hyungi_document_server/app/api/study_topics.py

"""학습 워크스페이스(study_topic) API — 필기 세션 + 자료(library document) 묶음 컨테이너

핵심 개념:
  - study_topic 은 단순 폴더/태그가 아니라 학습 자산 1차 컨테이너 (학습 워크스페이스).
  - 향후 단어장/오디오/문제 세트 같은 자산이 같은 컨테이너 아래로 들어올 수 있도록
    응답 구조를 sections + stats 형태로 설계 (현재는 sessions / documents 두 키만).
  - documents.category(자료실 UI 축) 와 직교한 별도 분류 축. 자료실 facet/카테고리는 미터치.
  - StudySession.certification/subject/topic 은 보존 — 본 컨테이너 와 직교한 세부 메타.

설계 제약:
  - study_type 은 강한 enum 미사용. VALID_STUDY_TYPES 는 단순 권장값 (DB/Pydantic 강제 안 함).
  - soft delete (deleted_at). active 행끼리만 (user_id, name) partial unique.
  - 권한: 모든 쿼리에 user_id 강제. 다른 사용자 자료를 묶지 못함.
  - 문서 매핑은 N:M (study_topic_documents). 세션 매핑은 1:N (study_sessions.study_topic_id).
  - polymorphic 단일 study_topic_items 테이블은 만들지 않는다 (영구 금지).
"""

import logging
from datetime import datetime, timezone
from typing import Annotated, Any

from fastapi import APIRouter, Depends, HTTPException, Query
from pydantic import BaseModel, Field
from sqlalchemy import and_, delete, func, select, text as sql_text, update
from sqlalchemy.exc import IntegrityError
from sqlalchemy.ext.asyncio import AsyncSession

from core.auth import get_current_user
from core.database import get_session
from core.library import LIBRARY_PREFIX, normalize_library_path
from models.document import Document
from models.study_session import StudySession
from models.study_topic import StudyTopic, StudyTopicDocument
from models.user import User

logger = logging.getLogger(__name__)
router = APIRouter()


# ─── 권장값 (강제 enum 아님, UI 안내용) ───

RECOMMENDED_STUDY_TYPES: set[str] = {
    "certification", "language", "school", "work", "general",
}


# ─── Pydantic 스키마 ───


class StudyTopicCreate(BaseModel):
    name: str = Field(min_length=1, max_length=120)
    description: str | None = None
    color: str | None = Field(default=None, max_length=20)
    study_type: str | None = Field(default=None, max_length=40)
    sort_order: int = 0
    # PR-6: 시험 메타
    exam_round_size: int | None = Field(default=None, ge=1, le=300)
    exam_subjects: list[str] = []


class StudyTopicUpdate(BaseModel):
    name: str | None = Field(default=None, min_length=1, max_length=120)
    description: str | None = None
    color: str | None = Field(default=None, max_length=20)
    study_type: str | None = Field(default=None, max_length=40)
    sort_order: int | None = None
    # PR-6: 시험 메타
    exam_round_size: int | None = Field(default=None, ge=1, le=300)
    exam_subjects: list[str] | None = None


class StudyTopicResponse(BaseModel):
    """주제 목록 응답 — 집계 카운트 포함."""

    id: int
    name: str
    description: str | None
    color: str | None
    study_type: str | None
    sort_order: int
    session_count: int = 0
    document_count: int = 0
    question_count: int = 0
    # PR-6: 시험 메타
    exam_round_size: int | None = None
    exam_subjects: list[str] = []
    created_at: datetime
    updated_at: datetime


class StudyTopicListResponse(BaseModel):
    items: list[StudyTopicResponse]
    total: int


class StudyTopicSessionSummary(BaseModel):
    """상세 뷰의 세션 카드 페이로드 — 통합 뷰 렌더용 최소 필드."""

    id: int
    study_type: str
    certification: str | None
    language_code: str | None
    learning_level: str | None
    subject: str | None
    topic: str | None
    mode: str
    repetition_count: int
    review_state: str | None
    created_at: datetime
    updated_at: datetime


class StudyTopicDocumentSummary(BaseModel):
    """상세 뷰의 자료 카드 페이로드.

