diff --git a/src/dev-dashboard/ui/vite-middleware.ts b/src/dev-dashboard/ui/vite-middleware.ts
index d7e45f4cee..08e882d825 100644
--- a/src/dev-dashboard/ui/vite-middleware.ts
+++ b/src/dev-dashboard/ui/vite-middleware.ts
@@ -29,14 +29,14 @@ import { listVault, readNote } from "@app/dev-dashboard/lib/obsidian/reader";
 import { renderSharePage } from "@app/dev-dashboard/lib/obsidian/share-template";
 import { createQaStream, todayLogFile } from "@app/dev-dashboard/lib/qa-sse";
 import { configureRetention, getCachedPulse, getSeries, startPulsePolling } from "@app/dev-dashboard/lib/system/poller";
-import { getAudioLibrary } from "@app/utils/audio/library";
-import { resolveSoundBuffer } from "@app/utils/audio/runner.server";
 import { addTodo, completeTodo, deleteTodo, listTodos } from "@app/dev-dashboard/lib/todos/service";
 import { killTtyd, listTtyd, renameTtyd, spawnTtyd } from "@app/dev-dashboard/lib/ttyd/manager";
 import { fetchWeather } from "@app/dev-dashboard/lib/weather/client";
 import logger from "@app/logger";
 import { defaultDbPath } from "@app/question/commands/log";
 import { openReadModel, queryEntries } from "@app/question/lib/read-model";
+import { getAudioLibrary } from "@app/utils/audio/library";
+import { resolveSoundBuffer } from "@app/utils/audio/runner.server";
 import { SafeJSON } from "@app/utils/json";
 import type { Connect } from "vite";
 
diff --git a/src/question/commands/config.ts b/src/question/commands/config.ts
index 19bafd19a1..c10671ff93 100644
--- a/src/question/commands/config.ts
+++ b/src/question/commands/config.ts
@@ -16,6 +16,7 @@ export function registerConfigCommand(program: Command): void {
         .option("--sound [spec]", "synth:<preset> | bundled:<file> | custom:<path> | off")
         .option("--sound-volume <n>", "0..1", (v) => Number.parseFloat(v))
         .option("--notify <onoff>", "on|off")
+        .option("--obsidian <onoff>", "on|off")
         .option("--obsidian-vault <path>", "set the Obsidian vault override")
         .option("--list-sounds", "list every available sound (bundled + synth) and exit")
         .action(
@@ -23,6 +24,7 @@ export function registerConfigCommand(program: Command): void {
                 sound?: string | boolean;
                 soundVolume?: number;
                 notify?: string;
+                obsidian?: string;
                 obsidianVault?: string;
                 listSounds?: boolean;
             }) => {
@@ -53,10 +55,24 @@ export function registerConfigCommand(program: Command): void {
                     next = saveConfig({ soundVolume: Math.max(0, Math.min(1, o.soundVolume)) });
                 }
 
-                if (o.notify === "on" || o.notify === "off") {
+                if (o.notify !== undefined) {
+                    if (o.notify !== "on" && o.notify !== "off") {
+                        process.stderr.write(`error: --notify expects on|off, got '${o.notify}'\n`);
+                        process.exit(1);
+                    }
+
                     next = saveConfig({ sinks: { ...next.sinks, notify: o.notify === "on" } });
                 }
 
+                if (o.obsidian !== undefined) {
+                    if (o.obsidian !== "on" && o.obsidian !== "off") {
+                        process.stderr.write(`error: --obsidian expects on|off, got '${o.obsidian}'\n`);
+                        process.exit(1);
+                    }
+
+                    next = saveConfig({ sinks: { ...next.sinks, obsidian: o.obsidian === "on" } });
+                }
+
                 if (o.obsidianVault) {
                     setVaultRoot(o.obsidianVault);
                 }
diff --git a/src/question/commands/log.ts b/src/question/commands/log.ts
index b129c94658..d1416e71f2 100644
--- a/src/question/commands/log.ts
+++ b/src/question/commands/log.ts
@@ -2,6 +2,8 @@ import { homedir } from "node:os";
 import { join } from "node:path";
 import { SafeJSON } from "@app/utils/json";
 import type { Command } from "commander";
+import pc from "picocolors";
+import { formatQaEntry } from "../lib/format";
 import { openReadModel, type QueryOpts, queryEntries } from "../lib/read-model";
 
