import { describe, it, expect } from "@effect/vitest";
import { env } from "cloudflare:workers";
import * as Cause from "effect/Cause";
import * as Data from "effect/Data";
import * as Effect from "effect/Effect";
import type { SandboxToolInvoker } from "@executor-js/codemode-core";
import { ExecutionToolError } from "@executor-js/execution";
import {
  classifySandboxFailure,
  ToolDispatcher,
  makeDynamicWorkerExecutor,
  renderWorkerError,
  serializeWorkerCause,
} from "./executor";

class TestToolError extends Data.TaggedError("TestToolError")<{
  readonly message: string;
}> {}

const makeInvoker = (
  fn: (input: { path: string; args: unknown }) => unknown,
): SandboxToolInvoker => ({
  invoke: (input) =>
    Effect.try({
      try: () => fn(input),
      catch: (error) => error,
    }),
});

const failingInvoker = (message: string): SandboxToolInvoker => ({
  invoke: () => Effect.fail(new TestToolError({ message })),
});

describe("ToolDispatcher", () => {
  it("returns a success envelope on successful tool call", async () => {
    const invoker = makeInvoker(({ args }) => args);
    const dispatcher = new ToolDispatcher(invoker, Effect.runPromise);

    const result = await dispatcher.call("test.tool", { key: "value" });
    expect(result).toEqual({ ok: true, result: { key: "value" } });
  });

  it("serializes tagged failures into a structured error envelope", async () => {
    const dispatcher = new ToolDispatcher(failingInvoker("tool broke"), Effect.runPromise);

    const result = await dispatcher.call("broken.tool", {});
    expect(result).toMatchObject({
      ok: false,
      error: {
        kind: "fail",
        message: "tool broke",
        primary: { __type: "Error", name: "TestToolError", message: "tool broke" },
        failures: [{ __type: "Error", name: "TestToolError", message: "tool broke" }],
        defects: [],
        interrupted: false,
      },
    });
  });

  it("serializes object-shaped tool errors without collapsing them", async () => {
    const dispatcher = new ToolDispatcher(
      {
        invoke: () =>
          Effect.fail({
            code: "forbidden",
            detail: "missing team access",
          }),
      },
      Effect.runPromise,
    );

    const result = await dispatcher.call("broken.tool", {});
    expect(result).toEqual({
      ok: false,
      error: {
        kind: "fail",
        message: '{"code":"forbidden","detail":"missing team access"}',
        primary: {
          code: "forbidden",
          detail: "missing team access",
        },
        failures: [
          {
            code: "forbidden",
            detail: "missing team access",
          },
        ],
        defects: [],
        interrupted: false,
      },
    });
  });

  it("handles undefined args", async () => {
    const invoker = makeInvoker(({ args }) => args);
    const dispatcher = new ToolDispatcher(invoker, Effect.runPromise);

    const result = await dispatcher.call("test.tool", undefined);
    expect(result).toEqual({ ok: true, result: undefined });
  });

  it("returns a failure envelope for circular RPC args", async () => {
    const invoker = makeInvoker(({ args }) => args);
    const dispatcher = new ToolDispatcher(invoker, Effect.runPromise);
    const cyclic: Record<string, unknown> = {};
    cyclic.self = cyclic;

    const result = await dispatcher.call("test.tool", cyclic);

    expect(result).toMatchObject({
      ok: false,
      error: {
        message: "Tool RPC payload contains a circular reference",
      },
    });
  });

  it("allows shared object references in RPC args", async () => {
    const invoker = makeInvoker(({ args }) => args);
    const dispatcher = new ToolDispatcher(invoker, Effect.runPromise);
    const shared = { value: 1 };

    const result = await dispatcher.call("test.tool", { first: shared, second: shared });

    expect(result).toEqual({
      ok: true,
      result: { first: { value: 1 }, second: { value: 1 } },
    });
  });

  it("passes the tool path correctly", async () => {
    let capturedPath = "";
    const invoker = makeInvoker(({ path }) => {
      capturedPath = path;
      return "ok";
    });
    const dispatcher = new ToolDispatcher(invoker, Effect.runPromise);

