diff --git a/src/hooks/bundled/session-memory/HOOK.md b/src/hooks/bundled/session-memory/HOOK.md
index 2a635a64541..0875486c94f 100644
--- a/src/hooks/bundled/session-memory/HOOK.md
+++ b/src/hooks/bundled/session-memory/HOOK.md
@@ -23,7 +23,7 @@ Automatically saves session context to your workspace memory when you issue the
 When you run `/new` to start a fresh session:
 
 1. **Finds the previous session** - Uses the pre-reset session entry to locate the correct transcript
-2. **Extracts conversation** - Reads the last 15 lines of conversation from the session
+2. **Extracts conversation** - Reads the last N user/assistant messages from the session (default: 15, configurable)
 3. **Generates descriptive slug** - Uses LLM to create a meaningful filename slug based on conversation content
 4. **Saves to memory** - Creates a new file at `<workspace>/memory/YYYY-MM-DD-slug.md`
 5. **Sends confirmation** - Notifies you with the file path
@@ -57,7 +57,30 @@ The hook uses your configured LLM provider to generate slugs, so it works with a
 
 ## Configuration
 
-No additional configuration required. The hook automatically:
+The hook supports optional configuration:
+
+| Option | Type | Default | Description |
+|--------|------|---------|-------------|
+| `messages` | number | 15 | Number of user/assistant messages to include in the memory file |
+
+Example configuration:
+
+```json
+{
+  "hooks": {
+    "internal": {
+      "entries": {
+        "session-memory": {
+          "enabled": true,
+          "messages": 25
+        }
+      }
+    }
+  }
+}
+```
+
+The hook automatically:
 