    library_paths: 통합뷰 자료 섹션의 카테고리 트리 그룹핑용. user_tags 의
    `@library/<path>` 태그에서 prefix 제거한 path 들. 한 자료가 여러 카테고리에
    속할 수 있으나(다중 분류), 트리 그룹핑 시 첫 번째 path 만 사용. 빈 리스트면
    "분류 없음" 그룹.
    """

    id: int
    title: str | None
    file_format: str
    file_type: str
    category: str | None
    ai_domain: str | None
    importance: str | None
    sort_order: int
    linked_at: datetime
    library_paths: list[str] = []


class StudyTopicQuestionSummary(BaseModel):
    """상세 뷰의 문제 카드 페이로드 — 정답·해설 비공개, 본문 80자 truncate."""

    id: int
    question_text: str
    subject: str | None
    scope: str | None
    exam_name: str | None
    exam_round: str | None
    is_active: bool
    attempt_count: int
    last_correct: bool | None
    created_at: datetime


class StudyTopicSections(BaseModel):
    """확장 친화 dict — 향후 audio_assets / vocab_decks 키 추가 가능."""

    sessions: list[StudyTopicSessionSummary]
    documents: list[StudyTopicDocumentSummary]
    questions: list[StudyTopicQuestionSummary] = []


class StudyTopicStats(BaseModel):
    """자산 카운트 — 0 으로 미리 노출해서 후속 PR 에서 필드만 채움.
    question_count = PR-2 단일 문제 수. question_set_count = 후속 PR 의 회차/모의고사 묶음 수 (둘은 의미 다름).
    """

    session_count: int
    document_count: int
    question_count: int = 0
    audio_count: int = 0
    vocab_count: int = 0
    question_set_count: int = 0


class StudyTopicMeta(BaseModel):
    id: int
    name: str
    description: str | None
    color: str | None
    study_type: str | None
    sort_order: int
    # PR-6: 시험 메타
    exam_round_size: int | None = None
    exam_subjects: list[str] = []
    created_at: datetime
    updated_at: datetime


class StudyTopicDetailResponse(BaseModel):
    topic: StudyTopicMeta
    sections: StudyTopicSections
    stats: StudyTopicStats


class StudyTopicDocumentLinkRequest(BaseModel):
    document_ids: list[int] = Field(min_length=1, max_length=100)


class StudyTopicDocumentLinkResponse(BaseModel):
    linked: list[int]
    skipped_existing: list[int]
    skipped_not_found: list[int]


class StudyTopicDocumentByPathRequest(BaseModel):
    """카테고리 트리 노드 일괄 추가용. path prefix 매칭으로 하위 자료 모두 매핑.
    include_subtree=True 면 path 와 그 하위 카테고리 전체, False 면 path 정확 일치만.
    """
    path: str = Field(min_length=1, max_length=500)
    include_subtree: bool = True


class StudyTopicDocumentByPathResponse(BaseModel):
    linked_count: int
    skipped_existing_count: int
    total_in_path: int
    path: str


# ─── Helpers ───


def _verify_topic_ownership(topic: StudyTopic | None, user: User) -> StudyTopic:
    """소유자 검증 + soft-deleted 행 차단. mismatch 도 404 (정보 누설 방지)."""
    if topic is None or topic.user_id != user.id or topic.deleted_at is not None:
        raise HTTPException(status_code=404, detail="학습 주제를 찾을 수 없습니다")
    return topic


def _meta_from_topic(t: StudyTopic) -> StudyTopicMeta:
    return StudyTopicMeta(
        id=t.id,
        name=t.name,
        description=t.description,
        color=t.color,
        study_type=t.study_type,
        sort_order=t.sort_order,
        exam_round_size=t.exam_round_size,
        exam_subjects=t.exam_subjects or [],
        created_at=t.created_at,
        updated_at=t.updated_at,
    )


# ─── 엔드포인트 ───


@router.get("/", response_model=StudyTopicListResponse)
async def list_study_topics(
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
    limit: int = Query(100, ge=1, le=500),
    offset: int = Query(0, ge=0),
):
    """사용자의 active 주제 목록. 세션 수·자료 수 집계 포함."""

