huskies: merge 1228 story Render agent questions as numbered options in chat protocols without question UI

server/src/chat/transport/matrix/bot/context.rs

@@ -318,6 +318,10 @@ mod tests {
             pending_perm_replies: PendingPermReplies::new(),
             permission_timeout_secs: 120,
             remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
             status: Arc::new(crate::service::status::StatusBroadcaster::new()),
             chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
         })

server/src/chat/transport/matrix/bot/messages/handle_message.rs

@@ -95,7 +95,8 @@ pub(in crate::chat::transport::matrix::bot) async fn handle_message(
         String::new()
     };
     let prompt = format!(
-        "{event_log_ctx}{seed_prefix}[Your name is {bot_name}. Refer to yourself as {bot_name}, not Claude.]\n{active_project_ctx}\n{}",
+        "{event_log_ctx}{seed_prefix}[Your name is {bot_name}. Refer to yourself as {bot_name}, not Claude.]\n[{}]\n{active_project_ctx}\n{}",
+        crate::chat::util::QUESTION_FORMAT_INSTRUCTION,
         format_user_prompt(&sender, &user_message)
     );
 

server/src/chat/transport/matrix/bot/messages/on_room_message.rs

@@ -336,6 +336,60 @@ async fn try_handle_stop_command(
     true
 }
 
+/// Parse a chat reply to a pending [`QuestionSpec`](crate::http::context::QuestionSpec)
+/// into the answer it represents (story 1228, AC2/AC4/AC5).
+///
+/// Tries, in order: a comma-separated list of 1-based option numbers (e.g.
+/// `"2"` or `"1,3"`, validated against `num_options` and `multi_select`); a
+/// case-insensitive exact match against one of `labels`; and finally free
+/// text (the always-available "Other" path). Returns `None` only when the
+/// reply looks like an attempted numeric selection but is out of range or
+/// violates `multi_select` — the caller must re-prompt in that case rather
+/// than guessing or picking a default (AC4).
+fn parse_question_reply(
+    body: &str,
+    num_options: usize,
+    multi_select: bool,
+    labels: &[String],
+) -> Option<crate::http::context::QuestionAnswer> {
+    let body_trimmed = body.trim();
+    // Strip a leading "@mention " prefix (e.g. "@timmy 1") entirely, not just
+    // the '@' character, so a mention-prefixed reply still parses as a
+    // number/label rather than falling through to free text.
+    let trimmed = if body_trimmed.starts_with('@') {
+        body_trimmed
+            .split_once(char::is_whitespace)
+            .map(|(_, rest)| rest.trim_start())
+            .unwrap_or(body_trimmed)
+    } else {
+        body_trimmed
+    };
+    let tokens: Vec<&str> = trimmed.split(',').map(str::trim).collect();
+    let parsed_indices: Option<Vec<usize>> =
+        tokens.iter().map(|t| t.parse::<usize>().ok()).collect();
+    match parsed_indices {
+        Some(indices) if !trimmed.is_empty() => {
+            if indices.iter().any(|&i| i == 0 || i > num_options) {
+                None
+            } else {
+                let mut zero_based: Vec<usize> = indices.into_iter().map(|i| i - 1).collect();
+                zero_based.dedup();
+                if zero_based.len() > 1 && !multi_select {
+                    None
+                } else {
+                    Some(crate::http::context::QuestionAnswer::Selected(zero_based))
+                }
+            }
+        }
+        _ => match labels.iter().position(|l| l.eq_ignore_ascii_case(trimmed)) {
+            Some(idx) => Some(crate::http::context::QuestionAnswer::Selected(vec![idx])),
+            None => Some(crate::http::context::QuestionAnswer::FreeText(
+                trimmed.to_string(),
+            )),
+        },
+    }
+}
+
 pub(in crate::chat::transport::matrix::bot) async fn on_room_message(
     ev: OriginalSyncRoomMessageEvent,
     room: Room,
@@ -471,6 +525,59 @@ pub(in crate::chat::transport::matrix::bot) async fn on_room_message(
         }
     }
 
