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packages/server/tests/local/chat-persistence.test.ts

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+/**
+ * Chat Persistence — I/O Tests
+ *
+ * Covers:
+ *   chat-persistence.ts: persistMessage, loadSessionMessages
+ *
+ * Uses real temp directories to exercise file system behavior.
+ */
+
+import { describe, it, expect, afterEach } from 'vitest';
+import fs from 'node:fs';
+import os from 'node:os';
+import path from 'node:path';
+import {
+  persistMessage,
+  loadSessionMessages,
+  stripTrailingFailedPair,
+} from '../../src/local/routes/chat-persistence.js';
+import { GENERATION_FAILED_PREFIX } from '@waggle/shared';
+
+// ─── Helpers ────────────────────────────────────────────────────────
+
+let tempDirs: string[] = [];
+
+function makeTempDir(): string {
+  const dir = fs.mkdtempSync(path.join(os.tmpdir(), 'waggle-persist-'));
+  tempDirs.push(dir);
+  return dir;
+}
+
+afterEach(() => {
+  for (const dir of tempDirs) {
+    try {
+      fs.rmSync(dir, { recursive: true, force: true });
+    } catch {
+      // best-effort cleanup
+    }
+  }
+  tempDirs = [];
+});
+
+// ─── persistMessage ─────────────────────────────────────────────────
+
+describe('persistMessage', () => {
+  it('creates sessions directory and .jsonl file when they do not exist', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'hello' });
+
+    const filePath = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-1.jsonl');
+    expect(fs.existsSync(filePath)).toBe(true);
+  });
+
+  it('writes a meta line as the first line of a new session file', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'hi' });
+
+    const filePath = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-1.jsonl');
+    const lines = fs.readFileSync(filePath, 'utf-8').trim().split('\n');
+
+    const meta = JSON.parse(lines[0]);
+    expect(meta.type).toBe('meta');
+    expect(meta).toHaveProperty('created');
+    expect(meta.title).toBeNull();
+  });
+
+  it('appends the message as a JSON line after the meta line', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'test message' });
+
+    const filePath = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-1.jsonl');
+    const lines = fs.readFileSync(filePath, 'utf-8').trim().split('\n');
+
+    expect(lines).toHaveLength(2);
+    const msg = JSON.parse(lines[1]);
+    expect(msg.role).toBe('user');
+    expect(msg.content).toBe('test message');
+    expect(msg).toHaveProperty('timestamp');
+  });
+
+  it('appends multiple messages to the same session file', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'first' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'assistant', content: 'second' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'third' });
+
+    const filePath = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-1.jsonl');
+    const lines = fs.readFileSync(filePath, 'utf-8').trim().split('\n');
+
+    // 1 meta + 3 messages
+    expect(lines).toHaveLength(4);
+  });
+
+  it('creates separate files for different session IDs', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-a', { role: 'user', content: 'a' });
+    persistMessage(dataDir, 'ws-1', 'sess-b', { role: 'user', content: 'b' });
+
+    const fileA = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-a.jsonl');
+    const fileB = path.join(dataDir, 'workspaces', 'ws-1', 'sessions', 'sess-b.jsonl');
+    expect(fs.existsSync(fileA)).toBe(true);
+    expect(fs.existsSync(fileB)).toBe(true);
+  });
+});
+
+// ─── loadSessionMessages ────────────────────────────────────────────
+
+describe('loadSessionMessages', () => {
+  it('returns an empty array when the session file does not exist', () => {
+    const dataDir = makeTempDir();
+    const result = loadSessionMessages(dataDir, 'ws-1', 'nonexistent');
+    expect(result).toEqual([]);
+  });
+
+  it('returns an empty array for an empty file', () => {
+    const dataDir = makeTempDir();
+    const sessDir = path.join(dataDir, 'workspaces', 'ws-1', 'sessions');
+    fs.mkdirSync(sessDir, { recursive: true });
+    fs.writeFileSync(path.join(sessDir, 'sess-1.jsonl'), '', 'utf-8');
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(result).toEqual([]);
+  });
+
+  it('skips meta lines and returns only chat messages', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'hello' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'assistant', content: 'hi there' });
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(result).toEqual([
+      { role: 'user', content: 'hello' },
+      { role: 'assistant', content: 'hi there' },
+    ]);
+  });
+
+  it('strips timestamp from returned messages (only role + content)', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'test' });
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(result).toHaveLength(1);
+    expect(Object.keys(result[0])).toEqual(['role', 'content']);
+  });
+
+  it('skips malformed JSON lines without throwing', () => {
+    const dataDir = makeTempDir();
+    const sessDir = path.join(dataDir, 'workspaces', 'ws-1', 'sessions');
+    fs.mkdirSync(sessDir, { recursive: true });
+
+    const lines = [
+      JSON.stringify({ type: 'meta', title: null, created: new Date().toISOString() }),
+      '{ INVALID JSON',
