Merge pull request #1271 from Whoaa512/feat/session-picker-mvp

feat: session picker MVP - fuzzy search, derived titles, relative time
2026-01-20 16:46:48 +00:00
parent 5c5745dee5 faa5838147
commit 40e928a4c4
16 changed files with 1216 additions and 126 deletions
--- a/src/agents/system-prompt.ts
+++ b/src/agents/system-prompt.ts
@@ -1,6 +1,5 @@
 import type { ReasoningLevel, ThinkLevel } from "../auto-reply/thinking.js";
 import { SILENT_REPLY_TOKEN } from "../auto-reply/tokens.js";
-import { formatCliCommand } from "../cli/command-format.js";
 import { listDeliverableMessageChannels } from "../utils/message-channel.js";
 import type { ResolvedTimeFormat } from "./date-time.js";
 import type { EmbeddedContextFile } from "./pi-embedded-helpers.js";
@@ -86,22 +85,8 @@ function buildMessagingSection(params: {
  messageChannelOptions: string;
  inlineButtonsEnabled: boolean;
  runtimeChannel?: string;
-  channelActions?: string[];
 }) {
  if (params.isMinimal) return [];
-
-  // Build channel-specific action description
-  let actionsDescription: string;
-  if (params.channelActions && params.channelActions.length > 0 && params.runtimeChannel) {
-    // Include "send" as a base action plus channel-specific actions
-    const allActions = new Set(["send", ...params.channelActions]);
-    const actionList = Array.from(allActions).sort().join(", ");
-    actionsDescription = `- Use \`message\` for proactive sends + channel actions. Current channel (${params.runtimeChannel}) supports: ${actionList}.`;
-  } else {
-    actionsDescription =
-      "- Use `message` for proactive sends + channel actions (send, react, edit, delete, etc.).";
-  }
-
  return [
    "## Messaging",
    "- Reply in current session → automatically routes to the source channel (Signal, Telegram, etc.)",
@@ -111,7 +96,7 @@ function buildMessagingSection(params: {
      ? [
          "",
          "### message tool",
-          actionsDescription,
+          "- Use `message` for proactive sends + channel actions (polls, reactions, etc.).",
          "- For `action=send`, include `to` and `message`.",
          `- If multiple channels are configured, pass \`channel\` (${params.messageChannelOptions}).`,
          `- If you use \`message\` (\`action=send\`) to deliver your user-visible reply, respond with ONLY: ${SILENT_REPLY_TOKEN} (avoid duplicate replies).`,
@@ -139,7 +124,7 @@ function buildDocsSection(params: { docsPath?: string; isMinimal: boolean; readT
    "Community: https://discord.com/invite/clawd",
    "Find new skills: https://clawdhub.com",
    "For Clawdbot behavior, commands, config, or architecture: consult local docs first.",
-    `When diagnosing issues, run \`${formatCliCommand("clawdbot status")}\` yourself when possible; only ask the user if you lack access (e.g., sandboxed).`,
+    "When diagnosing issues, run `clawdbot status` yourself when possible; only ask the user if you lack access (e.g., sandboxed).",
    "",
  ];
 }
@@ -170,10 +155,9 @@ export function buildAgentSystemPrompt(params: {
    arch?: string;
    node?: string;
    model?: string;
+    defaultModel?: string;
    channel?: string;
    capabilities?: string[];
-    /** Supported message actions for the current channel (e.g., react, edit, unsend) */
-    channelActions?: string[];
  };
  sandboxInfo?: {
    enabled: boolean;
@@ -381,11 +365,11 @@ export function buildAgentSystemPrompt(params: {
    "## Clawdbot CLI Quick Reference",
    "Clawdbot is controlled via subcommands. Do not invent commands.",
    "To manage the Gateway daemon service (start/stop/restart):",
-    `- ${formatCliCommand("clawdbot daemon status")}`,
-    `- ${formatCliCommand("clawdbot daemon start")}`,
-    `- ${formatCliCommand("clawdbot daemon stop")}`,
-    `- ${formatCliCommand("clawdbot daemon restart")}`,
-    `If unsure, ask the user to run \`${formatCliCommand("clawdbot help")}\` (or \`${formatCliCommand("clawdbot daemon --help")}\`) and paste the output.`,
+    "- clawdbot daemon status",
+    "- clawdbot daemon start",
+    "- clawdbot daemon stop",
+    "- clawdbot daemon restart",
+    "If unsure, ask the user to run `clawdbot help` (or `clawdbot daemon --help`) and paste the output.",
    "",
    ...skillsSection,
    ...memorySection,
@@ -484,7 +468,6 @@ export function buildAgentSystemPrompt(params: {
      messageChannelOptions,
      inlineButtonsEnabled,
      runtimeChannel,
-      channelActions: runtimeInfo?.channelActions,
    }),
  ];

--- a/src/gateway/protocol/schema/sessions.ts
+++ b/src/gateway/protocol/schema/sessions.ts
@@ -3,81 +3,92 @@ import { Type } from "@sinclair/typebox";
 import { NonEmptyString, SessionLabelString } from "./primitives.js";

 export const SessionsListParamsSchema = Type.Object(
-  {
-    limit: Type.Optional(Type.Integer({ minimum: 1 })),
-    activeMinutes: Type.Optional(Type.Integer({ minimum: 1 })),
-    includeGlobal: Type.Optional(Type.Boolean()),
-    includeUnknown: Type.Optional(Type.Boolean()),
-    label: Type.Optional(SessionLabelString),
-    spawnedBy: Type.Optional(NonEmptyString),
-    agentId: Type.Optional(NonEmptyString),
-  },
-  { additionalProperties: false },
+	{
+		limit: Type.Optional(Type.Integer({ minimum: 1 })),
+		activeMinutes: Type.Optional(Type.Integer({ minimum: 1 })),
+		includeGlobal: Type.Optional(Type.Boolean()),
+		includeUnknown: Type.Optional(Type.Boolean()),
+		/**
+		 * Read first 8KB of each session transcript to derive title from first user message.
+		 * Performs a file read per session - use `limit` to bound result set on large stores.
+		 */
+		includeDerivedTitles: Type.Optional(Type.Boolean()),
+		/**
+		 * Read last 16KB of each session transcript to extract most recent message preview.
+		 * Performs a file read per session - use `limit` to bound result set on large stores.
+		 */
+		includeLastMessage: Type.Optional(Type.Boolean()),
+		label: Type.Optional(SessionLabelString),
+		spawnedBy: Type.Optional(NonEmptyString),
+		agentId: Type.Optional(NonEmptyString),
+		search: Type.Optional(Type.String()),
+	},
+	{ additionalProperties: false },
 );