+    // If there is a pending question for this room, interpret the message as
+    // an answer instead of starting a new chat (story 1228). Checked before
+    // the pending-permission block below so the two never conflate (AC4):
+    // each is a fully independent store, and this only fires when a question
+    // is actually pending for this room.
+    if let Some((num_options, multi_select, labels)) = ctx
+        .services
+        .pending_question_replies
+        .peek_oldest_meta(incoming_room_id.as_str())
+        .await
+    {
+        let outcome = parse_question_reply(&body, num_options, multi_select, &labels);
+
+        match outcome {
+            None => {
+                // Invalid attempted selection — re-prompt without consuming
+                // the pending question (AC4: never strand the agent or
+                // silently pick a default).
+                let msg = "I didn't understand that reply. Please reply with a number \
+                           (or numbers separated by commas), an option's label, or your \
+                           own answer.";
+                let html = markdown_to_html(msg);
+                if let Ok(msg_id) = ctx.transport.send_message(&room_id_str, msg, &html).await
+                    && let Ok(event_id) = msg_id.parse()
+                {
+                    ctx.bot_sent_event_ids.lock().await.insert(event_id);
+                }
+                return;
+            }
+            Some(answer) => {
+                if let Some(tx) = ctx
+                    .services
+                    .pending_question_replies
+                    .resolve_oldest(incoming_room_id.as_str())
+                    .await
+                {
+                    let _ = tx.send(Ok(answer));
+                }
+                let confirmation = "Got it — thanks for answering.";
+                let html = markdown_to_html(confirmation);
+                if let Ok(msg_id) = ctx
+                    .transport
+                    .send_message(&room_id_str, confirmation, &html)
+                    .await
+                    && let Ok(event_id) = msg_id.parse()
+                {
+                    ctx.bot_sent_event_ids.lock().await.insert(event_id);
+                }
+                return;
+            }
+        }
+    }
+
     // If there is a pending permission prompt for this room, interpret the
     // message as a yes/no response instead of starting a new chat.
     {
@@ -1496,14 +1603,74 @@ pub(in crate::chat::transport::matrix::bot) async fn on_room_message(
 mod tests {
     use super::{
         eval_gateway_overview_command, eval_gateway_status_command, eval_switch_command,
-        try_handle_compact_command, try_handle_stop_command,
+        parse_question_reply, try_handle_compact_command, try_handle_stop_command,
     };
     use crate::chat::{ChatTransport, MessageId};
+    use crate::http::context::QuestionAnswer;
     use crate::service::gateway::config::ProjectEntry;
     use async_trait::async_trait;
     use std::collections::BTreeMap;
     use tokio::sync::RwLock;
 
+    // -- parse_question_reply (story 1228) -----------------------------------
+
+    fn sample_labels() -> Vec<String> {
+        vec!["Fast".to_string(), "Safe".to_string()]
+    }
+
+    #[test]
+    fn parse_question_reply_single_number_selects_option() {
+        let outcome = parse_question_reply("2", 2, false, &sample_labels());
+        assert_eq!(outcome, Some(QuestionAnswer::Selected(vec![1])));
+    }
+
+    #[test]
+    fn parse_question_reply_multi_select_comma_list() {
+        let outcome = parse_question_reply("1,2", 2, true, &sample_labels());
+        assert_eq!(outcome, Some(QuestionAnswer::Selected(vec![0, 1])));
+    }
+
+    #[test]
+    fn parse_question_reply_multi_numbers_rejected_when_not_multi_select() {
+        let outcome = parse_question_reply("1,2", 2, false, &sample_labels());
+        assert_eq!(outcome, None, "must re-prompt, not silently pick one");
+    }
+
+    #[test]
+    fn parse_question_reply_out_of_range_number_is_invalid() {
+        let outcome = parse_question_reply("5", 2, false, &sample_labels());
+        assert_eq!(outcome, None);
+    }
+
+    #[test]
+    fn parse_question_reply_zero_is_invalid() {
+        let outcome = parse_question_reply("0", 2, false, &sample_labels());
+        assert_eq!(outcome, None);
+    }
+
+    #[test]
+    fn parse_question_reply_matches_option_label_case_insensitively() {
+        let outcome = parse_question_reply("fast", 2, false, &sample_labels());
+        assert_eq!(outcome, Some(QuestionAnswer::Selected(vec![0])));
+    }
+
+    #[test]
+    fn parse_question_reply_unmatched_text_is_free_text() {
+        let outcome = parse_question_reply("Let's do something else", 2, false, &sample_labels());
+        assert_eq!(
+            outcome,
+            Some(QuestionAnswer::FreeText(
+                "Let's do something else".to_string()
+            ))
+        );
+    }
+
+    #[test]
+    fn parse_question_reply_strips_leading_mention() {
+        let outcome = parse_question_reply("@timmy 1", 2, false, &sample_labels());
+        assert_eq!(outcome, Some(QuestionAnswer::Selected(vec![0])));
+    }
+
     /// Regression test: `switch` reads from the live store, not a snapshot Vec.
     ///
     /// Seeds an empty store, inserts a project at runtime, then asserts the

