Fix calendar routing and user-local time context (#408)

* fix(chat): add user-local time context * fix(chat): route calendar follow-up phrasing * refactor(chat): log tool intent routing reasons * test(chat): align user time prompt shim --------- Co-authored-by: Alex Kenley <Alex.Kenley@threatvectorsecurity.com>
2026-06-04 22:20:04 +10:00
parent f59edee611
commit 7b45a94b6d
12 changed files with 463 additions and 106 deletions
--- a/routes/calendar_routes.py
+++ b/routes/calendar_routes.py
@@ -161,26 +161,18 @@ def _ensure_default_calendar(db, owner: str = None) -> CalendarCal:
    return cal


-# Per-request user UTC offset (in minutes east of UTC). chat_routes sets this
-# from the `X-Tz-Offset` header so naive natural-language times the LLM
-# emits ("today at 9pm") are parsed in the USER's timezone, not the server's
-# clock.  None = unknown, fall back to legacy server-local behavior.
-from contextvars import ContextVar
-_USER_TZ_OFFSET_MIN: ContextVar = ContextVar("user_tz_offset_min", default=None)
-
-
-def set_user_tz_offset(offset_min):
-    """Set the current user's UTC offset for this async context."""
-    try:
-        v = int(offset_min)
-    except (TypeError, ValueError):
-        return
-    _USER_TZ_OFFSET_MIN.set(v)
-
-
-def get_user_tz_offset():
-    """Read the current user's UTC offset (minutes east of UTC), or None."""
-    return _USER_TZ_OFFSET_MIN.get()
+# Per-request user time context. chat_routes sets this from browser timezone
+# headers so natural-language times the LLM emits ("today at 9pm") are parsed
+# in the user's timezone, not the server's clock. None = unknown, fall back to
+# legacy server-local behavior.
+from src.user_time import (
+    get_user_tz_name,
+    get_user_tz_offset,
+    now_user_local,
+    set_user_tz_name,
+    set_user_tz_offset,
+    user_timezone,
+)


 def parse_due_for_user(s: str) -> str:
@@ -199,6 +191,7 @@ def parse_due_for_user(s: str) -> str:
    """
    from datetime import timezone as _tz, timedelta as _td
    offset = get_user_tz_offset()
+    tz_name = get_user_tz_name()
    s = (s or "").strip()
    if not s:
        return s
@@ -212,11 +205,11 @@ def parse_due_for_user(s: str) -> str:
    except ValueError:
        parsed = None

-    if offset is None:
+    if offset is None and not tz_name:
        # No user tz known — preserve legacy behavior (naive server-local).
        return _parse_dt(s).isoformat()

-    user_tz = _tz(_td(minutes=offset))
+    user_tz = user_timezone()

    # Naive ISO → tag with user tz.
    if parsed is not None and parsed.tzinfo is None:
@@ -224,7 +217,7 @@ def parse_due_for_user(s: str) -> str:

    # Natural language — evaluate against user's "now".
    server_now_utc = datetime.now(_tz.utc)
-    user_now = server_now_utc.astimezone(user_tz)
+    user_now = now_user_local(server_now_utc)
    # Patch datetime.now() inside _parse_dt by leveraging the user's clock:
    # we re-implement the small natural-language phrases here against user_now
    # so the result is naturally in the user's tz.
@@ -232,6 +225,7 @@ def parse_due_for_user(s: str) -> str:
    lower = s.lower().strip()

    def _parse_time(t):
+        t = _re.sub(r'\b([ap])\s*\.?\s*m\.?\b', r'\1m', t.strip(), flags=_re.IGNORECASE)
        m = _re.match(r'^\s*(\d{1,2})(?::(\d{2}))?\s*(am|pm)?\s*$', t, _re.IGNORECASE)
        if not m: return None
        h = int(m.group(1)); mn = int(m.group(2) or 0); ampm = (m.group(3) or "").lower()
@@ -341,6 +335,7 @@ def _parse_dt(s: str) -> datetime:

    def _parse_time(t: str):
        """Return (hour, minute) from '1pm', '1:30 PM', '13:00', etc., or None."""
+        t = _re.sub(r'\b([ap])\s*\.?\s*m\.?\b', r'\1m', t.strip(), flags=_re.IGNORECASE)
        m = _re.match(r'^\s*(\d{1,2})(?::(\d{2}))?\s*(am|pm)?\s*$', t, _re.IGNORECASE)
        if not m:
            return None
@@ -1210,7 +1205,20 @@ def setup_calendar_routes() -> APIRouter:
        text = (body.get("text") or "").strip()
        if not text:
            raise HTTPException(400, "text is required")
+        from src.user_time import (
+            clear_user_time_context,
+            current_datetime_prompt,
+            now_user_local,
+            set_user_tz_name,
+            set_user_tz_offset,
+        )
+
+        clear_user_time_context()
        tz_hint = (body.get("tz") or "").strip()
+        if body.get("tz_offset") is not None:
+            set_user_tz_offset(body.get("tz_offset"))
+        if tz_hint:
+            set_user_tz_name(tz_hint)

        url, model, headers = resolve_endpoint("utility")
        if not url:
@@ -1218,15 +1226,15 @@ def setup_calendar_routes() -> APIRouter:
        if not url or not model:
            return {"ok": False, "error": "No LLM endpoint configured"}

