diff --git a/src/gateway/protocol/schema/sessions.ts b/src/gateway/protocol/schema/sessions.ts
index 502af9230..3535e54ef 100644
--- a/src/gateway/protocol/schema/sessions.ts
+++ b/src/gateway/protocol/schema/sessions.ts
@@ -8,6 +8,7 @@ export const SessionsListParamsSchema = Type.Object(
     activeMinutes: Type.Optional(Type.Integer({ minimum: 1 })),
     includeGlobal: Type.Optional(Type.Boolean()),
     includeUnknown: Type.Optional(Type.Boolean()),
+    includeDerivedTitles: Type.Optional(Type.Boolean()),
     label: Type.Optional(SessionLabelString),
     spawnedBy: Type.Optional(NonEmptyString),
     agentId: Type.Optional(NonEmptyString),
diff --git a/src/gateway/session-utils.fs.test.ts b/src/gateway/session-utils.fs.test.ts
new file mode 100644
index 000000000..b2157a06d
--- /dev/null
+++ b/src/gateway/session-utils.fs.test.ts
@@ -0,0 +1,136 @@
+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 } 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("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");
+  });
+});
diff --git a/src/gateway/session-utils.fs.ts b/src/gateway/session-utils.fs.ts
index cee03bde1..d624632cb 100644
--- a/src/gateway/session-utils.fs.ts
+++ b/src/gateway/session-utils.fs.ts
@@ -79,3 +79,61 @@ 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.type === "text" && typeof part.text === "string" && part.text.trim()) {
+      return part.text.trim();
+    }
+  }
+  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;
+}
diff --git a/src/gateway/session-utils.test.ts b/src/gateway/session-utils.test.ts
index db24c17f4..d0076061e 100644
--- a/src/gateway/session-utils.test.ts
+++ b/src/gateway/session-utils.test.ts
@@ -6,6 +6,7 @@ import type { SessionEntry } from "../config/sessions.js";
 import {
   capArrayByJsonBytes,
   classifySessionKey,
+  deriveSessionTitle,
   parseGroupKey,
   resolveGatewaySessionStoreTarget,
   resolveSessionStoreKey,
@@ -91,3 +92,98 @@ 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");
+  });
+});
diff --git a/src/gateway/session-utils.ts b/src/gateway/session-utils.ts
index b17018ae3..ac067f930 100644
--- a/src/gateway/session-utils.ts
+++ b/src/gateway/session-utils.ts
@@ -22,6 +22,7 @@ import {
   parseAgentSessionKey,
 } from "../routing/session-key.js";
 import { normalizeSessionDeliveryFields } from "../utils/delivery-context.js";
+import { readFirstUserMessageFromTranscript } from "./session-utils.fs.js";
 import type {
   GatewayAgentRow,
   GatewaySessionRow,
@@ -32,6 +33,7 @@ import type {
 export {
   archiveFileOnDisk,
   capArrayByJsonBytes,
+  readFirstUserMessageFromTranscript,
   readSessionMessages,
   resolveSessionTranscriptCandidates,
 } from "./session-utils.fs.js";
@@ -43,6 +45,51 @@ 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()) {
+    return truncateTitle(firstUserMessage.trim(), 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;
@@ -341,6 +388,7 @@ export function listSessionsFromStore(params: {
 
   const includeGlobal = opts.includeGlobal === true;
   const includeUnknown = opts.includeUnknown === true;
+  const includeDerivedTitles = opts.includeDerivedTitles === 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) : "";
@@ -400,6 +448,7 @@ export function listSessionsFromStore(params: {
       const deliveryFields = normalizeSessionDeliveryFields(entry);
       return {
         key,
+        entry,
         kind: classifySessionKey(key, entry),
         label: entry?.label,
         displayName,
@@ -429,7 +478,7 @@ 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));
 
@@ -443,11 +492,25 @@ export function listSessionsFromStore(params: {
     sessions = sessions.slice(0, limit);
   }
 
+  const finalSessions: GatewaySessionRow[] = sessions.map((s) => {
+    const { entry, ...rest } = s;
+    let derivedTitle: string | undefined;
+    if (includeDerivedTitles && entry?.sessionId) {
+      const firstUserMsg = readFirstUserMessageFromTranscript(
+        entry.sessionId,
+        storePath,
+        entry.sessionFile,
+      );
+      derivedTitle = deriveSessionTitle(entry, firstUserMsg);
+    }
+    return { ...rest, derivedTitle } satisfies GatewaySessionRow;
+  });
+
   return {
     ts: now,
     path: storePath,
-    count: sessions.length,
+    count: finalSessions.length,
     defaults: getSessionDefaults(cfg),
-    sessions,
+    sessions: finalSessions,
   };
 }
diff --git a/src/gateway/session-utils.types.ts b/src/gateway/session-utils.types.ts
index 4735a0ff4..08d1eeb3a 100644
--- a/src/gateway/session-utils.types.ts
+++ b/src/gateway/session-utils.types.ts
@@ -13,6 +13,7 @@ export type GatewaySessionRow = {
   kind: "direct" | "group" | "global" | "unknown";
   label?: string;
   displayName?: string;
+  derivedTitle?: string;
   channel?: string;
   subject?: string;
   groupChannel?: string;