    await dispatcher.call("my.deep.tool.path", {});
    expect(capturedPath).toBe("my.deep.tool.path");
  });
});

describe("serializeWorkerCause", () => {
  it("captures defects", () => {
    const serialized = serializeWorkerCause(Cause.die({ defect: true }));
    expect(serialized.kind).toBe("die");
    expect(serialized.defects).toEqual([{ defect: true }]);
    expect(serialized.failures).toEqual([]);
  });

  it("captures interruptions", () => {
    const serialized = serializeWorkerCause(Cause.interrupt());
    expect(serialized.kind).toBe("interrupt");
    expect(serialized.interrupted).toBe(true);
    expect(renderWorkerError(serialized)).toBe("Interrupted");
  });
});

describe("classifySandboxFailure", () => {
  // Each string here is a real `status.message` seen on the
  // executor.runtime.* spans in production. They reject the worker loader
  // or the evaluate RPC and were collapsed to an opaque "Internal tool
  // error" before the model could act on them. CPU/memory/capacity limits
  // can't be triggered deterministically inside a unit-test isolate, so we
  // pin their classification here; the syntax and serialization paths also
  // have live WorkerLoader coverage above.
  it.each([
    ["Failed to start Worker:\nUncaught SyntaxError: Unexpected token '='", "compilation"],
    ["Unexpected token '{'", "compilation"],
    ["Invalid or unexpected token", "compilation"],
    ["Symbol(nope) could not be cloned.", "runtime"],
    [
      'Could not serialize object of type "Cloudflare". This type does not support serialization.',
      "runtime",
    ],
    ["Worker exceeded CPU time limit.", "runtime"],
    ["Worker exceeded memory limit.", "runtime"],
    ["Too many concurrent dynamic workers", "runtime"],
  ] as const)("classifies %j as %s", (message, expected) => {
    expect(classifySandboxFailure({ __type: "Error", name: "Error", message }, message)).toBe(
      expected,
    );
  });

  it("classifies a SyntaxError by name even when the message is bare", () => {
    expect(
      classifySandboxFailure({ __type: "Error", name: "SyntaxError", message: "boom" }, "boom"),
    ).toBe("compilation");
  });

  it("classifies a DataCloneError by name even when the message is bare", () => {
    expect(
      classifySandboxFailure({ __type: "Error", name: "DataCloneError", message: "boom" }, "boom"),
    ).toBe("runtime");
  });

  it("leaves an unrecognized defect opaque (internal)", () => {
    const message = "the RPC receiver does not implement the method";
    expect(classifySandboxFailure({ __type: "Error", name: "TypeError", message }, message)).toBe(
      "internal",
    );
  });
});

describe("makeDynamicWorkerExecutor", () => {
  const loader = (env as { LOADER: WorkerLoader }).LOADER;

  it("executes simple code and returns result", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(executor.execute("async () => 42", invoker));

    expect(result.error).toBeUndefined();
    expect(result.result).toBe(42);
  });

  it("recovers prose-wrapped fenced async arrow input", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute(
        ["Use this snippet.", "", "```ts", "async () => 42", "```"].join("\n"),
        invoker,
      ),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toBe(42);
  });

  it("executes code that returns an object", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute('async () => ({ hello: "world" })', invoker),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toEqual({ hello: "world" });
  });

  it("captures console output in logs", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute(
        'async () => { console.log("hello"); console.warn("careful"); return 1; }',
        invoker,
      ),
    );

    expect(result.error).toBeUndefined();
    expect(result.logs).toContain("hello");
    expect(result.logs).toContain("[warn] careful");
  });

  it("returns error for throwing code", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute('async () => { throw new Error("boom"); }', invoker),
    );

    expect(result.error).toBe("boom");
    expect(result.result).toBeNull();
  });

  it("serializes thrown objects into the user-facing error text", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute(
        'async () => { throw { code: "bad_request", detail: "team missing" }; }',
        invoker,
      ),
    );

    expect(result.error).toBe('{"code":"bad_request","detail":"team missing"}');
    expect(result.result).toBeNull();
  });