server/src/chat/transport/matrix/bot/mod.rs

@@ -12,6 +12,10 @@ pub mod messages;
 /// Permission listener — registers as a permission responder for the bot's
 /// lifetime and forwards permission requests to the configured Matrix room.
 pub mod permission_listener;
+/// Question listener — registers as a question responder for the bot's
+/// lifetime and forwards `ask_question` requests to the configured Matrix
+/// room, rendered as numbered text (story 1228).
+pub mod question_listener;
 /// Bot run loop — the main async task that drives the Matrix sync loop.
 pub mod run;
 /// Device verification — handles Matrix cross-signing and emoji verification flows.

server/src/chat/transport/matrix/bot/permission_listener.rs

@@ -174,6 +174,10 @@ mod tests {
             pending_perm_replies: PendingPermReplies::new(),
             permission_timeout_secs: 120,
             remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
             status: Arc::new(crate::service::status::StatusBroadcaster::new()),
             chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
         })

server/src/chat/transport/matrix/bot/question_listener.rs

@@ -0,0 +1,335 @@
+//! Background task that registers as a question responder for the bot's
+//! lifetime and forwards `ask_question` requests to the configured Matrix
+//! room, rendering them as numbered text (story 1228).
+//!
+//! Mirrors `permission_listener.rs`'s always-on registration pattern so an
+//! agent's question reaches chat even when the bot isn't mid-turn.
+
+use crate::chat::ChatTransport;
+use crate::http::context::QuestionSpec;
+use crate::services::Services;
+use crate::slog;
+use matrix_sdk::ruma::{OwnedEventId, OwnedRoomId};
+use std::collections::HashSet;
+use std::sync::Arc;
+use std::time::Duration;
+use tokio::sync::Mutex as TokioMutex;
+
+use super::format::markdown_to_html;
+
+/// Render a [`QuestionSpec`] as readable, numbered chat text — the question,
+/// then each option numbered with its label and description — never raw
+/// JSON (story 1228, AC1).
+pub fn format_question_as_text(question: &QuestionSpec) -> String {
+    let mut out = format!("**{}**\n\n{}\n\n", question.header, question.question);
+    for (i, opt) in question.options.iter().enumerate() {
+        out.push_str(&format!("{}. {} — {}\n", i + 1, opt.label, opt.description));
+    }
+    out.push('\n');
+    if question.multi_select {
+        out.push_str(
+            "Reply with a number, or multiple numbers separated by commas (e.g. \"1,3\"), \
+             or type your own answer.",
+        );
+    } else {
+        out.push_str("Reply with a number, or type your own answer.");
+    }
+    out
+}
+
+/// Spawn a background task that registers with `services.question_registry`
+/// for the bot's lifetime and forwards each incoming question request to
+/// `target_room` as a chat message. Replies are resolved by `on_room_message`
+/// via `pending_question_replies`.
+pub fn spawn_question_listener(
+    services: Arc<Services>,
+    transport: Arc<dyn ChatTransport>,
+    target_room: OwnedRoomId,
+    bot_sent_event_ids: Arc<TokioMutex<HashSet<OwnedEventId>>>,
+) -> tokio::task::JoinHandle<()> {
+    tokio::spawn(async move {
+        let (_responder_guard, mut question_rx) = services.question_registry.register();
+        let target_room_str = target_room.as_str().to_string();
+        slog!("[matrix-bot] question listener started; forwarding requests to {target_room_str}");
+
+        while let Some(q_fwd) = question_rx.recv().await {
+            let prompt_msg = format_question_as_text(&q_fwd.question);
+            let html = markdown_to_html(&prompt_msg);
+            if let Ok(msg_id) = transport
+                .send_message(&target_room_str, &prompt_msg, &html)
+                .await
+                && let Ok(event_id) = msg_id.parse::<OwnedEventId>()
+            {
+                bot_sent_event_ids.lock().await.insert(event_id);
+            }
+
+            let num_options = q_fwd.question.options.len();
+            let multi_select = q_fwd.question.multi_select;
+            let labels: Vec<String> = q_fwd
+                .question
+                .options
+                .iter()
+                .map(|o| o.label.clone())
+                .collect();
+            services
+                .pending_question_replies
+                .insert(
+                    target_room.to_string(),
+                    q_fwd.request_id.clone(),
+                    num_options,
+                    multi_select,
+                    labels,
+                    q_fwd.response_tx,
+                )
+                .await;
+