-        now = datetime.now()
+        now = now_user_local()
        now_iso = now.strftime("%Y-%m-%dT%H:%M:%S")
        # The model gets only the schema it needs to fill out; we re-validate
        # everything client-side too.
        system_prompt = (
-            "You are a calendar event parser. Read the user's one-line "
+            current_datetime_prompt()
+            + "You are a calendar event parser. Read the user's one-line "
            "description and emit STRICT JSON describing the event. "
-            f"Today is {now.strftime('%A, %Y-%m-%d')} ({now_iso}). "
-            + (f"User timezone: {tz_hint}. " if tz_hint else "")
+            f"The current user-local timestamp is {now_iso}. "
            + "Resolve relative dates (\"tomorrow\", \"friday\", \"next monday\", "
              "\"in 30 minutes\") against today. Default duration is 60 minutes "
              "when no end time is given. If the text mentions a date with no "
--- a/routes/chat_routes.py
+++ b/routes/chat_routes.py
@@ -37,7 +37,7 @@ from routes.chat_helpers import (
    clean_thinking_for_save,
    _enforce_chat_privileges,
 )
-from src.action_intents import message_needs_tools as _message_needs_tools
+from src.action_intents import classify_tool_intent as _classify_tool_intent

 logger = logging.getLogger(__name__)

@@ -229,6 +229,26 @@ def _recover_empty_session_model(sess, session_id: str, owner: str | None = None
        db.close()


+def _set_user_time_from_request(request: Request) -> None:
+    """Copy browser timezone headers into the per-request context.
+
+    This is intentionally ephemeral: it is used only while building prompts
+    and running tools for this request. It is not persisted or logged.
+    """
+    try:
+        tz_offset = request.headers.get("x-tz-offset")
+        tz_name = request.headers.get("x-tz-name")
+        from src.user_time import clear_user_time_context, set_user_tz_name, set_user_tz_offset
+
+        clear_user_time_context()
+        if tz_offset is not None:
+            set_user_tz_offset(tz_offset)
+        if tz_name:
+            set_user_tz_name(tz_name)
+    except Exception:
+        pass
+
+
 def setup_chat_routes(
    session_manager,
    chat_handler,
@@ -247,6 +267,8 @@ def setup_chat_routes(
    # ------------------------------------------------------------------ #
    @router.post("/api/chat", response_model=Dict[str, str])
    async def chat_endpoint(request: Request, chat_request: ChatRequest) -> Dict[str, str]:
+        _set_user_time_from_request(request)
+
        message = chat_request.message
        session = chat_request.session
        att_ids = chat_request.attachments or []
@@ -355,16 +377,7 @@ def setup_chat_routes(
        except Exception as e:
            raise HTTPException(400, f"Request parsing error: {e}")

-        # Stash the user's UTC offset (in minutes east of UTC) from the
-        # frontend so tools like manage_notes interpret natural-language
-        # times in the USER's tz, not the server's. See calendar_routes.
-        try:
-            _tz_hdr = request.headers.get("x-tz-offset")
-            if _tz_hdr is not None:
-                from routes.calendar_routes import set_user_tz_offset
-                set_user_tz_offset(_tz_hdr)
-        except Exception:
-            pass
+        _set_user_time_from_request(request)

        form_data = await request.form()
        message = form_data.get("message")
@@ -393,10 +406,15 @@ def setup_chat_routes(
        # its way through a plain chat request (and fail, especially with the
        # shell disabled).
        auto_escalated = False
-        if chat_mode == "chat" and isinstance(message, str) and _message_needs_tools(message):
+        _tool_intent = _classify_tool_intent(message) if isinstance(message, str) else None
+        if chat_mode == "chat" and _tool_intent and _tool_intent.needs_tools:
            chat_mode = "agent"
            auto_escalated = True
-            logger.info("chat→agent auto-escalation: message matched tool-intent pattern")
+            logger.info(
+                "chat→agent auto-escalation: category=%s reason=%s",
+                _tool_intent.category,
+                _tool_intent.reason,
+            )
        active_doc_id = form_data.get("active_doc_id", "").strip()
        logger.info(f"[doc-inject] chat_mode={chat_mode}, active_doc_id={active_doc_id!r}")

--- a/src/action_intents.py
+++ b/src/action_intents.py
@@ -8,74 +8,121 @@ user asks how a feature works.
 from __future__ import annotations

 import re
+from dataclasses import dataclass
 from typing import Iterable, Pattern


-_ACTION_QUESTION = r"\b(?:can|could|would|will)\s+you\s+"
-_PLEASE = r"^\s*(?:please\s+)?"
+@dataclass(frozen=True)
+class ToolIntent:
+    """A cheap, deterministic chat-to-agent routing decision."""

-_CALENDAR_ACTION = r"(?:add|create|schedule|book|put|set\s+up|make)"
+    needs_tools: bool
+    category: str = ""
+    reason: str = ""
+
+
+_ACTION_QUESTION = r"\b(?:can|could|would|will)\s+you\s+"
+_ACTION_FOLLOWUP = (
+    r"\b(?:you\s+should\s+be\s+able\s+to|"
+    r"(?:can|could|would|will|should)\s+you|"
+    r"you\s+(?:can|could|would|will|should|need\s+to|have\s+to))\s+"
+)
+_PLEASE = r"^\s*(?:(?:please|ok(?:ay)?|alright|right|sure|cool|great|thanks)[\s,.!-]+)*"
+
+_CALENDAR_ACTION = (
+    r"(?:add|adding|create|creating|recreate|recreating|schedule|scheduling|"
+    r"reschedule|rescheduling|book|booking|put|set\s+up|make|making|"
+    r"delete|deleting|remove|removing|cancel|cancelling|canceling)"
+)
 _CALENDAR_THING = r"(?:calendar|calendar\s+(?:entry|item)|event|meeting|appointment|entry|call)"
+_EXPLANATORY_PREFIX = re.compile(
+    r"^\s*(?:how\s+(?:do|can)\s+i|can\s+you\s+explain|what\s+about|tell\s+me\s+how|show\s+me\s+how)\b",
+    re.I,
+)