  it("invokes tools via the proxy and returns results", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(({ path, args }) => {
      if (path === "math.add") {
        const { a, b } = args as { a: number; b: number };
        return a + b;
      }
      return null;
    });

    const result = await Effect.runPromise(
      executor.execute(
        "async () => { const sum = await tools.math.add({ a: 3, b: 4 }); return sum; }",
        invoker,
      ),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toBe(7);
  });

  it("surfaces infra defects through the worker bridge as an opaque generic", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = failingInvoker("not authorized");

    const result = await Effect.runPromise(
      executor.execute("async () => { return await tools.secret.read({}); }", invoker),
    );

    expect(result.error).toBe("Internal tool error");
  });

  it("surfaces a syntax error with the parser's descriptive message, not an opaque generic", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    // A genuine parse error: `const` with no binding name. Before the fix
    // this threw in stripTypeScript, became a DynamicWorkerExecutionError
    // on the failure channel, and the host collapsed it to the opaque
    // "Internal tool error". The model needs the real reason to self-correct.
    const result = await Effect.runPromise(
      executor.execute("async () => { const = 5; return 1; }", invoker),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBeDefined();
    expect(result.error).not.toBe("Internal tool error");
    expect(result.error).not.toContain("Internal tool error");
    expect(result.error?.toLowerCase()).toContain("unexpected");
  });

  it("surfaces smart-quote paste errors descriptively", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    // Curly quotes from a copy-paste are the most common real-world cause:
    // the snippet looks fine to a human but is invalid JavaScript.
    const result = await Effect.runPromise(
      executor.execute("async () => { return “hello”; }", invoker),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBeDefined();
    expect(result.error).not.toBe("Internal tool error");
  });

  it("surfaces a non-serializable return value descriptively, not opaquely", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    // Returning a value that can't cross the sandbox boundary (a Symbol, a
    // host object) rejects the evaluate RPC with a DataCloneError. That is
    // the user's own code, not a sandbox defect, so the model needs to be
    // told what it returned can't be serialized rather than getting an
    // opaque "Internal tool error". Production analog: "Could not serialize
    // object of type Cloudflare".
    const result = await Effect.runPromise(executor.execute("async () => Symbol('nope')", invoker));

    expect(result.result).toBeNull();
    expect(result.error).toBeDefined();
    expect(result.error).not.toBe("Internal tool error");
    expect(result.error).not.toContain("Internal tool error");
    expect(result.error?.toLowerCase()).toContain("could not be cloned");
  });

  it("preserves public ExecutionToolError messages across the worker bridge", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = {
      invoke: () =>
        Effect.fail(
          new ExecutionToolError({
            message:
              "tools.search expects an object: { query?: string; namespace?: string; limit?: number; offset?: number }",
          }),
        ),
    } satisfies SandboxToolInvoker;

    const result = await Effect.runPromise(
      executor.execute("async () => await tools.search('github')", invoker),
    );

    expect(result.error).toBe(
      "tools.search expects an object: { query?: string; namespace?: string; limit?: number; offset?: number }",
    );
  });

  it("does not expose host error stack details to sandbox error handlers", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = {
      invoke: () => {
        const error = new Error("not authorized");
        error.stack = "secret host stack";
        return Effect.fail(error);
      },
    } satisfies SandboxToolInvoker;

    const result = await Effect.runPromise(
      executor.execute(
        `async () => {
          try {
            await tools.secret.read({});
          } catch (error) {
            return {
              message: error && error.message,
              stack: error && error.stack,
            };
          }
        }`,
        invoker,
      ),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toMatchObject({ message: "Internal tool error" });
    expect((result.result as { stack?: string }).stack).not.toContain("secret host stack");
    expect((result.result as { message?: string }).message).not.toContain("not authorized");
  });

  it("collapses object-shaped tool defects to an opaque generic", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = {
      invoke: () =>
        Effect.fail({
          code: "forbidden",
          detail: "missing team access",
        }),
    } satisfies SandboxToolInvoker;

    const result = await Effect.runPromise(
      executor.execute("async () => { return await tools.secret.read({}); }", invoker),
    );

