diff --git a/README.md b/README.md
index 87f251cd4..51823969a 100644
--- a/README.md
+++ b/README.md
@@ -129,6 +129,12 @@ clawdis relay      # Start listening
 | `clawdis status` | Show recent messages |
 | `clawdis heartbeat` | Trigger a heartbeat |
 
+### Sessions, surfaces, and WebChat
+
+- Direct chats now share a canonical session key `main` by default (configurable via `inbound.reply.session.mainKey`). Groups stay isolated as `group:<jid>`.
+- WebChat always attaches to the `main` session and hydrates the full Tau history from `~/.clawdis/sessions/<SessionId>.jsonl`, so desktop view mirrors WhatsApp/Telegram turns.
+- Inbound contexts carry a `Surface` hint (e.g., `whatsapp`, `webchat`, `telegram`) for logging; replies still go back to the originating surface deterministically.
+
 ## Credits
 
 - **Peter Steinberger** ([@steipete](https://twitter.com/steipete)) — Creator
diff --git a/apps/macos/Sources/Clawdis/AppMain.swift b/apps/macos/Sources/Clawdis/AppMain.swift
index 1cf3f5e49..a86a093c2 100644
--- a/apps/macos/Sources/Clawdis/AppMain.swift
+++ b/apps/macos/Sources/Clawdis/AppMain.swift
@@ -90,6 +90,11 @@ final class AppState: ObservableObject {
         didSet { UserDefaults.standard.set(self.voiceWakeAdditionalLocaleIDs, forKey: voiceWakeAdditionalLocalesKey) }
     }
 
+    @Published var isWorking: Bool = false
+    @Published var earBoostActive: Bool = false
+
+    private var earBoostTask: Task<Void, Never>? = nil
+
     init() {
         self.isPaused = UserDefaults.standard.bool(forKey: pauseDefaultsKey)
         self.defaultSound = UserDefaults.standard.string(forKey: "clawdis.defaultSound") ?? ""
@@ -106,6 +111,19 @@ final class AppState: ObservableObject {
         self.voiceWakeAdditionalLocaleIDs = UserDefaults.standard
             .stringArray(forKey: voiceWakeAdditionalLocalesKey) ?? []
     }
+
+    func triggerVoiceEars(ttl: TimeInterval = 5) {
+        self.earBoostTask?.cancel()
+        self.earBoostActive = true
+        self.earBoostTask = Task { [weak self] in
+            try? await Task.sleep(nanoseconds: UInt64(ttl * 1_000_000_000))
+            await MainActor.run { [weak self] in self?.earBoostActive = false }
+        }
+    }
+
+    func setWorking(_ working: Bool) {
+        self.isWorking = working
+    }
 }
 
 @MainActor
@@ -578,7 +596,12 @@ struct ClawdisApp: App {
     }
 
     var body: some Scene {
-        MenuBarExtra { MenuContent(state: self.state) } label: { CritterStatusLabel(isPaused: self.state.isPaused) }
+        MenuBarExtra { MenuContent(state: self.state) } label: {
+            CritterStatusLabel(
+                isPaused: self.state.isPaused,
+                isWorking: self.state.isWorking,
+                earBoostActive: self.state.earBoostActive)
+        }
             .menuBarExtraStyle(.menu)
             .menuBarExtraAccess(isPresented: self.$isMenuPresented) { item in
                 self.statusItem = item
@@ -632,19 +655,19 @@ private struct MenuContent: View {
     }
 
     private func primarySessionKey() -> String {
-        // Prefer the most recently updated session from the store; fall back to default
+        // Prefer canonical main session; fall back to most recent.
         let storePath = SessionLoader.defaultStorePath
         if let data = try? Data(contentsOf: URL(fileURLWithPath: storePath)),
            let decoded = try? JSONDecoder().decode([String: SessionEntryRecord].self, from: data)
         {
+            if decoded.keys.contains("main") { return "main" }
+
             let sorted = decoded.sorted { a, b -> Bool in
                 let lhs = a.value.updatedAt ?? 0
                 let rhs = b.value.updatedAt ?? 0
                 return lhs > rhs
             }
-            if let first = sorted.first {
-                return first.key
-            }
+            if let first = sorted.first { return first.key }
         }
         return "+1003"
     }
@@ -652,6 +675,8 @@ private struct MenuContent: View {
 
 private struct CritterStatusLabel: View {
     var isPaused: Bool
+    var isWorking: Bool
+    var earBoostActive: Bool
 
