"""TurnEngine — the owned agent loop.

Async, but with blocking provider/tool calls wrapped in `asyncio.to_thread` so the loop
(and any UI consuming its events) stays responsive. One user turn spans many model↔tool
iterations until the model stops requesting tools, a rail trips, or it's interrupted.
When the model requests several tool calls in one turn, low-risk ones (reads, searches)
execute concurrently; writes/shell stay strictly ordered.

Approvals are handled out-of-band via an injected async `approver`: when the permission
engine says `needs_user`, the engine emits `PERMISSION_REQUIRED` and awaits the approver.
"""

from __future__ import annotations

import asyncio
import json
import time
from dataclasses import dataclass
from enum import Enum
from typing import Any, AsyncIterator, Awaitable, Callable, Optional

from .events import Event, EventType
from .permissions import Mode, PermissionEngine
from .providers import AssistantTurn, ProviderClient, ToolCall
from .providers.errors import friendly_model_error
from .tools import ToolRegistry


class ApprovalOutcome(str, Enum):
    ONCE = "once"
    ALWAYS_TOOL = "always_tool"
    ALWAYS_COMMAND = "always_command"
    DENY = "deny"


@dataclass
class PermissionRequest:
    tool_name: str
    arguments: dict[str, Any]
    metadata: Any
    reason: str
    tool_call_id: Optional[str] = None  # for durable resume (idempotent inbox item)


Approver = Callable[[PermissionRequest], Awaitable[ApprovalOutcome]]


async def _deny_all(_request: PermissionRequest) -> ApprovalOutcome:
    return ApprovalOutcome.DENY


class TurnEngine:
    def __init__(
        self,
        *,
        provider: ProviderClient,
        registry: ToolRegistry,
        permissions: PermissionEngine,
        model: str,
        instructions: Optional[str] = None,
        approver: Optional[Approver] = None,
        max_iterations: int = 12,
        model_settings: Optional[dict[str, Any]] = None,
        messages: Optional[list[dict[str, Any]]] = None,
        audit_sink: Optional[Callable[[dict[str, Any]], None]] = None,
        context_provider: Optional[Callable[[], str]] = None,
        directory_requester: Optional[
            Callable[[dict[str, Any]], "Awaitable[dict[str, Any]]"]
        ] = None,
        plan_approver: Optional[
            Callable[[dict[str, Any]], "Awaitable[dict[str, Any]]"]
        ] = None,
        question_asker: Optional[
            Callable[[dict[str, Any]], "Awaitable[dict[str, Any]]"]
        ] = None,
    ) -> None:
        self.provider = provider
        self.registry = registry
        self.permissions = permissions
        self.model = model
        self.approver = approver or _deny_all
        self.max_iterations = max_iterations
        self.model_settings = dict(model_settings or {})
        self.messages: list[dict[str, Any]] = list(messages or [])
        self.audit_sink = audit_sink
        # Returns an ephemeral `<system-context>` block appended to the LAST user message at
        # send-time only (never persisted). We can't reliably inject system messages mid-thread
        # across providers, so dynamic per-turn context (e.g. the live directory list) rides on
        # the latest user turn. Returns "" when there's nothing to add.
        self.context_provider = context_provider
        # Handles the `request_directory` tool: emits a DIRECTORY_REQUESTED prompt, waits for the
        # user to grant/decline a folder out-of-band, applies the grant to this live session, and
        # returns the outcome. None on surfaces that can't prompt (the tool then no-ops).
        self.directory_requester = directory_requester
        # Handles the `propose_plan` tool: emits PLAN_PROPOSED, waits for the user's decision.
        # An approving result flips the live PermissionEngine out of plan mode (same session,
        # context kept). None on surfaces that can't prompt (the tool then no-ops).
        self.plan_approver = plan_approver
        # Handles the `ask_user` tool: turns a question into an Inbox item and waits for the answer
        # (answerable inline in a live session or from the Inbox when unattended). None on surfaces
        # that can't ask (the tool then no-ops).
        self.question_asker = question_asker
        self.audit_context: dict[str, Any] = {}
        if instructions and not (
            self.messages and self.messages[0].get("role") == "system"
        ):
            self.messages.insert(0, {"role": "system", "content": instructions})
        self._cancel = asyncio.Event()
        # Each pending steering message: (text, optional MessageSource sidecar dict).
        self._steering: list[tuple[str, Optional[dict[str, Any]]]] = []
        # tool_call.id → the standing rule that auto-allowed it ("tool → target"), so the
        # TOOL_FINISHED event can carry the note to the tool card (§25).
        self._standing_notes: dict[str, str] = {}