    expect(result.error).toBe("Internal tool error");
    expect(result.result).toBeNull();
  });

  it("collapses message-bearing object tool defects to an opaque generic", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = {
      invoke: () =>
        Effect.fail({
          code: "invalid_query",
          message: 'Field with name "DisplayName" does not exist',
        }),
    } satisfies SandboxToolInvoker;

    const result = await Effect.runPromise(
      executor.execute("async () => { return await tools.records.query({}); }", invoker),
    );

    expect(result.error).toBe("Internal tool error");
    expect(result.error).not.toContain("DisplayName");
    expect(result.result).toBeNull();
  });

  it("handles multiple tool calls in sequence", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(({ path }) => {
      if (path === "data.first") return 10;
      if (path === "data.second") return 20;
      return 0;
    });

    const result = await Effect.runPromise(
      executor.execute(
        `async () => {
          const a = await tools.data.first({});
          const b = await tools.data.second({});
          return a + b;
        }`,
        invoker,
      ),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toBe(30);
  });

  it("suspends the execution deadline while a tool dispatch is in flight", async () => {
    const timeoutMs = 200;
    const executor = makeDynamicWorkerExecutor({
      loader,
      timeoutMs,
      hostTimeoutGraceMs: 5_000,
    });
    const invoker: SandboxToolInvoker = {
      invoke: () => Effect.sleep(timeoutMs * 3).pipe(Effect.as("slow result")),
    };

    const result = await Effect.runPromise(
      executor.execute("async () => await tools.slow.wait({})", invoker),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toBe("slow result");
  });

  it("still times out continuous autonomous compute", async () => {
    const timeoutMs = 200;
    const executor = makeDynamicWorkerExecutor({
      loader,
      timeoutMs,
      hostTimeoutGraceMs: 5_000,
    });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute("async () => await new Promise(() => {})", invoker),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBe(`Execution timed out after ${timeoutMs}ms`);
  });

  it("resets the execution deadline after a tool dispatch returns", async () => {
    const timeoutMs = 200;
    const executor = makeDynamicWorkerExecutor({
      loader,
      timeoutMs,
      hostTimeoutGraceMs: 5_000,
    });
    const invoker: SandboxToolInvoker = {
      invoke: () => Effect.sleep(timeoutMs * 3).pipe(Effect.as("done")),
    };

    const result = await Effect.runPromise(
      executor.execute(
        "async () => { await tools.slow.wait({}); await new Promise(() => {}); }",
        invoker,
      ),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBe(`Execution timed out after ${timeoutMs}ms`);
  });

  it("returns an execution error for circular tool args", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute(
        `async () => {
          const payload = {};
          payload.self = payload;
          return await tools.cycles.send(payload);
        }`,
        invoker,
      ),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBe("Tool RPC payload contains a circular reference");
  });

  it("returns an opaque generic when a tool result can't be serialized", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const cyclic: Record<string, unknown> = {};
    cyclic.self = cyclic;
    const invoker = makeInvoker(() => cyclic);

    const result = await Effect.runPromise(
      executor.execute("async () => await tools.cycles.read({})", invoker),
    );

    expect(result.result).toBeNull();
    expect(result.error).toBe("Internal tool error");
  });

  it("returns shared object references from tool results", async () => {
    const executor = makeDynamicWorkerExecutor({ loader });
    const shared = { _tag: "None" };
    const invoker = makeInvoker(() => ({ first: shared, second: shared }));

    const result = await Effect.runPromise(
      executor.execute("async () => await tools.shared.read({})", invoker),
    );

    expect(result.error).toBeUndefined();
    expect(result.result).toEqual({ first: { _tag: "None" }, second: { _tag: "None" } });
  });

  it("respects timeout", async () => {
    const executor = makeDynamicWorkerExecutor({ loader, timeoutMs: 500 });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute("async () => { await new Promise(r => setTimeout(r, 5000)); }", invoker),
    );

    expect(result.error).toContain("timed out");
  });

  it("blocks fetch when globalOutbound is null", async () => {
    const executor = makeDynamicWorkerExecutor({ loader, globalOutbound: null });
    const invoker = makeInvoker(() => null);

    const result = await Effect.runPromise(
      executor.execute('async () => { await fetch("https://example.com"); }', invoker),
    );

    expect(result.error).toBeDefined();
  });