     @State private var blinkAmount: CGFloat = 0
     @State private var nextBlink = Date().addingTimeInterval(Double.random(in: 3.5...8.5))
@@ -672,8 +697,9 @@ private struct CritterStatusLabel: View {
             } else {
                 Image(nsImage: CritterIconRenderer.makeIcon(
                     blink: self.blinkAmount,
-                    legWiggle: self.legWiggle,
-                    earWiggle: self.earWiggle))
+                    legWiggle: max(self.legWiggle, self.isWorking ? 0.6 : 0),
+                    earWiggle: self.earWiggle,
+                    earScale: self.earBoostActive ? 1.9 : 1.0))
                     .frame(width: 18, height: 16)
                     .rotationEffect(.degrees(self.wiggleAngle), anchor: .center)
                     .offset(x: self.wiggleOffset)
@@ -697,6 +723,10 @@ private struct CritterStatusLabel: View {
                             self.wiggleEars()
                             self.nextEarWiggle = now.addingTimeInterval(Double.random(in: 7.0...14.0))
                         }
+
+                        if self.isWorking {
+                            self.scurry()
+                        }
                     }
                     .onChange(of: self.isPaused) { _, _ in self.resetMotion() }
             }
@@ -743,6 +773,20 @@ private struct CritterStatusLabel: View {
         }
     }
 
+    private func scurry() {
+        let target = CGFloat.random(in: 0.7...1.0)
+        withAnimation(.easeInOut(duration: 0.12)) {
+            self.legWiggle = target
+            self.wiggleOffset = CGFloat.random(in: -0.6...0.6)
+        }
+        DispatchQueue.main.asyncAfter(deadline: .now() + 0.18) {
+            withAnimation(.easeOut(duration: 0.16)) {
+                self.legWiggle = 0.25
+                self.wiggleOffset = 0
+            }
+        }
+    }
+
     private func wiggleEars() {
         let target = CGFloat.random(in: -1.2...1.2)
         withAnimation(.interpolatingSpring(stiffness: 260, damping: 19)) {
@@ -757,7 +801,12 @@ private struct CritterStatusLabel: View {
 enum CritterIconRenderer {
     private static let size = NSSize(width: 18, height: 16)
 
-    static func makeIcon(blink: CGFloat, legWiggle: CGFloat = 0, earWiggle: CGFloat = 0) -> NSImage {
+    static func makeIcon(
+        blink: CGFloat,
+        legWiggle: CGFloat = 0,
+        earWiggle: CGFloat = 0,
+        earScale: CGFloat = 1
+    ) -> NSImage {
         let image = NSImage(size: size)
         image.lockFocus()
         defer { image.unlockFocus() }
@@ -774,7 +823,7 @@ enum CritterIconRenderer {
         let bodyCorner = w * 0.09
 
         let earW = w * 0.22
-        let earH = bodyH * 0.66 * (1 - 0.08 * abs(earWiggle))
+        let earH = bodyH * 0.66 * earScale * (1 - 0.08 * abs(earWiggle))
         let earCorner = earW * 0.24
 
         let legW = w * 0.11
@@ -2009,6 +2058,7 @@ final class VoiceWakeTester {
     {
         if matched, !text.isEmpty {
             self.stop()
+            AppStateStore.shared.triggerVoiceEars()
             onUpdate(.detected(text))
             return
         }
diff --git a/apps/macos/Sources/Clawdis/WebChatWindow.swift b/apps/macos/Sources/Clawdis/WebChatWindow.swift
index 2347184cd..4b8130091 100644
--- a/apps/macos/Sources/Clawdis/WebChatWindow.swift
+++ b/apps/macos/Sources/Clawdis/WebChatWindow.swift
@@ -1,13 +1,18 @@
 import AppKit
 import Foundation
+import OSLog
 import WebKit
 
