToolSpec {
+        let properties = BTreeMap::from([(
+            "message".to_string(),
+            JsonSchema::string(Some(
+                "The concise question or update to send to the user.".to_string(),
+            )),
+        )]);
+
+        ToolSpec::Function(ResponsesApiTool {
+            name: TOOL_NAME.to_string(),
+            description: "Send a concise message that needs the user's attention during ongoing work. The tool returns immediately without ending the turn or waiting for a reply; any reply arrives asynchronously as a new user message. Use this tool to ask for missing information, preferences, constraints, clarification, or approval; report a critical blocker or a finding that may change the task's direction; or answer a user question or status request received while work is still in progress. Use this tool when a message needs the user's immediate attention; use commentary for routine progress and intermediate context. Use clear formatting, such as bolding questions, to make requests easy to notice and answer."
+                .to_string(),
+            strict: false,
+            defer_loading: None,
+            parameters: JsonSchema::object(
+                properties,
+                Some(vec!["message".to_string()]),
+                /*additional_properties*/ Some(false.into()),
+            ),
+            output_schema: None,
+        })
+    }
+
+    fn handle<'a>(&'a self, invocation: ToolInvocation) -> codex_tools::ToolExecutorFuture<'a>
+    where
+        ToolInvocation: 'a,
+    {
+        Box::pin(async move {
+            let ToolInvocation {
+                session,
+                turn,
+                call_id,
+                payload,
+                ..
+            } = invocation;
+            let ToolPayload::Function { arguments } = payload else {
+                return Err(FunctionCallError::RespondToModel(format!(
+                    "{TOOL_NAME} handler received unsupported payload"
+                )));
+            };
+            let args: SendMessageToUserAsyncArgs = parse_arguments(&arguments)?;
+            let message = args.message.trim();
+            if message.is_empty() {
+                return Err(FunctionCallError::RespondToModel(
+                    "message must not be empty".to_string(),
+                ));
+            }
+
+            let item = TurnItem::AgentMessage(AgentMessageItem {
+                id: call_id,
+                content: vec![AgentMessageContent::Text {
+                    text: message.to_string(),
+                }],
+                phase: Some(MessagePhase::FinalAnswer),
+                memory_citation: None,
+                delivery: Some(AgentMessageDelivery::Async),
+                questions: None,
+            });
+            session.emit_turn_item_started(turn.as_ref(), &item).await;
+            session.emit_turn_item_completed(turn.as_ref(), item).await;
+
+            Ok(boxed_tool_output(FunctionToolOutput::from_text(
+                r#"{"accepted":true}"#.to_string(),
+                /*success*/ Some(true),
+            )))
+        })
+    }
+}
+
+impl CoreToolRuntime for SendMessageToUserAsyncHandler {
+    fn is_builtin_control_tool(&self) -> bool {
+        true
+    }
+}
diff --git a/codex-rs/core/src/tools/spec_plan.rs b/codex-rs/core/src/tools/spec_plan.rs
index 908bb143af..ef31ab2034 100644
--- a/codex-rs/core/src/tools/spec_plan.rs
+++ b/codex-rs/core/src/tools/spec_plan.rs
@@ -25,6 +25,7 @@ use crate::tools::handlers::RequestPermissionsHandler;
 use crate::tools::handlers::RequestPluginInstallHandler;
 use crate::tools::handlers::RequestUserInputAsyncHandler;
 use crate::tools::handlers::RequestUserInputHandler;
+use crate::tools::handlers::SendMessageToUserAsyncHandler;
 use crate::tools::handlers::SleepHandler;
 use crate::tools::handlers::TestSyncHandler;
 use crate::tools::handlers::ToolSearchHandlerCache;
@@ -1183,6 +1184,16 @@ fn add_core_utility_tools(context: &CoreToolPlanContext<'_>, registry: &mut Tool
         );
     }
 
+    if !turn_context.session_source.is_non_root_agent()
+        && context
+            .model_info
+            .experimental_supported_tools