 export const SessionsResolveParamsSchema = Type.Object(
-  {
-    key: Type.Optional(NonEmptyString),
-    label: Type.Optional(SessionLabelString),
-    agentId: Type.Optional(NonEmptyString),
-    spawnedBy: Type.Optional(NonEmptyString),
-    includeGlobal: Type.Optional(Type.Boolean()),
-    includeUnknown: Type.Optional(Type.Boolean()),
-  },
-  { additionalProperties: false },
+	{
+		key: Type.Optional(NonEmptyString),
+		label: Type.Optional(SessionLabelString),
+		agentId: Type.Optional(NonEmptyString),
+		spawnedBy: Type.Optional(NonEmptyString),
+		includeGlobal: Type.Optional(Type.Boolean()),
+		includeUnknown: Type.Optional(Type.Boolean()),
+	},
+	{ additionalProperties: false },
 );

 export const SessionsPatchParamsSchema = Type.Object(
-  {
-    key: NonEmptyString,
-    label: Type.Optional(Type.Union([SessionLabelString, Type.Null()])),
-    thinkingLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    verboseLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    reasoningLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    responseUsage: Type.Optional(
-      Type.Union([
-        Type.Literal("off"),
-        Type.Literal("tokens"),
-        Type.Literal("full"),
-        // Backward compat with older clients/stores.
-        Type.Literal("on"),
-        Type.Null(),
-      ]),
-    ),
-    elevatedLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    execHost: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    execSecurity: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    execAsk: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    execNode: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    model: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    spawnedBy: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
-    sendPolicy: Type.Optional(
-      Type.Union([Type.Literal("allow"), Type.Literal("deny"), Type.Null()]),
-    ),
-    groupActivation: Type.Optional(
-      Type.Union([Type.Literal("mention"), Type.Literal("always"), Type.Null()]),
-    ),
-  },
-  { additionalProperties: false },
+	{
+		key: NonEmptyString,
+		label: Type.Optional(Type.Union([SessionLabelString, Type.Null()])),
+		thinkingLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		verboseLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		reasoningLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		responseUsage: Type.Optional(
+			Type.Union([
+				Type.Literal("off"),
+				Type.Literal("tokens"),
+				Type.Literal("full"),
+				// Backward compat with older clients/stores.
+				Type.Literal("on"),
+				Type.Null(),
+			]),
+		),
+		elevatedLevel: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		execHost: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		execSecurity: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		execAsk: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		execNode: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		model: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		spawnedBy: Type.Optional(Type.Union([NonEmptyString, Type.Null()])),
+		sendPolicy: Type.Optional(
+			Type.Union([Type.Literal("allow"), Type.Literal("deny"), Type.Null()]),
+		),
+		groupActivation: Type.Optional(
+			Type.Union([Type.Literal("mention"), Type.Literal("always"), Type.Null()]),
+		),
+	},
+	{ additionalProperties: false },
 );

 export const SessionsResetParamsSchema = Type.Object(
-  { key: NonEmptyString },
-  { additionalProperties: false },
+	{ key: NonEmptyString },
+	{ additionalProperties: false },
 );

 export const SessionsDeleteParamsSchema = Type.Object(
-  {
-    key: NonEmptyString,
-    deleteTranscript: Type.Optional(Type.Boolean()),
-  },
-  { additionalProperties: false },
+	{
+		key: NonEmptyString,
+		deleteTranscript: Type.Optional(Type.Boolean()),
+	},
+	{ additionalProperties: false },
 );

