import { Context, Data, Effect, Layer, Option, Schema } from "effect"; import { sha256Hex } from "@executor-js/sdk"; import { ApiKeyManagementError } from "./errors";import { WorkOSClient } from "./workos"; /** * Which view a validated key resolves to. *   - `"user"` — the product view. The key belongs to a member; the request *     binds to that member as the acting subject. Every key today is this. *   - `"org"` — the PLATFORM view. The key belongs to the organization itself, *     so there is no acting member: the request gets tenant-wide READ-ONLY *     reach and no bound subject. Privileged; minted separately (PR 1.5). */export type ApiKeyScope = "user" | "org"; /** The owner an api key resolves to — NOT a full {@link Principal} (no email / * name / roles), so it carries an honest, distinct name. */export type ApiKeyOwner = {  readonly scope: ApiKeyScope;  /** The acting member for a `"user"` key; `null` for an `"org"` key, which   *  has no member behind it. Nullable rather than a sentinel so nothing can   *  accidentally bind an org key to a subject. */  readonly accountId: string | null;  readonly organizationId: string;  readonly keyId: string;}; export type ApiKeySummary = {  readonly id: string;  readonly name: string;  readonly obfuscatedValue: string;  readonly createdAt: string;  readonly updatedAt: string;  readonly lastUsedAt: string | null;}; export type CreatedApiKey = ApiKeySummary & {  readonly value: string;}; export class ApiKeyValidationError extends Data.TaggedError("ApiKeyValidationError")<{  readonly cause: unknown;}> {} /** * The requested key id is not an org-owned key of this organization — it does * not exist, belongs to a member rather than the org, or belongs to a different * org in the same WorkOS workspace. Distinct from `ApiKeyManagementError` (an * upstream failure) so callers can answer "not found" without a 500. */export class OrgApiKeyNotFound extends Data.TaggedError("OrgApiKeyNotFound")<{  readonly keyId: string;}> {} // WorkOS keys are owned by either a user or an organization. The user shape// carries the member id in `id` and the org in `organization_id`; the org shape// carries the ORG in `id` and no member at all. Both decode here — the// distinction is a branch (`ownerFromApiKey`), not a decode failure, so an// org-owned key is no longer indistinguishable from an invalid one.const UserApiKeyOwner = Schema.Struct({  type: Schema.Literal("user"),  id: Schema.String,  organizationId: Schema.optional(Schema.String),  organization_id: Schema.optional(Schema.String),}); const OrgApiKeyOwner = Schema.Struct({  type: Schema.Literal("organization"),  id: Schema.String,}); const WorkOSApiKeyOwner = Schema.Union([UserApiKeyOwner, OrgApiKeyOwner]); const ApiKey = Schema.Struct({  id: Schema.String,  owner: UserApiKeyOwner,  name: Schema.optional(Schema.String),  obfuscatedValue: Schema.optional(Schema.String),  obfuscated_value: Schema.optional(Schema.String),  createdAt: Schema.optional(Schema.String),  created_at: Schema.optional(Schema.String),  updatedAt: Schema.optional(Schema.String),  updated_at: Schema.optional(Schema.String),  lastUsedAt: Schema.optional(Schema.NullOr(Schema.String)),  last_used_at: Schema.optional(Schema.NullOr(Schema.String)),}); // Validation accepts BOTH owner shapes. The user list/create paths below stay// user-only on purpose (they are the console's personal-key CRUD); the ORG// list/create paths are the separate, privileged surface beside them, gated to// admins at the account-provider boundary.const ValidatedApiKey = Schema.Struct({  id: Schema.String,  owner: WorkOSApiKeyOwner,}); const ValidateApiKeyResponse = Schema.Struct({  apiKey: Schema.NullOr(ValidatedApiKey),}); const RawCreatedApiKey = Schema.Struct({  id: Schema.String,  owner: UserApiKeyOwner,  name: Schema.optional(Schema.String),  obfuscatedValue: Schema.optional(Schema.String),  obfuscated_value: Schema.optional(Schema.String),  createdAt: Schema.optional(Schema.String),  created_at: Schema.optional(Schema.String),  updatedAt: Schema.optional(Schema.String),  updated_at: Schema.optional(Schema.String),  lastUsedAt: Schema.optional(Schema.NullOr(Schema.String)),  last_used_at: Schema.optional(Schema.NullOr(Schema.String)),  value: Schema.String,}); const ListApiKeysResponse = Schema.Struct({  data: Schema.Array(ApiKey),}); // The ORG-owned mirror of `ApiKey` / `RawCreatedApiKey`. A separate shape// rather than a widened one: `summaryFromApiKey` reads the user shape's// `organization_id` to prove the key belongs to the caller's org, and an// org-owned row carries the org in `owner.id` instead. Merging them would mean// one nullable field standing for two different things.const OrgApiKey = Schema.Struct({  id: Schema.String,  owner: OrgApiKeyOwner,  name: Schema.optional(Schema.String),  obfuscatedValue: Schema.optional(Schema.String),  obfuscated_value: Schema.optional(Schema.String),  createdAt: Schema.optional(Schema.String),  created_at: Schema.optional(Schema.String),  updatedAt: Schema.optional(Schema.String),  updated_at: Schema.optional(Schema.String),  lastUsedAt: Schema.optional(Schema.NullOr(Schema.String)),  last_used_at: Schema.optional(Schema.NullOr(Schema.String)),}); const RawCreatedOrgApiKey = Schema.Struct({  ...OrgApiKey.fields,  value: Schema.String,}); // `data` is decoded element-by-element, NOT as `Schema.Array(OrgApiKey)`: WorkOS// may return user-owned keys alongside org-owned ones, and a whole-array decode// fails on the first non-org element — blanking the entire list rather than// dropping the one row that doesn't belong. Same per-row tolerance the user-key// path gets from `summaryFromApiKey` returning null.const ListOrgApiKeysResponse = Schema.Struct({  data: Schema.Array(Schema.Unknown),}); const CreateOrgApiKeyResponse = Schema.Union([  RawCreatedOrgApiKey,  Schema.Struct({ apiKey: RawCreatedOrgApiKey }),  Schema.Struct({ api_key: RawCreatedOrgApiKey }),]); const CreateApiKeyResponse = Schema.Union([  RawCreatedApiKey,  Schema.Struct({ apiKey: RawCreatedApiKey }),  Schema.Struct({ api_key: RawCreatedApiKey }),]); const decodeValidateApiKeyResponse = Schema.decodeUnknownOption(ValidateApiKeyResponse);const decodeListApiKeysResponse = Schema.decodeUnknownOption(ListApiKeysResponse);const decodeCreateApiKeyResponse = Schema.decodeUnknownOption(CreateApiKeyResponse);const decodeListOrgApiKeysResponse = Schema.decodeUnknownOption(ListOrgApiKeysResponse);const decodeOrgApiKey = Schema.decodeUnknownOption(OrgApiKey);const decodeCreateOrgApiKeyResponse = Schema.decodeUnknownOption(CreateOrgApiKeyResponse); const ownerFromApiKey = (apiKey: typeof ValidatedApiKey.Type): ApiKeyOwner | null => {  if (apiKey.owner.type === "organization") {    // An org-owned key IS the org: `owner.id` is the organization, and there    // is no member to act as. This resolves to the platform view.    return {      scope: "org",      accountId: null,      organizationId: apiKey.owner.id,      keyId: apiKey.id,    };  }  const organizationId = apiKey.owner.organizationId ?? apiKey.owner.organization_id;  if (!organizationId) return null;  return {    scope: "user",    accountId: apiKey.owner.id,    organizationId,    keyId: apiKey.id,  };}; const ownerFromResponse = (value: unknown): ApiKeyOwner | null =>  Option.match(decodeValidateApiKeyResponse(value), {    onNone: () => null,    onSome: ({ apiKey }) => (apiKey ? ownerFromApiKey(apiKey) : null),  }); const summaryFromApiKey = (apiKey: typeof ApiKey.Type): ApiKeySummary | null => {  const organizationId = apiKey.owner.organizationId ?? apiKey.owner.organization_id;  if (!organizationId) return null;  return {    id: apiKey.id,    name: apiKey.name ?? "API key",    obfuscatedValue: apiKey.obfuscatedValue ?? apiKey.obfuscated_value ?? "",    createdAt: apiKey.createdAt ?? apiKey.created_at ?? "",    updatedAt: apiKey.updatedAt ?? apiKey.updated_at ?? "",    lastUsedAt: apiKey.lastUsedAt ?? apiKey.last_used_at ?? null,  };}; const listFromResponse = (value: unknown): readonly ApiKeySummary[] =>  Option.match(decodeListApiKeysResponse(value), {    onNone: () => [],    onSome: ({ data }) =>      data.flatMap((apiKey) => {        const summary = summaryFromApiKey(apiKey);        return summary ? [summary] : [];      }),  }); // The org-owned mirror of `summaryFromApiKey`. `organizationId` is checked by// the CALLER against the org it asked for: WorkOS's workspace api key is// workspace-wide, so a response naming a different org than the one requested// must not be surfaced as that org's key.const summaryFromOrgApiKey = (  apiKey: typeof OrgApiKey.Type,  organizationId: string,): ApiKeySummary | null => {  if (apiKey.owner.id !