 _PANEL = (
    r"(?:calendar|notes?|inbox|email|mail|documents?|docs|library|gallery|"
    r"settings|cookbook|sessions?|chats?|skills|memories|memory|brain)"
 )

-_TOOL_INTENT_PATTERNS: tuple[Pattern[str], ...] = tuple(
-    re.compile(pattern, re.I)
-    for pattern in (
+_ROUTING_PATTERNS: tuple[tuple[str, str, Pattern[str]], ...] = tuple(
+    (category, reason, re.compile(pattern, re.I))
+    for category, reason, pattern in (
        # Calendar/event creation. Covers "Can you add an entry to my
-        # calendar?" and imperatives like "add lunch to my calendar".
-        rf"{_ACTION_QUESTION}{_CALENDAR_ACTION}\b.{{0,120}}\b{_CALENDAR_THING}\b",
-        rf"{_PLEASE}{_CALENDAR_ACTION}\b.{{0,120}}\b(?:to|on|in|into|for)\s+(?:my\s+|the\s+|this\s+)?calendar\b",
-        rf"{_PLEASE}{_CALENDAR_ACTION}\s+(?:a\s+|an\s+)?(?:calendar\s+)?(?:event|meeting|appointment|entry|item|call)\b",
-        r"\bput\s+.+\bon\s+(?:my\s+)?calendar\b",
+        # calendar?", imperatives like "add lunch to my calendar", and
+        # follow-ups such as "you should be able to create that event now".
+        ("calendar", "assistant calendar action request", rf"{_ACTION_QUESTION}{_CALENDAR_ACTION}\b.{{0,120}}\b{_CALENDAR_THING}\b"),
+        ("calendar", "calendar follow-up action request", rf"{_ACTION_FOLLOWUP}{_CALENDAR_ACTION}\b.{{0,120}}\b{_CALENDAR_THING}\b"),
+        ("calendar", "calendar imperative action request", rf"{_PLEASE}{_CALENDAR_ACTION}\b.{{0,120}}\b{_CALENDAR_THING}\b"),
+        ("calendar", "calendar target action request", rf"{_PLEASE}{_CALENDAR_ACTION}\b.{{0,120}}\b(?:to|on|in|into|for)\s+(?:my\s+|the\s+|this\s+)?calendar\b"),
+        ("calendar", "calendar item action request", rf"{_PLEASE}{_CALENDAR_ACTION}\s+(?:it\s+)?(?:a\s+|an\s+)?(?:calendar\s+)?(?:event|meeting|appointment|entry|item|call)\b"),
+        ("calendar", "calendar target action request", rf"\b{_CALENDAR_ACTION}\b.{{0,120}}\b(?:to|on|in|into|for)\s+(?:my\s+|the\s+|this\s+)?calendar\b"),
+        ("calendar", "put item on calendar request", r"\bput\s+.+\bon\s+(?:my\s+)?calendar\b"),

        # Notes, todos, checklists, and reminders.
-        r"\bremind\s+me\b",
-        rf"{_ACTION_QUESTION}(?:add|create|make|take|jot|write\s+down|set)\b.{{0,120}}\b(?:note|todo|task|checklist|reminder)\b",
-        rf"{_PLEASE}(?:add|create|make)\s+(?:a\s+|an\s+)?(?:todo|task|reminder|note|checklist)\b",
-        rf"{_PLEASE}(?:take|jot|write\s+down)\s+(?:a\s+|an\s+)?note\b",
-        rf"{_PLEASE}(?:add|jot|write\s+down)\b.{{0,120}}\b(?:to|in|into)\s+(?:my\s+|the\s+)?(?:todo(?:\s+list)?|task\s+list|notes?|checklist)\b",
-        rf"{_PLEASE}set\s+(?:a\s+)?reminder\b",
-        rf"{_ACTION_QUESTION}set\s+(?:a\s+)?reminder\b",
+        ("notes", "reminder request", r"\bremind\s+me\b"),
+        ("notes", "assistant note/todo action request", rf"{_ACTION_QUESTION}(?:add|create|make|take|jot|write\s+down|set)\b.{{0,120}}\b(?:note|todo|task|checklist|reminder)\b"),
+        ("notes", "note/todo imperative request", rf"{_PLEASE}(?:add|create|make)\s+(?:a\s+|an\s+)?(?:todo|task|reminder|note|checklist)\b"),
+        ("notes", "take note request", rf"{_PLEASE}(?:take|jot|write\s+down)\s+(?:a\s+|an\s+)?note\b"),
+        ("notes", "add item to notes/todo request", rf"{_PLEASE}(?:add|jot|write\s+down)\b.{{0,120}}\b(?:to|in|into)\s+(?:my\s+|the\s+)?(?:todo(?:\s+list)?|task\s+list|notes?|checklist)\b"),
+        ("notes", "set reminder request", rf"{_PLEASE}set\s+(?:a\s+)?reminder\b"),
+        ("notes", "assistant reminder request", rf"{_ACTION_QUESTION}set\s+(?:a\s+)?reminder\b"),