  // Multipart/form-data uploads (OpenAI Files API, any spec with a
  // `multipart/form-data` body) need Blob/File/Uint8Array values to
  // survive the sandbox→host RPC hop intact. JSON.stringify turns a Blob
  // into "{}" and a Uint8Array into a numeric-keyed object, so
  // `coerceFormDataRecord` produces a malformed multipart part and the
  // upstream server 400s.
  it.effect("preserves Uint8Array tool args across the dispatcher boundary", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: { file?: unknown } = {};
      const invoker = makeInvoker(({ args }) => {
        captured = (args ?? {}) as { file?: unknown };
        return null;
      });

      yield* executor.execute(
        `async () => {
          const bytes = new Uint8Array([0xde, 0xad, 0xbe, 0xef]);
          await tools.uploads.send({ file: bytes });
        }`,
        invoker,
      );

      expect(captured.file).toBeInstanceOf(Uint8Array);
      expect(Array.from(captured.file as Uint8Array)).toEqual([0xde, 0xad, 0xbe, 0xef]);
    }),
  );

  it.effect("preserves Blob tool args across the dispatcher boundary", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: { file?: unknown } = {};
      const invoker = makeInvoker(({ args }) => {
        captured = (args ?? {}) as { file?: unknown };
        return null;
      });

      const result = yield* executor.execute(
        `async () => {
          const file = new Blob(["hello multipart"], { type: "text/plain" });
          await tools.uploads.send({ file });
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(captured.file).toBeInstanceOf(Blob);
      const blob = captured.file as Blob;
      expect(blob.type).toBe("text/plain");
      const body = yield* Effect.promise(() => blob.text());
      expect(body).toBe("hello multipart");
    }),
  );

  // Symmetric direction: tool RESULT contains Blob/Uint8Array/File. Workers
  // RPC has the same "Could not serialize Blob" limit on the way back, so
  // tool implementations that return file-like data need the host→sandbox
  // codec too. This pins down which types survive both directions.
  it.effect("returns Uint8Array tool results to the sandbox intact", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => new Uint8Array([0xca, 0xfe, 0xba, 0xbe]));

      const result = yield* executor.execute(
        `async () => {
          const bytes = await tools.download.fetch({});
          if (!(bytes instanceof Uint8Array)) return { kind: typeof bytes, ctor: bytes && bytes.constructor && bytes.constructor.name };
          return { kind: 'Uint8Array', length: bytes.length, bytes: Array.from(bytes) };
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toEqual({
        kind: "Uint8Array",
        length: 4,
        bytes: [0xca, 0xfe, 0xba, 0xbe],
      });
    }),
  );

  it.effect("returns Blob tool results to the sandbox intact", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => new Blob(["DOWNLOAD"], { type: "text/plain" }));

      const result = yield* executor.execute(
        `async () => {
          const blob = await tools.download.fetch({});
          if (!(blob instanceof Blob)) return { kind: typeof blob };
          return { kind: 'Blob', type: blob.type, text: await blob.text() };
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toEqual({ kind: "Blob", type: "text/plain", text: "DOWNLOAD" });
    }),
  );

  it.effect("accumulates helper output separately from returned data", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => ({
        _tag: "ToolFile",
        name: "photo.png",
        mimeType: "image/png",
        encoding: "base64",
        data: "iVBORw0KGgo=",
        byteLength: 8,
      }));

