PaperClipAI/server/src/services/native-runtime/chat-attachment-reuse.ts

import { createHash } from "node:crypto";

import { and, desc, eq, inArray, isNull, sql } from "drizzle-orm";
import type { Db } from "@paperclipai/db";
import {
  assets,
  agents,
  chatConversations,
  chatDeliveries,
  chatEndpointResources,
  chatEndpoints,
  chatExternalPrincipals,
  chatIdentityLinks,
  chatMessageLinks,
  chatPublications,
  companyMemberships,
  heartbeatRuns,
  issueAttachments,
  issueComments,
  issues,
  issueWorkProducts,
  runIdentityContexts,
} from "@paperclipai/db";

import {
  isAllowedContentType,
  MAX_ATTACHMENT_BYTES,
  normalizeContentType,
} from "../../attachment-types.js";
import { getStorageService } from "../../storage/index.js";
import type { StorageService } from "../../storage/types.js";
import { loadConfig } from "../../config.js";
import { HttpError } from "../../errors.js";
import { voiceSessionStore, type VoiceTransaction } from "../voice/voice-session-store.js";
import { issueService } from "../issues.js";
import { readInheritedGitHubReviewWait } from "../chat-channels/github/review-wait.js";
import { boundExternalChatProvider } from "./external-chat-provider.js";
import { resolveExternalChatQuestionResponse } from "./external-chat-question-response.js";
import { githubRunReplyState } from "../chat-run-publications.js";

// This boundary reads identity and wake authority, never launch renderings,
// saved provider profiles, or run output. Keep the nested wake proof narrow too.
const responseWaitContextKeys = ["source", "issueId", "wakeReason", "wakeCommentId", "wakeCommentIds",
  "interactionId", "interactionKind", "interactionStatus", "sourceRunId", "sourceCommentId",
  "externalChatContinuation", "paperclipExternalChatQuestionResponse", "paperclipHarnessCheckedOut",
  "paperclipExternalChatExecutionBound"] as const;
const responseWaitRun = {
  id: heartbeatRuns.id, companyId: heartbeatRuns.companyId, agentId: heartbeatRuns.agentId,
  nativeIssueId: heartbeatRuns.nativeIssueId, issueId: heartbeatRuns.issueId, status: heartbeatRuns.status,
  responsibleUserId: heartbeatRuns.responsibleUserId, activeIdentityContextId: heartbeatRuns.activeIdentityContextId,
  contextSnapshot: sql<Record<string, unknown> | null>`case when jsonb_typeof(${heartbeatRuns.contextSnapshot}) = 'object'
    then (select coalesce(jsonb_object_agg(field.key, field.value), '{}'::jsonb)
      from jsonb_each(${heartbeatRuns.contextSnapshot}) as field(key, value)
      where field.key in (${sql.join(responseWaitContextKeys.map(key => sql`${key}`), sql`, `)}))
      || jsonb_build_object('paperclipWake', jsonb_build_object(
        'checkedOutByHarness', ${heartbeatRuns.contextSnapshot}#>'{paperclipWake,checkedOutByHarness}',
        'externalChatExecutionBound', ${heartbeatRuns.contextSnapshot}#>'{paperclipWake,externalChatExecutionBound}',
        'externalChatProvider', ${heartbeatRuns.contextSnapshot}#>'{paperclipWake,externalChatProvider}',
        'issue', jsonb_build_object('id', ${heartbeatRuns.contextSnapshot}#>'{paperclipWake,issue,id}'),
        'commentIds', ${heartbeatRuns.contextSnapshot}#>'{paperclipWake,commentIds}'))
    else null end`,
};

export const LIST_CHAT_ATTACHMENTS_TOOL_NAME = "list_chat_attachments";
export const REUSE_CHAT_ATTACHMENT_TOOL_NAME = "reuse_chat_attachment";

export const LIST_CHAT_ATTACHMENTS_TOOL_DEFINITION = Object.freeze({
  name: LIST_CHAT_ATTACHMENTS_TOOL_NAME,
  description:
    "List metadata for files already received or delivered in this same external-chat conversation. Call with {} for the latest page (default 20), or set limit to an integer from 1 through 50. Page through nextCursor to find older files, or filter by an exact sourceCommentId when known. File bytes and private storage locations are never returned.",
  inputSchema: {
    type: "object",
    properties: {
      sourceCommentId: {
        type: ["string", "null"],
        description:
          "Optional exact sourceCommentId returned by this tool on an earlier page.",
      },
      limit: { type: "integer", minimum: 1, maximum: 50, default: 20 },
      cursor: {
        type: ["string", "null"],
        maxLength: 1024,
        description: "Opaque nextCursor from the immediately preceding page.",
      },
    },
    required: [],
    additionalProperties: false,
  },
  annotations: {
    semanticContract: "paperclip.server-chat-attachment-reuse.v1",
    operationId: LIST_CHAT_ATTACHMENTS_TOOL_NAME,
    version: 1,
    exposure: "run_scoped",
    requiredClaims: [],
  },
});

export const REUSE_CHAT_ATTACHMENT_TOOL_DEFINITION = Object.freeze({
  name: REUSE_CHAT_ATTACHMENT_TOOL_NAME,
  description:
    "Prepare one exact file previously received or delivered in this same external-chat conversation for the current response. All four arguments are required: copy sourceCommentId and attachmentId from list_chat_attachments, provide a nonempty title, and choose a nonempty idempotencyKey of at most 200 characters once for this reuse; send that same key unchanged on every retry. This queues a verified copy for final publication; it does not confirm provider delivery.",
  inputSchema: {
    type: "object",
    properties: {
      idempotencyKey: { type: "string", minLength: 1, maxLength: 200 },
      sourceCommentId: { type: "string", format: "uuid" },
      attachmentId: { type: "string", format: "uuid" },
      title: { type: "string", minLength: 1, maxLength: 500 },
    },
    required: ["idempotencyKey", "sourceCommentId", "attachmentId", "title"],
    additionalProperties: false,
  },
  annotations: {
    semanticContract: "paperclip.server-chat-attachment-reuse.v1",
    operationId: REUSE_CHAT_ATTACHMENT_TOOL_NAME,
    version: 1,
    exposure: "run_scoped",
    requiredClaims: [],
  },
});

export type ChatReuseBinding = {
  companyId: string;
  issueId: string;
  runId: string;
  agentId: string;
};

type AuthorizedConversation = {
  conversationId: string;
  endpointId: string;
};

export type ExternalChatResponseWaitAuthorization =
  | "authorized"
  | "revoked"
  | "not_applicable";

type AuthorizationLockMode = "blocking" | "nonblocking" | "read";

type AuthorizationEndpoint = Pick<typeof chatEndpoints.$inferSelect,
  "id" | "companyId" | "provider" | "providerAccountId" | "status" | "setup"
  | "allowDirectMessages" | "allowGroupChats" | "allowUnlinkedPeople" | "sponsorUserId"
>;
type AuthorizationConversation = Pick<typeof chatConversations.$inferSelect,
  "id" | "resourceId" | "isDirectMessage"
>;
type AuthorizationResource = Pick<typeof chatEndpointResources.$inferSelect,
  "availability" | "type" | "enabled"
>;

class ExternalChatWaitAuthorizationContentionError extends Error {
  constructor() {
    super("paperclip_external_chat_wait_authorization_contended");
    this.name = "ExternalChatWaitAuthorizationContentionError";
  }
}