 export function defaultDbPath(): string {
@@ -13,17 +15,10 @@ export function renderDigest(opts: QueryOpts & { dbPath: string }): string {
     try {
         const rows = queryEntries(db, opts);
         if (rows.length === 0) {
-            return "No questions recorded.";
+            return pc.dim("No questions recorded.");
         }
 
-        return rows
-            .map((r) => {
-                const when = new Date(r.ts).toISOString().slice(0, 16).replace("T", " ");
-                const head = `${when}  ${r.project} · ${r.branch ?? "-"}  [${r.tag}]`;
-                const preview = r.answerMd.split("\n").slice(0, 3).join("\n");
-                return `${head}\n❯ ${r.question}\n${preview}\n`;
-            })
-            .join("\n");
+        return rows.map(formatQaEntry).join("\n");
     } finally {
         db.close();
     }
diff --git a/src/question/commands/tail.ts b/src/question/commands/tail.ts
index 60bfb80b97..869e8f57d4 100644
--- a/src/question/commands/tail.ts
+++ b/src/question/commands/tail.ts
@@ -1,19 +1,33 @@
 import { FileTailer } from "@app/utils/fs/file-tailer";
 import type { Command } from "commander";
+import pc from "picocolors";
+import { formatQaEntry } from "../lib/format";
 import { logFilePathFor } from "../lib/log-store";
+import { openReadModel, queryEntries } from "../lib/read-model";
 import type { QaEntry } from "../lib/types";
+import { defaultDbPath } from "./log";
+
+function watchToday(opts: { lines?: number }): void {
+    const backlog = opts.lines ?? 10;
+
+    // Backlog: last N entries oldest→newest (chronological, like `tail -f`),
+    // rendered identically to `tools question log` via the shared formatter.
+    if (backlog > 0) {
+        const db = openReadModel(defaultDbPath());
+        try {
+            const rows = queryEntries(db, { limit: backlog });
+            if (rows.length > 0) {
+                process.stdout.write(`${[...rows].reverse().map(formatQaEntry).join("\n")}\n`);
+            }
+        } finally {
+            db.close();
+        }
+    }
 
-function watchToday(): void {
     const file = logFilePathFor({ ts: Date.now() });
-    process.stdout.write(`tailing ${file} (Ctrl-C to stop)\n`);
+    process.stdout.write(pc.dim(`\n— live: tailing ${file} (Ctrl-C to stop) —\n`));
     const t = new FileTailer<QaEntry>(file, {
-        onLine: (e) => {
-            const when = new Date(e.ts).toISOString().slice(11, 16);
-            const preview = e.answerMd.split("\n").slice(0, 3).join("\n");
-            process.stdout.write(
-                `\n${when} ${e.project} · ${e.branch ?? "-"} [${e.tag}]\n❯ ${e.question}\n${preview}\n`
-            );
-        },
+        onLine: (e) => process.stdout.write(`\n${formatQaEntry(e)}`),
     });
     t.start();
     process.on("SIGINT", () => {
@@ -23,5 +37,10 @@ function watchToday(): void {
 }
 