      const result = yield* executor.execute(
        `async () => {
          const attachment = await tools.download.fetch({});
          const values = [
            emit("hello"),
            emit(attachment),
            emit({ type: "text", text: "mcp hello" }),
            emit({ type: "image", data: "Zm9v", mimeType: "image/png" }),
            emit({ type: "audio", data: "SUQz", mimeType: "audio/mpeg" }),
            emit({
              type: "resource",
              resource: { uri: "executor-file:///report.pdf", mimeType: "application/pdf", blob: "JVBERg==" },
            }),
            emit({
              type: "resource_link",
              uri: "executor-file:///remote.pdf",
              name: "remote.pdf",
              mimeType: "application/pdf",
            }),
            emit({ arbitrary: true }),
          ];
          return { values: values.map((value) => value === undefined), keptReturn: true };
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toEqual({
        values: [true, true, true, true, true, true, true, true],
        keptReturn: true,
      });
      expect(result.output).toEqual([
        { type: "content", content: { type: "text", text: "hello" } },
        {
          type: "file",
          file: {
            _tag: "ToolFile",
            name: "photo.png",
            mimeType: "image/png",
            encoding: "base64",
            data: "iVBORw0KGgo=",
            byteLength: 8,
          },
        },
        { type: "content", content: { type: "text", text: "mcp hello" } },
        { type: "content", content: { type: "image", data: "Zm9v", mimeType: "image/png" } },
        { type: "content", content: { type: "audio", data: "SUQz", mimeType: "audio/mpeg" } },
        {
          type: "content",
          content: {
            type: "resource",
            resource: {
              uri: "executor-file:///report.pdf",
              mimeType: "application/pdf",
              blob: "JVBERg==",
            },
          },
        },
        {
          type: "content",
          content: {
            type: "resource_link",
            uri: "executor-file:///remote.pdf",
            name: "remote.pdf",
            mimeType: "application/pdf",
          },
        },
        { type: "content", content: { type: "text", text: '{"arbitrary":true}' } },
      ]);
    }),
  );

  it.effect("preserves File tool args (name + lastModified survive)", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: { upload?: unknown } = {};
      const invoker = makeInvoker(({ args }) => {
        captured = (args ?? {}) as { upload?: unknown };
        return null;
      });

      const result = yield* executor.execute(
        `async () => {
          const upload = new File(["hi"], "report.txt", {
            type: "text/plain",
            lastModified: 1700000000000,
          });
          await tools.uploads.send({ upload });
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(captured.upload).toBeInstanceOf(File);
      const file = captured.upload as File;
      expect(file.name).toBe("report.txt");
      expect(file.type).toBe("text/plain");
      expect(file.lastModified).toBe(1700000000000);
    }),
  );

  // Codec recursion: Blob nested inside an array inside an object inside
  // an array. The structural concern is that `__encodeBinary` walks plain
  // objects + arrays symmetrically. If it stopped at the first level the
  // inner Blob would arrive as `{}`.
  it.effect("preserves Blob args nested deep in arrays and objects", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: unknown;
      const invoker = makeInvoker(({ args }) => {
        captured = args;
        return null;
      });

      yield* executor.execute(
        `async () => {
          const inner = new Blob(["MARKER"], { type: "text/plain" });
          await tools.deep.send({
            payload: { items: [{ blob: inner, name: "first" }, { name: "second" }] },
          });
        }`,
        invoker,
      );

      const root = captured as {
        payload: { items: Array<{ blob?: unknown; name: string }> };
      };
      expect(root.payload.items).toHaveLength(2);
      expect(root.payload.items[0]!.blob).toBeInstanceOf(Blob);
      expect(root.payload.items[0]!.name).toBe("first");
      expect(root.payload.items[1]!.name).toBe("second");
      expect(root.payload.items[1]!.blob).toBeUndefined();
      const blob = root.payload.items[0]!.blob as Blob;
      const body = yield* Effect.promise(() => blob.text());
      expect(body).toBe("MARKER");
    }),
  );