    # -- external controls ------------------------------------------------------
    def request_interrupt(self) -> None:
        self._cancel.set()

    def queue_steering(
        self, text: str, source: Optional[dict[str, Any]] = None
    ) -> None:
        self._steering.append((text, source))

    # -- main loop --------------------------------------------------------------
    async def run(
        self, user_input: "str | list", *, source: Optional[dict[str, Any]] = None
    ) -> AsyncIterator[Event]:
        # `user_input` is a string, or OpenAI content-parts (text + image_url) for attachments.
        # `source` (a MessageSource dict) is a display-only sidecar for connector messages: it
        # rides on the persisted user message + the TURN_START event, but is stripped before the
        # message reaches a provider (see `_outbound_messages`). `content` stays the framed text.
        # `ts` (unix seconds, stamped on every appended message) is the same kind of sidecar.
        message: dict[str, Any] = {
            "role": "user",
            "content": user_input,
            "ts": time.time(),
        }
        if source is not None:
            message["source"] = source
        self.messages.append(message)
        self._cancel.clear()
        data: dict[str, Any] = {"input": user_input}
        if source is not None:
            data["source"] = source
        yield Event(EventType.TURN_START, data)
        async for event in self._loop():
            yield event

    async def resume(self) -> AsyncIterator[Event]:
        """Continue a turn that was suspended at a prompt and persisted — durable resume after a
        restart (or engine eviction). Re-process the trailing assistant message's UNANSWERED
        tool-calls (the prompt callbacks find the already-resolved Inbox item and return without
        re-prompting; answered calls are skipped, so nothing double-executes), then run the model
        loop to finish the turn."""
        pending = self._unanswered_trailing_tool_calls()
        if not pending:
            return
        self._cancel.clear()
        yield Event(EventType.TURN_START, {"input": "(resumed)"})
        async for event in self._handle_tool_calls(pending):
            yield event
        yield Event(EventType.ITERATION_END, {"iteration": 0})
        if not self._cancel.is_set():
            async for event in self._loop():
                yield event

    def _unanswered_trailing_tool_calls(self) -> list[ToolCall]:
        """The tool-calls of the last assistant message that don't yet have a tool result —
        i.e. the prompt we suspended on (+ any after it). Reconstructed from the persisted thread.
        """
        answered = {
            m.get("tool_call_id") for m in self.messages if m.get("role") == "tool"
        }
        for msg in reversed(self.messages):
            if msg.get("role") == "user":
                return []
            if msg.get("role") == "assistant" and msg.get("tool_calls"):
                out: list[ToolCall] = []
                for tc in msg["tool_calls"]:
                    if tc.get("id") in answered:
                        continue
                    fn = tc.get("function") or {}
                    try:
                        args = json.loads(fn.get("arguments") or "{}")
                    except Exception:
                        args = {}
                    out.append(
                        ToolCall(id=tc.get("id"), name=fn.get("name"), arguments=args)
                    )
                return out
        return []

    async def _loop(self) -> AsyncIterator[Event]:
        iterations = 0
        while True:
            if iterations >= self.max_iterations:
                yield Event(
                    EventType.TURN_END,
                    {"status": "max_iterations_exceeded", "iterations": iterations},
                )
                return
            iterations += 1