export function isExternalChatWaitAuthorizationContention(
  error: unknown,
): boolean {
  let current: unknown = error;
  for (let depth = 0; depth < 4 && current; depth += 1) {
    if (current instanceof ExternalChatWaitAuthorizationContentionError) {
      return true;
    }
    const value = record(current);
    if (value.code === "55P03") return true;
    current = value.cause;
  }
  return false;
}

export type ChatAttachmentReuseSource = {
  sourceCommentId: string;
  attachmentId: string;
  filename: string;
  contentType: string;
  byteSize: number;
  sha256: string;
  objectKey: string;
  createdAt: Date;
};

export type ListedChatAttachment = Omit<
  ChatAttachmentReuseSource,
  "objectKey" | "createdAt"
> & {
  createdAt: string;
  contentAccess: "metadata_only";
};

export type ListedChatAttachmentPage = {
  attachments: ListedChatAttachment[];
  nextCursor: string | null;
  complete: boolean;
};

type ListCursor = {
  schema: "paperclip.chat-attachment-list-cursor.v1";
  conversationId: string;
  sourceCommentId: string | null;
  createdAt: string;
  attachmentId: string;
  sourceCommentIdTieBreak: string;
};

export type PreparedReusedChatAttachment = {
  result: {
    commandId: string;
    disposition: "applied";
    stateRevision: number;
    entityRefs: string[];
    scheduledWakeIds: never[];
    source: {
      commentId: string;
      attachmentId: string;
      sha256: string;
    };
    prepared: {
      attachmentId: string;
      workProductId: string;
      commentId: string;
      filename: string;
      byteSize: number;
      sha256: string;
    };
  };
  rollbackDefinitePreCommitFailure: (() => Promise<void>) | null;
};

function record(value: unknown): Record<string, unknown> {
  return typeof value === "object" && value !== null && !Array.isArray(value)
    ? (value as Record<string, unknown>)
    : {};
}

function wakeCommentIds(contextSnapshot: unknown): string[] {
  const context = record(contextSnapshot);
  const raw = context.wakeCommentIds;
  if (!Array.isArray(raw)) return [];
  return [
    ...new Set(
      raw
        .filter(
          (value): value is string =>
            typeof value === "string" && value.trim().length > 0,
        )
        .map((value) => value.trim()),
    ),
  ];
}

function publicationAttachmentIds(payload: unknown): string[] {
  const raw = record(payload).attachmentIds;
  return Array.isArray(raw)
    ? raw.filter((value): value is string => typeof value === "string")
    : [];
}

function isUuid(value: unknown): value is string {
  return (
    typeof value === "string" &&
    /^[0-9a-f]{8}-[0-9a-f]{4}-[1-5][0-9a-f]{3}-[89ab][0-9a-f]{3}-[0-9a-f]{12}$/iu.test(
      value,
    )
  );
}

function encodeListCursor(cursor: ListCursor): string {
  return Buffer.from(JSON.stringify(cursor), "utf8").toString("base64url");
}

function decodeListCursor(
  value: unknown,
  conversationId: string,
  sourceCommentId: string | null,
): ListCursor | null {
  if (value === null || value === undefined) return null;
  if (typeof value !== "string" || value.length === 0 || value.length > 1024) {
    throw new Error("paperclip_runner_chat_attachment_cursor_invalid");
  }
  try {
    const parsed = record(
      JSON.parse(Buffer.from(value, "base64url").toString("utf8")),
    );
    const createdAt =
      typeof parsed.createdAt === "string" ? parsed.createdAt : "";
    const parsedDate = new Date(createdAt);
    if (
      parsed.schema !== "paperclip.chat-attachment-list-cursor.v1" ||
      parsed.conversationId !== conversationId ||
      (parsed.sourceCommentId ?? null) !== sourceCommentId ||
      Number.isNaN(parsedDate.getTime()) ||
      !isUuid(parsed.attachmentId) ||
      !isUuid(parsed.sourceCommentIdTieBreak)
    ) {
      throw new Error("invalid");
    }
    return parsed as ListCursor;
  } catch {
    throw new Error("paperclip_runner_chat_attachment_cursor_invalid");
  }
}

function destinationAllowed(
  endpoint: AuthorizationEndpoint,
  conversation: AuthorizationConversation,
  resource: AuthorizationResource | null,
): boolean {
  if (conversation.isDirectMessage) return endpoint.allowDirectMessages;
  if (!resource || resource.availability !== "available") return false;
  if (
    endpoint.provider === "microsoft-teams" &&
    resource.type === "group_chat"
  ) {
    return endpoint.allowGroupChats;
  }
  return resource.enabled;
}

function currentSetupTestAcceptsBoundDeliveries(
  endpoint: AuthorizationEndpoint,
  deliveries: Array<{
    normalizedEvent: unknown;
    processedAt: Date | null;
    receivedAt: Date;
  }>,
): boolean {
  if (endpoint.status === "active") return true;
  if (endpoint.status !== "verifying" || deliveries.length === 0) return false;
  const setup = record(endpoint.setup);
  const testStartedAt =
    typeof setup.testStartedAt === "string"
      ? new Date(setup.testStartedAt)
      : null;
  const generation = setup.runtimeGeneration;
  if (
    setup.step !== "test" ||
    !testStartedAt ||
    Number.isNaN(testStartedAt.getTime()) ||
    typeof generation !== "number" ||
    !Number.isSafeInteger(generation) ||
    generation < 0
  ) {
    return false;
  }
  return deliveries.every((delivery) => {
    const runtimeContext = record(
      record(delivery.normalizedEvent).runtimeContext,
    );
    return (
      delivery.receivedAt >= testStartedAt &&
      delivery.processedAt !== null &&
      delivery.processedAt >= testStartedAt &&
      delivery.processedAt >= delivery.receivedAt &&
      runtimeContext.generation === generation &&
      typeof runtimeContext.credentialFingerprint === "string" &&
      /^[a-f0-9]{64}$/u.test(runtimeContext.credentialFingerprint)
    );
  });
}