 export function registerTailCommand(program: Command): void {
-    program.command("tail").alias("answers").description("Live feed of Q→A as they are recorded").action(watchToday);
+    program
+        .command("tail")
+        .alias("answers")
+        .description("Live feed of Q→A as they are recorded (with last-N backlog)")
+        .option("-n, --lines <n>", "show the last N entries before tailing (0 = none)", (v) => Number.parseInt(v, 10))
+        .action((o: { lines?: number }) => watchToday(o));
 }
diff --git a/src/question/lib/format.ts b/src/question/lib/format.ts
new file mode 100644
index 0000000000..8d705c0995
--- /dev/null
+++ b/src/question/lib/format.ts
@@ -0,0 +1,28 @@
+import pc from "picocolors";
+import type { QaEntry } from "./types";
+
+// picocolors (the codebase convention over chalk) auto-detects stdout: full
+// color on a TTY, no-ops when piped/redirected — colorful in a terminal,
+// clean ANSI-free for `| tools json`.
+const TAG_TINT: Record<string, (s: string) => string> = {
+    question: (s) => pc.bold(pc.blue(s)),
+    action: (s) => pc.bold(pc.yellow(s)),
+    directive: (s) => pc.bold(pc.green(s)),
+};
+
+type FormattableEntry = Pick<QaEntry, "ts" | "project" | "branch" | "tag" | "question" | "answerMd" | "sessionId">;
+
+/**
+ * Single source of truth for one Q→A entry's terminal rendering. Used by both
+ * `tools question log` (newest-first digest) and `tools question tail` (live
+ * feed) so they are visually identical per entry.
+ */
+export function formatQaEntry(e: FormattableEntry): string {
+    const when = new Date(e.ts).toISOString().slice(0, 16).replace("T", " ");
+    const tint = TAG_TINT[e.tag] ?? ((s: string) => pc.bold(pc.gray(s)));
+    const head = `${pc.dim(when)}  ${pc.bold(pc.cyan(e.project))} ${pc.dim("·")} ${pc.magenta(e.branch ?? "-")}  ${tint(`[${e.tag}]`)}`;
+    const preview = pc.yellow(e.answerMd.split("\n").slice(0, 3).join("\n"));
+    const sid = e.sessionId && e.sessionId !== "unknown" ? e.sessionId.slice(0, 8) : null;
+    const resume = sid ? pc.dim(`  ↩ ${sid} · tools claude resume ${sid}\n`) : "";
+    return `${head}\n${pc.green("❯")} ${pc.bold(e.question)}\n${preview}\n${resume}`;
+}
diff --git a/src/question/lib/sinks/notification.ts b/src/question/lib/sinks/notification.ts
index 5edc601935..6e480c87bc 100644
--- a/src/question/lib/sinks/notification.ts
+++ b/src/question/lib/sinks/notification.ts
@@ -4,13 +4,18 @@ import { registerSink, type Sink } from "./registry-exports";
 
 export function formatNotification(e: QaEntry): { title: string; message: string } {
     return {
-        title: `${e.project} · ${e.tag}`,
+        // Same header shape as `tools question log`/`tail`: project · branch [tag].
+        title: `${e.project} · ${e.branch ?? "-"} [${e.tag}]`,
         message: `❯ ${e.question}\n\n${e.answerMd}`,
     };
 }
 
 export const notificationSink: Sink = {
     name: "notification",
+    // Telegram = cold `await import(@app/telegram-bot)` + HTTP; the 2s default
+    // fan-out budget gets truncated by the CLI's process.exit(0) before the
+    // send completes (system banner is fast, telegram isn't). Give it room.
+    timeoutMs: 9000,
     isEnabled: (c) => c.sinks.notify,
     emit: async (entry) => {
         const { title, message } = formatNotification(entry);
diff --git a/src/question/lib/sinks/registry.ts b/src/question/lib/sinks/registry.ts
index dbcc4098a2..5135cc6876 100644
--- a/src/question/lib/sinks/registry.ts
+++ b/src/question/lib/sinks/registry.ts
@@ -38,7 +38,7 @@ export async function runFanOut(
     });
     return Promise.all(
         enabled.map(async (s): Promise<SinkResult> => {
-            const t = timeout(timeoutMs);
+            const t = timeout(s.timeoutMs ?? timeoutMs);
             try {
                 await Promise.race([Promise.resolve(s.emit(entry, config)), t.promise]);
                 return { name: s.name, ok: true };
diff --git a/src/question/lib/sinks/types.ts b/src/question/lib/sinks/types.ts
index 00b27eed66..120198f698 100644
--- a/src/question/lib/sinks/types.ts
+++ b/src/question/lib/sinks/types.ts
@@ -15,6 +15,10 @@ export interface Sink {
     name: string;
     isEnabled(config: QuestionConfig): boolean;
     emit(entry: QaEntry, config: QuestionConfig): Promise<void> | void;
+    /** Optional per-sink fan-out budget (ms). Network sinks (Telegram does a
+     *  cold dynamic import + HTTP) need more than the 2s default or they get
+     *  cut off by process.exit(0) before delivery. */
+    timeoutMs?: number;
 }
 