  // Native types that Workers RPC structured-clone supports natively. If
  // any of these stops working it almost certainly means the dispatcher's
  // contract regressed back toward JSON-only.
  it.effect("preserves Date tool args", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: { when?: unknown } = {};
      const invoker = makeInvoker(({ args }) => {
        captured = (args ?? {}) as { when?: unknown };
        return null;
      });

      yield* executor.execute(
        `async () => {
          await tools.events.log({ when: new Date("2026-05-03T12:00:00Z") });
        }`,
        invoker,
      );

      expect(captured.when).toBeInstanceOf(Date);
      expect((captured.when as Date).toISOString()).toBe("2026-05-03T12:00:00.000Z");
    }),
  );

  it.effect("preserves Map and Set tool args", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let captured: { tags?: unknown; index?: unknown } = {};
      const invoker = makeInvoker(({ args }) => {
        captured = (args ?? {}) as { tags?: unknown; index?: unknown };
        return null;
      });

      yield* executor.execute(
        `async () => {
          await tools.search.run({
            tags: new Set(["red", "blue"]),
            index: new Map([["a", 1], ["b", 2]]),
          });
        }`,
        invoker,
      );

      expect(captured.tags).toBeInstanceOf(Set);
      expect([...(captured.tags as Set<string>)].sort()).toEqual(["blue", "red"]);
      expect(captured.index).toBeInstanceOf(Map);
      expect((captured.index as Map<string, number>).get("a")).toBe(1);
      expect((captured.index as Map<string, number>).get("b")).toBe(2);
    }),
  );

  // The `tools` Proxy has guards (`then`, symbol props, empty path) that
  // never had tests. Each one is a foot-gun for sandbox code: if `then`
  // ever stopped returning undefined, awaiting `tools.foo` would hang.
  it.effect("tools proxy returns undefined for `then` (so it isn't thenable)", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => null);

      const result = yield* executor.execute(
        `async () => {
          // If the proxy were thenable, awaiting it would call .then(...)
          // and either hang or invoke a phantom tool. We expect a plain
          // object whose .then is undefined.
          return {
            thenIsUndefined: tools.foo.then === undefined,
            thenableCheck: typeof tools.foo.then,
          };
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toEqual({ thenIsUndefined: true, thenableCheck: "undefined" });
    }),
  );

  it.effect("tools proxy throws when called with no path", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => null);

      const result = yield* executor.execute(
        `async () => {
          try {
            await tools({});
            return "no error";
          } catch (e) {
            return e instanceof Error ? e.message : String(e);
          }
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toBe("Tool path missing in invocation");
    }),
  );

  it.effect("tools proxy supports deep paths (>2 segments)", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      let capturedPath = "";
      const invoker = makeInvoker(({ path }) => {
        capturedPath = path;
        return path;
      });

      const result = yield* executor.execute("async () => tools.a.b.c.d.e({})", invoker);

      expect(result.error).toBeUndefined();
      expect(capturedPath).toBe("a.b.c.d.e");
      expect(result.result).toBe("a.b.c.d.e");
    }),
  );

  it.effect("tools proxy throws a search hint on enumeration", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(() => null);

      const result = yield* executor.execute(
        `async () => {
          const outcomes = {};
          try {
            Object.keys(tools);
            outcomes.keys = "no error";
          } catch (e) {
            outcomes.keys = e instanceof Error ? e.message : String(e);
          }
          try {
            ({ ...tools.github });
            outcomes.spread = "no error";
          } catch (e) {
            outcomes.spread = e instanceof Error ? e.message : String(e);
          }
          return outcomes;
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toEqual({
        keys: 'tools is a lazy proxy and cannot be enumerated. Use tools.search({ query: "..." }) to find tools, tools.search({ namespace: "<integration>", query: "" }) to list every tool in an integration, or tools.executor.coreTools.connections.list({}) to list saved connections.',
        spread:
          'tools.github is a lazy proxy and cannot be enumerated. Use tools.search({ query: "..." }) to find tools, tools.search({ namespace: "<integration>", query: "" }) to list every tool in an integration, or tools.executor.coreTools.connections.list({}) to list saved connections.',
      });
    }),
  );

  it.effect("tools proxy still invokes and chains after the enumeration traps", () =>
    Effect.gen(function* () {
      const executor = makeDynamicWorkerExecutor({ loader });
      const invoker = makeInvoker(({ path }) => path);

      const result = yield* executor.execute(
        `async () => {
          try { Object.keys(tools); } catch {}
          return tools.a.b.c({});
        }`,
        invoker,
      );

      expect(result.error).toBeUndefined();
      expect(result.result).toBe("a.b.c");
    }),
  );
});