async function principalAuthorized(
  tx: Db,
  endpoint: AuthorizationEndpoint,
  principalId: string,
  lockMode: AuthorizationLockMode = "blocking",
): Promise<boolean> {
  if (lockMode === "blocking") {
    await tx.execute(
      sql`select pg_advisory_xact_lock(hashtextextended(${`chat-identity:${endpoint.companyId}:${principalId}`}, 0))`,
    );
  } else if (lockMode === "nonblocking") {
    const [lock] = (await tx.execute(
      sql`select pg_try_advisory_xact_lock(hashtextextended(${`chat-identity:${endpoint.companyId}:${principalId}`}, 0)) as acquired`,
    )) as unknown as Array<{ acquired: boolean }>;
    if (!lock?.acquired) {
      throw new ExternalChatWaitAuthorizationContentionError();
    }
  }
  const principalQuery = tx
    .select({ id: chatExternalPrincipals.id, externalId: chatExternalPrincipals.externalId })
    .from(chatExternalPrincipals)
    .where(
      and(
        eq(chatExternalPrincipals.id, principalId),
        eq(chatExternalPrincipals.companyId, endpoint.companyId),
        eq(chatExternalPrincipals.provider, endpoint.provider),
        eq(
          chatExternalPrincipals.providerAccountId,
          endpoint.providerAccountId ?? "",
        ),
      ),
    );
  const [principal] = await (lockMode === "read"
    ? principalQuery.limit(1)
    : lockMode === "nonblocking"
      ? principalQuery.for("update", { noWait: true }).limit(1)
      : principalQuery.for("update").limit(1));
  if (!principal) return false;
  if (endpoint.provider === "speko") {
    try {
      await voiceSessionStore(tx, { allowLocalBoard: loadConfig().deploymentMode === "local_trusted", nonblockingAuthority: lockMode === "nonblocking" })
        .authorizePrincipal(tx as unknown as VoiceTransaction, endpoint.companyId, endpoint.id, principal.externalId);
      return true;
    } catch (error) {
      if (error instanceof HttpError && [403, 404].includes(error.status)) return false;
      throw error;
    }
  }
  const linkQuery = tx
    .select({
      status: chatIdentityLinks.status,
      userId: chatIdentityLinks.paperclipUserId,
    })
    .from(chatIdentityLinks)
    .where(
      and(
        eq(chatIdentityLinks.companyId, endpoint.companyId),
        eq(chatIdentityLinks.endpointId, endpoint.id),
        eq(chatIdentityLinks.principalId, principalId),
      ),
    );
  const [link] = await (lockMode === "read"
    ? linkQuery.limit(1)
    : lockMode === "nonblocking"
      ? linkQuery.for("update", { noWait: true }).limit(1)
      : linkQuery.for("update").limit(1));
  const activeMember = async (userId: string) => {
    const membershipQuery = tx
      .select({
        status: companyMemberships.status,
        role: companyMemberships.membershipRole,
      })
      .from(companyMemberships)
      .where(
        and(
          eq(companyMemberships.companyId, endpoint.companyId),
          eq(companyMemberships.principalType, "user"),
          eq(companyMemberships.principalId, userId),
        ),
      );
    const [membership] = await (lockMode === "read"
      ? membershipQuery.limit(1)
      : lockMode === "nonblocking"
        ? membershipQuery.for("update", { noWait: true }).limit(1)
        : membershipQuery.for("update").limit(1));
    return membership?.status === "active" && membership.role !== "viewer";
  };
  if (link?.status === "linked") {
    return Boolean(link.userId && (await activeMember(link.userId)));
  }
  if (!endpoint.allowUnlinkedPeople) return false;
  return endpoint.sponsorUserId ? activeMember(endpoint.sponsorUserId) : true;
}

/** Caller must independently verify the current run/issue execution owner. */
export async function authorizeChatConversationForBoundRun(
  tx: Db,
  binding: ChatReuseBinding,
  contextSnapshot: unknown,
  lockMode: AuthorizationLockMode = "blocking",
): Promise<AuthorizedConversation> {
  let context = record(contextSnapshot);
  if (context.source === "issue.interaction.respond") {
    const answer = await resolveExternalChatQuestionResponse(tx, binding, context, lockMode);
    if (!answer) throw new Error("paperclip_runner_chat_attachment_binding_denied");
    context = answer.authorizationContext;
  }
  const source = typeof context.source === "string" ? context.source : "";
  const provider = boundExternalChatProvider(source);
  const commentIds = wakeCommentIds(context);
  if (
    !provider ||
    (context.paperclipHarnessCheckedOut !== true &&
      context.paperclipExternalChatExecutionBound !== true) ||
    commentIds.length === 0
  ) {
    throw new Error("paperclip_runner_chat_attachment_binding_denied");
  }
  const linksQuery = tx
    .select({
      commentId: chatMessageLinks.commentId,
      conversation: {
        id: chatConversations.id,
        resourceId: chatConversations.resourceId,
        isDirectMessage: chatConversations.isDirectMessage,
      },
      endpoint: {
        id: chatEndpoints.id,
        companyId: chatEndpoints.companyId,
        provider: chatEndpoints.provider,
        providerAccountId: chatEndpoints.providerAccountId,
        status: chatEndpoints.status,
        allowDirectMessages: chatEndpoints.allowDirectMessages,
        allowGroupChats: chatEndpoints.allowGroupChats,
        allowUnlinkedPeople: chatEndpoints.allowUnlinkedPeople,
        sponsorUserId: chatEndpoints.sponsorUserId,
        setup: sql<AuthorizationEndpoint["setup"]>`jsonb_build_object(
          'step', ${chatEndpoints.setup}->'step',
          'testStartedAt', ${chatEndpoints.setup}->'testStartedAt',
          'runtimeGeneration', ${chatEndpoints.setup}->'runtimeGeneration'
        )`,
      },
      principalId: chatDeliveries.principalId,
      normalizedEvent: sql<unknown>`jsonb_build_object('runtimeContext', jsonb_build_object(
        'generation', ${chatDeliveries.normalizedEvent}->'runtimeContext'->'generation',
        'credentialFingerprint', ${chatDeliveries.normalizedEvent}->'runtimeContext'->'credentialFingerprint'
      ))`,
      processedAt: chatDeliveries.processedAt,
      receivedAt: chatDeliveries.receivedAt,
    })
    .from(chatMessageLinks)
    .innerJoin(
      chatDeliveries,
      and(
        eq(chatDeliveries.id, chatMessageLinks.deliveryId),
        eq(chatDeliveries.companyId, chatMessageLinks.companyId),
        eq(chatDeliveries.endpointId, chatMessageLinks.endpointId),
        eq(chatDeliveries.conversationId, chatMessageLinks.conversationId),
      ),
    )
    .innerJoin(
      chatConversations,
      and(
        eq(chatConversations.id, chatMessageLinks.conversationId),
        eq(chatConversations.companyId, chatMessageLinks.companyId),
        eq(chatConversations.endpointId, chatMessageLinks.endpointId),
      ),
    )
    .innerJoin(
      chatEndpoints,
      and(
        eq(chatEndpoints.id, chatConversations.endpointId),
        eq(chatEndpoints.companyId, chatConversations.companyId),
      ),
    )
    .where(
      and(
        eq(chatMessageLinks.companyId, binding.companyId),
        eq(chatMessageLinks.direction, "inbound"),
        inArray(chatMessageLinks.commentId, commentIds),
        eq(chatDeliveries.state, "processed"),
        eq(chatConversations.issueId, binding.issueId),
        inArray(chatConversations.state, ["active", "waiting"]),
        eq(
          chatEndpoints.provider,
          provider as typeof chatEndpoints.$inferSelect.provider,
        ),
        eq(chatEndpoints.assignedAgentId, binding.agentId),
        inArray(chatEndpoints.status, ["active", "verifying"]),
      ),
    );
  const links = await (lockMode === "read"
    ? linksQuery
    : lockMode === "nonblocking"
      ? linksQuery.for("update", { noWait: true })
      : linksQuery.for("update"));
  const linkedCommentIds = new Set(links.map((row) => row.commentId));
  const conversationIds = new Set(links.map((row) => row.conversation.id));
  const endpointIds = new Set(links.map((row) => row.endpoint.id));
  if (
    links.length === 0 ||
    conversationIds.size !== 1 ||
    endpointIds.size !== 1 ||
    !commentIds.every((id) => linkedCommentIds.has(id)) ||
    links.some((row) => !row.principalId)
  ) {
    throw new Error("paperclip_runner_chat_attachment_binding_denied");
  }
  const conversation = links[0]!.conversation;
  const endpoint = links[0]!.endpoint;
  if (!currentSetupTestAcceptsBoundDeliveries(endpoint, links)) {
    throw new Error("paperclip_runner_chat_attachment_binding_denied");
  }
  const resource = conversation.resourceId
    ? await (() => {
        const query = tx
          .select({
            availability: chatEndpointResources.availability,
            type: chatEndpointResources.type,
            enabled: chatEndpointResources.enabled,
          })
          .from(chatEndpointResources)
          .where(
            and(
              eq(chatEndpointResources.id, conversation.resourceId!),
              eq(chatEndpointResources.companyId, binding.companyId),
              eq(chatEndpointResources.endpointId, endpoint.id),
            ),
          );
        return lockMode === "read"
          ? query.then((rows) => rows[0] ?? null)
          : lockMode === "nonblocking"
            ? query
                .for("update", { noWait: true })
                .then((rows) => rows[0] ?? null)
            : query.for("update").then((rows) => rows[0] ?? null);
      })()
    : null;
  if (!destinationAllowed(endpoint, conversation, resource)) {
    throw new Error("paperclip_runner_chat_attachment_destination_denied");
  }
  for (const principalId of new Set(links.map((row) => row.principalId!))) {
    if (!(await principalAuthorized(tx, endpoint, principalId, lockMode))) {
      throw new Error("paperclip_runner_chat_attachment_principal_denied");
    }
  }
  return { conversationId: conversation.id, endpointId: endpoint.id };
}