    # active 주제 + 세션 수 (LEFT JOIN study_sessions)
    sess_count_sub = (
        select(
            StudySession.study_topic_id.label("topic_id"),
            func.count().label("c"),
        )
        .where(StudySession.user_id == user.id)
        .where(StudySession.study_topic_id.is_not(None))
        .group_by(StudySession.study_topic_id)
        .subquery()
    )

    doc_count_sub = (
        select(
            StudyTopicDocument.study_topic_id.label("topic_id"),
            func.count().label("c"),
        )
        .where(StudyTopicDocument.user_id == user.id)
        .group_by(StudyTopicDocument.study_topic_id)
        .subquery()
    )

    # PR-2 — 활성 문제 카운트 (soft-deleted 제외)
    from models.study_question import StudyQuestion as _SQ
    q_count_sub = (
        select(
            _SQ.study_topic_id.label("topic_id"),
            func.count().label("c"),
        )
        .where(_SQ.user_id == user.id, _SQ.deleted_at.is_(None))
        .group_by(_SQ.study_topic_id)
        .subquery()
    )

    base = (
        select(
            StudyTopic,
            func.coalesce(sess_count_sub.c.c, 0).label("session_count"),
            func.coalesce(doc_count_sub.c.c, 0).label("document_count"),
            func.coalesce(q_count_sub.c.c, 0).label("question_count"),
        )
        .outerjoin(sess_count_sub, sess_count_sub.c.topic_id == StudyTopic.id)
        .outerjoin(doc_count_sub, doc_count_sub.c.topic_id == StudyTopic.id)
        .outerjoin(q_count_sub, q_count_sub.c.topic_id == StudyTopic.id)
        .where(StudyTopic.user_id == user.id, StudyTopic.deleted_at.is_(None))
        .order_by(StudyTopic.sort_order.asc(), StudyTopic.id.desc())
    )

    total_query = select(func.count()).select_from(
        select(StudyTopic.id)
        .where(StudyTopic.user_id == user.id, StudyTopic.deleted_at.is_(None))
        .subquery()
    )
    total = (await session.execute(total_query)).scalar() or 0

    rows = (await session.execute(base.offset(offset).limit(limit))).all()

    items = [
        StudyTopicResponse(
            id=t.id,
            name=t.name,
            description=t.description,
            color=t.color,
            study_type=t.study_type,
            sort_order=t.sort_order,
            session_count=int(sc),
            document_count=int(dc),
            question_count=int(qc),
            exam_round_size=t.exam_round_size,
            exam_subjects=t.exam_subjects or [],
            created_at=t.created_at,
            updated_at=t.updated_at,
        )
        for t, sc, dc, qc in rows
    ]
    return StudyTopicListResponse(items=items, total=total)


class ExamRoundProgress(BaseModel):
    exam_round: str
    question_count: int
    max_question_number: int  # 0 = exam_question_number 가 모두 NULL
    next_question_number: int | None  # 도달 시 None
    is_complete: bool


class ExamRoundsResponse(BaseModel):
    exam_round_size: int | None  # 토픽 메타. NULL = 미설정
    items: list[ExamRoundProgress]


@router.get("/{topic_id}/exam-rounds", response_model=ExamRoundsResponse)
async def list_exam_rounds(
    topic_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """토픽 안 회차별 진행률 집계. 진행률 표시 + 재개 UX 용.