+            .iter()
+            .any(|tool| tool == "send_message_to_user_async")
+    {
+        registry.add_with_exposure(SendMessageToUserAsyncHandler, ToolExposure::DirectModelOnly);
+    }
+
     if environment_mode.has_environment() && features.enabled(Feature::RequestPermissionsTool) {
         registry.add(RequestPermissionsHandler);
     }
diff --git a/codex-rs/core/tests/suite/request_user_input_async.rs b/codex-rs/core/tests/suite/request_user_input_async.rs
index fdb6cb93fb..7e20abf110 100644
--- a/codex-rs/core/tests/suite/request_user_input_async.rs
+++ b/codex-rs/core/tests/suite/request_user_input_async.rs
@@ -120,6 +120,195 @@ async fn persistent_async_message_guidance_follows_tool_availability(
     Ok(())
 }
 
+#[test_case(SessionSource::Exec, None, false; "root_without_opt_in")]
+#[test_case(SessionSource::Exec, Some("send_user_message_async"), false; "root_with_legacy_question_tool")]
+#[test_case(SessionSource::Exec, Some("request_user_input_async"), false; "root_with_question_tool")]
+#[test_case(SessionSource::Exec, Some("send_message_to_user_async"), true; "root_with_freeform_tool")]
+#[test_case(SessionSource::SubAgent(SubAgentSource::Other("test".to_string())), Some("send_message_to_user_async"), false; "subagent_with_freeform_tool")]
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn freeform_async_message_requires_root_and_exact_catalog_opt_in(
+    session_source: SessionSource,
+    catalog_tool: Option<&'static str>,
+    expected: bool,
+) -> Result<()> {
+    skip_if_no_network!(Ok(()));
+
+    let server = start_mock_server().await;
+    let responses = mount_sse_once(
+        &server,
+        sse(vec![ev_response_created("resp-1"), ev_completed("resp-1")]),
+    )
+    .await;
+    let test = test_codex()
+        .with_model_info_override("gpt-5.2", move |model| {
+            model.tool_mode = Some(ToolMode::CodeModeOnly);
+            model.experimental_supported_tools =
+                catalog_tool.map(str::to_string).into_iter().collect();
+        })
+        .build_with_auto_env(&server)
+        .await?;
+    let thread = test
+        .thread_manager
+        .start_thread(StartThreadOptions {
+            session_source: Some(session_source),
+            ..StartThreadOptions::new(test.config.clone())
+        })
+        .await?
+        .thread;
+    thread
+        .start_or_steer_turn(TurnInputRequest::user_input(vec![UserInput::Text {
+            text: "Report progress.".to_string(),
+            text_elements: Vec::new(),
+        }]))
+        .await?;
+    wait_for_event(&thread, |event| matches!(event, EventMsg::TurnComplete(_))).await;
+
+    let body = responses.single_request().body_json();
+    let tools = body["tools"].as_array().expect("request tools");
+    assert_eq!(
+        tools
+            .iter()
+            .any(|tool| tool["name"] == "send_message_to_user_async"),
+        expected,
+    );
+    Ok(())
+}
+
+#[tokio::test(flavor = "multi_thread", worker_threads = 2)]
+async fn freeform_async_message_emits_an_item_without_ending_the_turn() -> Result<()> {
+    skip_if_no_network!(Ok(()));
+
+    const CALL_ID: &str = "freeform-message";
+    const MESSAGE: &str = "I found a blocker that changes the plan.";
+    let server = start_mock_server().await;
+    let responses = mount_sse_sequence(
+        &server,
+        vec![
+            sse(vec![
+                ev_response_created("resp-1"),
+                ev_function_call_with_namespace(
+                    CALL_ID,
+                    "functions",
+                    "send_message_to_user_async",
+                    &json!({ "message": format!("  {MESSAGE}  ") }).to_string(),
+                ),
+                ev_completed("resp-1"),
+            ]),
+            sse(vec![
+                ev_response_created("resp-2"),
+                ev_function_call_with_namespace(
+                    "blank-message",
+                    "functions",
+                    "send_message_to_user_async",
+                    &json!({ "message": "  " }).to_string(),
+                ),
+                ev_completed("resp-2"),
+            ]),
+            sse(vec![
+                ev_response_created("resp-3"),