function externalChatWaitCandidate(
  contextSnapshot: unknown,
  binding: ChatReuseBinding,
): { provider: string; commentIds: string[] } | null {
  const context = record(contextSnapshot);
  const source = typeof context.source === "string" ? context.source : "";
  const provider = boundExternalChatProvider(source);
  const commentIds = wakeCommentIds(context);
  const wake = record(context.paperclipWake);
  const wakeIssue = record(wake.issue);
  const payloadCommentIds = Array.isArray(wake.commentIds)
    ? wake.commentIds.filter(
        (value): value is string =>
          typeof value === "string" && value.trim().length > 0,
      )
    : [];
  if (
    !provider ||
    !(
      (context.paperclipHarnessCheckedOut === true &&
        wake.checkedOutByHarness === true) ||
      (context.paperclipExternalChatExecutionBound === true &&
        wake.externalChatExecutionBound === true)
    ) ||
    commentIds.length === 0 ||
    wake.externalChatProvider !== provider ||
    wakeIssue.id !== binding.issueId ||
    payloadCommentIds.length !== commentIds.length ||
    payloadCommentIds.some((id, index) => id !== commentIds[index])
  ) {
    return null;
  }
  return { provider, commentIds };
}

/**
 * Authorize a no-work external-chat wait from the same durable boundary used
 * by historical file reuse. The nested wake payload proves that this was a
 * server-built chat turn; current destination and principal policy remain
 * authoritative at the instant the status decision commits.
 */
export async function resolveExternalChatResponseWaitAuthorizationInTransaction(
  tx: Db,
  binding: ChatReuseBinding,
  lockMode: AuthorizationLockMode = "blocking",
): Promise<ExternalChatResponseWaitAuthorization> {
  // Preserve the native mutation lock order (issue -> run -> actor). The
  // status committer already holds the issue lock; PostgreSQL treats this
  // repeated lock as a no-op.
  const issueQuery = tx
    .select({
      assigneeAgentId: issues.assigneeAgentId,
      executionRunId: issues.executionRunId,
    })
    .from(issues)
    .where(
      and(
        eq(issues.id, binding.issueId),
        eq(issues.companyId, binding.companyId),
      ),
    );
  const [issue] = await (lockMode === "read"
    ? issueQuery.limit(1)
    : lockMode === "nonblocking"
      ? issueQuery.for("update", { noWait: true }).limit(1)
      : issueQuery.for("update").limit(1));

  const runQuery = tx
    .select(responseWaitRun)
    .from(heartbeatRuns)
    .where(
      and(
        eq(heartbeatRuns.id, binding.runId),
        eq(heartbeatRuns.companyId, binding.companyId),
        eq(heartbeatRuns.agentId, binding.agentId),
        eq(heartbeatRuns.nativeIssueId, binding.issueId),
        eq(heartbeatRuns.runtimeMode, "native"),
      ),
    );
  const [run] = await (lockMode === "read"
    ? runQuery.limit(1)
    : lockMode === "nonblocking"
      ? runQuery.for("update", { noWait: true }).limit(1)
      : runQuery.for("update").limit(1));
  const answerContext =
    run && record(run.contextSnapshot).source === "issue.interaction.respond"
      ? await resolveExternalChatQuestionResponse(
          tx,
          binding,
          run.contextSnapshot,
          lockMode,
        )
      : null;
  if (
    run &&
    record(run.contextSnapshot).source === "issue.interaction.respond" &&
    record(run.contextSnapshot).paperclipExternalChatQuestionResponse &&
    !answerContext
  )
    return "revoked";
  const directContext = answerContext?.authorizationContext ?? run?.contextSnapshot;
  const inheritedReviewWait = run && !externalChatWaitCandidate(directContext, binding)
    ? await readInheritedGitHubReviewWait(tx, run) : null;
  if (inheritedReviewWait?.kind === "revoked") return "revoked";
  const authorizationContext = inheritedReviewWait?.context ?? directContext;
  const candidate = run ? externalChatWaitCandidate(authorizationContext, binding) : null;
  if (!candidate) return "not_applicable";

  const actorQuery = tx
    .select({ status: agents.status })
    .from(agents)
    .where(
      and(
        eq(agents.id, binding.agentId),
        eq(agents.companyId, binding.companyId),
      ),
    );
  const [actor] = await (lockMode === "read"
    ? actorQuery.limit(1)
    : lockMode === "nonblocking"
      ? actorQuery.for("update", { noWait: true }).limit(1)
      : actorQuery.for("update").limit(1));
  if (
    !issue ||
    !actor ||
    run.status !== "running" ||
    issue.assigneeAgentId !== binding.agentId ||
    issue.executionRunId !== binding.runId ||
    ["paused", "terminated", "pending_approval", "error"].includes(
      actor.status,
    )
  ) {
    return "revoked";
  }

  const links = await tx
    .select({
      commentId: chatMessageLinks.commentId,
      conversationId: chatConversations.id,
      endpointId: chatEndpoints.id,
      principalId: chatDeliveries.principalId,
    })
    .from(chatMessageLinks)
    .innerJoin(
      chatDeliveries,
      and(
        eq(chatDeliveries.id, chatMessageLinks.deliveryId),
        eq(chatDeliveries.companyId, chatMessageLinks.companyId),
        eq(chatDeliveries.endpointId, chatMessageLinks.endpointId),
        eq(chatDeliveries.conversationId, chatMessageLinks.conversationId),
      ),
    )
    .innerJoin(
      chatConversations,
      and(
        eq(chatConversations.id, chatMessageLinks.conversationId),
        eq(chatConversations.companyId, chatMessageLinks.companyId),
        eq(chatConversations.endpointId, chatMessageLinks.endpointId),
      ),
    )
    .innerJoin(
      chatEndpoints,
      and(
        eq(chatEndpoints.id, chatConversations.endpointId),
        eq(chatEndpoints.companyId, chatConversations.companyId),
      ),
    )
    .where(
      and(
        eq(chatMessageLinks.companyId, binding.companyId),
        eq(chatMessageLinks.direction, "inbound"),
        inArray(chatMessageLinks.commentId, candidate.commentIds),
        eq(chatDeliveries.state, "processed"),
        eq(chatConversations.issueId, binding.issueId),
        eq(
          chatEndpoints.provider,
          candidate.provider as typeof chatEndpoints.$inferSelect.provider,
        ),
        eq(chatEndpoints.assignedAgentId, binding.agentId),
      ),
    );
  const linkedCommentIds = new Set(links.map((row) => row.commentId));
  if (
    links.length === 0 ||
    new Set(links.map((row) => row.conversationId)).size !== 1 ||
    new Set(links.map((row) => row.endpointId)).size !== 1 ||
    links.some((row) => !row.principalId) ||
    !candidate.commentIds.every((id) => linkedCommentIds.has(id))
  ) {
    return "revoked";
  }
  try {
    await authorizeChatConversationForBoundRun(
      tx,
      binding,
      authorizationContext,
      lockMode,
    );
    return "authorized";
  } catch (error) {
    if (
      error instanceof Error &&
      [
        "paperclip_runner_chat_attachment_binding_denied",
        "paperclip_runner_chat_attachment_destination_denied",
        "paperclip_runner_chat_attachment_principal_denied",
      ].includes(error.message)
    ) {
      return "revoked";
    }
    throw error;
  }
}