    is_complete = (exam_round_size IS NOT NULL AND question_count >= exam_round_size).
    next_question_number = max + 1 (도달 시 NULL).
    """
    topic = await session.get(StudyTopic, topic_id)
    _verify_topic_ownership(topic, user)

    from models.study_question import StudyQuestion as _SQ

    rows = (
        await session.execute(
            select(
                _SQ.exam_round,
                func.count().label("question_count"),
                func.coalesce(func.max(_SQ.exam_question_number), 0).label("max_qnum"),
            )
            .where(
                _SQ.user_id == user.id,
                _SQ.study_topic_id == topic_id,
                _SQ.deleted_at.is_(None),
                _SQ.exam_round.is_not(None),
            )
            .group_by(_SQ.exam_round)
            .order_by(_SQ.exam_round.desc())
        )
    ).all()

    size = topic.exam_round_size
    items: list[ExamRoundProgress] = []
    for r in rows:
        cnt = int(r.question_count)
        mx = int(r.max_qnum)
        is_complete = bool(size is not None and cnt >= size)
        # 도달했으면 next None, 아니면 max+1 (max=0 이면 1번부터)
        next_n = None if is_complete else (mx + 1 if mx > 0 else 1)
        items.append(ExamRoundProgress(
            exam_round=r.exam_round,
            question_count=cnt,
            max_question_number=mx,
            next_question_number=next_n,
            is_complete=is_complete,
        ))

    return ExamRoundsResponse(exam_round_size=size, items=items)


@router.get("/by-document/{document_id}", response_model=list[StudyTopicMeta])
async def list_topics_for_document(
    document_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """이 자료가 매핑된 active 주제 목록.
    /study/sources 카드의 "이 자료가 속한 주제" 배지·컨텍스트 메뉴용.
    """
    rows = (
        await session.execute(
            select(StudyTopic)
            .join(StudyTopicDocument, StudyTopicDocument.study_topic_id == StudyTopic.id)
            .where(
                StudyTopicDocument.document_id == document_id,
                StudyTopicDocument.user_id == user.id,
                StudyTopic.deleted_at.is_(None),
            )
            .order_by(StudyTopic.sort_order.asc(), StudyTopic.id.desc())
        )
    ).scalars().all()
    return [_meta_from_topic(t) for t in rows]


@router.post("/", response_model=StudyTopicResponse, status_code=201)
async def create_study_topic(
    body: StudyTopicCreate,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """주제 생성. 같은 이름의 active 주제가 이미 있으면 409.
    soft-deleted 동명 주제는 partial unique index 에서 빠지므로 신규 생성 가능.
    """
    topic = StudyTopic(
        user_id=user.id,
        name=body.name.strip(),
        description=body.description,
        color=body.color,
        study_type=body.study_type,
        sort_order=body.sort_order,
        exam_round_size=body.exam_round_size,
        exam_subjects=body.exam_subjects or [],
    )
    session.add(topic)
    try:
        await session.flush()
        await session.commit()
    except IntegrityError:
        await session.rollback()
        raise HTTPException(status_code=409, detail="이미 같은 이름의 학습 주제가 있습니다")

    return StudyTopicResponse(
        id=topic.id,
        name=topic.name,
        description=topic.description,
        color=topic.color,
        study_type=topic.study_type,
        sort_order=topic.sort_order,
        session_count=0,
        document_count=0,
        question_count=0,
        exam_round_size=topic.exam_round_size,
        exam_subjects=topic.exam_subjects or [],
        created_at=topic.created_at,
        updated_at=topic.updated_at,
    )


@router.get("/{topic_id}", response_model=StudyTopicDetailResponse)
async def get_study_topic(
    topic_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """통합 뷰: 주제 메타 + 세션 목록 + 자료 목록 + stats.
    응답 형태는 후속 PR(오디오/단어장/문제세트 추가) 에서 sections / stats 키만 늘리면 되도록 dict 구조.
    """
    topic = await session.get(StudyTopic, topic_id)
    topic = _verify_topic_ownership(topic, user)