            turn: Optional[AssistantTurn] = None
            try:
                async for chunk in self._astream():
                    if chunk.text_delta:
                        yield Event(
                            EventType.ASSISTANT_DELTA, {"text": chunk.text_delta}
                        )
                    if chunk.turn is not None:
                        turn = chunk.turn
            except Exception as exc:  # provider failure
                friendly = friendly_model_error(self.model, exc)
                payload = {
                    "error": friendly or str(exc),
                    "error_type": type(exc).__name__,
                }
                if friendly:
                    payload["raw"] = str(exc)
                yield Event(EventType.ERROR, payload)
                return
            if turn is None:
                turn = AssistantTurn()

            self.messages.append(_assistant_message(turn))
            yield Event(
                EventType.ASSISTANT_MESSAGE,
                {"text": turn.text, "tool_calls": [tc.name for tc in turn.tool_calls]},
            )

            if not turn.tool_calls:
                if self._steering:
                    self._inject_steering()
                    continue
                yield Event(
                    EventType.TURN_END,
                    {"status": "completed", "iterations": iterations},
                )
                return

            async for event in self._handle_tool_calls(turn.tool_calls):
                yield event

            yield Event(EventType.ITERATION_END, {"iteration": iterations})

            if self._cancel.is_set():
                yield Event(EventType.INTERRUPTED, {"iterations": iterations})
                return
            if self._steering:
                self._inject_steering()

    # -- helpers ----------------------------------------------------------------
    async def _astream(self):
        """Bridge the provider's blocking stream generator to the async loop via a
        thread + queue, so text deltas surface live without blocking the event loop."""
        loop = asyncio.get_running_loop()
        queue: asyncio.Queue = asyncio.Queue()
        tools = self.registry.schemas() or None
        model, messages, settings = (
            self.model,
            self._outbound_messages(),
            self.model_settings,
        )
        provider = self.provider

        def produce():
            try:
                for chunk in provider.stream(
                    model=model, messages=messages, tools=tools, **settings
                ):
                    loop.call_soon_threadsafe(queue.put_nowait, ("chunk", chunk))
            except Exception as exc:  # surfaced to the awaiting consumer
                loop.call_soon_threadsafe(queue.put_nowait, ("error", exc))
            finally:
                loop.call_soon_threadsafe(queue.put_nowait, ("done", None))

        loop.run_in_executor(None, produce)
        while True:
            kind, payload = await queue.get()
            if kind == "chunk":
                yield payload
            elif kind == "error":
                raise payload
            else:
                return

    async def _handle_tool_calls(
        self, tool_calls: list[ToolCall]
    ) -> AsyncIterator[Event]:
        """Run one assistant turn's tool calls: authorize all of them first (sequentially —
        approval prompts are interactive), then execute. Low-risk calls (reads, searches)
        run concurrently; everything else runs one at a time in call order."""
        cleared: list[ToolCall] = []
        for tool_call in tool_calls:
            yield Event(
                EventType.TOOL_PROPOSED,
                {"name": tool_call.name, "arguments": tool_call.arguments},
            )
            self._audit(tool_call, stage="proposed")
            # `request_directory` and `propose_plan` are interactive: the user decides
            # out-of-band and that decision IS the consent, so they skip the
            # permission/registry path.
            if tool_call.name == "request_directory":
                async for event in self._handle_directory_request(tool_call):
                    yield event
                continue
            if tool_call.name == "propose_plan":
                async for event in self._handle_plan_proposal(tool_call):
                    yield event
                continue
            if tool_call.name == "ask_user":
                async for event in self._handle_ask_user(tool_call):
                    yield event
                continue
            allowed = False
            async for item in self._authorize(tool_call):
                if isinstance(item, Event):
                    yield item
                else:
                    allowed = item
            if allowed:
                cleared.append(tool_call)

        concurrent = (
            [tc for tc in cleared if self._parallel_safe(tc)]
            if len(cleared) > 1
            else []
        )
        serial = [tc for tc in cleared if tc not in concurrent]