        # Email actions.
-        rf"{_ACTION_QUESTION}(?:send|write|reply|email|message|archive|delete|mark)\b.{{0,120}}\b(?:emails?|mail|messages?|inbox|unread|read)\b",
-        rf"{_PLEASE}(?:send|write|reply)\b.{{0,120}}\b(?:emails?|mail|messages?)\b",
-        rf"{_PLEASE}(?:archive|delete|mark)\b.{{0,120}}\b(?:emails?|mail|messages?|inbox)\b",
-        r"\b(?:send|write|reply)\s+(?:an?\s+)?(?:email|message|mail)\b",
-        r"\bemail\s+\w+\b",
-        r"\bcheck\s+(?:my\s+)?(?:email|inbox|mail)\b",
-        r"\bunread\s+(?:email|mail)s?\b",
+        ("email", "assistant email action request", rf"{_ACTION_QUESTION}(?:send|write|reply|email|message|archive|delete|mark)\b.{{0,120}}\b(?:emails?|mail|messages?|inbox|unread|read)\b"),
+        ("email", "send/write/reply email request", rf"{_PLEASE}(?:send|write|reply)\b.{{0,120}}\b(?:emails?|mail|messages?)\b"),
+        ("email", "archive/delete/mark email request", rf"{_PLEASE}(?:archive|delete|mark)\b.{{0,120}}\b(?:emails?|mail|messages?|inbox)\b"),
+        ("email", "email composition request", r"\b(?:send|write|reply)\s+(?:an?\s+)?(?:email|message|mail)\b"),
+        ("email", "email contact request", r"\bemail\s+\w+\b"),
+        ("email", "check inbox request", r"\bcheck\s+(?:my\s+)?(?:email|inbox|mail)\b"),
+        ("email", "unread email request", r"\bunread\s+(?:email|mail)s?\b"),

        # UI/control-plane actions that should open panels or flip toggles.
-        rf"{_PLEASE}(?:open|show|bring\s+up)\s+(?:me\s+)?(?:my\s+|the\s+)?{_PANEL}\b",
-        r"\b(?:disable|enable|turn\s+(?:on|off))\s+(?:the\s+)?(?:shell|search|web|browser|documents?|memory|skills|images?|calendar|email|mail|research|incognito)\b",
+        ("ui", "open/show panel request", rf"{_PLEASE}(?:open|show|bring\s+up)\s+(?:me\s+)?(?:my\s+|the\s+)?{_PANEL}\b"),
+        ("ui", "tool or feature toggle request", r"\b(?:disable|enable|turn\s+(?:on|off))\s+(?:the\s+)?(?:shell|search|web|browser|documents?|memory|skills|images?|calendar|email|mail|research|incognito)\b"),

        # Deep research jobs, not quick conceptual mentions of research.
-        rf"{_PLEASE}(?:research|deep\s+dive|look\s+into|investigate)\s+.+",
-        rf"{_ACTION_QUESTION}(?:research|do\s+research|deep\s+dive|look\s+into|investigate)\s+.+",
+        ("research", "deep research imperative request", rf"{_PLEASE}(?:research|deep\s+dive|look\s+into|investigate)\s+.+"),
+        ("research", "assistant deep research request", rf"{_ACTION_QUESTION}(?:research|do\s+research|deep\s+dive|look\s+into|investigate)\s+.+"),

        # Shell / remote-host intent.
-        r"\bssh\s+(?:in)?to\b",
-        r"\bssh\s+\w+",
-        r"\b(run|execute)\s+.{1,40}\bon\s+\w+",
-        r"\b(can|could|please|would)\s+you\s+(run|execute|exec)\b",
+        ("shell", "ssh request", r"\bssh\s+(?:in)?to\b"),
+        ("shell", "ssh target request", r"\bssh\s+\w+"),
+        ("shell", "remote command request", r"\b(run|execute)\s+.{1,40}\bon\s+\w+"),
+        ("shell", "assistant command execution request", r"\b(can|could|please|would)\s+you\s+(run|execute|exec)\b"),
        # Shell verbs only count in imperative position (start of message,
        # optionally after "please") or as a "can you ..." request. A bare
        # word match promoted informational questions ("What does the grep
        # command do?") and incidental uses ("My cat ate my homework").
-        rf"{_PLEASE}(deploy|build|install|restart|reboot|kill|tail|grep|cat|ls|cd|cp|mv|rm)\b\s+\S+",
-        rf"{_ACTION_QUESTION}(deploy|build|install|restart|reboot|kill|tail|grep|cat|ls|cd|cp|mv|rm)\b\s+\S+",
-        r"\b(check|see)\s+(if|whether|what)\s+.{1,40}\b(running|process|service|port|file|exists?)\b",
+        ("shell", "imperative shell command request", rf"{_PLEASE}(deploy|build|install|restart|reboot|kill|tail|grep|cat|ls|cd|cp|mv|rm)\b\s+\S+"),
+        ("shell", "assistant shell command request", rf"{_ACTION_QUESTION}(deploy|build|install|restart|reboot|kill|tail|grep|cat|ls|cd|cp|mv|rm)\b\s+\S+"),
+        ("shell", "system/file check request", r"\b(check|see)\s+(if|whether|what)\s+.{1,40}\b(running|process|service|port|file|exists?)\b"),
    )
 )

+_TOOL_INTENT_PATTERNS: tuple[Pattern[str], ...] = tuple(
+    pattern for _, _, pattern in _ROUTING_PATTERNS
+)
+
+
+def classify_tool_intent(text: str) -> ToolIntent:
+    """Classify whether a chat message should be promoted to agent mode."""
+    if not text:
+        return ToolIntent(False, reason="empty message")
+    if _EXPLANATORY_PREFIX.search(text):
+        return ToolIntent(False, reason="explanatory feature question")
+    for category, reason, pattern in _ROUTING_PATTERNS:
+        if pattern.search(text):
+            return ToolIntent(True, category=category, reason=reason)
+    return ToolIntent(False, reason="no tool-action pattern matched")
+

 def message_needs_tools(text: str, patterns: Iterable[Pattern[str]] = _TOOL_INTENT_PATTERNS) -> bool:
    """Return True when a plain chat message should be promoted to agent mode."""
    if not text:
        return False
+    if _EXPLANATORY_PREFIX.search(text):
+        return False
+    if patterns is _TOOL_INTENT_PATTERNS:
+        return classify_tool_intent(text).needs_tools
    return any(pattern.search(text) for pattern in patterns)
--- a/src/agent_loop.py
+++ b/src/agent_loop.py
@@ -636,28 +636,11 @@ def _build_system_prompt(

    set_active_model(model)