    # 세션 목록 — 최근순
    sess_rows = (
        await session.execute(
            select(StudySession)
            .where(
                StudySession.user_id == user.id,
                StudySession.study_topic_id == topic_id,
            )
            .order_by(StudySession.created_at.desc(), StudySession.id.desc())
        )
    ).scalars().all()

    sessions_payload = [
        StudyTopicSessionSummary(
            id=s.id,
            study_type=s.study_type,
            certification=s.certification,
            language_code=s.language_code,
            learning_level=s.learning_level,
            subject=s.subject,
            topic=s.topic,
            mode=s.mode,
            repetition_count=s.repetition_count,
            review_state=s.review_state,
            created_at=s.created_at,
            updated_at=s.updated_at,
        )
        for s in sess_rows
    ]

    # 자료 목록 — 매핑 sort_order → created_at desc
    doc_rows = (
        await session.execute(
            select(Document, StudyTopicDocument)
            .join(
                StudyTopicDocument,
                and_(
                    StudyTopicDocument.document_id == Document.id,
                    StudyTopicDocument.study_topic_id == topic_id,
                    StudyTopicDocument.user_id == user.id,
                ),
            )
            .where(Document.deleted_at.is_(None))
            .order_by(
                StudyTopicDocument.sort_order.asc(),
                StudyTopicDocument.created_at.desc(),
            )
        )
    ).all()

    def _extract_library_paths(tags: list | None) -> list[str]:
        if not tags:
            return []
        out: list[str] = []
        for t in tags:
            if isinstance(t, str) and t.startswith(LIBRARY_PREFIX):
                out.append(t[len(LIBRARY_PREFIX):])
        return out

    documents_payload = [
        StudyTopicDocumentSummary(
            id=d.id,
            title=d.title,
            file_format=d.file_format,
            file_type=str(d.file_type) if d.file_type is not None else "immutable",
            category=str(d.category) if d.category is not None else None,
            ai_domain=d.ai_domain,
            importance=d.importance,
            sort_order=link.sort_order,
            linked_at=link.created_at,
            library_paths=_extract_library_paths(d.user_tags),
        )
        for d, link in doc_rows
    ]

    # 문제 목록 (PR-2) — 본문 truncate, 정답·해설 비공개. attempt 통계 batch 로 끌어옴.
    from models.study_question import StudyQuestion, StudyQuestionAttempt

    q_rows = (
        await session.execute(
            select(StudyQuestion)
            .where(
                StudyQuestion.user_id == user.id,
                StudyQuestion.study_topic_id == topic_id,
                StudyQuestion.deleted_at.is_(None),
            )
            .order_by(StudyQuestion.created_at.desc(), StudyQuestion.id.desc())
        )
    ).scalars().all()

    qids = [q.id for q in q_rows]
    q_attempt_count: dict[int, int] = {}
    q_last_correct: dict[int, bool] = {}
    if qids:
        from sqlalchemy import case as _case
        cnt_rows = (
            await session.execute(
                select(
                    StudyQuestionAttempt.study_question_id,
                    func.count().label("total"),
                )
                .where(
                    StudyQuestionAttempt.user_id == user.id,
                    StudyQuestionAttempt.study_question_id.in_(qids),
                )
                .group_by(StudyQuestionAttempt.study_question_id)
            )
        ).all()
        for r in cnt_rows:
            q_attempt_count[r.study_question_id] = int(r.total)

        latest_rows = (
            await session.execute(
                select(
                    StudyQuestionAttempt.study_question_id,
                    StudyQuestionAttempt.is_correct,
                )
                .where(
                    StudyQuestionAttempt.user_id == user.id,
                    StudyQuestionAttempt.study_question_id.in_(qids),
                )
                .order_by(
                    StudyQuestionAttempt.study_question_id,
                    StudyQuestionAttempt.answered_at.desc(),
                )
                .distinct(StudyQuestionAttempt.study_question_id)
            )
        ).all()
        for r in latest_rows:
            q_last_correct[r.study_question_id] = bool(r.is_correct)

    def _truncate_q(text: str, n: int = 80) -> str:
        return text if len(text) <= n else text[:n].rstrip() + "…"