        if concurrent:
            for tool_call in concurrent:
                yield Event(EventType.TOOL_STARTED, {"name": tool_call.name})
                self._audit(tool_call, stage="started")
            outcomes = await asyncio.gather(
                *[asyncio.to_thread(self._execute_sync, tc) for tc in concurrent]
            )
            for tool_call, (result, status) in zip(concurrent, outcomes):
                yield self._record_result(tool_call, result, status)

        for tool_call in serial:
            yield Event(EventType.TOOL_STARTED, {"name": tool_call.name})
            self._audit(tool_call, stage="started")
            result, status = await asyncio.to_thread(self._execute_sync, tool_call)
            yield self._record_result(tool_call, result, status)

    def _parallel_safe(self, tool_call: ToolCall) -> bool:
        # Only metadata-declared low-risk tools (reads, searches, git queries) run
        # concurrently; writes, shell, and anything unannotated stay strictly ordered.
        spec = self.registry.get(tool_call.name)
        metadata = spec.metadata if spec else None
        return getattr(metadata, "risk_level", "") == "low" and not getattr(
            metadata, "requires_approval", False
        )

    async def _authorize(self, tool_call: ToolCall) -> "AsyncIterator[Event | bool]":
        """Permission flow for one call (TOOL_PROPOSED is emitted by the caller). Yields
        its events, then True/False (allowed) last. Denied/unknown calls get their
        tool-error message appended here."""
        from .permissions import standing_rule_candidate

        spec = self.registry.get(tool_call.name)
        metadata = spec.metadata if spec else None

        decision = self.permissions.evaluate(
            tool_call.name, tool_call.arguments, metadata
        )
        allowed = decision.allowed
        reason = decision.reason

        if allowed and decision.rule:
            # A task-scoped standing rule auto-allowed this call: audit the exact rule
            # (§25 invariant — every auto-allowed call cites its rule) and remember it so
            # the tool card can say "allowed by standing rule".
            self._standing_notes[tool_call.id] = decision.rule
            self._audit(
                tool_call, stage="auto_allowed", status="allowed", reason=reason
            )

        if not allowed and decision.needs_user:
            yield Event(
                EventType.PERMISSION_REQUIRED,
                {
                    "name": tool_call.name,
                    "arguments": tool_call.arguments,
                    "reason": decision.reason,
                    "category": getattr(metadata, "category", ""),
                    # The exact target a standing rule could pin, or None when the call
                    # isn't eligible (no declared target arg / exec risk). Surfaces use it
                    # to offer "Allow every time" on automation-run approval cards only.
                    "standing_target": standing_rule_candidate(
                        tool_call.name,
                        tool_call.arguments,
                        metadata,
                        self.permissions.risk_overrides,
                    ),
                },
            )
            self._audit(tool_call, stage="approval_requested", reason=decision.reason)
            outcome = await self.approver(
                PermissionRequest(
                    tool_name=tool_call.name,
                    arguments=tool_call.arguments,
                    metadata=metadata,
                    reason=decision.reason,
                    tool_call_id=tool_call.id,
                )
            )
            if outcome is ApprovalOutcome.DENY:
                allowed, reason = False, "denied by user"
                self._audit(
                    tool_call,
                    stage="approval_resolved",
                    status="denied",
                    approval=outcome.value,
                    reason=reason,
                )
            else:
                if outcome is ApprovalOutcome.ALWAYS_TOOL:
                    self.permissions.allow_tool_for_session(tool_call.name)
                elif outcome is ApprovalOutcome.ALWAYS_COMMAND:
                    self.permissions.allow_command_for_session(
                        str(tool_call.arguments.get("command", ""))
                    )
                allowed, reason = True, "approved by user"
                self._audit(
                    tool_call,
                    stage="approval_resolved",
                    status="approved",
                    approval=outcome.value,
                    reason=reason,
                )