-final class WebChatWindowController: NSWindowController, WKScriptMessageHandler {
+private let webChatLogger = Logger(subsystem: "com.steipete.clawdis", category: "WebChat")
+
+final class WebChatWindowController: NSWindowController, WKScriptMessageHandler, WKNavigationDelegate {
     private let webView: WKWebView
     private let sessionKey: String
+    private let initialMessagesJSON: String
 
     init(sessionKey: String) {
         self.sessionKey = sessionKey
+        self.initialMessagesJSON = WebChatWindowController.loadInitialMessagesJSON(for: sessionKey)
 
         let config = WKWebViewConfiguration()
         let contentController = WKUserContentController()
@@ -40,6 +45,11 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
             window.webkit?.messageHandlers?.clawdis?.postMessage({ id: 'log', log: String(msg) });
           } catch (_) {}
         };
+        const __origConsoleLog = console.log;
+        console.log = function(...args) {
+          try { window.__clawdisLog(args.join(' ')); } catch (_) {}
+          __origConsoleLog.apply(console, args);
+        };
         """
         let userScript = WKUserScript(source: callbackScript, injectionTime: .atDocumentStart, forMainFrameOnly: true)
         contentController.addUserScript(userScript)
@@ -53,6 +63,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
         window.title = "Clawd Web Chat"
         window.contentView = self.webView
         super.init(window: window)
+        self.webView.navigationDelegate = self
         contentController.add(self, name: "clawdis")
         self.loadPage()
     }
@@ -61,6 +72,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
     required init?(coder: NSCoder) { fatalError() }
 
     private func loadPage() {
+        let messagesJSON = self.initialMessagesJSON.replacingOccurrences(of: "</script>", with: "<\\/script>")
         guard let webChatURL = Bundle.main.url(forResource: "WebChat", withExtension: nil) else {
             NSLog("WebChat resources missing")
             return
@@ -119,6 +131,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
         <body>
           <div id="app"></div>
           <script type="module">
+            const initialMessages = \(messagesJSON);
             const status = (msg) => {
               console.log(msg);
               window.__clawdisLog(msg);
@@ -169,7 +182,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
                     systemPrompt: 'You are Clawd (primary session).',
                     model: getModel('anthropic', 'claude-opus-4-5'),
                     thinkingLevel: 'off',
-                    messages: []
+                    messages: initialMessages
                   },
                   transport: new NativeTransport()
                 });
@@ -212,6 +225,16 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
         self.webView.loadHTMLString(html, baseURL: webChatURL)
     }
 
+    func webView(_ webView: WKWebView, didFinish navigation: WKNavigation!) {
+        webView.evaluateJavaScript("document.body.innerText") { result, error in
+            if let error {
+                webChatLogger.error("eval error: \(error.localizedDescription, privacy: .public)")
+            } else if let text = result as? String {
+                webChatLogger.debug("body text snapshot: \(String(text.prefix(200)), privacy: .public)")
+            }
+        }
+    }
+
     func userContentController(_ userContentController: WKUserContentController, didReceive message: WKScriptMessage) {
         guard let body = message.body as? [String: Any],
               let id = body["id"] as? String,
@@ -219,7 +242,7 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
         else { return }
 
         if id == "log", let log = body["log"] as? String {
-            NSLog("WebChat JS: %@", log)
+            webChatLogger.debug("JS: \(log, privacy: .public)")
             return
         }
 