 // SinkResult is defined once, canonically, in ../types (Task 2 — RecordResult.sinks uses it).
diff --git a/src/utils/agent-runtime.ts b/src/utils/agent-runtime.ts
index 7427148de6..a5968c5cbe 100644
--- a/src/utils/agent-runtime.ts
+++ b/src/utils/agent-runtime.ts
@@ -53,8 +53,7 @@ export function getAgentRuntimeContext(
         project: detectCurrentProject() ?? basename(repoRoot),
         repoRoot,
         cwd,
-        isWorktree:
-            gitDir != null && gitCommonDir != null && resolve(cwd, gitDir) !== resolve(cwd, gitCommonDir),
+        isWorktree: gitDir != null && gitCommonDir != null && resolve(cwd, gitDir) !== resolve(cwd, gitCommonDir),
         worktreePath: null,
         branch: gitSync(["rev-parse", "--abbrev-ref", "HEAD"], cwd),
         commitSha: gitSync(["rev-parse", "--short", "HEAD"], cwd),
diff --git a/src/utils/audio/library.ts b/src/utils/audio/library.ts
index 1b93561d9a..18bdcf8b5d 100644
--- a/src/utils/audio/library.ts
+++ b/src/utils/audio/library.ts
@@ -1,5 +1,5 @@
 import { existsSync } from "node:fs";
-import { type BundledSound, BUNDLED_SOUNDS } from "./assets/manifest";
+import { BUNDLED_SOUNDS, type BundledSound } from "./assets/manifest";
 import { DING_PRESETS } from "./ding-presets";
 import type { SoundChoice } from "./runner.server";
 
@@ -57,9 +57,7 @@ export function getAudioLibrary(): AudioLibrary {
     return { bundled, synth, default: def };
 }
 
-export type ParseSoundResult =
-    | { ok: true; sound?: SoundChoice; enabled: boolean }
-    | { ok: false; error: string };
+export type ParseSoundResult = { ok: true; sound?: SoundChoice; enabled: boolean } | { ok: false; error: string };
 
 /**
  * Parse a `--sound` / dashboard spec into a validated `SoundChoice`.
@@ -112,9 +110,7 @@ export function parseSoundSpec(spec: string): ParseSoundResult {
 /** Human-readable list of every available sound (for `--list-sounds` / errors). */
 export function formatAudioLibrary(): string {
     const lib = getAudioLibrary();
-    const bundled = lib.bundled
-        .map((e) => `  ${e.id}${e.isDefault ? "  (default)" : ""}  — ${e.label}`)
-        .join("\n");
+    const bundled = lib.bundled.map((e) => `  ${e.id}${e.isDefault ? "  (default)" : ""}  — ${e.label}`).join("\n");
     const synth = lib.synth.map((e) => `  ${e.id}  — ${e.label}`).join("\n");
     return `Available sounds:\n\nBundled (Kenney CC0):\n${bundled}\n\nSynth presets:\n${synth}\n\nAlso valid:  custom:/abs/path.wav  |  off`;
 }