        if not allowed:
            if spec is None:
                reason = f"unknown tool: {tool_call.name}"
            self.messages.append(_tool_error_message(tool_call, reason))
            yield Event(
                EventType.TOOL_FINISHED,
                {"name": tool_call.name, "status": "denied", "reason": reason},
            )
            self._audit(tool_call, stage="finished", status="denied", reason=reason)
            yield False
            return

        if spec is None:
            self.messages.append(
                _tool_error_message(tool_call, f"unknown tool: {tool_call.name}")
            )
            yield Event(
                EventType.TOOL_FINISHED,
                {"name": tool_call.name, "status": "error", "reason": "unknown tool"},
            )
            yield False
            return

        yield True

    def _execute_sync(self, tool_call: ToolCall) -> tuple[Any, str]:
        """Execute one authorized call (runs in a worker thread)."""
        try:
            return self.registry.execute(tool_call.name, tool_call.arguments), "ok"
        except Exception as exc:
            return {"error": str(exc), "error_type": type(exc).__name__}, "error"

    def _record_result(self, tool_call: ToolCall, result: Any, status: str) -> Event:
        # A `_display` key on a tool result is user-facing metadata the AGENT must
        # never see (e.g. how many gmail hits the privacy filters hid — a count
        # the model could probe around). Lift it onto the message as a sidecar
        # (like `source`), stripped from every provider feed in
        # `_outbound_messages` but persisted for the GUI's tool card.
        display: Optional[dict[str, Any]] = None
        if isinstance(result, dict) and "_display" in result:
            display = result.get("_display") or None
            result = {k: v for k, v in result.items() if k != "_display"}
        message = _tool_result_message(tool_call, result)
        if display:
            message["_display"] = display
        self.messages.append(message)
        hidden = int((display or {}).get("hidden_by_filters") or 0)
        stripped = int((display or {}).get("hidden_fields") or 0)
        if hidden or stripped:
            # The out-of-band trace the user CAN see: rule class + count, never content.
            parts = []
            if hidden:
                parts.append(f"{hidden} result(s) hidden")
            if stripped:
                parts.append(f"{stripped} field value(s) stripped")
            self._audit(
                tool_call,
                stage="filtered",
                status="hidden",
                reason=" · ".join(parts) + " by privacy filters",
            )
        self._audit(
            tool_call,
            stage="finished",
            status=status,
            result=result,
            result_preview=_preview(result),
        )
        rule = self._standing_notes.pop(tool_call.id, "")
        return Event(
            EventType.TOOL_FINISHED,
            {
                "name": tool_call.name,
                "status": status,
                "result_preview": _preview(result),
                **({"display": display} if display else {}),
                **({"standing_rule": rule} if rule else {}),
            },
        )

    def _audit(self, tool_call: ToolCall, **event: Any) -> None:
        if self.audit_sink is None:
            return
        payload = {
            **self.audit_context,
            "tool": tool_call.name,
            "arguments": tool_call.arguments,
            **event,
        }
        try:
            self.audit_sink(payload)
        except Exception:
            pass

    async def _handle_plan_proposal(self, tool_call: ToolCall) -> AsyncIterator[Event]:
        """Emit the plan for review, await the user's out-of-band decision, and apply it:
        approval flips the live PermissionEngine out of plan mode (the same session keeps
        going, with all its exploration context); rejection keeps plan mode and returns
        the user's feedback so the agent can revise."""
        args = tool_call.arguments or {}
        plan = str(args.get("plan", ""))
        if self.permissions.mode is not Mode.PLAN:
            # The tool is always registered (mode can flip mid-session), but proposing a
            # plan only means something while the session is actually in plan mode. The
            # right next step differs by mode: discuss stays read-only, so the agent
            # should talk through the change; write-capable modes should just do it.
            if self.permissions.mode is Mode.DISCUSS:
                error = (
                    "not in plan mode — this is discuss mode (read-only), so describe "
                    "the proposed changes in chat instead"
                )
            else:
                error = "not in plan mode — proceed with the work directly"
            result: dict[str, Any] = {"approved": False, "error": error}
        elif self.plan_approver is None:
            result = {
                "approved": False,
                "error": "plan approval isn't available here",
            }
        else:
            yield Event(EventType.PLAN_PROPOSED, {"plan": plan})
            self._audit(tool_call, stage="plan_proposed")
            result = await self.plan_approver(dict(args), tool_call.id) or {
                "approved": False,
                "error": "no response",
            }