== organizationId) return null;  return {    id: apiKey.id,    name: apiKey.name ?? "API key",    obfuscatedValue: apiKey.obfuscatedValue ?? apiKey.obfuscated_value ?? "",    createdAt: apiKey.createdAt ?? apiKey.created_at ?? "",    updatedAt: apiKey.updatedAt ?? apiKey.updated_at ?? "",    lastUsedAt: apiKey.lastUsedAt ?? apiKey.last_used_at ?? null,  };}; const orgListFromResponse = (value: unknown, organizationId: string): readonly ApiKeySummary[] =>  Option.match(decodeListOrgApiKeysResponse(value), {    onNone: () => [],    onSome: ({ data }) =>      data.flatMap((entry) =>        Option.match(decodeOrgApiKey(entry), {          // Not an org-owned key (a user key sharing the listing, or a shape we          // don't recognize) — skip the row, keep the rest.          onNone: () => [],          onSome: (apiKey) => {            const summary = summaryFromOrgApiKey(apiKey, organizationId);            return summary ? [summary] : [];          },        }),      ),  }); const orgCreatedFromResponse = (value: unknown, organizationId: string): CreatedApiKey | null =>  Option.match(decodeCreateOrgApiKeyResponse(value), {    onNone: () => null,    onSome: (response) => {      const apiKey =        "value" in response ? response : "apiKey" in response ? response.apiKey : response.api_key;      const summary = summaryFromOrgApiKey(apiKey, organizationId);      return summary ? { ...summary, value: apiKey.value } : null;    },  }); const createdFromResponse = (value: unknown): CreatedApiKey | null =>  Option.match(decodeCreateApiKeyResponse(value), {    onNone: () => null,    onSome: (response) => {      const apiKey =        "value" in response ? response : "apiKey" in response ? response.apiKey : response.api_key;      const summary = summaryFromApiKey(apiKey);      return summary ? { ...summary, value: apiKey.value } : null;    },  }); // ---------------------------------------------------------------------------// Per-isolate validation cache.//// Every /mcp request and every api-key-authenticated /api/* request funnels// through `validate`, and each call is a live WorkOS round trip (~100-150ms).// The JWT bearer path beside it verifies locally against a JWKS cached for an// hour; api keys had no cache at all. This is the same bounded TTL map the// engine already uses for billing outcomes (engine/execution-gate.ts).//// Security shape, stated explicitly because this is auth code://   - The map key is the SHA-256 digest of the presented key value, never the//     raw credential, so the map's keys cannot be reversed into a usable key.//     The digest reaches no log, span, or error message.//   - Only SUCCESSFUL validations are cached. An invalid key and an upstream//     failure always miss: an attacker probing bad keys cannot poison the map//     (the size bound alone handles memory), and a just-created key works//     immediately instead of waiting out a stale negative entry.//   - REVOCATION WINDOW: the isolate that serves the revoke drops its own//     entries for that key id immediately (`invalidateKeyId`, called by both//     revoke paths below), so revoking a key through the console refuses it//     on the next request wherever the same isolate validates. OTHER isolates//     that validated the key before revocation keep serving it for up to the//     TTL (60s). That residual window is the price of the cache, and it is//     far tighter than the 1h JWKS rotation window the JWT path already//     accepts.//   - Concurrent misses for the same key each call WorkOS; there is no//     in-flight dedupe. The duplicate window is one round trip per key per//     TTL per isolate — exactly the cost EVERY request paid before this//     cache — and dedupe would add interruption-safety machinery (a//     cancelled leader must not strand its waiters) to auth-critical code.