@@ -245,6 +268,8 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
     }
 
     private func runAgent(text: String, sessionKey: String) async -> (text: String?, error: String?) {
+        await MainActor.run { AppStateStore.shared.setWorking(true) }
+        defer { Task { await MainActor.run { AppStateStore.shared.setWorking(false) } } }
         let data: Data
         do {
             data = try await Task.detached(priority: .utility) { () -> Data in
@@ -280,6 +305,48 @@ final class WebChatWindowController: NSWindowController, WKScriptMessageHandler
         }
         return (String(data: data, encoding: .utf8), nil)
     }
+
+    private static func loadInitialMessagesJSON(for sessionKey: String) -> String {
+        guard let sessionId = self.sessionId(for: sessionKey) else { return "[]" }
+        let path = self.expand("~/.clawdis/sessions/\(sessionId).jsonl")
+        guard FileManager.default.fileExists(atPath: path) else { return "[]" }
+        guard let content = try? String(contentsOfFile: path, encoding: .utf8) else { return "[]" }
+
+        var messages: [[String: Any]] = []
+        for line in content.split(whereSeparator: { $0.isNewline }) {
+            guard let data = String(line).data(using: .utf8),
+                  let obj = try? JSONSerialization.jsonObject(with: data) as? [String: Any]
+            else { continue }
+            let message = (obj["message"] as? [String: Any]) ?? obj
+            guard let role = message["role"] as? String,
+                  ["user", "assistant", "system"].contains(role)
+            else { continue }
+
+            var contentPayload = message["content"] as? [[String: Any]]
+            if contentPayload == nil, let text = message["text"] as? String {
+                contentPayload = [["type": "text", "text": text]]
+            }
+            guard let finalContent = contentPayload else { continue }
+            messages.append(["role": role, "content": finalContent])
+        }
+
+        guard let data = try? JSONSerialization.data(withJSONObject: messages, options: []) else {
+            return "[]"
+        }
+        return String(data: data, encoding: .utf8) ?? "[]"
+    }
+
+    private static func sessionId(for key: String) -> String? {
+        let storePath = self.expand("~/.clawdis/sessions/sessions.json")
+        guard let data = try? Data(contentsOf: URL(fileURLWithPath: storePath)) else { return nil }
+        guard let decoded = try? JSONSerialization.jsonObject(with: data) as? [String: Any] else { return nil }
+        guard let entry = decoded[key] as? [String: Any] else { return nil }
+        return entry["sessionId"] as? String
+    }
+
+    private static func expand(_ path: String) -> String {
+        (path as NSString).expandingTildeInPath
+    }
 }
 
 @MainActor
diff --git a/docs/mac/icon.md b/docs/mac/icon.md
new file mode 100644
index 000000000..06a102d10
--- /dev/null
+++ b/docs/mac/icon.md
@@ -0,0 +1,21 @@
+# Menu Bar Icon States
+
+Author: steipete · Updated: 2025-12-06 · Scope: macOS app (`apps/macos`)
+
+- **Idle:** Normal icon animation (blink, occasional wiggle).
+- **Paused:** Status item uses `appearsDisabled`; no motion.
+- **Voice trigger (big ears):** Voice wake detector calls `AppState.triggerVoiceEars()` → `earBoostActive=true` for ~5s. Ears scale up (1.9x) then auto-reset. Only fired from the in-app voice pipeline.
+- **Working (agent running):** `AppState.isWorking=true` drives a “tail/leg scurry” micro-motion: faster leg wiggle and slight offset while work is in-flight. Currently toggled around WebChat agent runs; add the same toggle around other long tasks when you wire them.
+
+Wiring points
+- Voice wake: see `VoiceWakeTester.handleResult` in `AppMain.swift`—on detection it calls `triggerVoiceEars()`.
+- Agent activity: set `AppStateStore.shared.setWorking(true/false)` around work spans (already done in WebChat agent call). Keep spans short and reset in `defer` blocks to avoid stuck animations.
+
+Shapes & sizes
+- Base icon drawn in `CritterIconRenderer.makeIcon(blink:legWiggle:earWiggle:earScale:)`.
+- Ear scale defaults to `1.0`; voice boost sets `earScale=1.9` without changing overall frame (18×16pt template image).
+- Scurry uses leg wiggle up to ~1.0 with a small horizontal jiggle; it’s additive to any existing idle wiggle.
+
+Behavioral notes
+- No external CLI/XPC toggle for ears/working; keep it internal to the app’s own signals to avoid accidental flapping.
+- Keep TTLs short (<10s) so the icon returns to baseline quickly if a job hangs.
diff --git a/docs/session.md b/docs/session.md
index f92faa0b7..9a31b00e1 100644
--- a/docs/session.md
+++ b/docs/session.md
@@ -10,11 +10,13 @@ CLAWDIS keeps lightweight session state so your agent can remember context betwe
 
 ## How session keys are chosen
 
-- Direct chats: normalized E.164 sender number (e.g., `+15551234567`).
+- Direct chats: by default collapse to the canonical key `main` so all 1:1 channels (WhatsApp, WebChat, Telegram) share a single session.
 - Group chats: `group:<whatsapp-jid>` so group history stays isolated from DMs.
 - Global mode: set `inbound.reply.session.scope = "global"` to force a single shared session for all chats.
 - Unknown senders fall back to `unknown`.
 