 export const SessionsCompactParamsSchema = Type.Object(
-  {
-    key: NonEmptyString,
-    maxLines: Type.Optional(Type.Integer({ minimum: 1 })),
-  },
-  { additionalProperties: false },
+	{
+		key: NonEmptyString,
+		maxLines: Type.Optional(Type.Integer({ minimum: 1 })),
+	},
+	{ additionalProperties: false },
 );
--- a/src/gateway/session-utils.fs.test.ts
+++ b/src/gateway/session-utils.fs.test.ts
@@ -0,0 +1,343 @@
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+import { afterEach, beforeEach, describe, expect, test } from "vitest";
+import {
+  readFirstUserMessageFromTranscript,
+  readLastMessagePreviewFromTranscript,
+} from "./session-utils.fs.js";
+
+describe("readFirstUserMessageFromTranscript", () => {
+  let tmpDir: string;
+  let storePath: string;
+
+  beforeEach(() => {
+    tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), "clawdbot-session-fs-test-"));
+    storePath = path.join(tmpDir, "sessions.json");
+  });
+
+  afterEach(() => {
+    fs.rmSync(tmpDir, { recursive: true, force: true });
+  });
+
+  test("returns null when transcript file does not exist", () => {
+    const result = readFirstUserMessageFromTranscript("nonexistent-session", storePath);
+    expect(result).toBeNull();
+  });
+
+  test("returns first user message from transcript with string content", () => {
+    const sessionId = "test-session-1";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({ message: { role: "user", content: "Hello world" } }),
+      JSON.stringify({ message: { role: "assistant", content: "Hi there" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Hello world");
+  });
+
+  test("returns first user message from transcript with array content", () => {
+    const sessionId = "test-session-2";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({
+        message: {
+          role: "user",
+          content: [{ type: "text", text: "Array message content" }],
+        },
+      }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Array message content");
+  });
+
+  test("returns first user message from transcript with input_text content", () => {
+    const sessionId = "test-session-2b";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({
+        message: {
+          role: "user",
+          content: [{ type: "input_text", text: "Input text content" }],
+        },
+      }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Input text content");
+  });
+  test("skips non-user messages to find first user message", () => {
+    const sessionId = "test-session-3";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({ message: { role: "system", content: "System prompt" } }),
+      JSON.stringify({ message: { role: "assistant", content: "Greeting" } }),
+      JSON.stringify({ message: { role: "user", content: "First user question" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("First user question");
+  });
+
+  test("returns null when no user messages exist", () => {
+    const sessionId = "test-session-4";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({ message: { role: "system", content: "System prompt" } }),
+      JSON.stringify({ message: { role: "assistant", content: "Greeting" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBeNull();
+  });
+
+  test("handles malformed JSON lines gracefully", () => {
+    const sessionId = "test-session-5";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      "not valid json",
+      JSON.stringify({ message: { role: "user", content: "Valid message" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Valid message");
+  });
+
+  test("uses sessionFile parameter when provided", () => {
+    const sessionId = "test-session-6";
+    const customPath = path.join(tmpDir, "custom-transcript.jsonl");
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({ message: { role: "user", content: "Custom file message" } }),
+    ];
+    fs.writeFileSync(customPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath, customPath);
+    expect(result).toBe("Custom file message");
+  });
+
+  test("trims whitespace from message content", () => {
+    const sessionId = "test-session-7";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [JSON.stringify({ message: { role: "user", content: "  Padded message  " } })];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Padded message");
+  });
+
+  test("returns null for empty content", () => {
+    const sessionId = "test-session-8";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "user", content: "" } }),
+      JSON.stringify({ message: { role: "user", content: "Second message" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readFirstUserMessageFromTranscript(sessionId, storePath);
+    expect(result).toBe("Second message");
+  });
+});
+
+describe("readLastMessagePreviewFromTranscript", () => {
+  let tmpDir: string;
+  let storePath: string;
+
+  beforeEach(() => {
+    tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), "clawdbot-session-fs-test-"));
+    storePath = path.join(tmpDir, "sessions.json");
+  });
+
+  afterEach(() => {
+    fs.rmSync(tmpDir, { recursive: true, force: true });
+  });
+
+  test("returns null when transcript file does not exist", () => {
+    const result = readLastMessagePreviewFromTranscript("nonexistent-session", storePath);
+    expect(result).toBeNull();
+  });
+
+  test("returns null for empty file", () => {
+    const sessionId = "test-last-empty";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    fs.writeFileSync(transcriptPath, "", "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBeNull();
+  });
+
+  test("returns last user message from transcript", () => {
+    const sessionId = "test-last-user";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "user", content: "First user" } }),
+      JSON.stringify({ message: { role: "assistant", content: "First assistant" } }),
+      JSON.stringify({ message: { role: "user", content: "Last user message" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Last user message");
+  });
+
+  test("returns last assistant message from transcript", () => {
+    const sessionId = "test-last-assistant";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "user", content: "User question" } }),
+      JSON.stringify({ message: { role: "assistant", content: "Final assistant reply" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Final assistant reply");
+  });
+
+  test("skips system messages to find last user/assistant", () => {
+    const sessionId = "test-last-skip-system";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "user", content: "Real last" } }),
+      JSON.stringify({ message: { role: "system", content: "System at end" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Real last");
+  });
+
+  test("returns null when no user/assistant messages exist", () => {
+    const sessionId = "test-last-no-match";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ type: "session", version: 1, id: sessionId }),
+      JSON.stringify({ message: { role: "system", content: "Only system" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBeNull();
+  });
+
+  test("handles malformed JSON lines gracefully", () => {
+    const sessionId = "test-last-malformed";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "user", content: "Valid first" } }),
+      "not valid json at end",
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Valid first");
+  });
+
+  test("handles array content format", () => {
+    const sessionId = "test-last-array";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({
+        message: {
+          role: "assistant",
+          content: [{ type: "text", text: "Array content response" }],
+        },
+      }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Array content response");
+  });
+
+  test("handles output_text content format", () => {
+    const sessionId = "test-last-output-text";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({
+        message: {
+          role: "assistant",
+          content: [{ type: "output_text", text: "Output text response" }],
+        },
+      }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Output text response");
+  });
+  test("uses sessionFile parameter when provided", () => {
+    const sessionId = "test-last-custom";
+    const customPath = path.join(tmpDir, "custom-last.jsonl");
+    const lines = [JSON.stringify({ message: { role: "user", content: "Custom file last" } })];
+    fs.writeFileSync(customPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath, customPath);
+    expect(result).toBe("Custom file last");
+  });
+
+  test("trims whitespace from message content", () => {
+    const sessionId = "test-last-trim";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "assistant", content: "  Padded response  " } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Padded response");
+  });
+
+  test("skips empty content to find previous message", () => {
+    const sessionId = "test-last-skip-empty";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const lines = [
+      JSON.stringify({ message: { role: "assistant", content: "Has content" } }),
+      JSON.stringify({ message: { role: "user", content: "" } }),
+    ];
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Has content");
+  });
+
+  test("reads from end of large file (16KB window)", () => {
+    const sessionId = "test-last-large";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const padding = JSON.stringify({ message: { role: "user", content: "x".repeat(500) } });
+    const lines: string[] = [];
+    for (let i = 0; i < 50; i++) {
+      lines.push(padding);
+    }
+    lines.push(JSON.stringify({ message: { role: "assistant", content: "Last in large file" } }));
+    fs.writeFileSync(transcriptPath, lines.join("\n"), "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Last in large file");
+  });
+
+  test("handles valid UTF-8 content", () => {
+    const sessionId = "test-last-utf8";
+    const transcriptPath = path.join(tmpDir, `${sessionId}.jsonl`);
+    const validLine = JSON.stringify({
+      message: { role: "user", content: "Valid UTF-8: 你好世界 🌍" },
+    });
+    fs.writeFileSync(transcriptPath, validLine, "utf-8");
+
+    const result = readLastMessagePreviewFromTranscript(sessionId, storePath);
+    expect(result).toBe("Valid UTF-8: 你好世界 🌍");
+  });
+});
--- a/src/gateway/session-utils.fs.ts
+++ b/src/gateway/session-utils.fs.ts
@@ -79,3 +79,113 @@ export function capArrayByJsonBytes<T>(
  const next = start > 0 ? items.slice(start) : items;
  return { items: next, bytes };
 }
+
+const MAX_LINES_TO_SCAN = 10;
+
+type TranscriptMessage = {
+  role?: string;
+  content?: string | Array<{ type: string; text?: string }>;
+};
+
+function extractTextFromContent(content: TranscriptMessage["content"]): string | null {
+  if (typeof content === "string") return content.trim() || null;
+  if (!Array.isArray(content)) return null;
+  for (const part of content) {
+    if (!part || typeof part.text !== "string") continue;
+    if (part.type === "text" || part.type === "output_text" || part.type === "input_text") {
+      const trimmed = part.text.trim();
+      if (trimmed) return trimmed;
+    }
+  }
+  return null;
+}
+
+export function readFirstUserMessageFromTranscript(
+  sessionId: string,
+  storePath: string | undefined,
+  sessionFile?: string,
+  agentId?: string,
+): string | null {
+  const candidates = resolveSessionTranscriptCandidates(sessionId, storePath, sessionFile, agentId);
+  const filePath = candidates.find((p) => fs.existsSync(p));
+  if (!filePath) return null;
+
+  let fd: number | null = null;
+  try {
+    fd = fs.openSync(filePath, "r");
+    const buf = Buffer.alloc(8192);
+    const bytesRead = fs.readSync(fd, buf, 0, buf.length, 0);
+    if (bytesRead === 0) return null;
+    const chunk = buf.toString("utf-8", 0, bytesRead);
+    const lines = chunk.split(/\r?\n/).slice(0, MAX_LINES_TO_SCAN);
+
+    for (const line of lines) {
+      if (!line.trim()) continue;
+      try {
+        const parsed = JSON.parse(line);
+        const msg = parsed?.message as TranscriptMessage | undefined;
+        if (msg?.role === "user") {
+          const text = extractTextFromContent(msg.content);
+          if (text) return text;
+        }
+      } catch {
+        // skip malformed lines
+      }
+    }
+  } catch {
+    // file read error
+  } finally {
+    if (fd !== null) fs.closeSync(fd);
+  }
+  return null;
+}
+
+const LAST_MSG_MAX_BYTES = 16384;
+const LAST_MSG_MAX_LINES = 20;
+
+export function readLastMessagePreviewFromTranscript(
+  sessionId: string,
+  storePath: string | undefined,
+  sessionFile?: string,
+  agentId?: string,
+): string | null {
+  const candidates = resolveSessionTranscriptCandidates(sessionId, storePath, sessionFile, agentId);
+  const filePath = candidates.find((p) => fs.existsSync(p));
+  if (!filePath) return null;
+
+  let fd: number | null = null;
+  try {
+    fd = fs.openSync(filePath, "r");
+    const stat = fs.fstatSync(fd);
+    const size = stat.size;
+    if (size === 0) return null;
+
+    const readStart = Math.max(0, size - LAST_MSG_MAX_BYTES);
+    const readLen = Math.min(size, LAST_MSG_MAX_BYTES);
+    const buf = Buffer.alloc(readLen);
+    fs.readSync(fd, buf, 0, readLen, readStart);
+
+    const chunk = buf.toString("utf-8");
+    const lines = chunk.split(/\r?\n/).filter((l) => l.trim());
+    const tailLines = lines.slice(-LAST_MSG_MAX_LINES);
+
+    for (let i = tailLines.length - 1; i >= 0; i--) {
+      const line = tailLines[i];
+      try {
+        const parsed = JSON.parse(line);
+        const msg = parsed?.message as TranscriptMessage | undefined;
+        if (msg?.role === "user" || msg?.role === "assistant") {
+          const text = extractTextFromContent(msg.content);
+          if (text) return text;
+        }
+      } catch {
+        // skip malformed
+      }
+    }
+  } catch {
+    // file error
+  } finally {
+    if (fd !== null) fs.closeSync(fd);
+  }
+  return null;
+}
--- a/src/gateway/session-utils.test.ts
+++ b/src/gateway/session-utils.test.ts
@@ -6,6 +6,8 @@ import type { SessionEntry } from "../config/sessions.js";
 import {
  capArrayByJsonBytes,
  classifySessionKey,
+  deriveSessionTitle,
+  listSessionsFromStore,
  parseGroupKey,
  resolveGatewaySessionStoreTarget,
  resolveSessionStoreKey,
@@ -91,3 +93,242 @@ describe("gateway session utils", () => {
    expect(target.storePath).toBe(path.resolve(storeTemplate.replace("{agentId}", "ops")));
  });
 });
+
+describe("deriveSessionTitle", () => {
+  test("returns undefined for undefined entry", () => {
+    expect(deriveSessionTitle(undefined)).toBeUndefined();
+  });
+
+  test("prefers displayName when set", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+      displayName: "My Custom Session",
+      subject: "Group Chat",
+    } as SessionEntry;
+    expect(deriveSessionTitle(entry)).toBe("My Custom Session");
+  });
+
+  test("falls back to subject when displayName is missing", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+      subject: "Dev Team Chat",
+    } as SessionEntry;
+    expect(deriveSessionTitle(entry)).toBe("Dev Team Chat");
+  });
+
+  test("uses first user message when displayName and subject missing", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+    } as SessionEntry;
+    expect(deriveSessionTitle(entry, "Hello, how are you?")).toBe("Hello, how are you?");
+  });
+
+  test("truncates long first user message to 60 chars with ellipsis", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+    } as SessionEntry;
+    const longMsg =
+      "This is a very long message that exceeds sixty characters and should be truncated appropriately";
+    const result = deriveSessionTitle(entry, longMsg);
+    expect(result).toBeDefined();
+    expect(result!.length).toBeLessThanOrEqual(60);
+    expect(result!.endsWith("…")).toBe(true);
+  });
+
+  test("truncates at word boundary when possible", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+    } as SessionEntry;
+    const longMsg = "This message has many words and should be truncated at a word boundary nicely";
+    const result = deriveSessionTitle(entry, longMsg);
+    expect(result).toBeDefined();
+    expect(result!.endsWith("…")).toBe(true);
+    expect(result!.includes("  ")).toBe(false);
+  });
+
+  test("falls back to sessionId prefix with date", () => {
+    const entry = {
+      sessionId: "abcd1234-5678-90ef-ghij-klmnopqrstuv",
+      updatedAt: new Date("2024-03-15T10:30:00Z").getTime(),
+    } as SessionEntry;
+    const result = deriveSessionTitle(entry);
+    expect(result).toBe("abcd1234 (2024-03-15)");
+  });
+
+  test("falls back to sessionId prefix without date when updatedAt missing", () => {
+    const entry = {
+      sessionId: "abcd1234-5678-90ef-ghij-klmnopqrstuv",
+      updatedAt: 0,
+    } as SessionEntry;
+    const result = deriveSessionTitle(entry);
+    expect(result).toBe("abcd1234");
+  });
+
+  test("trims whitespace from displayName", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+      displayName: "  Padded Name  ",
+    } as SessionEntry;
+    expect(deriveSessionTitle(entry)).toBe("Padded Name");
+  });
+
+  test("ignores empty displayName and falls through", () => {
+    const entry = {
+      sessionId: "abc123",
+      updatedAt: Date.now(),
+      displayName: "   ",
+      subject: "Actual Subject",
+    } as SessionEntry;
+    expect(deriveSessionTitle(entry)).toBe("Actual Subject");
+  });
+});
+
+describe("listSessionsFromStore search", () => {
+  const baseCfg = {
+    session: { mainKey: "main" },
+    agents: { list: [{ id: "main", default: true }] },
+  } as ClawdbotConfig;
+
+  const makeStore = (): Record<string, SessionEntry> => ({
+    "agent:main:work-project": {
+      sessionId: "sess-work-1",
+      updatedAt: Date.now(),
+      displayName: "Work Project Alpha",
+      label: "work",
+    } as SessionEntry,
+    "agent:main:personal-chat": {
+      sessionId: "sess-personal-1",
+      updatedAt: Date.now() - 1000,
+      displayName: "Personal Chat",
+      subject: "Family Reunion Planning",
+    } as SessionEntry,
+    "agent:main:discord:group:dev-team": {
+      sessionId: "sess-discord-1",
+      updatedAt: Date.now() - 2000,
+      label: "discord",
+      subject: "Dev Team Discussion",
+    } as SessionEntry,
+  });
+
+  test("returns all sessions when search is empty", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "" },
+    });
+    expect(result.sessions.length).toBe(3);
+  });
+
+  test("returns all sessions when search is undefined", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: {},
+    });
+    expect(result.sessions.length).toBe(3);
+  });
+
+  test("filters by displayName case-insensitively", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "WORK PROJECT" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].displayName).toBe("Work Project Alpha");
+  });
+
+  test("filters by subject", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "reunion" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].subject).toBe("Family Reunion Planning");
+  });
+
+  test("filters by label", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "discord" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].label).toBe("discord");
+  });
+
+  test("filters by sessionId", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "sess-personal" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].sessionId).toBe("sess-personal-1");
+  });
+
+  test("filters by key", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "dev-team" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].key).toBe("agent:main:discord:group:dev-team");
+  });
+
+  test("returns empty array when no matches", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "nonexistent-term" },
+    });
+    expect(result.sessions.length).toBe(0);
+  });
+
+  test("matches partial strings", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "alpha" },
+    });
+    expect(result.sessions.length).toBe(1);
+    expect(result.sessions[0].displayName).toBe("Work Project Alpha");
+  });
+
+  test("trims whitespace from search query", () => {
+    const store = makeStore();
+    const result = listSessionsFromStore({
+      cfg: baseCfg,
+      storePath: "/tmp/sessions.json",
+      store,
+      opts: { search: "  personal  " },
+    });
+    expect(result.sessions.length).toBe(1);
+  });
+});
--- a/src/gateway/session-utils.ts
+++ b/src/gateway/session-utils.ts
@@ -22,6 +22,10 @@ import {
  parseAgentSessionKey,
 } from "../routing/session-key.js";
 import { normalizeSessionDeliveryFields } from "../utils/delivery-context.js";
+import {
+  readFirstUserMessageFromTranscript,
+  readLastMessagePreviewFromTranscript,
+} from "./session-utils.fs.js";
 import type {
  GatewayAgentRow,
  GatewaySessionRow,
@@ -32,6 +36,8 @@ import type {
 export {
  archiveFileOnDisk,
  capArrayByJsonBytes,
+  readFirstUserMessageFromTranscript,
+  readLastMessagePreviewFromTranscript,
  readSessionMessages,
  resolveSessionTranscriptCandidates,
 } from "./session-utils.fs.js";
@@ -43,6 +49,52 @@ export type {
  SessionsPatchResult,
 } from "./session-utils.types.js";