export async function resolveExternalChatResponseWaitAuthorization(input: {
  db: Db;
  binding: ChatReuseBinding;
}): Promise<ExternalChatResponseWaitAuthorization> {
  return input.db.transaction((tx) =>
    resolveExternalChatResponseWaitAuthorizationInTransaction(
      tx as unknown as Db,
      input.binding,
      "read",
    ),
  );
}

const publishedGitHubReviewWaitKey = "github-review-response:";

export function isPublishedGitHubReviewCompletionContinuation(value: unknown): boolean {
  const continuation = record(value);
  return continuation.kind === "response_wake" && typeof continuation.idempotencyKey === "string" &&
    continuation.idempotencyKey.startsWith(publishedGitHubReviewWaitKey);
}

/** Project a wait from the same saved publication and current authority used
 * by finalization. Inherited waits need an accepted tree resume or a confirmed
 * reply from this run to its exact current source. An arbitrary old review does
 * not assign an unanswered new turn a wait. */
export async function readPublishedGitHubReviewCompletionContinuationInTransaction(
  tx: Db, binding: ChatReuseBinding, lockMode: AuthorizationLockMode = "read",
) {
  const [run] = await tx.select(responseWaitRun).from(heartbeatRuns).where(and(
    eq(heartbeatRuns.id, binding.runId), eq(heartbeatRuns.companyId, binding.companyId),
    eq(heartbeatRuns.agentId, binding.agentId), eq(heartbeatRuns.nativeIssueId, binding.issueId),
    eq(heartbeatRuns.runtimeMode, "native"),
  )).limit(1);
  if (!run || run.status !== "running") return null;
  const wait = await readInheritedGitHubReviewWait(tx, run);
  if (wait?.kind !== "published") return null;
  if (wait.reviewRunId !== run.id) {
    const [identity] = await tx.select({ cause: runIdentityContexts.cause, parentContextId: runIdentityContexts.parentContextId })
      .from(runIdentityContexts).where(and(eq(runIdentityContexts.id, run.activeIdentityContextId!),
        eq(runIdentityContexts.companyId, run.companyId), eq(runIdentityContexts.runId, run.id),
        eq(runIdentityContexts.status, "accepted"))).limit(1);
    const resumed = run.contextSnapshot?.source === "issue.tree_resume" && identity?.cause === "issue_tree_resumed" &&
      Boolean(identity.parentContextId);
    if (!resumed && !(run.contextSnapshot?.source === "chat:github" &&
        await githubRunReplyState(tx, { ...binding, endpointId: wait.endpointId,
          sourceCommentId: wait.context.wakeCommentId, requireSettled: true }) === "confirmed")) return null;
  }
  if (await resolveExternalChatResponseWaitAuthorizationInTransaction(tx, binding, lockMode) !== "authorized") return null;
  return { kind: "response_wake" as const, summary: "Wait for the next authorized GitHub response to the published review.",
    idempotencyKey: `${publishedGitHubReviewWaitKey}${run.id}:${wait.reviewId}:${wait.headSha}` };
}

export async function readPublishedGitHubReviewCompletionContinuation(input: { db: Db; binding: ChatReuseBinding }) {
  return input.db.transaction(tx => readPublishedGitHubReviewCompletionContinuationInTransaction(tx as unknown as Db, input.binding));
}

async function sourceLineageExists(
  tx: Db,
  binding: ChatReuseBinding,
  conversation: AuthorizedConversation,
  source: Pick<
    ChatAttachmentReuseSource,
    "sourceCommentId" | "attachmentId"
  > & {
    parentCommentId: string;
  },
): Promise<boolean> {
  const [inbound] = await tx
    .select({ providerEventId: chatDeliveries.providerEventId })
    .from(chatMessageLinks)
    .innerJoin(
      chatDeliveries,
      and(
        eq(chatDeliveries.id, chatMessageLinks.deliveryId),
        eq(chatDeliveries.companyId, chatMessageLinks.companyId),
        eq(chatDeliveries.endpointId, chatMessageLinks.endpointId),
        eq(chatDeliveries.conversationId, chatMessageLinks.conversationId),
      ),
    )
    .where(
      and(
        eq(chatMessageLinks.companyId, binding.companyId),
        eq(chatMessageLinks.endpointId, conversation.endpointId),
        eq(chatMessageLinks.conversationId, conversation.conversationId),
        eq(chatMessageLinks.direction, "inbound"),
        eq(chatMessageLinks.commentId, source.sourceCommentId),
        eq(chatDeliveries.state, "processed"),
      ),
    )
    .limit(1);
  if (inbound && source.parentCommentId === source.sourceCommentId) {
    const [lifecycle] = await tx
      .select({ id: chatDeliveries.id })
      .from(chatDeliveries)
      .where(
        and(
          eq(chatDeliveries.companyId, binding.companyId),
          eq(chatDeliveries.endpointId, conversation.endpointId),
          eq(chatDeliveries.conversationId, conversation.conversationId),
          inArray(chatDeliveries.eventKind, [
            "message_updated",
            "message_deleted",
            "message_restored",
          ]),
          eq(chatDeliveries.state, "processed"),
          sql`${chatDeliveries.normalizedEvent}->'message'->>'targetProviderEventId' = ${inbound.providerEventId}`,
        ),
      )
      .limit(1);
    return !lifecycle;
  }
  const publications = await tx
    .select({
      payload: chatPublications.payload,
      providerMessageId: chatPublications.providerMessageId,
      publishedAt: chatPublications.publishedAt,
    })
    .from(chatPublications)
    .where(
      and(
        eq(chatPublications.companyId, binding.companyId),
        eq(chatPublications.endpointId, conversation.endpointId),
        eq(chatPublications.conversationId, conversation.conversationId),
        eq(chatPublications.issueId, binding.issueId),
        eq(chatPublications.commentId, source.sourceCommentId),
        eq(chatPublications.state, "published"),
      ),
    );
  const matchingPublications = publications.filter(
    (row) =>
      row.providerMessageId !== null &&
      row.publishedAt !== null &&
      publicationAttachmentIds(row.payload).includes(source.attachmentId),
  );
  if (matchingPublications.length === 0) return false;
  for (const publication of matchingPublications) {
    const [lifecycle] = await tx
      .select({ id: chatDeliveries.id })
      .from(chatDeliveries)
      .where(
        and(
          eq(chatDeliveries.companyId, binding.companyId),
          eq(chatDeliveries.endpointId, conversation.endpointId),
          eq(chatDeliveries.conversationId, conversation.conversationId),
          inArray(chatDeliveries.eventKind, [
            "message_updated",
            "message_deleted",
            "message_restored",
          ]),
          eq(chatDeliveries.state, "processed"),
          eq(
            sql<string>`${chatDeliveries.normalizedEvent}->'message'->>'providerMessageId'`,
            publication.providerMessageId!,
          ),
        ),
      )
      .limit(1);
    if (!lifecycle) return true;
  }
  return false;
}