-    # Current date/time — every request. Models default to their
-    # training-cutoff date when "today" is asked otherwise (was
-    # rendering April 2026 dates as "today" when the actual date is
-    # May 19, 2026). System TZ-local so calendar/email date math
-    # matches what the user sees.
+    # Current date/time for every agent request. This is user-local when the
+    # browser provided timezone headers, with a server-local fallback.
    try:
-        from datetime import datetime as _dt, timezone as _tz
-        _now = _dt.now().astimezone()
-        _utc = _dt.now(_tz.utc)
-        _off = _now.strftime('%z')  # e.g. +0900
-        _off_fmt = (f"{_off[:3]}:{_off[3:]}" if _off else "+00:00")
-        agent_prompt = (
-            f"## Current date and time\n"
-            f"Today is {_now.strftime('%A, %B %-d, %Y')} ({_now.strftime('%Y-%m-%d')}). "
-            f"Local time is {_now.strftime('%-I:%M %p')} ({_now.strftime('%Z')}, UTC{_off_fmt}); "
-            f"current UTC time is {_utc.strftime('%H:%M')}. "
-            f"Use this for any 'today'/'tomorrow'/'this week' reasoning — do NOT "
-            f"infer the date from training data or from event timestamps.\n"
-            f"When scheduling a task (manage_tasks), scheduled_time is in UTC: "
-            f"subtract the offset above from the user's local time "
-            f"(local {_now.strftime('%H:%M')} = {_utc.strftime('%H:%M')} UTC right now).\n\n"
-        ) + agent_prompt
+        from src.user_time import current_datetime_prompt
+        agent_prompt = current_datetime_prompt() + agent_prompt
    except Exception:
        pass