// --------------------------------------------------------------------------- const API_KEY_VALIDATION_CACHE_TTL_MS = 60_000;// Sweep guard so a long-lived isolate serving many keys can't grow the cache// map unbounded (mirrors BALANCE_CACHE_MAX_ENTRIES in execution-gate.ts).const API_KEY_VALIDATION_CACHE_MAX_ENTRIES = 10_000; type ApiKeyValidationCacheEntry = {  readonly owner: ApiKeyOwner;  readonly expiresAtMs: number;}; // The map lives at MODULE scope — one per isolate — not inside// `makeCachedApiKeyValidate`, because the `ApiKeyService.WorkOS` layer is NOT// built once per isolate on every plane: the account middleware rebuilds it// per request. A map owned by each build would give the revoke paths a fresh// empty cache to invalidate while the long-lived identity plane kept serving// the revoked key from its own. Every build shares this map instead (entries// are pure validation RESULTS, so which build's WorkOS client wrote them does// not matter), which is also what makes the entries survive between requests// on the per-request plane at all.const isolateApiKeyValidationCache = new Map<string, ApiKeyValidationCacheEntry>(); /** Test-only: module state outlives a single test case (mirrors *  `resetBuildSlotsForTest` in mcp/session-build-semaphore.ts). */export const resetApiKeyValidationCacheForTest = (): void => {  isolateApiKeyValidationCache.clear();}; export type ApiKeyValidate = (  value: string,) => Effect.Effect<ApiKeyOwner | null, ApiKeyValidationError>; /** * Wrap a `validate` function with the success cache described above. Exported * for tests only — production use is the `ApiKeyService.WorkOS` layer below, * every build of which shares the module-scope map. * * The `ttlMs` / `maxEntries` / `now` / `cache` knobs exist so tests can * exercise expiry, the size bound, and map sharing without wall time or * module state; production passes only `cache`. */export const makeCachedApiKeyValidate = (  validate: ApiKeyValidate,  options?: {    readonly ttlMs?: number;    readonly maxEntries?: number;    readonly now?: () => number;    /** The map to cache into. Production passes the module-scope     *  `isolateApiKeyValidationCache`; tests default to a private map. */    readonly cache?: Map<string, ApiKeyValidationCacheEntry>;  },): {  readonly validate: ApiKeyValidate;  /**   * Drop every cached entry that resolved to this key id. The cache is keyed   * by the digest of the presented VALUE and a revoke only knows the key ID,   * so this walks the map — bounded by `maxEntries`, and revocation is a rare   * human action, not a hot path.   */  readonly invalidateKeyId: (keyId: string) => void;  /** Test seam: the digests currently cached, so tests can assert the raw   *  credential never appears as a map key. */  readonly cacheKeys: () => ReadonlyArray<string>;} => {  const ttlMs = options?.ttlMs ?? API_KEY_VALIDATION_CACHE_TTL_MS;  const maxEntries = options?.maxEntries ?? API_KEY_VALIDATION_CACHE_MAX_ENTRIES;  const now = options?.now ?? Date.now;  const cache = options?.cache ?? new Map<string, ApiKeyValidationCacheEntry>();   const writeCache = (digest: string, owner: ApiKeyOwner, nowMs: number): void => {    if (cache.size >= maxEntries) {      for (const [key, entry] of cache) {        if (entry.expiresAtMs <= nowMs) cache.delete(key);      }      // Still saturated after dropping expired entries: reset rather than grow.      if (cache.size >= maxEntries) cache.clear();    }    cache.set(digest, { owner, expiresAtMs: nowMs + ttlMs });  };   return {    cacheKeys: () => [...cache.keys()],    invalidateKeyId: (keyId) => {      for (const [digest, entry] of cache) {        if (entry.owner.keyId === keyId) cache.delete(digest);      }    },    validate: (value) =>      Effect.gen(function* () {        const digest = yield* sha256Hex(value);        const nowMs = now();        const cached = cache.get(digest);        if (cached && cached.expiresAtMs > nowMs) return cached.owner;        const owner = yield* validate(value);        // Cache only a resolved owner — see the block comment above for why        // null results and failures always stay misses.        