+            // Spawn a per-request timeout: give up (fail-closed) if the user
+            // does not respond within `question_timeout_secs`.
+            let pending = Arc::clone(&services.pending_question_replies);
+            let timeout_room_key = target_room.to_string();
+            let timeout_request_id = q_fwd.request_id.clone();
+            let timeout_transport = Arc::clone(&transport);
+            let timeout_room_str = target_room_str.clone();
+            let timeout_sent_ids = Arc::clone(&bot_sent_event_ids);
+            let timeout_secs = services.question_timeout_secs;
+            tokio::spawn(async move {
+                tokio::time::sleep(Duration::from_secs(timeout_secs)).await;
+                if let Some(tx) = pending
+                    .remove_by_request_id(&timeout_room_key, &timeout_request_id)
+                    .await
+                {
+                    let _ = tx.send(Err("Question timed out waiting for a reply.".to_string()));
+                    let msg = "Question timed out — no answer received.";
+                    let html = markdown_to_html(msg);
+                    if let Ok(msg_id) = timeout_transport
+                        .send_message(&timeout_room_str, msg, &html)
+                        .await
+                        && let Ok(event_id) = msg_id.parse::<OwnedEventId>()
+                    {
+                        timeout_sent_ids.lock().await.insert(event_id);
+                    }
+                }
+            });
+        }
+
+        slog!("[matrix-bot] question listener exiting (channel closed)");
+    })
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::http::context::{QuestionAnswer, QuestionForward, QuestionOption};
+    use async_trait::async_trait;
+
+    struct RecordingTransport {
+        sent: Arc<std::sync::Mutex<Vec<(String, String)>>>,
+    }
+
+    #[async_trait]
+    impl crate::chat::ChatTransport for RecordingTransport {
+        async fn send_message(
+            &self,
+            room_id: &str,
+            plain: &str,
+            _html: &str,
+        ) -> Result<crate::chat::MessageId, String> {
+            self.sent
+                .lock()
+                .unwrap()
+                .push((room_id.to_string(), plain.to_string()));
+            Ok("$test_event_id:example.com".to_string())
+        }
+
+        async fn edit_message(&self, _: &str, _: &str, _: &str, _: &str) -> Result<(), String> {
+            Ok(())
+        }
+
+        async fn send_typing(&self, _: &str, _: bool) -> Result<(), String> {
+            Ok(())
+        }
+    }
+
+    async fn wait_until(mut cond: impl FnMut() -> bool, timeout: std::time::Duration) -> bool {
+        let start = tokio::time::Instant::now();
+        loop {
+            if cond() {
+                return true;
+            }
+            if start.elapsed() > timeout {
+                return false;
+            }
+            tokio::time::sleep(std::time::Duration::from_millis(5)).await;
+        }
+    }
+
+    fn test_services() -> Arc<Services> {
+        Arc::new(Services {
+            project_root: std::path::PathBuf::from("/tmp/test"),
+            agents: Arc::new(crate::agents::AgentPool::new_test(3000)),
+            bot_name: "Assistant".to_string(),
+            bot_user_id: "@bot:example.com".to_string(),
+            ambient_rooms: Arc::new(std::sync::Mutex::new(std::collections::HashSet::new())),
+            permission_registry: crate::service::permission_router::ResponderRegistry::new(),
+            pending_perm_replies: crate::service::permission_router::PendingPermReplies::new(),
+            permission_timeout_secs: 120,
+            remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
+            status: Arc::new(crate::service::status::StatusBroadcaster::new()),
+            chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
+        })
+    }
+
+    fn sample_question(multi_select: bool) -> QuestionSpec {
+        QuestionSpec {
+            header: "Approach".to_string(),
+            question: "Which approach should we use?".to_string(),
+            options: vec![
+                QuestionOption {
+                    label: "Fast".to_string(),
+                    description: "Ship quickly".to_string(),
+                },
+                QuestionOption {
+                    label: "Safe".to_string(),
+                    description: "Take more time".to_string(),
+                },
+            ],
+            multi_select,
+        }
+    }
+
+    #[test]
+    fn format_question_as_text_renders_numbered_options_never_json() {
+        let text = format_question_as_text(&sample_question(false));
+        assert!(text.contains("**Approach**"));