--- a/src/chat_processor.py
+++ b/src/chat_processor.py
@@ -185,6 +185,15 @@ class ChatProcessor:
                "role": "system",
                "content": preset_system_prompt
            })
+        if not agent_mode:
+            try:
+                from src.user_time import current_datetime_prompt
+                preface.append({
+                    "role": "system",
+                    "content": current_datetime_prompt(),
+                })
+            except Exception:
+                logger.debug("Failed to add current date/time context", exc_info=True)
        preface.append({
            "role": "system",
            "content": UNTRUSTED_CONTEXT_POLICY,
--- a/src/tool_index.py
+++ b/src/tool_index.py
@@ -102,7 +102,7 @@ BUILTIN_TOOL_DESCRIPTIONS: Dict[str, str] = {
    "resolve_contact": "Look up a contact's email address by name. Searches CardDAV address book and sent email history. Use when the user says 'message [name]', 'email [name]', or 'send to [name]' without an email address.",
    "manage_contact": "Create, update, delete, or list CardDAV contacts. Use to save a new contact, change an existing one's email/phone, or remove one. Action=list returns uids needed for update/delete. Use when the user says 'save this contact', 'add [name] to contacts', 'update [name]'s email', 'delete [name] from contacts'. Do not use for user identity facts like 'my name is <name>'; those are memory.",
    "manage_notes": "Create and manage notes and checklists (Google Keep-style). ALWAYS use this for note/todo/checklist/reminder creation — NEVER hit /api/notes via app_api. Accepts natural-language `due_date` like 'tomorrow at 9am' or '11pm today' (parsed in the USER'S timezone). The due_date IS the reminder — it fires a notification at that time, so do NOT also create a calendar event for the same reminder. Set colors, labels, pin, archive. Do NOT use manage_memory for note content.",
-    "manage_calendar": "Calendar event management: list, create, update, delete. Each event can carry a tag/category (event_type — work/personal/health/travel/meal/social/admin/other) and importance (low/normal/high/critical). Use ISO datetimes; supports all-day events. For event reminders/alarms, pass reminder_minutes; this creates the Notes reminder, so do not also call manage_notes for the same reminder.",
+    "manage_calendar": "Calendar event management: list, create, update, delete. Each event can carry a tag/category (event_type — work/personal/health/travel/meal/social/admin/other) and importance (low/normal/high/critical). Resolve today/tomorrow using the Current date and time context, then use ISO datetimes in the user's local wall time; supports all-day events. For event reminders/alarms, pass reminder_minutes; this creates the Notes reminder, so do not also call manage_notes for the same reminder.",
    "download_model": "Download a HuggingFace model to a local or remote server. Specify repo_id (e.g. 'Qwen/Qwen3-8B'), optional server host, and optional include filter for specific files.",
    "serve_model": "Start serving a model with vLLM, SGLang, llama.cpp, Ollama, or Diffusers. For image/inpainting/diffusion use python3 scripts/diffusion_server.py --model <repo> --port 8100. After launch, call list_served_models for readiness/errors and retry suggestions.",
    "list_served_models": "List currently running model servers in the Cookbook — shows status (loading, ready, idle, error), model name, port, throughput, and serve failure diagnosis/retry suggestions. Use when the user asks 'what's running', 'show my cookbook', 'which models are up', 'what's serving'.",
--- a/src/tool_schemas.py
+++ b/src/tool_schemas.py
@@ -422,7 +422,7 @@ FUNCTION_TOOL_SCHEMAS = [
        "type": "function",
        "function": {
            "name": "manage_calendar",
-            "description": "Manage calendar events: list events in a date range, create, update, delete. Each event can carry a tag/category (event_type) and importance level. Use ISO 8601 datetimes; for all-day events set all_day=true and pass YYYY-MM-DD. For event reminders/alarms, pass reminder_minutes; the tool creates the Odysseus note reminder, so do not also call manage_notes for the same reminder.",
+            "description": "Manage calendar events: list events in a date range, create, update, delete. Each event can carry a tag/category (event_type) and importance level. Resolve relative dates like today/tomorrow against the 'Current date and time' system context, then pass ISO 8601 datetimes in the user's local wall time; for all-day events set all_day=true and pass YYYY-MM-DD. For event reminders/alarms, pass reminder_minutes; the tool creates the Odysseus note reminder, so do not also call manage_notes for the same reminder.",
            "parameters": {
                "type": "object",
                "properties": {
--- a/src/user_time.py
+++ b/src/user_time.py
@@ -0,0 +1,138 @@
+"""Per-request user-local time helpers.
+
+Chat routes set this context from browser headers. Prompt builders and tools
+can then resolve relative dates against the user's clock instead of the server.
+"""
+
+from __future__ import annotations
+
+import re
+from contextvars import ContextVar
+from datetime import datetime, timedelta, timezone
+from typing import Optional
+
+
+_USER_TZ_OFFSET_MIN: ContextVar[Optional[int]] = ContextVar("user_tz_offset_min", default=None)
+_USER_TZ_NAME: ContextVar[Optional[str]] = ContextVar("user_tz_name", default=None)
+
+
+def set_user_tz_offset(offset_min) -> None:
+    """Set the current user's UTC offset in minutes east of UTC."""
+    if offset_min in (None, ""):
+        _USER_TZ_OFFSET_MIN.set(None)
+        return
+    try:
+        value = int(offset_min)
+    except (TypeError, ValueError):
+        return
+    if -14 * 60 <= value <= 14 * 60:
+        _USER_TZ_OFFSET_MIN.set(value)
+
+
+def get_user_tz_offset() -> Optional[int]:
+    """Return minutes east of UTC for the current user, if known."""
+    return _USER_TZ_OFFSET_MIN.get()
+
+
+def set_user_tz_name(name) -> None:
+    """Set a safe IANA timezone label for the current request context."""
+    if not name:
+        _USER_TZ_NAME.set(None)
+        return
+    first_token = str(name).strip().split()[0] if str(name).strip() else ""
+    cleaned = re.sub(r"[^A-Za-z0-9_+\-./]", "", first_token)[:80]
+    _USER_TZ_NAME.set(cleaned or None)
+
+
+def get_user_tz_name() -> Optional[str]:
+    """Return the current user's browser timezone name, if provided."""
+    return _USER_TZ_NAME.get()
+
+
+def clear_user_time_context() -> None:
+    """Clear user-local time context for tests and non-browser entry points."""
+    _USER_TZ_OFFSET_MIN.set(None)
+    _USER_TZ_NAME.set(None)
+
+
+def format_utc_offset(offset_min: Optional[int]) -> str:
+    """Format minutes east of UTC as +HH:MM or -HH:MM."""
+    if offset_min is None:
+        offset_min = 0
+    sign = "+" if offset_min >= 0 else "-"
+    total = abs(int(offset_min))
+    hours, minutes = divmod(total, 60)
+    return f"{sign}{hours:02d}:{minutes:02d}"
+
+
+def user_timezone() -> timezone:
+    """Return the best known user timezone as a fixed-offset tzinfo."""
+    offset = get_user_tz_offset()
+    if offset is None:
+        name = get_user_tz_name()
+        if name:
+            try:
+                from zoneinfo import ZoneInfo
+                return ZoneInfo(name)
+            except Exception:
+                pass
+        return datetime.now().astimezone().tzinfo or timezone.utc
+    return timezone(timedelta(minutes=offset))
+
+
+def now_user_local(now_utc: Optional[datetime] = None) -> datetime:
+    """Return the current time in the user's timezone."""
+    if now_utc is None:
+        now_utc = datetime.now(timezone.utc)
+    elif now_utc.tzinfo is None:
+        now_utc = now_utc.replace(tzinfo=timezone.utc)
+    return now_utc.astimezone(user_timezone())
+
+
+def _date_label(dt: datetime) -> str:
+    return f"{dt.strftime('%A')}, {dt.strftime('%B')} {dt.day}, {dt.year}"
+
+
+def _clock_label(dt: datetime) -> str:
+    hour = dt.hour % 12 or 12
+    return f"{hour}:{dt.minute:02d} {dt.strftime('%p')}"
+
+
+def timezone_label(dt: Optional[datetime] = None) -> str:
+    """Return a concise display label such as Australia/Brisbane, UTC+10:00."""
+    offset = get_user_tz_offset()
+    if offset is None:
+        if dt is None:
+            dt = datetime.now().astimezone()
+        offset = int((dt.utcoffset() or timedelta()).total_seconds() // 60)
+    offset_label = f"UTC{format_utc_offset(offset)}"
+    name = get_user_tz_name()
+    return f"{name}, {offset_label}" if name else offset_label
+
+
+def current_datetime_prompt(now_utc: Optional[datetime] = None) -> str:
+    """Build reusable system prompt text for date/time reasoning."""
+    if now_utc is None:
+        utc_now = datetime.now(timezone.utc)
+    elif now_utc.tzinfo is None:
+        utc_now = now_utc.replace(tzinfo=timezone.utc)
+    else:
+        utc_now = now_utc.astimezone(timezone.utc)
+
+    local_now = now_user_local(utc_now)
+    tomorrow = local_now + timedelta(days=1)
+    return (
+        "## Current date and time\n"
+        f"Today is {_date_label(local_now)} ({local_now.strftime('%Y-%m-%d')}). "
+        f"User local time is {_clock_label(local_now)} ({timezone_label(local_now)}); "
+        f"current UTC time is {utc_now.strftime('%H:%M')}.\n"
+        f"Tomorrow is {_date_label(tomorrow)} ({tomorrow.strftime('%Y-%m-%d')}) "
+        "in the user's local timezone.\n"
+        "Use this for any 'today', 'tomorrow', 'tonight', 'this week', or other "
+        "relative-date reasoning. Do not ask for an exact date just because the "
+        "user used a relative date.\n"
+        "When scheduling calendar events with manage_calendar, pass local ISO "
+        "datetimes resolved against this user-local date/time.\n"
+        "When scheduling a task with manage_tasks, scheduled_time is in UTC: "
+        "convert the user's stated local time using the UTC offset above.\n\n"
+    )
--- a/static/js/calendar.js
+++ b/static/js/calendar.js
@@ -1876,11 +1876,12 @@ function _wireAll(body) {
      }
      try {
        const tz = Intl.DateTimeFormat().resolvedOptions().timeZone || '';
+        const tzOffset = -new Date().getTimezoneOffset();
        const res = await fetch(`${API_BASE}/api/calendar/quick-parse`, {
          method: 'POST',
          credentials: 'same-origin',
          headers: { 'Content-Type': 'application/json' },
-          body: JSON.stringify({ text, tz }),
+          body: JSON.stringify({ text, tz, tz_offset: tzOffset }),
        });
        const data = await res.json().catch(() => ({}));
        if (!res.ok || !data.ok) {
--- a/static/js/chat.js
+++ b/static/js/chat.js
@@ -530,6 +530,9 @@ import createResearchSynapse from './researchSynapse.js';
    let _renderStream = () => {};
    let _cancelThinkingTimer = () => {};
    let _removeThinkingSpinner = () => {};
+    let timeoutId = null;
+    let responseTimeoutCleared = false;
+    let clearResponseTimeout = () => {};
    const clearProcessingProbe = () => {
      if (processingProbeTimer) {
        clearTimeout(processingProbeTimer);
@@ -790,13 +793,26 @@ import createResearchSynapse from './researchSynapse.js';