        if result.get("approved"):
            # The approver may pick the post-plan mode ("interactive" asks per write,
            # "auto" executes the approved plan without further prompts).
            try:
                self.permissions.mode = Mode(str(result.get("mode", "interactive")))
            except ValueError:
                self.permissions.mode = Mode.INTERACTIVE
            result = {
                **result,
                "mode": self.permissions.mode.value,
                "note": "plan approved — implement it now",
            }

        status = "ok" if result.get("approved") else "denied"
        self.messages.append(_tool_result_message(tool_call, result))
        self._audit(
            tool_call,
            stage="finished",
            status=status,
            result=result,
            result_preview=_preview(result),
        )
        yield Event(
            EventType.TOOL_FINISHED,
            {
                "name": tool_call.name,
                "status": status,
                "result_preview": _preview(result),
            },
        )

    async def _handle_directory_request(
        self, tool_call: ToolCall
    ) -> AsyncIterator[Event]:
        """Emit the grant prompt, await the user's out-of-band decision (which the requester also
        applies to this session's roots), and return the outcome as the tool result."""
        args = tool_call.arguments or {}
        if self.directory_requester is None:
            result: dict[str, Any] = {
                "granted": False,
                "error": "directory requests aren't available here",
            }
        else:
            yield Event(
                EventType.DIRECTORY_REQUESTED,
                {
                    "reason": str(args.get("reason", "")),
                    "path": str(args.get("path", "")),
                    "writable": bool(args.get("writable", False)),
                },
            )
            self._audit(
                tool_call,
                stage="directory_requested",
                reason=str(args.get("reason", "")),
            )
            result = await self.directory_requester(dict(args), tool_call.id) or {
                "granted": False,
                "error": "no response",
            }

        status = "ok" if result.get("granted") else "denied"
        self.messages.append(_tool_result_message(tool_call, result))
        self._audit(
            tool_call,
            stage="finished",
            status=status,
            result=result,
            result_preview=_preview(result),
        )
        yield Event(
            EventType.TOOL_FINISHED,
            {
                "name": tool_call.name,
                "status": status,
                "result_preview": _preview(result),
            },
        )

    async def _handle_ask_user(self, tool_call: ToolCall) -> AsyncIterator[Event]:
        """Emit the question, await the user's out-of-band answer (inline in the live session or
        from the Inbox when unattended), and return it as the tool result."""
        args = tool_call.arguments or {}
        question = str(args.get("question", "")).strip()
        if self.question_asker is None or not question:
            result: dict[str, Any] = {
                "answer": "",
                "error": (
                    "no question was asked"
                    if not question
                    else "asking isn't available here"
                ),
            }
        else:
            # The asker is mode-aware (attended → live inline prompt; unattended → Inbox), so it
            # owns surfacing the question. The engine just awaits the answer.
            self._audit(tool_call, stage="question_requested", reason=question)
            result = await self.question_asker(dict(args), tool_call.id) or {
                "answer": "",
                "error": "no response",
            }

        status = "ok" if result.get("answer") else "denied"
        self.messages.append(_tool_result_message(tool_call, result))
        self._audit(
            tool_call,
            stage="finished",
            status=status,
            result=result,
            result_preview=_preview(result),
        )
        yield Event(
            EventType.TOOL_FINISHED,
            {
                "name": tool_call.name,
                "status": status,
                "result_preview": _preview(result),
            },
        )

    def _inject_steering(self) -> None:
        for text, source in self._steering:
            message: dict[str, Any] = {
                "role": "user",
                "content": text,
                "ts": time.time(),
            }
            if source is not None:
                message["source"] = source
            self.messages.append(message)
        self._steering = []

    def _outbound_messages(self) -> list[dict[str, Any]]:
        """`self.messages` prepared for the provider. The SOLE provider feed (see `_astream`).