+To change the canonical key (or disable collapsing), set `inbound.reply.session.mainKey` to another string or leave it empty.
+
 ## When sessions reset
 
 - Idle timeout: `inbound.reply.session.idleMinutes` (default 60). If no messages arrive within this window, a new `sessionId` is created on the next message.
@@ -32,11 +34,20 @@ CLAWDIS keeps lightweight session state so your agent can remember context betwe
         scope: "per-sender",      // or "global"
         resetTriggers: ["/new"],   // additional triggers allowed
         idleMinutes: 120,           // extend or shrink timeout (min 1)
-        store: "~/state/clawdis-sessions.json" // optional custom path
+        store: "~/state/clawdis-sessions.json", // optional custom path
+        mainKey: "main"             // canonical direct-chat bucket
       }
     }
   }
 }
+
+## Surfaces (channel labels)
+
+Each inbound message can carry a `Surface` hint in the templating context (e.g., `whatsapp`, `webchat`, `telegram`, `voice`). Routing stays deterministic: replies are sent back to the origin surface, but the shared `main` session keeps context unified across direct channels. Groups retain their `group:<jid>` buckets.
+
+## WebChat history
+
+WebChat always attaches to the `main` session and hydrates the full Tau JSONL transcript from `~/.clawdis/sessions/<SessionId>.jsonl`, so desktop view reflects all turns, even those that arrived via WhatsApp/Telegram.
 ```
 
 Other session-related behaviors:
diff --git a/docs/surface.md b/docs/surface.md
new file mode 100644
index 000000000..5adf96b94
--- /dev/null
+++ b/docs/surface.md
@@ -0,0 +1,14 @@
+# Surfaces & Routing
+
+Updated: 2025-12-06
+
+Goal: make replies deterministic per channel while keeping one shared context for direct chats.
+
+- **Surfaces** (channel labels): `whatsapp`, `webchat`, `telegram`, `voice`, etc. Add `Surface` to inbound `MsgContext` so templates/agents can log which channel a turn came from. Routing is fixed: replies go back to the origin surface; the model doesn’t choose.
+- **Canonical direct session:** Direct chats collapse into `main` by default via `inbound.reply.session.mainKey` (configurable). Groups stay `group:<jid>`. This keeps context unified across WhatsApp/WebChat/Telegram while preserving group isolation.
+- **Session store:** Keys are resolved via `resolveSessionKey(scope, ctx, mainKey)`; the Tau JSONL path still lives under `~/.clawdis/sessions/<SessionId>.jsonl`.
+- **WebChat:** Always attaches to `main`, loads the full Tau transcript so desktop reflects cross-surface history, and writes new turns back to the same session.
+- **Implementation hints:**
+  - Set `Surface` in each ingress (WhatsApp relay, WebChat bridge, future Telegram). 
+  - Keep routing deterministic: originate → same surface. Use IPC/web senders accordingly.
+  - Do not let the agent emit “send to X” decisions; keep that policy in the host code.
diff --git a/docs/webchat.md b/docs/webchat.md
index 3a4bf17d1..4561a758f 100644
--- a/docs/webchat.md
+++ b/docs/webchat.md
@@ -6,7 +6,7 @@ The macOS Clawdis app ships a built-in web chat window that reuses your primary
 
 - UI: `pi-mono/packages/web-ui` bundle loaded in a `WKWebView`.
 - Bridge: `WKScriptMessageHandler` named `clawdis` (see `apps/macos/Sources/Clawdis/WebChatWindow.swift`). The page posts `sessionKey` + message; Swift shells `pnpm clawdis agent --to <sessionKey> --message <text> --json` and returns the first payload text to the page. No sockets are opened.
-- Session selection: picks the most recently updated entry in `~/.clawdis/sessions/sessions.json`; falls back to `+1003` if none exist. This keeps the web chat on the same primary conversation as the relay/CLI.
+- Session selection: always uses the canonical `main` session key (or `inbound.reply.session.mainKey`), hydrating from the Tau JSONL session file so you see the full history even when messages arrived via WhatsApp/Telegram.