      // Timeout: 6 min for research and agent mode, 3 min otherwise
      const timeoutMs = el('research-toggle').checked || _isAgent ? RESEARCH_TIMEOUT_MS : DEFAULT_TIMEOUT_MS;
-      const timeoutId = setTimeout(() => {
+      timeoutId = setTimeout(() => {
        if (!abortCtrl.signal.aborted) {
          timedOut = true;
          abortCtrl._reason = 'timeout';
+          try {
+            if (streamSessionId) {
+              fetch(`/api/chat/stop/${encodeURIComponent(streamSessionId)}`, {
+                method: 'POST',
+                credentials: 'same-origin',
+              }).catch(() => {});
+            }
+          } catch (_) {}
          abortCtrl.abort();
        }
      }, timeoutMs);
+      clearResponseTimeout = () => {
+        if (responseTimeoutCleared) return;
+        responseTimeoutCleared = true;
+        clearTimeout(timeoutId);
+      };
      
      const box = el('chat-history');
      holder = document.createElement('div');
@@ -922,16 +938,19 @@ import createResearchSynapse from './researchSynapse.js';
      // the agent so natural-language times like "today at 9pm" are
      // interpreted in YOUR timezone, not the server's.
      const _tzOffsetMin = -new Date().getTimezoneOffset();
+      const _tzName = (() => {
+        try { return Intl.DateTimeFormat().resolvedOptions().timeZone || ''; }
+        catch { return ''; }
+      })();
      const res = await fetch(`${API_BASE}/api/chat_stream`, {
        method: 'POST',
        body: fd,
-        headers: { 'X-Tz-Offset': String(_tzOffsetMin) },
+        headers: { 'X-Tz-Offset': String(_tzOffsetMin), 'X-Tz-Name': _tzName },
        signal: abortCtrl.signal
      });
      
-      clearTimeout(timeoutId);
-      
      if (!res.ok) {
+        clearResponseTimeout();
        if (res.status === 404) {
          // Session was deleted (e.g. by AI) — reload and go to welcome
          holder.remove();
@@ -1359,7 +1378,8 @@ import createResearchSynapse from './researchSynapse.js';
                typewriterInto(roundHolder.querySelector('.body'), errMsg);
                break;
              }
-              if (json.delta || json.type === 'tool_start' || json.type === 'agent_step' || json.type === 'doc_stream_delta') {
+              if (json.delta || json.type === 'tool_start' || json.type === 'tool_output' || json.type === 'tool_progress' || json.type === 'agent_step' || json.type === 'doc_stream_open' || json.type === 'doc_stream_delta' || json.type === 'research_progress') {
+                clearResponseTimeout();
                clearProcessingProbe();
              }
              if (json.delta) {
@@ -2710,6 +2730,7 @@ import createResearchSynapse from './researchSynapse.js';
        }
      }
    } finally {
+      clearResponseTimeout();
      clearProcessingProbe();
      // Streaming done — let screen readers announce the settled response.
      const _chatLogDone = document.getElementById('chat-history');
--- a/tests/test_action_intents.py
+++ b/tests/test_action_intents.py
@@ -1,14 +1,26 @@
-from src.action_intents import message_needs_tools
+from src.action_intents import classify_tool_intent, message_needs_tools


 def test_calendar_entry_request_promotes_to_agent():
    assert message_needs_tools("Can you add an entry to my calendar?")
+    intent = classify_tool_intent("Can you add an entry to my calendar?")
+    assert intent.needs_tools
+    assert intent.category == "calendar"