 - Uses your workspace directory (`~/clawd` by default)
 - Uses your configured LLM for slug generation
diff --git a/src/hooks/bundled/session-memory/handler.test.ts b/src/hooks/bundled/session-memory/handler.test.ts
new file mode 100644
index 00000000000..525e210599c
--- /dev/null
+++ b/src/hooks/bundled/session-memory/handler.test.ts
@@ -0,0 +1,379 @@
+import fs from "node:fs/promises";
+import path from "node:path";
+
+import { describe, expect, it } from "vitest";
+
+import handler from "./handler.js";
+import { createHookEvent } from "../../hooks.js";
+import type { ClawdbotConfig } from "../../../config/config.js";
+import { makeTempWorkspace, writeWorkspaceFile } from "../../../test-helpers/workspace.js";
+
+/**
+ * Create a mock session JSONL file with various entry types
+ */
+function createMockSessionContent(
+  entries: Array<{ role: string; content: string } | { type: string }>,
+): string {
+  return entries
+    .map((entry) => {
+      if ("role" in entry) {
+        return JSON.stringify({
+          type: "message",
+          message: {
+            role: entry.role,
+            content: entry.content,
+          },
+        });
+      }
+      // Non-message entry (tool call, system, etc.)
+      return JSON.stringify(entry);
+    })
+    .join("\n");
+}
+
+describe("session-memory hook", () => {
+  it("skips non-command events", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+
+    const event = createHookEvent("agent", "bootstrap", "agent:main:main", {
+      workspaceDir: tempDir,
+    });
+
+    await handler(event);
+
+    // Memory directory should not be created for non-command events
+    const memoryDir = path.join(tempDir, "memory");
+    await expect(fs.access(memoryDir)).rejects.toThrow();
+  });
+
+  it("skips commands other than new", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+
+    const event = createHookEvent("command", "help", "agent:main:main", {
+      workspaceDir: tempDir,
+    });
+
+    await handler(event);
+
+    // Memory directory should not be created for other commands
+    const memoryDir = path.join(tempDir, "memory");
+    await expect(fs.access(memoryDir)).rejects.toThrow();
+  });
+
+  it("creates memory file with session content on /new command", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    // Create a mock session file with user/assistant messages
+    const sessionContent = createMockSessionContent([
+      { role: "user", content: "Hello there" },
+      { role: "assistant", content: "Hi! How can I help?" },
+      { role: "user", content: "What is 2+2?" },
+      { role: "assistant", content: "2+2 equals 4" },
+    ]);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    // Memory file should be created
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    expect(files.length).toBe(1);
+
+    // Read the memory file and verify content
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+    expect(memoryContent).toContain("user: Hello there");
+    expect(memoryContent).toContain("assistant: Hi! How can I help?");
+    expect(memoryContent).toContain("user: What is 2+2?");
+    expect(memoryContent).toContain("assistant: 2+2 equals 4");
+  });
+
+  it("filters out non-message entries (tool calls, system)", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    // Create session with mixed entry types
+    const sessionContent = createMockSessionContent([
+      { role: "user", content: "Hello" },
+      { type: "tool_use", tool: "search", input: "test" },
+      { role: "assistant", content: "World" },
+      { type: "tool_result", result: "found it" },
+      { role: "user", content: "Thanks" },
+    ]);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+
+    // Only user/assistant messages should be present
+    expect(memoryContent).toContain("user: Hello");
+    expect(memoryContent).toContain("assistant: World");
+    expect(memoryContent).toContain("user: Thanks");
+    // Tool entries should not appear
+    expect(memoryContent).not.toContain("tool_use");
+    expect(memoryContent).not.toContain("tool_result");
+    expect(memoryContent).not.toContain("search");
+  });
+
+  it("filters out command messages starting with /", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    const sessionContent = createMockSessionContent([
+      { role: "user", content: "/help" },
+      { role: "assistant", content: "Here is help info" },
+      { role: "user", content: "Normal message" },
+      { role: "user", content: "/new" },
+    ]);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+
+    // Command messages should be filtered out
+    expect(memoryContent).not.toContain("/help");
+    expect(memoryContent).not.toContain("/new");
+    // Normal messages should be present
+    expect(memoryContent).toContain("assistant: Here is help info");
+    expect(memoryContent).toContain("user: Normal message");
+  });
+
+  it("respects custom messages config (limits to N messages)", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    // Create 10 messages
+    const entries = [];
+    for (let i = 1; i <= 10; i++) {
+      entries.push({ role: "user", content: `Message ${i}` });
+    }
+    const sessionContent = createMockSessionContent(entries);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    // Configure to only include last 3 messages
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+      hooks: {
+        internal: {
+          entries: {
+            "session-memory": { enabled: true, messages: 3 },
+          },
+        },
+      },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+
+    // Only last 3 messages should be present
+    expect(memoryContent).not.toContain("user: Message 1\n");
+    expect(memoryContent).not.toContain("user: Message 7\n");
+    expect(memoryContent).toContain("user: Message 8");
+    expect(memoryContent).toContain("user: Message 9");
+    expect(memoryContent).toContain("user: Message 10");
+  });
+
+  it("filters messages before slicing (fix for #2681)", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    // Create session with many tool entries interspersed with messages
+    // This tests that we filter FIRST, then slice - not the other way around
+    const entries = [
+      { role: "user", content: "First message" },
+      { type: "tool_use", tool: "test1" },
+      { type: "tool_result", result: "result1" },
+      { role: "assistant", content: "Second message" },
+      { type: "tool_use", tool: "test2" },
+      { type: "tool_result", result: "result2" },
+      { role: "user", content: "Third message" },
+      { type: "tool_use", tool: "test3" },
+      { type: "tool_result", result: "result3" },
+      { role: "assistant", content: "Fourth message" },
+    ];
+    const sessionContent = createMockSessionContent(entries);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    // Request 3 messages - if we sliced first, we'd only get 1-2 messages
+    // because the last 3 lines include tool entries
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+      hooks: {
+        internal: {
+          entries: {
+            "session-memory": { enabled: true, messages: 3 },
+          },
+        },
+      },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+
+    // Should have exactly 3 user/assistant messages (the last 3)
+    expect(memoryContent).not.toContain("First message");
+    expect(memoryContent).toContain("user: Third message");
+    expect(memoryContent).toContain("assistant: Second message");
+    expect(memoryContent).toContain("assistant: Fourth message");
+  });
+
+  it("handles empty session files gracefully", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: "",
+    });
+
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    // Should not throw
+    await handler(event);
+
+    // Memory file should still be created with metadata
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    expect(files.length).toBe(1);
+  });
+
+  it("handles session files with fewer messages than requested", async () => {
+    const tempDir = await makeTempWorkspace("clawdbot-session-memory-");
+    const sessionsDir = path.join(tempDir, "sessions");
+    await fs.mkdir(sessionsDir, { recursive: true });
+
+    // Only 2 messages but requesting 15 (default)
+    const sessionContent = createMockSessionContent([
+      { role: "user", content: "Only message 1" },
+      { role: "assistant", content: "Only message 2" },
+    ]);
+    const sessionFile = await writeWorkspaceFile({
+      dir: sessionsDir,
+      name: "test-session.jsonl",
+      content: sessionContent,
+    });
+
+    const cfg: ClawdbotConfig = {
+      agents: { defaults: { workspace: tempDir } },
+    };
+
+    const event = createHookEvent("command", "new", "agent:main:main", {
+      cfg,
+      previousSessionEntry: {
+        sessionId: "test-123",
+        sessionFile,
+      },
+    });
+
+    await handler(event);
+
+    const memoryDir = path.join(tempDir, "memory");
+    const files = await fs.readdir(memoryDir);
+    const memoryContent = await fs.readFile(path.join(memoryDir, files[0]!), "utf-8");
+
+    // Both messages should be included
+    expect(memoryContent).toContain("user: Only message 1");
+    expect(memoryContent).toContain("assistant: Only message 2");
+  });
+});
diff --git a/src/hooks/bundled/session-memory/handler.ts b/src/hooks/bundled/session-memory/handler.ts
index c087d73e823..c38a46e7b5f 100644
--- a/src/hooks/bundled/session-memory/handler.ts
+++ b/src/hooks/bundled/session-memory/handler.ts
@@ -11,22 +11,23 @@ import os from "node:os";
 import type { MoltbotConfig } from "../../../config/config.js";
 import { resolveAgentWorkspaceDir } from "../../../agents/agent-scope.js";
 import { resolveAgentIdFromSessionKey } from "../../../routing/session-key.js";
+import { resolveHookConfig } from "../../config.js";
 import type { HookHandler } from "../../hooks.js";
 