+        assert!(text.contains("Which approach should we use?"));
+        assert!(text.contains("1. Fast — Ship quickly"));
+        assert!(text.contains("2. Safe — Take more time"));
+        assert!(!text.contains('{'), "must never render raw JSON: {text}");
+    }
+
+    #[test]
+    fn format_question_as_text_mentions_multi_select_syntax_when_enabled() {
+        let text = format_question_as_text(&sample_question(true));
+        assert!(text.contains("1,3"));
+    }
+
+    #[tokio::test]
+    async fn listener_forwards_question_to_target_room_and_registers_pending_reply() {
+        let services = test_services();
+        let sent: Arc<std::sync::Mutex<Vec<(String, String)>>> =
+            Arc::new(std::sync::Mutex::new(Vec::new()));
+        let transport: Arc<dyn crate::chat::ChatTransport> = Arc::new(RecordingTransport {
+            sent: Arc::clone(&sent),
+        });
+        let target_room: OwnedRoomId = "!question:example.com".parse().unwrap();
+        let bot_sent_event_ids = Arc::new(TokioMutex::new(HashSet::new()));
+
+        spawn_question_listener(
+            Arc::clone(&services),
+            Arc::clone(&transport),
+            target_room.clone(),
+            Arc::clone(&bot_sent_event_ids),
+        );
+
+        assert!(
+            wait_until(
+                || !services.question_registry.is_empty(),
+                std::time::Duration::from_secs(2)
+            )
+            .await,
+            "listener never registered as a responder"
+        );
+
+        let (response_tx, _response_rx) = tokio::sync::oneshot::channel();
+        services.question_registry.dispatch(QuestionForward {
+            request_id: "req-1".to_string(),
+            question: sample_question(false),
+            response_tx,
+        });
+
+        assert!(
+            wait_until(
+                || !sent.lock().unwrap().is_empty(),
+                std::time::Duration::from_secs(2)
+            )
+            .await,
+            "listener never sent the question prompt"
+        );
+
+        let recorded = sent.lock().unwrap().clone();
+        assert_eq!(recorded[0].0, target_room.as_str());
+        assert!(recorded[0].1.contains("1. Fast — Ship quickly"));
+
+        let mut resolved = None;
+        for _ in 0..50 {
+            resolved = services
+                .pending_question_replies
+                .peek_oldest_meta(target_room.as_str())
+                .await;
+            if resolved.is_some() {
+                break;
+            }
+            tokio::time::sleep(std::time::Duration::from_millis(5)).await;
+        }
+        assert_eq!(
+            resolved,
+            Some((2, false, vec!["Fast".to_string(), "Safe".to_string()])),
+            "pending_question_replies missing entry with correct option count"
+        );
+    }
+
+    #[tokio::test]
+    async fn resolved_reply_delivers_answer_through_response_channel() {
+        let services = test_services();
+        let sent: Arc<std::sync::Mutex<Vec<(String, String)>>> =
+            Arc::new(std::sync::Mutex::new(Vec::new()));
+        let transport: Arc<dyn crate::chat::ChatTransport> = Arc::new(RecordingTransport {
+            sent: Arc::clone(&sent),
+        });
+        let target_room: OwnedRoomId = "!question2:example.com".parse().unwrap();
+        let bot_sent_event_ids = Arc::new(TokioMutex::new(HashSet::new()));
+
+        spawn_question_listener(
+            Arc::clone(&services),
+            Arc::clone(&transport),
+            target_room.clone(),
+            Arc::clone(&bot_sent_event_ids),
+        );
+        assert!(
+            wait_until(
+                || !services.question_registry.is_empty(),
+                std::time::Duration::from_secs(2)
+            )
+            .await
+        );
+
+        let (response_tx, response_rx) = tokio::sync::oneshot::channel();
+        services.question_registry.dispatch(QuestionForward {
+            request_id: "req-2".to_string(),
+            question: sample_question(false),
+            response_tx,
+        });
+
+        let mut tx = None;
+        for _ in 0..50 {
+            tx = services
+                .pending_question_replies
+                .resolve_oldest(target_room.as_str())
+                .await;
+            if tx.is_some() {
+                break;
+            }
+            tokio::time::sleep(std::time::Duration::from_millis(5)).await;
+        }
+        let tx = tx.expect("pending reply must be present");
+        let _ = tx.send(Ok(QuestionAnswer::Selected(vec![1])));
+        assert_eq!(
+            response_rx.await.unwrap().unwrap(),
+            QuestionAnswer::Selected(vec![1])
+        );
+    }
+}