    questions_payload = [
        StudyTopicQuestionSummary(
            id=q.id,
            question_text=_truncate_q(q.question_text, 80),
            subject=q.subject,
            scope=q.scope,
            exam_name=q.exam_name,
            exam_round=q.exam_round,
            is_active=q.is_active,
            attempt_count=q_attempt_count.get(q.id, 0),
            last_correct=q_last_correct.get(q.id),
            created_at=q.created_at,
        )
        for q in q_rows
    ]

    return StudyTopicDetailResponse(
        topic=_meta_from_topic(topic),
        sections=StudyTopicSections(
            sessions=sessions_payload,
            documents=documents_payload,
            questions=questions_payload,
        ),
        stats=StudyTopicStats(
            session_count=len(sessions_payload),
            document_count=len(documents_payload),
            question_count=len(questions_payload),
            # 후속 PR 에서 채움
            audio_count=0,
            vocab_count=0,
            question_set_count=0,
        ),
    )


@router.patch("/{topic_id}", response_model=StudyTopicResponse)
async def update_study_topic(
    topic_id: int,
    body: StudyTopicUpdate,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    topic = await session.get(StudyTopic, topic_id)
    topic = _verify_topic_ownership(topic, user)

    fields_set = body.model_fields_set
    if "name" in fields_set and body.name is not None:
        topic.name = body.name.strip()
    for fname in {"description", "color", "study_type", "sort_order"} & fields_set:
        setattr(topic, fname, getattr(body, fname))
    # PR-6: 시험 메타. exam_subjects 가 None 이면 (PATCH 미명시) 기존 유지, 빈 배열은 명시적 클리어
    if "exam_round_size" in fields_set:
        topic.exam_round_size = body.exam_round_size
    if "exam_subjects" in fields_set and body.exam_subjects is not None:
        topic.exam_subjects = body.exam_subjects

    topic.updated_at = datetime.now(timezone.utc)
    try:
        await session.commit()
    except IntegrityError:
        await session.rollback()
        raise HTTPException(status_code=409, detail="이미 같은 이름의 학습 주제가 있습니다")

    # 응답용 카운트 별도 조회
    sc = (await session.execute(
        select(func.count())
        .select_from(StudySession)
        .where(StudySession.user_id == user.id, StudySession.study_topic_id == topic.id)
    )).scalar() or 0
    dc = (await session.execute(
        select(func.count())
        .select_from(StudyTopicDocument)
        .where(StudyTopicDocument.study_topic_id == topic.id)
    )).scalar() or 0
    from models.study_question import StudyQuestion as _SQ2
    qc = (await session.execute(
        select(func.count())
        .select_from(_SQ2)
        .where(
            _SQ2.user_id == user.id,
            _SQ2.study_topic_id == topic.id,
            _SQ2.deleted_at.is_(None),
        )
    )).scalar() or 0

    return StudyTopicResponse(
        id=topic.id,
        name=topic.name,
        description=topic.description,
        color=topic.color,
        study_type=topic.study_type,
        sort_order=topic.sort_order,
        session_count=int(sc),
        document_count=int(dc),
        question_count=int(qc),
        exam_round_size=topic.exam_round_size,
        exam_subjects=topic.exam_subjects or [],
        created_at=topic.created_at,
        updated_at=topic.updated_at,
    )


@router.delete("/{topic_id}", status_code=204)
async def delete_study_topic(
    topic_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """주제 soft delete. 세션의 study_topic_id 는 SET NULL, 문서 매핑은 cascade 제거.
    같은 이름 재생성을 위해 partial unique index 가 deleted_at IS NULL 인 행만 본다.
    """
    topic = await session.get(StudyTopic, topic_id)
    topic = _verify_topic_ownership(topic, user)

    # 세션 FK SET NULL — 명시적으로 (DB ON DELETE SET NULL 은 hard delete 시에만 동작)
    await session.execute(
        update(StudySession)
        .where(
            StudySession.user_id == user.id,
            StudySession.study_topic_id == topic_id,
        )
        .values(study_topic_id=None)
    )
    # 문서 매핑 명시 제거 (soft delete 라 FK CASCADE 안 탐)
    await session.execute(
        delete(StudyTopicDocument).where(
            StudyTopicDocument.study_topic_id == topic_id,
        )
    )

    topic.deleted_at = datetime.now(timezone.utc)
    await session.commit()


