diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2ace486db..2383eb8cd 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 ### Security
 - Hardened the relay IPC socket: now lives under `~/.warelay/ipc`, enforces 0700 dir / 0600 socket perms, rejects symlink or foreign-owned paths, and includes unit tests to lock in the behavior.
 - `warelay logout` now also prunes the shared session store (`~/.warelay/sessions.json`) alongside WhatsApp Web credentials, reducing leftover state after unlinking.
+- Logging now rolls daily to `/tmp/warelay/warelay-YYYY-MM-DD.log` (or custom dir) and prunes files older than 24h to reduce data retention.
 
 ## 1.3.0 — 2025-12-02
 
diff --git a/README.md b/README.md
index 70cd06569..6524c35ea 100644
--- a/README.md
+++ b/README.md
@@ -137,6 +137,16 @@ warelay supports running on the same phone number you message from—you chat wi
 }
 ```
 
+#### Abort trigger words
+- If an inbound body is exactly `stop`, `esc`, `abort`, `wait`, or `exit`, the command/agent run is skipped and the user immediately gets `Agent was aborted.`.
+- The session is tagged so the *next* prompt sent to the agent is prefixed with a short reminder that the previous run was aborted; the hint clears after that turn.
+
+#### Agent choices
+- `inbound.reply.agent.kind` can be `claude`, `opencode`, `pi`, `codex`, or `gemini`.
+- Gemini CLI supports `--output-format text|json|stream-json`; warelay auto-adds it when you set `agent.format`.
+- Session defaults: Claude uses `--session-id/--resume`, Codex/Opencode/Pi use `--session`, and Gemini defaults to `--resume` for session resumes (new sessions need no flag). Override via `sessionArgNew/sessionArgResume` if you prefer custom flags.
+- Reliability note: only Claude reliably returns a `session_id` that warelay can persist and reuse. Other harnesses currently don’t emit a stable session identifier, so multi-turn continuity may reset between runs for those agents (Pi does not auto-compact, but still doesn’t expose a session id).
+
 #### Heartbeat pings (command mode)
 - When `heartbeatMinutes` is set (default 10 for `mode: "command"`), the relay periodically runs your command/Claude session with a heartbeat prompt.
 - Heartbeat body is `HEARTBEAT ultrathink` (so the model can recognize the probe); if Claude replies exactly `HEARTBEAT_OK`, the message is suppressed; otherwise the reply (or media) is forwarded. Suppressions are still logged so you know the heartbeat ran.
@@ -145,7 +155,7 @@ warelay supports running on the same phone number you message from—you chat wi
 - When multiple active sessions exist, `warelay heartbeat` requires `--to <E.164>` or `--all`; if `allowFrom` is just `"*"`, you must choose a target with one of those flags.
 
 ### Logging (optional)
-- File logs are written to `/tmp/warelay/warelay.log` by default. Levels: `silent | fatal | error | warn | info | debug | trace` (CLI `--verbose` forces `debug`). Web-provider inbound/outbound entries include message bodies and auto-reply text for easier auditing.
+- File logs are written to `/tmp/warelay/warelay-YYYY-MM-DD.log` by default (rotated daily; files older than 24h are pruned). Levels: `silent | fatal | error | warn | info | debug | trace` (CLI `--verbose` forces `debug`). Web-provider inbound/outbound entries include message bodies and auto-reply text for easier auditing.
 - Override in `~/.warelay/warelay.json`:
 
 ```json5
@@ -208,7 +218,7 @@ Templating tokens: `{{Body}}`, `{{BodyStripped}}`, `{{From}}`, `{{To}}`, `{{Mess
 
 ## FAQ & Safety
 - Twilio errors: **63016 “permission to send an SMS has not been enabled”** → ensure your number is WhatsApp-enabled; **63007 template not approved** → send a free-form session message within 24h or use an approved template; **63112 policy violation** → adjust content, shorten to <1600 chars, avoid links that trigger spam filters. Re-run `pnpm warelay status` to see the exact Twilio response body.
-- Does this store my messages? warelay only writes `~/.warelay/warelay.json` (config), `~/.warelay/credentials/` (WhatsApp Web auth), and `~/.warelay/sessions.json` (session IDs + timestamps). It does **not** persist message bodies beyond the session store. Logs stream to stdout/stderr and also `/tmp/warelay/warelay.log` (configurable via `logging.file`).
+- Does this store my messages? warelay only writes `~/.warelay/warelay.json` (config), `~/.warelay/credentials/` (WhatsApp Web auth), and `~/.warelay/sessions.json` (session IDs + timestamps). It does **not** persist message bodies beyond the session store. Logs stream to stdout/stderr and also `/tmp/warelay/warelay-YYYY-MM-DD.log` (configurable via `logging.file`).
 - Personal WhatsApp safety: Automation on personal accounts can be rate-limited or logged out by WhatsApp. Use `--provider web` sparingly, keep messages human-like, and re-run `login` if the session is dropped.
 - Limits to remember: WhatsApp text limit ~1600 chars; avoid rapid bursts—space sends by a few seconds; keep webhook replies under a couple seconds for good UX; command auto-replies time out after 600s by default.
 - Deploy / keep running: Use `tmux` or `screen` for ad-hoc (`tmux new -s warelay -- pnpm warelay relay --provider twilio`). For long-running hosts, wrap `pnpm warelay relay ...` or `pnpm warelay webhook --ingress tailscale ...` in a systemd service or macOS LaunchAgent; ensure environment variables are loaded in that context.
diff --git a/src/logger.test.ts b/src/logger.test.ts
index 1e7d6aa63..709fcca35 100644
--- a/src/logger.test.ts
+++ b/src/logger.test.ts
@@ -7,7 +7,11 @@ import { afterEach, describe, expect, it, vi } from "vitest";
 