const HISTORICAL_ATTACHMENT_FILE_EXTENSIONS: ReadonlyMap<string, string> =
  new Map([
    ["image/png", "png"],
    ["image/jpeg", "jpg"],
    ["image/jpg", "jpg"],
    ["image/webp", "webp"],
    ["image/gif", "gif"],
    ["audio/mpeg", "mp3"],
    ["audio/mp4", "m4a"],
    ["audio/ogg", "ogg"],
    ["audio/wav", "wav"],
    ["audio/webm", "webm"],
    ["video/mp4", "mp4"],
    ["video/webm", "webm"],
    ["video/quicktime", "mov"],
    ["video/x-m4v", "m4v"],
    ["application/pdf", "pdf"],
    ["application/zip", "zip"],
    ["application/json", "json"],
    ["text/plain", "txt"],
    ["text/markdown", "md"],
    ["text/csv", "csv"],
    ["text/html", "html"],
  ]);

async function loadSource(
  tx: Db,
  binding: ChatReuseBinding,
  conversation: AuthorizedConversation,
  sourceCommentId: string,
  attachmentId: string,
  allowEmpty = false,
): Promise<ChatAttachmentReuseSource> {
  const [sourceComment] = await tx
    .select({ id: issueComments.id })
    .from(issueComments)
    .where(
      and(
        eq(issueComments.id, sourceCommentId),
        eq(issueComments.companyId, binding.companyId),
        eq(issueComments.issueId, binding.issueId),
        isNull(issueComments.deletedAt),
      ),
    )
    .for("update")
    .limit(1);
  if (!sourceComment) {
    throw new Error("paperclip_runner_chat_attachment_source_denied");
  }
  const [row] = await tx
    .select({
      attachmentId: issueAttachments.id,
      parentCommentId: issueComments.id,
      filename: assets.originalFilename,
      contentType: assets.contentType,
      byteSize: assets.byteSize,
      sha256: assets.sha256,
      objectKey: assets.objectKey,
      createdAt: issueAttachments.createdAt,
    })
    .from(issueAttachments)
    .innerJoin(
      assets,
      and(
        eq(assets.id, issueAttachments.assetId),
        eq(assets.companyId, binding.companyId),
      ),
    )
    .innerJoin(
      issueComments,
      and(
        eq(issueComments.id, issueAttachments.issueCommentId),
        eq(issueComments.companyId, binding.companyId),
        eq(issueComments.issueId, binding.issueId),
        isNull(issueComments.deletedAt),
      ),
    )
    .where(
      and(
        eq(issueAttachments.id, attachmentId),
        eq(issueAttachments.companyId, binding.companyId),
        eq(issueAttachments.issueId, binding.issueId),
      ),
    )
    .for("update")
    .limit(1);
  if (
    !row ||
    row.byteSize < (allowEmpty ? 0 : 1) ||
    row.byteSize > MAX_ATTACHMENT_BYTES ||
    !isAllowedContentType(normalizeContentType(row.contentType)) ||
    !/^[a-f0-9]{64}$/iu.test(row.sha256)
  ) {
    throw new Error("paperclip_runner_chat_attachment_source_denied");
  }
  const sourceWithParent = {
    sourceCommentId,
    attachmentId: row.attachmentId,
    parentCommentId: row.parentCommentId,
    // Provider photos/voice messages legitimately have no original filename.
    // Derive display metadata from the already-validated MIME and opaque id;
    // never infer a storage path or change the selected source bytes.
    filename: row.filename?.trim()
      ? row.filename
      : `attachment-${row.attachmentId}.${HISTORICAL_ATTACHMENT_FILE_EXTENSIONS.get(normalizeContentType(row.contentType)) ?? "bin"}`,
    contentType: normalizeContentType(row.contentType),
    byteSize: row.byteSize,
    sha256: row.sha256,
    objectKey: row.objectKey,
    createdAt: row.createdAt,
  };
  if (
    !(await sourceLineageExists(tx, binding, conversation, sourceWithParent))
  ) {
    throw new Error("paperclip_runner_chat_attachment_source_denied");
  }
  const { parentCommentId: _parentCommentId, ...source } = sourceWithParent;
  return source;
}

export async function listAuthorizedChatAttachments(input: {
  db: Db;
  binding: ChatReuseBinding;
  sourceCommentId?: string | null;
  cursor?: string | null;
  limit: number;
}): Promise<ListedChatAttachmentPage> {
  return input.db.transaction(async (tx) => {
    const [current] = await tx
      .select({ run: heartbeatRuns, actorStatus: agents.status })
      .from(heartbeatRuns)
      .innerJoin(
        issues,
        and(
          eq(issues.id, input.binding.issueId),
          eq(issues.companyId, heartbeatRuns.companyId),
        ),
      )
      .innerJoin(
        agents,
        and(
          eq(agents.id, input.binding.agentId),
          eq(agents.companyId, heartbeatRuns.companyId),
        ),
      )
      .where(
        and(
          eq(heartbeatRuns.id, input.binding.runId),
          eq(heartbeatRuns.companyId, input.binding.companyId),
          eq(heartbeatRuns.agentId, input.binding.agentId),
          eq(heartbeatRuns.nativeIssueId, input.binding.issueId),
          eq(heartbeatRuns.runtimeMode, "native"),
          eq(heartbeatRuns.status, "running"),
          eq(issues.assigneeAgentId, input.binding.agentId),
          eq(issues.executionRunId, input.binding.runId),
        ),
      )
      .for("update")
      .limit(1);
    if (
      !current ||
      ["paused", "terminated", "pending_approval", "error"].includes(
        current.actorStatus,
      )
    ) {
      throw new Error("paperclip_runner_tool_binding_not_authorized");
    }
    const conversation = await authorizeChatConversationForBoundRun(
      tx as unknown as Db,
      input.binding,
      current.run.contextSnapshot,
    );
    const sourceFilter = input.sourceCommentId ?? null;
    const cursor = decodeListCursor(
      input.cursor,
      conversation.conversationId,
      sourceFilter,
    );
    const rawCandidates = await tx.execute(sql<{
      attachment_id: string;
      source_comment_id: string;
      created_at: Date | string;
    }>`
      with candidate_pairs as (
        select
          attachment.id as attachment_id,
          link.comment_id as source_comment_id,
          attachment.created_at
        from issue_attachments attachment
        join issue_comments parent_comment
          on parent_comment.id = attachment.issue_comment_id
          and parent_comment.company_id = ${input.binding.companyId}::uuid
          and parent_comment.issue_id = ${input.binding.issueId}::uuid
          and parent_comment.deleted_at is null
        join chat_message_links link
          on link.company_id = ${input.binding.companyId}::uuid
          and link.endpoint_id = ${conversation.endpointId}::uuid
          and link.conversation_id = ${conversation.conversationId}::uuid
          and link.direction = 'inbound'
          and link.comment_id = attachment.issue_comment_id
        join chat_deliveries delivery
          on delivery.id = link.delivery_id
          and delivery.company_id = link.company_id
          and delivery.endpoint_id = link.endpoint_id
          and delivery.conversation_id = link.conversation_id
          and delivery.state = 'processed'
        where attachment.company_id = ${input.binding.companyId}::uuid
          and attachment.issue_id = ${input.binding.issueId}::uuid
          and (${sourceFilter}::uuid is null or link.comment_id = ${sourceFilter}::uuid)
          and not exists (
            select 1
            from chat_deliveries lifecycle
            where lifecycle.company_id = ${input.binding.companyId}::uuid
              and lifecycle.endpoint_id = ${conversation.endpointId}::uuid
              and lifecycle.conversation_id = ${conversation.conversationId}::uuid
              and lifecycle.state = 'processed'
              and lifecycle.event_kind in ('message_updated', 'message_deleted', 'message_restored')
              and lifecycle.normalized_event->'message'->>'targetProviderEventId' = delivery.provider_event_id
          )