if (owner) writeCache(digest, owner, nowMs);        return owner;      }),  };}; export class ApiKeyService extends Context.Service<  ApiKeyService,  {    readonly validate: (value: string) => Effect.Effect<ApiKeyOwner | null, ApiKeyValidationError>;    readonly listUserKeys: (input: {      readonly accountId: string;      readonly organizationId: string;    }) => Effect.Effect<readonly ApiKeySummary[], ApiKeyManagementError>;    readonly createUserKey: (input: {      readonly accountId: string;      readonly organizationId: string;      readonly name: string;    }) => Effect.Effect<CreatedApiKey, ApiKeyManagementError>;    readonly revokeUserKey: (input: {      readonly keyId: string;    }) => Effect.Effect<void, ApiKeyManagementError>;    /**     * The org-owned keys of an organization — the credentials that resolve to     * the read-only platform view. Privileged: callers gate on admin membership     * before reaching this.     */    readonly listOrgKeys: (input: {      readonly organizationId: string;    }) => Effect.Effect<readonly ApiKeySummary[], ApiKeyManagementError>;    readonly createOrgKey: (input: {      readonly organizationId: string;      readonly name: string;    }) => Effect.Effect<CreatedApiKey, ApiKeyManagementError>;    /**     * Revoke an org-owned key. Ownership is resolved against the ORG's own key     * listing — never the caller's personal keys — so a member's user key id     * (or another org's key id, since the WorkOS workspace key is     * workspace-wide) cannot be destroyed through this path.     */    readonly revokeOrgKey: (input: {      readonly organizationId: string;      readonly keyId: string;    }) => Effect.Effect<void, ApiKeyManagementError | OrgApiKeyNotFound>;  }>()("@executor-js/cloud/ApiKeyService") {  static WorkOS = Layer.effect(this)(    Effect.gen(function* () {      const workos = yield* WorkOSClient;      // The cache MAP is the module-scope per-isolate one (see its comment);      // this build only contributes the validate function that fills it, so      // however many times a plane rebuilds this layer, hits, misses, and      // invalidations all land in the same map.      const cachedValidate = makeCachedApiKeyValidate(        (value) =>          workos.validateApiKey(value).pipe(            Effect.map(ownerFromResponse),            Effect.mapError((cause) => new ApiKeyValidationError({ cause })),          ),        { cache: isolateApiKeyValidationCache },      );      return {        validate: cachedValidate.validate,        listUserKeys: ({ accountId, organizationId }) =>          workos.listUserApiKeys(accountId, organizationId).pipe(            Effect.map(listFromResponse),            Effect.mapError((cause) => new ApiKeyManagementError({ cause })),          ),        createUserKey: ({ accountId, organizationId, name }) =>          workos.createUserApiKey({ userId: accountId, organizationId, name }).pipe(            Effect.mapError((cause) => new ApiKeyManagementError({ cause })),            Effect.flatMap((response) => {              const created = createdFromResponse(response);              return created                ? Effect.succeed(created)                : Effect.fail(new ApiKeyManagementError({ cause: "invalid_create_response" }));            }),          ),        revokeUserKey: ({ keyId }) =>          workos.deleteApiKey(keyId).pipe(            Effect.mapError((cause) => new ApiKeyManagementError({ cause })),            Effect.tap(() => Effect.sync(() => cachedValidate.invalidateKeyId(keyId))),          ),        listOrgKeys: ({ organizationId }) =>          workos.listOrgApiKeys(organizationId).pipe(            Effect.map((response) => orgListFromResponse(response, organizationId)),            Effect.mapError((cause) => new ApiKeyManagementError({ cause })),          ),        createOrgKey: ({ organizationId, name }) =>          workos.createOrgApiKey({ organizationId, name }).pipe(            Effect.mapError((cause) => new ApiKeyManagementError({ cause })),            Effect.flatMap((response) => {

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