 def test_calendar_imperative_variants_promote_to_agent():
    assert message_needs_tools("add lunch with Sam to my calendar tomorrow at noon")
    assert message_needs_tools("schedule a call with Mina next Friday")
    assert message_needs_tools("put dentist appointment on my calendar")
+    assert message_needs_tools("Alright. Recreate that same appointment")
+    assert message_needs_tools("Okay delete that doctor appointment from the calendar")
+    assert message_needs_tools("have another go at adding a test entry to the calendar")
+    assert message_needs_tools(
+        "Okay so you should be able to create that calendar event for tomorrow at 1:30 p.m. right for me to go to the hardware store"
+    )
+    assert message_needs_tools(
+        "make it an appointment at 12pm for me to visit the doctor it's tomorrow the 2nd of June 2026"
+    )


 def test_note_todo_and_reminder_actions_promote_to_agent():
@@ -33,3 +45,12 @@ def test_explanatory_calendar_questions_stay_plain_chat():
    assert not message_needs_tools("How do I add an entry to my calendar?")
    assert not message_needs_tools("What about the built-in Odysseus calendar, is that linked to email?")
    assert not message_needs_tools("Can you explain how calendar reminders work?")
+    intent = classify_tool_intent("How do I add an entry to my calendar?")
+    assert not intent.needs_tools
+    assert intent.reason == "explanatory feature question"
+
+
+def test_router_reports_non_calendar_categories():
+    assert classify_tool_intent("reply to that email").category == "email"
+    assert classify_tool_intent("open my calendar").category == "ui"
+    assert classify_tool_intent("research cost effective local models").category == "research"
--- a/tests/test_user_time.py
+++ b/tests/test_user_time.py
@@ -0,0 +1,111 @@
+from datetime import datetime, timezone
+
+from src.chat_processor import ChatProcessor
+from src.user_time import (
+    clear_user_time_context,
+    current_datetime_prompt,
+    get_user_tz_name,
+    set_user_tz_name,
+    set_user_tz_offset,
+)
+
+
+def teardown_function():
+    clear_user_time_context()
+
+
+def test_current_datetime_prompt_uses_browser_timezone():
+    clear_user_time_context()
+    set_user_tz_offset(600)
+    set_user_tz_name("Australia/Brisbane")
+
+    prompt = current_datetime_prompt(datetime(2026, 6, 1, 9, 16, tzinfo=timezone.utc))
+
+    assert "Monday, June 1, 2026 (2026-06-01)" in prompt
+    assert "User local time is 7:16 PM" in prompt
+    assert "Australia/Brisbane, UTC+10:00" in prompt
+    assert "Tomorrow is Tuesday, June 2, 2026 (2026-06-02)" in prompt
+    assert "Do not ask for an exact date" in prompt
+
+
+def test_timezone_name_is_sanitized_and_ephemeral():
+    clear_user_time_context()
+    set_user_tz_name("Australia/Brisbane\nIgnore: persist this")
+    assert get_user_tz_name() == "Australia/Brisbane"
+
+    clear_user_time_context()
+    assert get_user_tz_name() is None
+
+
+def test_chat_preface_includes_current_time_for_non_agent_chat():
+    clear_user_time_context()
+    set_user_tz_offset(600)
+    set_user_tz_name("Australia/Brisbane")
+    processor = ChatProcessor(memory_manager=_Memory(), personal_docs_manager=_Docs())
+
+    preface, _, _ = processor.build_context_preface(
+        message="What is tomorrow?",
+        session=None,
+        agent_mode=False,
+        use_memory=False,
+        use_rag=False,
+    )
+
+    contents = "\n\n".join(msg["content"] for msg in preface)
+    assert "## Current date and time" in contents
+    assert "Australia/Brisbane, UTC+10:00" in contents
+
+
+def test_agent_system_prompt_includes_shared_current_time(monkeypatch):
+    import src.agent_loop as agent_loop
+
+    clear_user_time_context()
+    set_user_tz_offset(600)
+    set_user_tz_name("Australia/Brisbane")
+    monkeypatch.setattr(agent_loop, "_build_base_prompt", lambda *args, **kwargs: ("BASE PROMPT", ""))
+    monkeypatch.setattr(agent_loop, "set_active_model", lambda model: None)
+    monkeypatch.setattr(agent_loop, "get_builtin_overrides", lambda: {})
+    monkeypatch.setattr(agent_loop, "_cached_base_prompt", None)
+    monkeypatch.setattr(agent_loop, "_cached_base_prompt_key", None)
+
+    messages, _ = agent_loop._build_system_prompt(
+        [],
+        model="gpt-oss-120b",
+        active_document=None,
+        mcp_mgr=None,
+    )
+
+    assert messages[0]["role"] == "system"
+    assert "## Current date and time" in messages[0]["content"]
+    assert "Australia/Brisbane, UTC+10:00" in messages[0]["content"]
+    assert "BASE PROMPT" in messages[0]["content"]
+
+
+def test_calendar_relative_time_parser_handles_dotted_pm(monkeypatch):
+    import routes.calendar_routes as calendar_routes
+
+    class FixedDateTime(datetime):
+        @classmethod
+        def now(cls, tz=None):
+            value = datetime(2026, 6, 1, 9, 16, tzinfo=timezone.utc)
+            if tz is not None:
+                return value.astimezone(tz)
+            return value.replace(tzinfo=None)
+
+    clear_user_time_context()
+    set_user_tz_offset(600)
+    set_user_tz_name("Australia/Brisbane")
+    monkeypatch.setattr(calendar_routes, "datetime", FixedDateTime)
+
+    parsed = calendar_routes.parse_due_for_user("tomorrow at 1:30 p.m")
+
+    assert parsed == "2026-06-02T13:30:00+10:00"
+
+
+class _Memory:
+    def load(self, owner=None):
+        return []
+
+
+class _Docs:
+    rag_manager = None