        union all

        select
          attachment.id as attachment_id,
          publication.comment_id as source_comment_id,
          attachment.created_at
        from issue_attachments attachment
        join issue_comments parent_comment
          on parent_comment.id = attachment.issue_comment_id
          and parent_comment.company_id = ${input.binding.companyId}::uuid
          and parent_comment.issue_id = ${input.binding.issueId}::uuid
          and parent_comment.deleted_at is null
        join chat_publications publication
          on publication.company_id = ${input.binding.companyId}::uuid
          and publication.endpoint_id = ${conversation.endpointId}::uuid
          and publication.conversation_id = ${conversation.conversationId}::uuid
          and publication.issue_id = ${input.binding.issueId}::uuid
          and publication.state = 'published'
          and publication.published_at is not null
          and publication.provider_message_id is not null
          and publication.comment_id is not null
          and publication.payload->'attachmentIds' ? attachment.id::text
        join issue_comments source_comment
          on source_comment.id = publication.comment_id
          and source_comment.company_id = publication.company_id
          and source_comment.issue_id = publication.issue_id
          and source_comment.deleted_at is null
        where attachment.company_id = ${input.binding.companyId}::uuid
          and attachment.issue_id = ${input.binding.issueId}::uuid
          and (${sourceFilter}::uuid is null or publication.comment_id = ${sourceFilter}::uuid)
          and not exists (
            select 1
            from chat_deliveries lifecycle
            where lifecycle.company_id = ${input.binding.companyId}::uuid
              and lifecycle.endpoint_id = ${conversation.endpointId}::uuid
              and lifecycle.conversation_id = ${conversation.conversationId}::uuid
              and lifecycle.state = 'processed'
              and lifecycle.event_kind in ('message_updated', 'message_deleted', 'message_restored')
              and lifecycle.normalized_event->'message'->>'providerMessageId' = publication.provider_message_id
          )
      ), candidates as (
        select distinct on (attachment_id)
          attachment_id,
          source_comment_id,
          created_at
        from candidate_pairs
        order by attachment_id, created_at desc, source_comment_id desc
      )
      select attachment_id, source_comment_id, created_at
      from candidates
      where (
        ${cursor?.createdAt ?? null}::timestamptz is null
        or (created_at, attachment_id, source_comment_id) <
          (${cursor?.createdAt ?? null}::timestamptz, ${cursor?.attachmentId ?? null}::uuid, ${cursor?.sourceCommentIdTieBreak ?? null}::uuid)
      )
      order by created_at desc, attachment_id desc, source_comment_id desc
      limit ${input.limit + 1}
    `);
    const candidates = (
      Array.from(rawCandidates) as Array<{
        attachment_id: string;
        source_comment_id: string;
        created_at: Date | string;
      }>
    ).map((row) => ({
      sourceCommentId: row.source_comment_id,
      attachmentId: row.attachment_id,
      createdAt:
        row.created_at instanceof Date
          ? row.created_at
          : new Date(row.created_at),
    }));
    const listed: ListedChatAttachment[] = [];
    const scanned = candidates.slice(0, input.limit);
    for (const candidate of scanned) {
      if (listed.length >= input.limit) break;
      try {
        const source = await loadSource(
          tx as unknown as Db,
          input.binding,
          conversation,
          candidate.sourceCommentId,
          candidate.attachmentId,
          true,
        );
        listed.push({
          sourceCommentId: source.sourceCommentId,
          attachmentId: source.attachmentId,
          filename: source.filename,
          contentType: source.contentType,
          byteSize: source.byteSize,
          sha256: source.sha256,
          createdAt: source.createdAt.toISOString(),
          contentAccess: "metadata_only",
        });
      } catch (error) {
        // Metadata listing omits deleted, oversized, or no-longer-lineaged files.
        if (
          !(error instanceof Error) ||
          error.message !== "paperclip_runner_chat_attachment_source_denied"
        ) {
          throw error;
        }
      }
    }
    const lastScanned = scanned.at(-1) ?? null;
    const hasMore = candidates.length > input.limit;
    return {
      attachments: listed,
      nextCursor:
        hasMore && lastScanned
          ? encodeListCursor({
              schema: "paperclip.chat-attachment-list-cursor.v1",
              conversationId: conversation.conversationId,
              sourceCommentId: sourceFilter,
              createdAt: lastScanned.createdAt.toISOString(),
              attachmentId: lastScanned.attachmentId,
              sourceCommentIdTieBreak: lastScanned.sourceCommentId,
            })
          : null,
      complete: !hasMore,
    };
  });
}

export async function authorizeChatAttachmentReuse(input: {
  db: Db;
  binding: ChatReuseBinding;
  contextSnapshot: unknown;
  sourceCommentId: string;
  attachmentId: string;
  /** Inspection may open empty files; publication retains its nonempty bound. */
  allowEmpty?: boolean;
}): Promise<ChatAttachmentReuseSource> {
  const conversation = await authorizeChatConversationForBoundRun(
    input.db,
    input.binding,
    input.contextSnapshot,
  );
  return loadSource(
    input.db,
    input.binding,
    conversation,
    input.sourceCommentId,
    input.attachmentId,
    input.allowEmpty,
  );
}

async function readSourceBytes(
  storage: StorageService,
  companyId: string,
  source: ChatAttachmentReuseSource,
  timeoutMs: number,
): Promise<Buffer> {
  let acquisitionTimedOut = false;
  let rejectAcquisition!: (error: Error) => void;
  const acquisitionTimeout = new Promise<never>((_resolve, reject) => {
    rejectAcquisition = reject;
  });
  const acquisitionTimer = setTimeout(() => {
    acquisitionTimedOut = true;
    rejectAcquisition(
      new Error("paperclip_runner_chat_attachment_source_read_timed_out"),
    );
  }, timeoutMs);
  acquisitionTimer.unref?.();
  const objectPromise = storage
    .getObject(companyId, source.objectKey)
    .then((object) => {
      if (acquisitionTimedOut) object.stream.destroy();
      return object;
    });
  let object: Awaited<ReturnType<StorageService["getObject"]>>;
  try {
    object = await Promise.race([objectPromise, acquisitionTimeout]);
  } finally {
    clearTimeout(acquisitionTimer);
  }
  const timeout = setTimeout(() => {
    object.stream.destroy(
      new Error("paperclip_runner_chat_attachment_source_read_timed_out"),
    );
  }, timeoutMs);
  timeout.unref?.();
  const chunks: Buffer[] = [];
  let total = 0;
  try {
    for await (const chunk of object.stream) {
      const buffer = Buffer.isBuffer(chunk) ? chunk : Buffer.from(chunk);
      total += buffer.length;
      if (total > source.byteSize || total > MAX_ATTACHMENT_BYTES) {
        object.stream.destroy();
        throw new Error(
          "paperclip_runner_chat_attachment_source_size_mismatch",
        );
      }
      chunks.push(buffer);
    }
  } finally {
    clearTimeout(timeout);
  }
  const body = Buffer.concat(chunks);
  if (
    body.length !== source.byteSize ||
    createHash("sha256").update(body).digest("hex") !==
      source.sha256.toLowerCase()
  ) {
    if (!object.stream.destroyed) {
      object.stream.destroy();
    }
    throw new Error(
      "paperclip_runner_chat_attachment_source_integrity_mismatch",
    );
  }
  return body;
}