+const DERIVED_TITLE_MAX_LEN = 60;
+
+function formatSessionIdPrefix(sessionId: string, updatedAt?: number | null): string {
+  const prefix = sessionId.slice(0, 8);
+  if (updatedAt && updatedAt > 0) {
+    const d = new Date(updatedAt);
+    const date = d.toISOString().slice(0, 10);
+    return `${prefix} (${date})`;
+  }
+  return prefix;
+}
+
+function truncateTitle(text: string, maxLen: number): string {
+  if (text.length <= maxLen) return text;
+  const cut = text.slice(0, maxLen - 1);
+  const lastSpace = cut.lastIndexOf(" ");
+  if (lastSpace > maxLen * 0.6) return cut.slice(0, lastSpace) + "…";
+  return cut + "…";
+}
+
+export function deriveSessionTitle(
+  entry: SessionEntry | undefined,
+  firstUserMessage?: string | null,
+): string | undefined {
+  if (!entry) return undefined;
+
+  if (entry.displayName?.trim()) {
+    return entry.displayName.trim();
+  }
+
+  if (entry.subject?.trim()) {
+    return entry.subject.trim();
+  }
+
+  if (firstUserMessage?.trim()) {
+    const normalized = firstUserMessage.replace(/\s+/g, " ").trim();
+    return truncateTitle(normalized, DERIVED_TITLE_MAX_LEN);
+  }
+
+  if (entry.sessionId) {
+    return formatSessionIdPrefix(entry.sessionId, entry.updatedAt);
+  }
+
+  return undefined;
+}
+
 export function loadSessionEntry(sessionKey: string) {
  const cfg = loadConfig();
  const sessionCfg = cfg.session;
@@ -341,9 +393,12 @@ export function listSessionsFromStore(params: {