 import { setVerbose } from "./globals.js";
 import { logDebug, logError, logInfo, logSuccess, logWarn } from "./logger.js";
-import { resetLogger, setLoggerOverride } from "./logging.js";
+import {
+  DEFAULT_LOG_DIR,
+  resetLogger,
+  setLoggerOverride,
+} from "./logging.js";
 import type { RuntimeEnv } from "./runtime.js";
 
 describe("logger helpers", () => {
@@ -67,6 +71,28 @@ describe("logger helpers", () => {
     expect(content).toContain("warn-only");
     cleanup(logPath);
   });
+
+  it("uses daily rolling default log file and prunes old ones", () => {
+    resetLogger();
+    setLoggerOverride({}); // force defaults regardless of user config
+    const today = new Date().toISOString().slice(0, 10);
+    const todayPath = path.join(DEFAULT_LOG_DIR, `warelay-${today}.log`);
+
+    // create an old file to be pruned
+    const oldPath = path.join(DEFAULT_LOG_DIR, "warelay-2000-01-01.log");
+    fs.mkdirSync(DEFAULT_LOG_DIR, { recursive: true });
+    fs.writeFileSync(oldPath, "old");
+    fs.utimesSync(oldPath, new Date(0), new Date(0));
+    cleanup(todayPath);
+
+    logInfo("roll-me");
+
+    expect(fs.existsSync(todayPath)).toBe(true);
+    expect(fs.readFileSync(todayPath, "utf-8")).toContain("roll-me");
+    expect(fs.existsSync(oldPath)).toBe(false);
+
+    cleanup(todayPath);
+  });
 });
 
 function pathForTest() {
diff --git a/src/logging.ts b/src/logging.ts
index 3e0a6d21b..cabe9b277 100644
--- a/src/logging.ts
+++ b/src/logging.ts
@@ -6,8 +6,12 @@ import pino, { type Bindings, type LevelWithSilent, type Logger } from "pino";
 import { loadConfig, type WarelayConfig } from "./config/config.js";
 import { isVerbose } from "./globals.js";
 
-const DEFAULT_LOG_DIR = path.join(os.tmpdir(), "warelay");
-export const DEFAULT_LOG_FILE = path.join(DEFAULT_LOG_DIR, "warelay.log");
+export const DEFAULT_LOG_DIR = path.join(os.tmpdir(), "warelay");
+export const DEFAULT_LOG_FILE = path.join(DEFAULT_LOG_DIR, "warelay.log"); // legacy single-file path
+
+const LOG_PREFIX = "warelay";
+const LOG_SUFFIX = ".log";
+const MAX_LOG_AGE_MS = 24 * 60 * 60 * 1000; // 24h
 
 const ALLOWED_LEVELS: readonly LevelWithSilent[] = [
   "silent",
@@ -46,7 +50,7 @@ function resolveSettings(): ResolvedSettings {
   const cfg: WarelayConfig["logging"] | undefined =
     overrideSettings ?? loadConfig().logging;
   const level = normalizeLevel(cfg?.level);
-  const file = cfg?.file ?? DEFAULT_LOG_FILE;
+  const file = cfg?.file ?? defaultRollingPathForToday();
   return { level, file };
 }
 
@@ -57,6 +61,10 @@ function settingsChanged(a: ResolvedSettings | null, b: ResolvedSettings) {
 
 function buildLogger(settings: ResolvedSettings): Logger {
   fs.mkdirSync(path.dirname(settings.file), { recursive: true });
+  // Clean up stale rolling logs when using a dated log filename.
+  if (isRollingPath(settings.file)) {
+    pruneOldRollingLogs(path.dirname(settings.file));
+  }
   const destination = pino.destination({
     dest: settings.file,
     mkdir: true,
@@ -104,3 +112,39 @@ export function resetLogger() {
   cachedSettings = null;
   overrideSettings = null;
 }
+
+function defaultRollingPathForToday(): string {
+  const today = new Date().toISOString().slice(0, 10); // YYYY-MM-DD
+  return path.join(DEFAULT_LOG_DIR, `${LOG_PREFIX}-${today}${LOG_SUFFIX}`);
+}
+
+function isRollingPath(file: string): boolean {
+  const base = path.basename(file);
+  return (
+    base.startsWith(`${LOG_PREFIX}-`) &&
+    base.endsWith(LOG_SUFFIX) &&
+    base.length === `${LOG_PREFIX}-YYYY-MM-DD${LOG_SUFFIX}`.length
+  );
+}
+
+function pruneOldRollingLogs(dir: string): void {
+  try {
+    const entries = fs.readdirSync(dir, { withFileTypes: true });
+    const cutoff = Date.now() - MAX_LOG_AGE_MS;
+    for (const entry of entries) {
+      if (!entry.isFile()) continue;
+      if (!entry.name.startsWith(`${LOG_PREFIX}-`) || !entry.name.endsWith(LOG_SUFFIX)) continue;
+      const fullPath = path.join(dir, entry.name);
+      try {
+        const stat = fs.statSync(fullPath);
+        if (stat.mtimeMs < cutoff) {
+          fs.rmSync(fullPath, { force: true });
+        }
+      } catch {
+        // ignore errors during pruning
+      }
+    }
+  } catch {
+    // ignore missing dir or read errors
+  }
+}