 - Assets: the entire `pi-web-ui` dist plus dependencies (pi-ai, mini-lit, lit, lucide, pdfjs-dist, docx-preview, jszip) is bundled into `apps/macos/Sources/Clawdis/Resources/WebChat/` and shipped with the app. No external checkout is required at runtime.
 
 ## Requirements
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index dd05c9e66..d4fd1f4e2 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -6,8 +6,8 @@ import { loadConfig, type WarelayConfig } from "../config/config.js";
 import {
   DEFAULT_IDLE_MINUTES,
   DEFAULT_RESET_TRIGGER,
-  deriveSessionKey,
   loadSessionStore,
+  resolveSessionKey,
   resolveStorePath,
   type SessionEntry,
   saveSessionStore,
@@ -210,6 +210,7 @@ export async function getReplyFromConfig(
 
   // Optional session handling (conversation reuse + /new resets)
   const sessionCfg = reply?.session;
+  const mainKey = sessionCfg?.mainKey ?? "main";
   const resetTriggers = sessionCfg?.resetTriggers?.length
     ? sessionCfg.resetTriggers
     : [DEFAULT_RESET_TRIGGER];
@@ -261,7 +262,7 @@ export async function getReplyFromConfig(
       }
     }
 
-    sessionKey = deriveSessionKey(sessionScope, ctx);
+    sessionKey = resolveSessionKey(sessionScope, ctx, mainKey);
     sessionStore = loadSessionStore(storePath);
     const entry = sessionStore[sessionKey];
     const idleMs = idleMinutes * 60_000;
diff --git a/src/auto-reply/templating.ts b/src/auto-reply/templating.ts
index ece3add05..d88650f2c 100644
--- a/src/auto-reply/templating.ts
+++ b/src/auto-reply/templating.ts
@@ -12,6 +12,7 @@ export type MsgContext = {
   GroupMembers?: string;
   SenderName?: string;
   SenderE164?: string;
+  Surface?: string;
 };
 
 export type TemplateContext = MsgContext & {
diff --git a/src/commands/agent.ts b/src/commands/agent.ts
index c51311c53..23f0acb95 100644
--- a/src/commands/agent.ts
+++ b/src/commands/agent.ts
@@ -15,8 +15,8 @@ import { type CliDeps, createDefaultDeps } from "../cli/deps.js";
 import { loadConfig, type WarelayConfig } from "../config/config.js";
 import {
   DEFAULT_IDLE_MINUTES,
-  deriveSessionKey,
   loadSessionStore,
+  resolveSessionKey,
   resolveStorePath,
   type SessionEntry,
   saveSessionStore,
@@ -67,6 +67,7 @@ function resolveSession(opts: {
 }): SessionResolution {
   const sessionCfg = opts.replyCfg?.session;
   const scope = sessionCfg?.scope ?? "per-sender";
+  const mainKey = sessionCfg?.mainKey ?? "main";
   const idleMinutes = Math.max(
     sessionCfg?.idleMinutes ?? DEFAULT_IDLE_MINUTES,
     1,
@@ -78,7 +79,7 @@ function resolveSession(opts: {
 
   let sessionKey: string | undefined =
     sessionStore && opts.to
-      ? deriveSessionKey(scope, { From: opts.to } as MsgContext)
+      ? resolveSessionKey(scope, { From: opts.to } as MsgContext, mainKey)
       : undefined;
   let sessionEntry =
     sessionKey && sessionStore ? sessionStore[sessionKey] : undefined;
diff --git a/src/config/config.ts b/src/config/config.ts
index b01a97b18..093d355f3 100644
--- a/src/config/config.ts
+++ b/src/config/config.ts
@@ -23,6 +23,7 @@ export type SessionConfig = {
   sessionIntro?: string;
   typingIntervalSeconds?: number;
   heartbeatMinutes?: number;
+  mainKey?: string;
 };
 
 export type LoggingConfig = {
@@ -135,6 +136,7 @@ const ReplySchema = z
         sendSystemOnce: z.boolean().optional(),
         sessionIntro: z.string().optional(),
         typingIntervalSeconds: z.number().int().positive().optional(),
+        mainKey: z.string().optional(),
       })
       .optional(),
     heartbeatMinutes: z.number().int().nonnegative().optional(),
diff --git a/src/config/sessions.test.ts b/src/config/sessions.test.ts
index 0743d1503..df6b768a3 100644
--- a/src/config/sessions.test.ts
+++ b/src/config/sessions.test.ts
@@ -1,6 +1,6 @@
 import { describe, expect, it } from "vitest";
 
-import { deriveSessionKey } from "./sessions.js";