const DEFAULT_STORAGE_TIMEOUT_MS = 10_000;

async function deleteStorageObjectWithin(
  storage: StorageService,
  companyId: string,
  objectKey: string,
  timeoutMs: number,
): Promise<void> {
  const deletion = storage
    .deleteObject(companyId, objectKey)
    .catch(() => undefined);
  let timer: ReturnType<typeof setTimeout> | null = null;
  try {
    await Promise.race([
      deletion,
      new Promise<void>((resolve) => {
        timer = setTimeout(resolve, timeoutMs);
        timer.unref?.();
      }),
    ]);
  } finally {
    if (timer) clearTimeout(timer);
  }
}

async function putStorageObjectWithin(
  storage: StorageService,
  input: Parameters<StorageService["putFile"]>[0],
  timeoutMs: number,
): Promise<Awaited<ReturnType<StorageService["putFile"]>>> {
  let timedOut = false;
  let rejectTimeout!: (error: Error) => void;
  const timeout = new Promise<never>((_resolve, reject) => {
    rejectTimeout = reject;
  });
  const timer = setTimeout(() => {
    timedOut = true;
    rejectTimeout(
      new Error("paperclip_runner_chat_attachment_storage_write_timed_out"),
    );
  }, timeoutMs);
  timer.unref?.();
  const write = storage.putFile(input).then((stored) => {
    if (timedOut) {
      void deleteStorageObjectWithin(
        storage,
        input.companyId,
        stored.objectKey,
        timeoutMs,
      );
    }
    return stored;
  });
  try {
    return await Promise.race([write, timeout]);
  } finally {
    clearTimeout(timer);
  }
}

export async function prepareReusedChatAttachment(input: {
  db: Db;
  binding: ChatReuseBinding;
  source: ChatAttachmentReuseSource;
  title: string;
  storage?: StorageService;
  storageTimeoutMs?: number;
}): Promise<PreparedReusedChatAttachment> {
  const [issue] = await input.db
    .select({ statusVersion: issues.statusVersion })
    .from(issues)
    .innerJoin(
      heartbeatRuns,
      and(
        eq(heartbeatRuns.id, input.binding.runId),
        eq(heartbeatRuns.companyId, issues.companyId),
        eq(heartbeatRuns.nativeIssueId, issues.id),
      ),
    )
    .where(
      and(
        eq(issues.id, input.binding.issueId),
        eq(issues.companyId, input.binding.companyId),
        eq(issues.assigneeAgentId, input.binding.agentId),
        eq(issues.executionRunId, input.binding.runId),
        eq(heartbeatRuns.agentId, input.binding.agentId),
        eq(heartbeatRuns.status, "running"),
        eq(heartbeatRuns.runtimeMode, "native"),
      ),
    )
    .limit(1);
  if (!issue)
    throw new Error("paperclip_runner_chat_attachment_binding_denied");
  const storage = input.storage ?? getStorageService();
  const storageTimeoutMs =
    typeof input.storageTimeoutMs === "number" &&
    Number.isFinite(input.storageTimeoutMs) &&
    input.storageTimeoutMs > 0
      ? input.storageTimeoutMs
      : DEFAULT_STORAGE_TIMEOUT_MS;
  const body = await readSourceBytes(
    storage,
    input.binding.companyId,
    input.source,
    storageTimeoutMs,
  );
  const stored = await putStorageObjectWithin(
    storage,
    {
      companyId: input.binding.companyId,
      namespace: `issues/${input.binding.issueId}`,
      originalFilename: input.source.filename,
      contentType: input.source.contentType,
      body,
    },
    storageTimeoutMs,
  );
  try {
    if (
      stored.byteSize !== body.length ||
      stored.sha256.toLowerCase() !== input.source.sha256.toLowerCase() ||
      stored.contentType !== input.source.contentType
    ) {
      throw new Error("paperclip_runner_chat_attachment_storage_mismatch");
    }
    const attachment = await issueService(input.db).createAttachment({
      issueId: input.binding.issueId,
      provider: stored.provider,
      objectKey: stored.objectKey,
      contentType: stored.contentType,
      byteSize: stored.byteSize,
      sha256: stored.sha256,
      originalFilename: stored.originalFilename,
      createdByAgentId: input.binding.agentId,
      createdByRunId: input.binding.runId,
    });
    if (
      !attachment.artifactWorkProductId ||
      attachment.originatingRunId !== input.binding.runId
    ) {
      throw new Error("paperclip_runner_chat_attachment_origin_not_persisted");
    }
    const [workProduct] = await input.db
      .select({ metadata: issueWorkProducts.metadata })
      .from(issueWorkProducts)
      .where(
        and(
          eq(issueWorkProducts.id, attachment.artifactWorkProductId),
          eq(issueWorkProducts.companyId, input.binding.companyId),
          eq(issueWorkProducts.issueId, input.binding.issueId),
          eq(issueWorkProducts.createdByRunId, input.binding.runId),
        ),
      )
      .for("update")
      .limit(1);
    if (!workProduct) {
      throw new Error("paperclip_runner_chat_attachment_origin_not_persisted");
    }
    await input.db
      .update(issueWorkProducts)
      .set({
        title: input.title,
        metadata: {
          ...record(workProduct.metadata),
          reusedFromAttachmentId: input.source.attachmentId,
          reusedFromCommentId: input.source.sourceCommentId,
          reusedFromSha256: input.source.sha256,
        },
        updatedAt: new Date(),
      })
      .where(
        and(
          eq(issueWorkProducts.id, attachment.artifactWorkProductId),
          eq(issueWorkProducts.companyId, input.binding.companyId),
          eq(issueWorkProducts.issueId, input.binding.issueId),
          eq(issueWorkProducts.createdByRunId, input.binding.runId),
        ),
      );
    const comment = await issueService(input.db).addComment(
      input.binding.issueId,
      `Prepared ${input.title} for this response.`,
      { agentId: input.binding.agentId, runId: input.binding.runId },
      {
        attachmentIds: [attachment.id],
        authorizationReason: "paperclip_runner_protocol",
      },
      input.db,
    );
    return {
      result: {
        commandId: `chat-attachment-reused:${attachment.id}`,
        disposition: "applied",
        stateRevision: issue.statusVersion,
        entityRefs: [
          attachment.id,
          attachment.artifactWorkProductId,
          comment.id,
        ],
        scheduledWakeIds: [],
        source: {
          commentId: input.source.sourceCommentId,
          attachmentId: input.source.attachmentId,
          sha256: input.source.sha256,
        },
        prepared: {
          attachmentId: attachment.id,
          workProductId: attachment.artifactWorkProductId,
          commentId: comment.id,
          filename: input.source.filename,
          byteSize: body.length,
          sha256: attachment.sha256,
        },
      },
      rollbackDefinitePreCommitFailure: async () => {
        await deleteStorageObjectWithin(
          storage,
          input.binding.companyId,
          stored.objectKey,
          storageTimeoutMs,
        );
      },
    };
  } catch (error) {
    await deleteStorageObjectWithin(
      storage,
      input.binding.companyId,
      stored.objectKey,
      storageTimeoutMs,
    );
    throw error;
  }
}