server/src/chat/transport/matrix/bot/run.rs

@@ -306,6 +306,12 @@ pub async fn run_bot(
             target_room.clone(),
             Arc::clone(&bot_sent_event_ids),
         );
+        super::question_listener::spawn_question_listener(
+            Arc::clone(&services),
+            Arc::clone(&transport),
+            target_room.clone(),
+            Arc::clone(&bot_sent_event_ids),
+        );
     }
 
     // The forwarder only needs live (future) events — resubscribe is fine.

server/src/chat/transport/matrix/health.rs

@@ -625,6 +625,10 @@ mod tests {
             pending_perm_replies: PendingPermReplies::new(),
             permission_timeout_secs: 120,
             remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
             status: Arc::new(crate::service::status::StatusBroadcaster::new()),
             chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
         });
@@ -657,6 +661,10 @@ mod tests {
             pending_perm_replies: PendingPermReplies::new(),
             permission_timeout_secs: 120,
             remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
             status: Arc::new(crate::service::status::StatusBroadcaster::new()),
             chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
         });

server/src/chat/transport/whatsapp/commands/mod.rs

@@ -315,6 +315,10 @@ mod tests {
             pending_perm_replies: crate::service::permission_router::PendingPermReplies::new(),
             permission_timeout_secs: 120,
             remembered_permissions: crate::service::permission_router::RememberedPermissions::new(),
+            question_registry: crate::service::question_router::QuestionResponderRegistry::new(),
+            pending_question_replies: crate::service::question_router::PendingQuestionReplies::new(
+            ),
+            question_timeout_secs: 120,
             chat_dispatcher: Arc::new(crate::chat::dispatcher::ChatDispatcher::new(1_500)),
         });
         Arc::new(WhatsAppWebhookContext {

server/src/chat/util.rs

@@ -3,6 +3,23 @@
 //! These functions are transport-agnostic helpers for processing chat messages:
 //! prefix stripping, bot-mention handling, and paragraph buffering.
 
+/// Instruction prepended to chat-bot prompts telling the model how to ask a
+/// clarifying multiple-choice question over a chat protocol that has no
+/// interactive question UI (story 1228).
+///
+/// Claude Code's built-in `AskUserQuestion` tool requires an interactive
+/// terminal/IDE to render and answer; in the headless `claude -p` sessions
+/// this server spawns for chat transports it either isn't offered to the
+/// model at all, or (if forced into scope) degrades into the model emitting
+/// its attempted call as raw tool-call syntax in plain text. Disallowing it
+/// (`--disallowedTools AskUserQuestion` on the CLI invocation) closes that
+/// leak; this instruction points the model at the huskies-owned MCP
+/// `ask_question` tool as the replacement, which renders the numbered
+/// options in chat, blocks until a reply resolves it, and returns the
+/// answer directly to this tool call — the model does not need to format
+/// the question itself or wait for a future turn to see the reply.
+pub const QUESTION_FORMAT_INSTRUCTION: &str = "This chat has no interactive question UI, and the built-in AskUserQuestion tool is unavailable here. When you need to ask the user a clarifying multiple-choice question, call the `ask_question` MCP tool instead — never emit JSON or tool-call syntax as plain text. Pass a `question`, an optional `header`, and at least two `options` (each with a `label` and `description`); set `multi_select: true` if the user may choose more than one. The tool renders the options as a numbered list in chat and blocks until the user replies, then returns the selected option(s) or free-text answer for you to continue with.";
+
 /// Truncate `s` to at most `max_bytes` bytes without splitting a UTF-8 codepoint.
 ///
 /// If `s.len() <= max_bytes` the original slice is returned unchanged.
@@ -318,6 +335,29 @@ mod tests {
         assert_eq!(truncate_at_char_boundary("hi", 100), "hi");
     }
 
+    // -- QUESTION_FORMAT_INSTRUCTION (story 1228) ---------------------------
+
+    #[test]
+    fn question_format_instruction_directs_model_to_ask_question_tool() {
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("ask_question"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("AskUserQuestion"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("never emit JSON or tool-call syntax"));
+    }
+
+    #[test]
+    fn question_format_instruction_describes_required_arguments() {
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("question"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("options"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("label"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("multi_select"));
+    }
+
+    #[test]
+    fn question_format_instruction_explains_blocking_reply_behavior() {
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("blocks until the user replies"));
+        assert!(QUESTION_FORMAT_INSTRUCTION.contains("free-text"));
+    }
+
     // -- is_permission_approval ---------------------------------------------
 
     #[test]