 /**
  * Read recent messages from session file for slug generation
  */
-async function getRecentSessionContent(sessionFilePath: string): Promise<string | null> {
+async function getRecentSessionContent(
+  sessionFilePath: string,
+  messageCount: number = 15,
+): Promise<string | null> {
   try {
     const content = await fs.readFile(sessionFilePath, "utf-8");
     const lines = content.trim().split("\n");
 
-    // Get last 15 lines (recent conversation)
-    const recentLines = lines.slice(-15);
-
-    // Parse JSONL and extract messages
-    const messages: string[] = [];
-    for (const line of recentLines) {
+    // Parse JSONL and extract user/assistant messages first
+    const allMessages: string[] = [];
+    for (const line of lines) {
       try {
         const entry = JSON.parse(line);
         // Session files have entries with type="message" containing a nested message object
@@ -39,7 +40,7 @@ async function getRecentSessionContent(sessionFilePath: string): Promise<string
               ? msg.content.find((c: any) => c.type === "text")?.text
               : msg.content;
             if (text && !text.startsWith("/")) {
-              messages.push(`${role}: ${text}`);
+              allMessages.push(`${role}: ${text}`);
             }
           }
         }
@@ -48,7 +49,9 @@ async function getRecentSessionContent(sessionFilePath: string): Promise<string
       }
     }
 
-    return messages.join("\n");
+    // Then slice to get exactly messageCount messages
+    const recentMessages = allMessages.slice(-messageCount);
+    return recentMessages.join("\n");
   } catch {
     return null;
   }
@@ -93,12 +96,19 @@ const saveSessionToMemory: HookHandler = async (event) => {
 
     const sessionFile = currentSessionFile || undefined;
 
+    // Read message count from hook config (default: 15)
+    const hookConfig = resolveHookConfig(cfg, "session-memory");
+    const messageCount =
+      typeof hookConfig?.messages === "number" && hookConfig.messages > 0
+        ? hookConfig.messages
+        : 15;
+
     let slug: string | null = null;
     let sessionContent: string | null = null;
 
     if (sessionFile) {
       // Get recent conversation content
-      sessionContent = await getRecentSessionContent(sessionFile);
+      sessionContent = await getRecentSessionContent(sessionFile, messageCount);
       console.log("[session-memory] sessionContent length:", sessionContent?.length || 0);
 
       if (sessionContent && cfg) {