# ─── 자료(문서) 매핑 ───


@router.post(
    "/{topic_id}/documents",
    response_model=StudyTopicDocumentLinkResponse,
    status_code=201,
)
async def link_documents_to_topic(
    topic_id: int,
    body: StudyTopicDocumentLinkRequest,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """자료 N개를 주제에 일괄 매핑. 이미 연결된 건 skipped_existing 으로 보고."""
    topic = await session.get(StudyTopic, topic_id)
    topic = _verify_topic_ownership(topic, user)

    requested = list(dict.fromkeys(body.document_ids))  # 중복 제거 + 순서 보존

    # 존재 + 미삭제 documents 만 통과 (single-user 시스템: documents.user_id 부재 가능)
    valid_rows = (
        await session.execute(
            select(Document.id).where(
                Document.id.in_(requested),
                Document.deleted_at.is_(None),
            )
        )
    ).scalars().all()
    valid_set = set(valid_rows)
    not_found = [d for d in requested if d not in valid_set]

    # 이미 매핑된 것
    existing_rows = (
        await session.execute(
            select(StudyTopicDocument.document_id).where(
                StudyTopicDocument.study_topic_id == topic_id,
                StudyTopicDocument.document_id.in_(valid_set),
            )
        )
    ).scalars().all()
    existing_set = set(existing_rows)
    to_link = [d for d in requested if d in valid_set and d not in existing_set]

    # 기존 max sort_order 다음부터
    max_sort = (
        await session.execute(
            select(func.coalesce(func.max(StudyTopicDocument.sort_order), -1))
            .where(StudyTopicDocument.study_topic_id == topic_id)
        )
    ).scalar() or -1

    for i, doc_id in enumerate(to_link, start=1):
        session.add(StudyTopicDocument(
            study_topic_id=topic_id,
            document_id=doc_id,
            user_id=user.id,
            sort_order=int(max_sort) + i,
        ))

    try:
        await session.commit()
    except IntegrityError:
        await session.rollback()
        raise HTTPException(status_code=409, detail="자료 매핑 중 충돌이 발생했습니다")

    return StudyTopicDocumentLinkResponse(
        linked=to_link,
        skipped_existing=sorted(existing_set),
        skipped_not_found=not_found,
    )


@router.post(
    "/{topic_id}/documents/by-path",
    response_model=StudyTopicDocumentByPathResponse,
    status_code=201,
)
async def link_documents_by_library_path(
    topic_id: int,
    body: StudyTopicDocumentByPathRequest,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """자료실 카테고리 path 기준으로 하위 자료를 일괄 매핑.
    /api/documents/library?path=... 와 동일한 user_tags(@library/...) prefix 매칭 사용.
    100건 limit 우회 — 한 카테고리에 자료가 많아도 한 번에 처리.
    """
    topic = await session.get(StudyTopic, topic_id)
    topic = _verify_topic_ownership(topic, user)

    try:
        normalized = normalize_library_path(body.path)
    except ValueError as e:
        raise HTTPException(status_code=400, detail=str(e))

    exact_tag = f"{LIBRARY_PREFIX}{normalized}"
    prefix_tag = f"{LIBRARY_PREFIX}{normalized}/%"