  const includeGlobal = opts.includeGlobal === true;
  const includeUnknown = opts.includeUnknown === true;
+  const includeDerivedTitles = opts.includeDerivedTitles === true;
+  const includeLastMessage = opts.includeLastMessage === true;
  const spawnedBy = typeof opts.spawnedBy === "string" ? opts.spawnedBy : "";
  const label = typeof opts.label === "string" ? opts.label.trim() : "";
  const agentId = typeof opts.agentId === "string" ? normalizeAgentId(opts.agentId) : "";
+  const search = typeof opts.search === "string" ? opts.search.trim().toLowerCase() : "";
  const activeMinutes =
    typeof opts.activeMinutes === "number" && Number.isFinite(opts.activeMinutes)
      ? Math.max(1, Math.floor(opts.activeMinutes))
@@ -400,6 +455,7 @@ export function listSessionsFromStore(params: {
      const deliveryFields = normalizeSessionDeliveryFields(entry);
      return {
        key,
+        entry,
        kind: classifySessionKey(key, entry),
        label: entry?.label,
        displayName,
@@ -429,10 +485,17 @@ export function listSessionsFromStore(params: {
        lastChannel: deliveryFields.lastChannel ?? entry?.lastChannel,
        lastTo: deliveryFields.lastTo ?? entry?.lastTo,
        lastAccountId: deliveryFields.lastAccountId ?? entry?.lastAccountId,
-      } satisfies GatewaySessionRow;
+      };
    })
    .sort((a, b) => (b.updatedAt ?? 0) - (a.updatedAt ?? 0));

+  if (search) {
+    sessions = sessions.filter((s) => {
+      const fields = [s.displayName, s.label, s.subject, s.sessionId, s.key];
+      return fields.some((f) => typeof f === "string" && f.toLowerCase().includes(search));
+    });
+  }
+
  if (activeMinutes !== undefined) {
    const cutoff = now - activeMinutes * 60_000;
    sessions = sessions.filter((s) => (s.updatedAt ?? 0) >= cutoff);
@@ -443,11 +506,36 @@ export function listSessionsFromStore(params: {
    sessions = sessions.slice(0, limit);
  }