+      JSON.stringify({ role: 'user', content: 'valid message', timestamp: new Date().toISOString() }),
+      'not json at all',
+      JSON.stringify({ role: 'assistant', content: 'another valid', timestamp: new Date().toISOString() }),
+    ];
+    fs.writeFileSync(path.join(sessDir, 'sess-1.jsonl'), lines.join('\n') + '\n', 'utf-8');
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(result).toEqual([
+      { role: 'user', content: 'valid message' },
+      { role: 'assistant', content: 'another valid' },
+    ]);
+  });
+
+  it('skips lines that are valid JSON but lack role or content fields', () => {
+    const dataDir = makeTempDir();
+    const sessDir = path.join(dataDir, 'workspaces', 'ws-1', 'sessions');
+    fs.mkdirSync(sessDir, { recursive: true });
+
+    const lines = [
+      JSON.stringify({ type: 'meta', title: null, created: new Date().toISOString() }),
+      JSON.stringify({ role: 'user' }), // missing content
+      JSON.stringify({ content: 'orphan' }), // missing role
+      JSON.stringify({ role: 'user', content: 'complete', timestamp: new Date().toISOString() }),
+    ];
+    fs.writeFileSync(path.join(sessDir, 'sess-1.jsonl'), lines.join('\n') + '\n', 'utf-8');
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    // The line missing role is skipped because parsed.role is falsy
+    // The line missing content: content is undefined, and the check is `parsed.content !== undefined`
+    // so { role: 'user' } has content === undefined → skipped
+    expect(result).toEqual([
+      { role: 'user', content: 'complete' },
+    ]);
+  });
+
+  it('skips blank lines in the file', () => {
+    const dataDir = makeTempDir();
+    const sessDir = path.join(dataDir, 'workspaces', 'ws-1', 'sessions');
+    fs.mkdirSync(sessDir, { recursive: true });
+
+    const content = [
+      JSON.stringify({ type: 'meta', title: null, created: new Date().toISOString() }),
+      '',
+      '   ',
+      JSON.stringify({ role: 'user', content: 'msg', timestamp: new Date().toISOString() }),
+      '',
+    ].join('\n');
+    fs.writeFileSync(path.join(sessDir, 'sess-1.jsonl'), content, 'utf-8');
+
+    const result = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(result).toEqual([{ role: 'user', content: 'msg' }]);
+  });
+
+  // ── Round-trip ────────────────────────────────────────────────────
+
+  it('round-trips: persist then load returns the same messages in order', () => {
+    const dataDir = makeTempDir();
+    const messages = [
+      { role: 'user', content: 'What is 2+2?' },
+      { role: 'assistant', content: 'The answer is 4.' },
+      { role: 'user', content: 'Thanks!' },
+      { role: 'assistant', content: 'You are welcome.' },
+    ];
+
+    for (const msg of messages) {
+      persistMessage(dataDir, 'ws-1', 'sess-1', msg);
+    }
+
+    const loaded = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(loaded).toEqual(messages);
+  });
+
+  it('handles messages with empty string content', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: '' });
+
+    const loaded = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    // content '' is !== undefined → should be included
+    expect(loaded).toEqual([{ role: 'user', content: '' }]);
+  });
+
+  it('handles messages with special characters and newlines in content', () => {
+    const dataDir = makeTempDir();
+    const content = 'line1\nline2\ttab "quotes" {braces}';
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content });
+
+    const loaded = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(loaded).toEqual([{ role: 'user', content }]);
+  });
+});
+
+// ─── stripTrailingFailedPair ────────────────────────────────────────
+
+describe('stripTrailingFailedPair', () => {
+  it('strips a trailing failed user+assistant pair', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'ok turn' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'assistant', content: 'sure' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'reproduce this' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'assistant', content: `${GENERATION_FAILED_PREFIX}boom` });
+
+    const stripped = stripTrailingFailedPair(dataDir, 'ws-1', 'sess-1');
+    expect(stripped).toBe(true);
+
+    // Only the failed pair is dropped; the earlier successful pair survives.
+    const loaded = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(loaded).toEqual([
+      { role: 'user', content: 'ok turn' },
+      { role: 'assistant', content: 'sure' },
+    ]);
+  });
+
+  it('is a no-op on a normal (non-failed) tail', () => {
+    const dataDir = makeTempDir();
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'user', content: 'hi' });
+    persistMessage(dataDir, 'ws-1', 'sess-1', { role: 'assistant', content: 'hello' });
+
+    const stripped = stripTrailingFailedPair(dataDir, 'ws-1', 'sess-1');
+    expect(stripped).toBe(false);
+
+    const loaded = loadSessionMessages(dataDir, 'ws-1', 'sess-1');
+    expect(loaded).toEqual([
+      { role: 'user', content: 'hi' },
+      { role: 'assistant', content: 'hello' },
+    ]);
+  });
+
+  it('returns false when the session file does not exist', () => {
+    const dataDir = makeTempDir();
+    expect(stripTrailingFailedPair(dataDir, 'ws-1', 'missing')).toBe(false);
+  });
+});