+                ev_assistant_message("final-message", "Finished."),
+                ev_completed("resp-3"),
+            ]),
+        ],
+    )
+    .await;
+    let test = test_codex()
+        .with_model_info_override("gpt-5.2", |model| {
+            model.tool_mode = Some(ToolMode::CodeModeOnly);
+            model.experimental_supported_tools.extend([
+                "send_message_to_user_async".to_string(),
+                "request_user_input_async".to_string(),
+            ]);
+            model
+                .model_messages
+                .as_mut()
+                .expect("model instruction metadata")
+                .tools = Some(ToolMessages {
+                send_user_message_async: Some(ToolMessage {
+                    description: Some("Questions only.".to_string()),
+                }),
+            });
+        })
+        .build_with_auto_env(&server)
+        .await?;
+    test.codex
+        .start_or_steer_turn(TurnInputRequest::user_input(vec![UserInput::Text {
+            text: "Keep me updated.".to_string(),
+            text_elements: Vec::new(),
+        }]))
+        .await?;
+
+    let started = wait_for_event_match(test.codex.as_ref(), |event| match event {
+        EventMsg::ItemStarted(event) if event.item.id() == CALL_ID => Some(event.item.clone()),
+        _ => None,
+    })
+    .await;
+    let completed = wait_for_event_match(test.codex.as_ref(), |event| match event {
+        EventMsg::ItemCompleted(event) if event.item.id() == CALL_ID => Some(event.item.clone()),
+        _ => None,
+    })
+    .await;
+    let expected = serde_json::to_value(TurnItem::AgentMessage(AgentMessageItem {
+        id: CALL_ID.to_string(),
+        content: vec![AgentMessageContent::Text {
+            text: MESSAGE.to_string(),
+        }],
+        phase: Some(MessagePhase::FinalAnswer),
+        memory_citation: None,
+        delivery: Some(AgentMessageDelivery::Async),
+        questions: None,
+    }))?;
+    assert_eq!(serde_json::to_value(started)?, expected);
+    assert_eq!(serde_json::to_value(completed)?, expected);
+    wait_for_event(test.codex.as_ref(), |event| {
+        let item = match event {
+            EventMsg::ItemStarted(event) => Some(&event.item),
+            EventMsg::ItemCompleted(event) => Some(&event.item),
+            _ => None,
+        };
+        assert!(!matches!(item, Some(TurnItem::AgentMessage(message)) if message.delivery == Some(AgentMessageDelivery::Async)));
+        matches!(event, EventMsg::TurnComplete(_))
+    }).await;
+
+    let requests = responses.requests();
+    assert_eq!(requests.len(), 3);
+    let body = requests[0].body_json();
+    let tools = body["tools"].as_array().expect("request tools");
+    let freeform_tool = tools
+        .iter()
+        .find(|tool| tool["name"] == "send_message_to_user_async")
+        .expect("freeform tool is directly available");
+    assert_eq!(freeform_tool["parameters"]["required"], json!(["message"]));
+    assert!(
+        freeform_tool["description"]
+            .as_str()
+            .expect("description")
+            .contains("report a critical blocker")
+    );
+    let question_tool = tools
+        .iter()
+        .find(|tool| tool["name"] == "request_user_input_async")
+        .expect("question tool is still directly available");
+    assert_eq!(question_tool["description"], "Questions only.");
+    assert_eq!(
+        requests[1].function_call_output_text(CALL_ID),
+        Some(r#"{"accepted":true}"#.to_string())
+    );
+    assert_eq!(
+        requests[2].function_call_output_text("blank-message"),
+        Some("message must not be empty".to_string())
+    );
+    assert!(
+        !requests[1]
+            .input()
+            .into_iter()
+            .any(|item| item["type"] == "message"
+                && item["role"] == "assistant"
+                && item.to_string().contains(MESSAGE))
+    );
+    Ok(())
+}
+
 #[test_case(None, "send_user_message_async"; "fallback_description")]
 #[test_case(None, "request_user_input_async"; "current_catalog_name")]
 #[test_case(Some(ToolMessages { send_user_message_async: None }), "send_user_message_async"; "missing_tool")]