+  const finalSessions: GatewaySessionRow[] = sessions.map((s) => {
+    const { entry, ...rest } = s;
+    let derivedTitle: string | undefined;
+    let lastMessagePreview: string | undefined;
+    if (entry?.sessionId) {
+      if (includeDerivedTitles) {
+        const firstUserMsg = readFirstUserMessageFromTranscript(
+          entry.sessionId,
+          storePath,
+          entry.sessionFile,
+        );
+        derivedTitle = deriveSessionTitle(entry, firstUserMsg);
+      }
+      if (includeLastMessage) {
+        const lastMsg = readLastMessagePreviewFromTranscript(
+          entry.sessionId,
+          storePath,
+          entry.sessionFile,
+        );
+        if (lastMsg) lastMessagePreview = lastMsg;
+      }
+    }
+    return { ...rest, derivedTitle, lastMessagePreview } satisfies GatewaySessionRow;
+  });
+
  return {
    ts: now,
    path: storePath,
-    count: sessions.length,
+    count: finalSessions.length,
    defaults: getSessionDefaults(cfg),
-    sessions,
+    sessions: finalSessions,
  };
 }
--- a/src/gateway/session-utils.types.ts
+++ b/src/gateway/session-utils.types.ts
@@ -13,6 +13,8 @@ export type GatewaySessionRow = {
  kind: "direct" | "group" | "global" | "unknown";
  label?: string;
  displayName?: string;
+  derivedTitle?: string;
+  lastMessagePreview?: string;
  channel?: string;
  subject?: string;
  groupChannel?: string;
--- a/src/tui/components/filterable-select-list.ts
+++ b/src/tui/components/filterable-select-list.ts
@@ -0,0 +1,143 @@
+import {
+  Input,
+  matchesKey,
+  type SelectItem,
+  SelectList,
+  type SelectListTheme,
+  getEditorKeybindings,
+} from "@mariozechner/pi-tui";
+import type { Component } from "@mariozechner/pi-tui";
+import chalk from "chalk";
+import { fuzzyFilterLower, prepareSearchItems } from "./fuzzy-filter.js";
+
+export interface FilterableSelectItem extends SelectItem {
+  /** Additional searchable fields beyond label */
+  searchText?: string;
+  /** Pre-computed lowercase search text (label + description + searchText) for filtering */
+  searchTextLower?: string;
+}
+
+export interface FilterableSelectListTheme extends SelectListTheme {
+  filterLabel: (text: string) => string;
+}
+
+/**
+ * Combines text input filtering with a select list.
+ * User types to filter, arrows/j/k to navigate, Enter to select, Escape to clear/cancel.
+ */
+export class FilterableSelectList implements Component {
+  private input: Input;
+  private selectList: SelectList;
+  private allItems: FilterableSelectItem[];
+  private maxVisible: number;
+  private theme: FilterableSelectListTheme;
+  private filterText = "";
+
+  onSelect?: (item: SelectItem) => void;
+  onCancel?: () => void;
+
+  constructor(items: FilterableSelectItem[], maxVisible: number, theme: FilterableSelectListTheme) {
+    this.allItems = prepareSearchItems(items);
+    this.maxVisible = maxVisible;
+    this.theme = theme;
+    this.input = new Input();
+    this.selectList = new SelectList(this.allItems, maxVisible, theme);
+  }
+
+  private applyFilter(): void {
+    const queryLower = this.filterText.toLowerCase();
+    if (!queryLower.trim()) {
+      this.selectList = new SelectList(this.allItems, this.maxVisible, this.theme);
+      return;
+    }
+    const filtered = fuzzyFilterLower(this.allItems, queryLower);
+    this.selectList = new SelectList(filtered, this.maxVisible, this.theme);
+  }
+
+  invalidate(): void {
+    this.input.invalidate();
+    this.selectList.invalidate();
+  }
+
+  render(width: number): string[] {
+    const lines: string[] = [];
+
+    // Filter input row
+    const filterLabel = this.theme.filterLabel("Filter: ");
+    const inputLines = this.input.render(width - 8);
+    const inputText = inputLines[0] ?? "";
+    lines.push(filterLabel + inputText);
+
+    // Separator
+    lines.push(chalk.dim("─".repeat(width)));
+
+    // Select list
+    const listLines = this.selectList.render(width);
+    lines.push(...listLines);
+
+    return lines;
+  }
+
+  handleInput(keyData: string): void {
+    const allowVimNav = !this.filterText.trim();
+
+    // Navigation: arrows, vim j/k, or ctrl+p/ctrl+n
+    if (
+      matchesKey(keyData, "up") ||
+      matchesKey(keyData, "ctrl+p") ||
+      (allowVimNav && keyData === "k")
+    ) {
+      this.selectList.handleInput("\x1b[A");
+      return;
+    }
+
+    if (
+      matchesKey(keyData, "down") ||
+      matchesKey(keyData, "ctrl+n") ||
+      (allowVimNav && keyData === "j")
+    ) {
+      this.selectList.handleInput("\x1b[B");
+      return;
+    }
+
+    // Enter selects
+    if (matchesKey(keyData, "enter")) {
+      const selected = this.selectList.getSelectedItem();
+      if (selected) {
+        this.onSelect?.(selected);
+      }
+      return;
+    }
+
+    // Escape: clear filter or cancel
+    const kb = getEditorKeybindings();
+    if (kb.matches(keyData, "selectCancel")) {
+      if (this.filterText) {
+        this.filterText = "";
+        this.input.setValue("");
+        this.applyFilter();
+      } else {
+        this.onCancel?.();
+      }
+      return;
+    }
+
+    // All other input goes to filter
+    const prevValue = this.input.getValue();
+    this.input.handleInput(keyData);
+    const newValue = this.input.getValue();
+
+    if (newValue !== prevValue) {
+      this.filterText = newValue;
+      this.applyFilter();
+    }
+  }
+
+  getSelectedItem(): SelectItem | null {
+    return this.selectList.getSelectedItem();
+  }
+
+  getFilterText(): string {
+    return this.filterText;
+  }
+}
--- a/src/tui/components/fuzzy-filter.ts
+++ b/src/tui/components/fuzzy-filter.ts
@@ -0,0 +1,114 @@
+/**
+ * Shared fuzzy filtering utilities for select list components.
+ */
+
+/**
+ * Word boundary characters for matching.
+ */
+const WORD_BOUNDARY_CHARS = /[\s\-_./:#@]/;
+
+/**
+ * Check if position is at a word boundary.
+ */
+export function isWordBoundary(text: string, index: number): boolean {
+	return index === 0 || WORD_BOUNDARY_CHARS.test(text[index - 1] ?? "");
+}
+
+/**
+ * Find index where query matches at a word boundary in text.
+ * Returns null if no match.
+ */
+export function findWordBoundaryIndex(text: string, query: string): number | null {
+	if (!query) return null;
+	const textLower = text.toLowerCase();
+	const queryLower = query.toLowerCase();
+	const maxIndex = textLower.length - queryLower.length;
+	if (maxIndex < 0) return null;
+	for (let i = 0; i <= maxIndex; i++) {
+		if (textLower.startsWith(queryLower, i) && isWordBoundary(textLower, i)) {
+			return i;
+		}
+	}
+	return null;
+}
+
+/**
+ * Fuzzy match with pre-lowercased inputs (avoids toLowerCase on every keystroke).
+ * Returns score (lower = better) or null if no match.
+ */
+export function fuzzyMatchLower(queryLower: string, textLower: string): number | null {
+	if (queryLower.length === 0) return 0;
+	if (queryLower.length > textLower.length) return null;
+
+	let queryIndex = 0;
+	let score = 0;
+	let lastMatchIndex = -1;
+	let consecutiveMatches = 0;
+
+	for (let i = 0; i < textLower.length && queryIndex < queryLower.length; i++) {
+		if (textLower[i] === queryLower[queryIndex]) {
+			const isAtWordBoundary = isWordBoundary(textLower, i);
+			if (lastMatchIndex === i - 1) {
+				consecutiveMatches++;
+				score -= consecutiveMatches * 5; // Reward consecutive matches
+			} else {
+				consecutiveMatches = 0;
+				if (lastMatchIndex >= 0) score += (i - lastMatchIndex - 1) * 2; // Penalize gaps
+			}
+			if (isAtWordBoundary) score -= 10; // Reward word boundary matches
+			score += i * 0.1; // Slight penalty for later matches
+			lastMatchIndex = i;
+			queryIndex++;
+		}
+	}
+	return queryIndex < queryLower.length ? null : score;
+}
+
+/**
+ * Filter items using pre-lowercased searchTextLower field.
+ * Supports space-separated tokens (all must match).
+ */
+export function fuzzyFilterLower<T extends { searchTextLower?: string }>(
+	items: T[],
+	queryLower: string,
+): T[] {
+	const trimmed = queryLower.trim();
+	if (!trimmed) return items;
+
+	const tokens = trimmed.split(/\s+/).filter((t) => t.length > 0);
+	if (tokens.length === 0) return items;
+
+	const results: { item: T; score: number }[] = [];
+	for (const item of items) {
+		const text = item.searchTextLower ?? "";
+		let totalScore = 0;
+		let allMatch = true;
+		for (const token of tokens) {
+			const score = fuzzyMatchLower(token, text);
+			if (score !== null) {
+				totalScore += score;
+			} else {
+				allMatch = false;
+				break;
+			}
+		}
+		if (allMatch) results.push({ item, score: totalScore });
+	}
+	results.sort((a, b) => a.score - b.score);
+	return results.map((r) => r.item);
+}
+
+/**
+ * Prepare items for fuzzy filtering by pre-computing lowercase search text.
+ */
+export function prepareSearchItems<T extends { label?: string; description?: string; searchText?: string }>(
+	items: T[],
+): (T & { searchTextLower: string })[] {
+	return items.map((item) => {
+		const parts: string[] = [];
+		if (item.label) parts.push(item.label);
+		if (item.description) parts.push(item.description);
+		if (item.searchText) parts.push(item.searchText);
+		return { ...item, searchTextLower: parts.join(" ").toLowerCase() };
+	});
+}
--- a/src/tui/components/searchable-select-list.ts
+++ b/src/tui/components/searchable-select-list.ts
@@ -1,6 +1,7 @@
 import {
  type Component,
  fuzzyFilter,
+  getEditorKeybindings,
  Input,
  isKeyRelease,
  matchesKey,
@@ -9,6 +10,7 @@ import {
  truncateToWidth,
 } from "@mariozechner/pi-tui";
 import { visibleWidth } from "../../terminal/ansi.js";
+import { findWordBoundaryIndex } from "./fuzzy-filter.js";