    # @library/<path> 정확 일치 또는 (subtree 옵션 시) 그 하위까지 prefix 매칭
    if body.include_subtree:
        tag_filter = sql_text("""
            EXISTS (
                SELECT 1 FROM jsonb_array_elements_text(documents.user_tags) AS t
                WHERE t = :exact OR t LIKE :prefix
            )
        """).bindparams(exact=exact_tag, prefix=prefix_tag)
    else:
        tag_filter = sql_text("""
            EXISTS (
                SELECT 1 FROM jsonb_array_elements_text(documents.user_tags) AS t
                WHERE t = :exact
            )
        """).bindparams(exact=exact_tag)

    candidate_rows = (
        await session.execute(
            select(Document.id).where(
                Document.deleted_at.is_(None),
                Document.category == "library",
                tag_filter,
            )
        )
    ).scalars().all()
    candidate_set = set(candidate_rows)
    total_in_path = len(candidate_set)

    if total_in_path == 0:
        return StudyTopicDocumentByPathResponse(
            linked_count=0,
            skipped_existing_count=0,
            total_in_path=0,
            path=normalized,
        )

    existing_rows = (
        await session.execute(
            select(StudyTopicDocument.document_id).where(
                StudyTopicDocument.study_topic_id == topic_id,
                StudyTopicDocument.document_id.in_(candidate_set),
            )
        )
    ).scalars().all()
    existing_set = set(existing_rows)
    to_link = [d for d in candidate_rows if d not in existing_set]

    max_sort = (
        await session.execute(
            select(func.coalesce(func.max(StudyTopicDocument.sort_order), -1))
            .where(StudyTopicDocument.study_topic_id == topic_id)
        )
    ).scalar() or -1

    for i, doc_id in enumerate(to_link, start=1):
        session.add(StudyTopicDocument(
            study_topic_id=topic_id,
            document_id=doc_id,
            user_id=user.id,
            sort_order=int(max_sort) + i,
        ))

    try:
        await session.commit()
    except IntegrityError:
        await session.rollback()
        raise HTTPException(status_code=409, detail="자료 매핑 중 충돌이 발생했습니다")

    return StudyTopicDocumentByPathResponse(
        linked_count=len(to_link),
        skipped_existing_count=len(existing_set),
        total_in_path=total_in_path,
        path=normalized,
    )


@router.delete("/{topic_id}/documents/{document_id}", status_code=204)
async def unlink_document_from_topic(
    topic_id: int,
    document_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    topic = await session.get(StudyTopic, topic_id)
    _verify_topic_ownership(topic, user)

    result = await session.execute(
        delete(StudyTopicDocument).where(
            StudyTopicDocument.study_topic_id == topic_id,
            StudyTopicDocument.document_id == document_id,
            StudyTopicDocument.user_id == user.id,
        )
    )
    await session.commit()
    if result.rowcount == 0:
        raise HTTPException(status_code=404, detail="매핑을 찾을 수 없습니다")


# ─── 세션 매핑 ───


@router.post("/{topic_id}/sessions/{session_id}", status_code=204)
async def attach_session_to_topic(
    topic_id: int,
    session_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """기존 세션을 주제에 연결. 다른 주제에 이미 연결돼 있으면 새 주제로 갱신 (1:N)."""
    topic = await session.get(StudyTopic, topic_id)
    _verify_topic_ownership(topic, user)

    sess = await session.get(StudySession, session_id)
    if sess is None or sess.user_id != user.id:
        raise HTTPException(status_code=404, detail="학습 세션을 찾을 수 없습니다")
    sess.study_topic_id = topic_id
    sess.updated_at = datetime.now(timezone.utc)
    await session.commit()


@router.delete("/{topic_id}/sessions/{session_id}", status_code=204)
async def detach_session_from_topic(
    topic_id: int,
    session_id: int,
    user: Annotated[User, Depends(get_current_user)],
    session: Annotated[AsyncSession, Depends(get_session)],
):
    """세션 분리. 현재 study_topic_id 가 topic_id 가 아니면 404."""
    topic = await session.get(StudyTopic, topic_id)
    _verify_topic_ownership(topic, user)

    sess = await session.get(StudySession, session_id)
    if sess is None or sess.user_id != user.id:
        raise HTTPException(status_code=404, detail="학습 세션을 찾을 수 없습니다")
    if sess.study_topic_id != topic_id:
        raise HTTPException(status_code=404, detail="해당 주제에 연결된 세션이 아닙니다")
    sess.study_topic_id = None
    sess.updated_at = datetime.now(timezone.utc)
    await session.commit()