+import { deriveSessionKey, resolveSessionKey } from "./sessions.js";
 
 describe("sessions", () => {
   it("returns normalized per-sender key", () => {
@@ -22,4 +22,16 @@ describe("sessions", () => {
       "group:12345-678@g.us",
     );
   });
+
+  it("maps direct chats to main key when provided", () => {
+    expect(
+      resolveSessionKey("per-sender", { From: "whatsapp:+1555" }, "main"),
+    ).toBe("main");
+  });
+
+  it("leaves groups untouched even with main key", () => {
+    expect(
+      resolveSessionKey("per-sender", { From: "12345-678@g.us" }, "main"),
+    ).toBe("group:12345-678@g.us");
+  });
 });
diff --git a/src/config/sessions.ts b/src/config/sessions.ts
index a512a61c9..17b5a9502 100644
--- a/src/config/sessions.ts
+++ b/src/config/sessions.ts
@@ -77,3 +77,20 @@ export function deriveSessionKey(scope: SessionScope, ctx: MsgContext) {
   }
   return from || "unknown";
 }
+
+/**
+ * Resolve the session key with an optional canonical direct-chat key (e.g., "main").
+ * All non-group direct chats collapse to `mainKey` when provided, keeping group isolation.
+ */
+export function resolveSessionKey(
+  scope: SessionScope,
+  ctx: MsgContext,
+  mainKey?: string,
+) {
+  const raw = deriveSessionKey(scope, ctx);
+  if (scope === "global") return raw;
+  const canonical = (mainKey ?? "").trim();
+  const isGroup = raw.startsWith("group:") || raw.includes("@g.us");
+  if (!isGroup && canonical) return canonical;
+  return raw;
+}
diff --git a/src/index.ts b/src/index.ts
index b46c8f5b3..a175c0280 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -12,6 +12,7 @@ import { loadConfig } from "./config/config.js";
 import {
   deriveSessionKey,
   loadSessionStore,
+  resolveSessionKey,
   resolveStorePath,
   saveSessionStore,
 } from "./config/sessions.js";
@@ -52,6 +53,7 @@ export {
   normalizeE164,
   PortInUseError,
   promptYesNo,
+  resolveSessionKey,
   resolveStorePath,
   runCommandWithTimeout,
   runExec,
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index f11163140..a232971d5 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -5,8 +5,8 @@ import { waitForever } from "../cli/wait.js";
 import { loadConfig } from "../config/config.js";
 import {
   DEFAULT_IDLE_MINUTES,
-  deriveSessionKey,
   loadSessionStore,
+  resolveSessionKey,
   resolveStorePath,
   saveSessionStore,
 } from "../config/sessions.js";
@@ -213,11 +213,15 @@ export async function runWebHeartbeatOnce(opts: {
   });
 
   const cfg = cfgOverride ?? loadConfig();
+  const sessionCfg = cfg.inbound?.reply?.session;
+  const mainKey = sessionCfg?.mainKey ?? "main";
+  const sessionScope = sessionCfg?.scope ?? "per-sender";
+  const sessionKey = resolveSessionKey(sessionScope, { From: to }, mainKey);
   if (sessionId) {
     const storePath = resolveStorePath(cfg.inbound?.reply?.session?.store);
     const store = loadSessionStore(storePath);
-    store[to] = {
-      ...(store[to] ?? {}),
+    store[sessionKey] = {
+      ...(store[sessionKey] ?? {}),
       sessionId,
       updatedAt: Date.now(),
     };
@@ -432,7 +436,11 @@ function getSessionSnapshot(
 ) {
   const sessionCfg = cfg.inbound?.reply?.session;
   const scope = sessionCfg?.scope ?? "per-sender";
-  const key = deriveSessionKey(scope, { From: from, To: "", Body: "" });
+  const key = resolveSessionKey(
+    scope,
+    { From: from, To: "", Body: "" },
+    sessionCfg?.mainKey ?? "main",
+  );
   const store = loadSessionStore(resolveStorePath(sessionCfg?.store));
   const entry = store[key];
   const idleMinutes = Math.max(
@@ -790,6 +798,7 @@ export async function monitorWebProvider(
           GroupMembers: latest.groupParticipants?.join(", "),
           SenderName: latest.senderName,
           SenderE164: latest.senderE164,
+          Surface: "whatsapp",
         },
         {
           onReplyStart: latest.sendComposing,