 export interface SearchableSelectListTheme extends SelectListTheme {
  searchPrompt: (text: string) => string;
@@ -80,7 +82,7 @@ export class SearchableSelectList implements Component {
        continue;
      }
      // Tier 2: Word-boundary prefix in label (score 100-199)
-      const wordBoundaryIndex = this.findWordBoundaryIndex(label, q);
+      const wordBoundaryIndex = findWordBoundaryIndex(label, q);
      if (wordBoundaryIndex !== null) {
        wordBoundary.push({ item, score: wordBoundaryIndex });
        continue;
@@ -111,28 +113,6 @@ export class SearchableSelectList implements Component {
    ];
  }

-  /**
-   * Check if query matches at a word boundary in text.
-   * E.g., "gpt" matches "openai/gpt-4" at the "gpt" word boundary.
-   */
-  private matchesWordBoundary(text: string, query: string): boolean {
-    return this.findWordBoundaryIndex(text, query) !== null;
-  }
-
-  private findWordBoundaryIndex(text: string, query: string): number | null {
-    if (!query) return null;
-    const maxIndex = text.length - query.length;
-    if (maxIndex < 0) return null;
-    for (let i = 0; i <= maxIndex; i++) {
-      if (text.startsWith(query, i)) {
-        if (i === 0 || /[\s\-_./:]/.test(text[i - 1] ?? "")) {
-          return i;
-        }
-      }
-    }
-    return null;
-  }
-
  private escapeRegex(str: string): string {
    return str.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
  }
@@ -258,14 +238,24 @@ export class SearchableSelectList implements Component {
  handleInput(keyData: string): void {
    if (isKeyRelease(keyData)) return;

+    const allowVimNav = !this.searchInput.getValue().trim();
+
    // Navigation keys
-    if (matchesKey(keyData, "up") || matchesKey(keyData, "ctrl+p")) {
+    if (
+      matchesKey(keyData, "up") ||
+      matchesKey(keyData, "ctrl+p") ||
+      (allowVimNav && keyData === "k")
+    ) {
      this.selectedIndex = Math.max(0, this.selectedIndex - 1);
      this.notifySelectionChange();
      return;
    }