        Every message is stripped of the display-only sidecars — `source`, `_display`, and
        `ts` — (providers reject unknown keys), unconditionally — whether or not a
        `<system-context>` block is added. When a context
        provider yields a non-empty string, an ephemeral `<system-context>` block is appended to the
        last user message. Never mutates `self.messages`, so neither the strip nor the block is
        persisted/replayed.
        """
        # Strip the display-only sidecars — `source` (connector cards), `_display`
        # (e.g. filter-hidden counts), and `ts` (append-time timestamps) — copying only
        # messages that carry one.
        _SIDECARS = ("source", "_display", "ts")
        out = [
            (
                {k: v for k, v in msg.items() if k not in _SIDECARS}
                if any(s in msg for s in _SIDECARS)
                else msg
            )
            for msg in self.messages
        ]
        # PDF attachments (stored as `file` parts) are adapted to the ACTIVE model right
        # here — never in the persisted history — so a mid-session model switch always
        # re-decides: native PDF models get the real document, the rest get the local
        # text-extract/page-image fallback (pdf_support.py).
        if any(
            isinstance(p, dict) and p.get("type") == "file"
            for msg in out
            if isinstance(msg.get("content"), list)
            for p in msg["content"]
        ):
            caps = self.provider.capabilities(self.model)
            if not getattr(caps, "pdf", False):
                from . import pdf_support

                out = [
                    (
                        {
                            **msg,
                            "content": pdf_support.adapt_content(msg["content"], caps),
                        }
                        if isinstance(msg.get("content"), list)
                        else msg
                    )
                    for msg in out
                ]

        context = (
            self.context_provider() if self.context_provider is not None else ""
        ) or ""
        if not context:
            return out
        block = f"\n\n<system-context>\n{context}\n</system-context>"
        for i in range(len(out) - 1, -1, -1):
            if out[i].get("role") != "user":
                continue
            msg = dict(out[i])
            content = msg.get("content")
            if isinstance(content, str):
                msg["content"] = content + block
            elif isinstance(content, list):  # content-parts (text + images)
                msg["content"] = [*content, {"type": "text", "text": block}]
            else:
                msg["content"] = block
            out[i] = msg
            break
        return out


def _assistant_message(turn: AssistantTurn) -> dict[str, Any]:
    message: dict[str, Any] = {
        "role": "assistant",
        "content": turn.text or "",
        "ts": time.time(),
    }
    if turn.tool_calls:
        message["tool_calls"] = [
            {
                "id": tc.id,
                "type": "function",
                "function": {"name": tc.name, "arguments": json.dumps(tc.arguments)},
            }
            for tc in turn.tool_calls
        ]
    return message


def _tool_result_message(tool_call: ToolCall, result: Any) -> dict[str, Any]:
    content = result if isinstance(result, str) else json.dumps(result, default=str)
    return {
        "role": "tool",
        "tool_call_id": tool_call.id,
        "content": content,
        "ts": time.time(),
    }


def _tool_error_message(tool_call: ToolCall, reason: str) -> dict[str, Any]:
    return {
        "role": "tool",
        "tool_call_id": tool_call.id,
        "content": json.dumps({"error": "tool call not executed", "reason": reason}),
        "ts": time.time(),
    }


def _preview(value: Any, max_chars: int = 300) -> str:
    text = value if isinstance(value, str) else json.dumps(value, default=str)
    text = text.replace("\n", "\\n")
    return text if len(text) <= max_chars else text[: max_chars - 3] + "..."