-    if (matchesKey(keyData, "down") || matchesKey(keyData, "ctrl+n")) {
+    if (
+      matchesKey(keyData, "down") ||
+      matchesKey(keyData, "ctrl+n") ||
+      (allowVimNav && keyData === "j")
+    ) {
      this.selectedIndex = Math.min(this.filteredItems.length - 1, this.selectedIndex + 1);
      this.notifySelectionChange();
      return;
@@ -279,7 +269,8 @@ export class SearchableSelectList implements Component {
      return;
    }

-    if (matchesKey(keyData, "escape")) {
+    const kb = getEditorKeybindings();
+    if (kb.matches(keyData, "selectCancel")) {
      if (this.onCancel) {
        this.onCancel();
      }
--- a/src/tui/components/selectors.ts
+++ b/src/tui/components/selectors.ts
@@ -1,5 +1,14 @@
 import { type SelectItem, SelectList, type SettingItem, SettingsList } from "@mariozechner/pi-tui";
-import { searchableSelectListTheme, selectListTheme, settingsListTheme } from "../theme/theme.js";
+import {
+  filterableSelectListTheme,
+  searchableSelectListTheme,
+  selectListTheme,
+  settingsListTheme,
+} from "../theme/theme.js";
+import {
+  FilterableSelectList,
+  type FilterableSelectItem,
+} from "./filterable-select-list.js";
 import { SearchableSelectList } from "./searchable-select-list.js";

 export function createSelectList(items: SelectItem[], maxVisible = 7) {
@@ -10,6 +19,10 @@ export function createSearchableSelectList(items: SelectItem[], maxVisible = 7)
  return new SearchableSelectList(items, maxVisible, searchableSelectListTheme);
 }

+export function createFilterableSelectList(items: FilterableSelectItem[], maxVisible = 7) {
+  return new FilterableSelectList(items, maxVisible, filterableSelectListTheme);
+}
+
 export function createSettingsList(
  items: SettingItem[],
  onChange: (id: string, value: string) => void,
--- a/src/tui/gateway-chat.ts
+++ b/src/tui/gateway-chat.ts
@@ -64,6 +64,8 @@ export type GatewaySessionList = {
    lastProvider?: string;
    lastTo?: string;
    lastAccountId?: string;
+    derivedTitle?: string;
+    lastMessagePreview?: string;
  }>;
 };

@@ -183,6 +185,8 @@ export class GatewayChatClient {
      activeMinutes: opts?.activeMinutes,
      includeGlobal: opts?.includeGlobal,
      includeUnknown: opts?.includeUnknown,
+      includeDerivedTitles: opts?.includeDerivedTitles,
+      includeLastMessage: opts?.includeLastMessage,
      agentId: opts?.agentId,
    });
  }
--- a/src/tui/theme/theme.ts
+++ b/src/tui/theme/theme.ts
@@ -106,6 +106,11 @@ export const selectListTheme: SelectListTheme = {
  noMatch: (text) => fg(palette.dim)(text),
 };

+export const filterableSelectListTheme = {
+  ...selectListTheme,
+  filterLabel: (text: string) => fg(palette.dim)(text),
+};
+
 export const settingsListTheme: SettingsListTheme = {
  label: (text, selected) =>
    selected ? chalk.bold(fg(palette.accent)(text)) : fg(palette.text)(text),
--- a/src/tui/tui-command-handlers.ts
+++ b/src/tui/tui-command-handlers.ts
@@ -5,9 +5,14 @@ import {
  resolveResponseUsageMode,
 } from "../auto-reply/thinking.js";
 import { normalizeAgentId } from "../routing/session-key.js";
+import { formatRelativeTime } from "../utils/time-format.js";
 import { helpText, parseCommand } from "./commands.js";
 import type { ChatLog } from "./components/chat-log.js";
-import { createSearchableSelectList, createSettingsList } from "./components/selectors.js";
+import {
+  createFilterableSelectList,
+  createSearchableSelectList,
+  createSettingsList,
+} from "./components/selectors.js";
 import type { GatewayChatClient } from "./gateway-chat.js";
 import { formatStatusSummary } from "./tui-status-summary.js";
 import type {
@@ -134,16 +139,37 @@ export function createCommandHandlers(context: CommandHandlerContext) {
      const result = await client.listSessions({
        includeGlobal: false,
        includeUnknown: false,
+        includeDerivedTitles: true,
+        includeLastMessage: true,
        agentId: state.currentAgentId,
      });
-      const items = result.sessions.map((session) => ({
-        value: session.key,
-        label: session.displayName
-          ? `${session.displayName} (${formatSessionKey(session.key)})`
-          : formatSessionKey(session.key),
-        description: session.updatedAt ? new Date(session.updatedAt).toLocaleString() : "",
-      }));
-      const selector = createSearchableSelectList(items, 9);
+      const items = result.sessions.map((session) => {
+        const title = session.derivedTitle ?? session.displayName;
+        const formattedKey = formatSessionKey(session.key);
+        // Avoid redundant "title (key)" when title matches key
+        const label = title && title !== formattedKey ? `${title} (${formattedKey})` : formattedKey;
+        // Build description: time + message preview
+        const timePart = session.updatedAt ? formatRelativeTime(session.updatedAt) : "";
+        const preview = session.lastMessagePreview?.replace(/\s+/g, " ").trim();
+        const description =
+          timePart && preview ? `${timePart} · ${preview}` : (preview ?? timePart);
+        return {
+          value: session.key,
+          label,
+          description,
+          searchText: [
+            session.displayName,
+            session.label,
+            session.subject,
+            session.sessionId,
+            session.key,
+            session.lastMessagePreview,
+          ]
+            .filter(Boolean)
+            .join(" "),
+        };
+      });
+      const selector = createFilterableSelectList(items, 9);
      selector.onSelect = (item) => {
        void (async () => {
          closeOverlay();
--- a/src/utils/time-format.ts
+++ b/src/utils/time-format.ts
@@ -0,0 +1,15 @@
+export function formatRelativeTime(timestamp: number): string {
+	const now = Date.now();
+	const diff = now - timestamp;
+	const seconds = Math.floor(diff / 1000);
+	const minutes = Math.floor(seconds / 60);
+	const hours = Math.floor(minutes / 60);
+	const days = Math.floor(hours / 24);
+
+	if (seconds < 60) return "just now";
+	if (minutes < 60) return `${minutes}m ago`;
+	if (hours < 24) return `${hours}h ago`;
+	if (days === 1) return "Yesterday";
+	if (days < 7) return `${days}d ago`;
+	return new Date(timestamp).toLocaleDateString(undefined, { month: "short", day: "numeric" });
+}