diff --git a/apps/macos/Sources/Clawdis/AgentRPC.swift b/apps/macos/Sources/Clawdis/AgentRPC.swift
index 87d0540c6..6c5d7b53b 100644
--- a/apps/macos/Sources/Clawdis/AgentRPC.swift
+++ b/apps/macos/Sources/Clawdis/AgentRPC.swift
@@ -62,17 +62,19 @@ actor AgentRPC {
     func send(
         text: String,
         thinking: String?,
-        session: String,
+        sessionKey: String,
         deliver: Bool,
-        to: String?) async -> (ok: Bool, text: String?, error: String?)
+        to: String?,
+        channel: String? = nil) async -> (ok: Bool, text: String?, error: String?)
     {
         do {
             let params: [String: Any] = [
                 "message": text,
-                "sessionId": session,
+                "sessionKey": sessionKey,
                 "thinking": thinking ?? "default",
                 "deliver": deliver,
                 "to": to ?? "",
+                "channel": channel ?? "",
                 "idempotencyKey": UUID().uuidString,
             ]
             _ = try await self.controlRequest(method: "agent", params: ControlRequestParams(raw: params))
diff --git a/apps/macos/Sources/Clawdis/ControlRequestHandler.swift b/apps/macos/Sources/Clawdis/ControlRequestHandler.swift
index 43da27283..30a578c33 100644
--- a/apps/macos/Sources/Clawdis/ControlRequestHandler.swift
+++ b/apps/macos/Sources/Clawdis/ControlRequestHandler.swift
@@ -57,9 +57,10 @@ enum ControlRequestHandler {
             let rpcResult = await AgentRPC.shared.send(
                 text: trimmed,
                 thinking: thinking,
-                session: sessionKey,
+                sessionKey: sessionKey,
                 deliver: deliver,
-                to: to)
+                to: to,
+                channel: nil)
             return rpcResult.ok
                 ? Response(ok: true, message: rpcResult.text ?? "sent")
                 : Response(ok: false, message: rpcResult.error ?? "failed to send")
diff --git a/apps/macos/Sources/Clawdis/VoiceWakeForwarder.swift b/apps/macos/Sources/Clawdis/VoiceWakeForwarder.swift
index 91e2e2576..cc2b368e1 100644
--- a/apps/macos/Sources/Clawdis/VoiceWakeForwarder.swift
+++ b/apps/macos/Sources/Clawdis/VoiceWakeForwarder.swift
@@ -33,10 +33,11 @@ enum VoiceWakeForwarder {
     }
 
     struct ForwardOptions: Sendable {
-        var session: String = "main"
+        var sessionKey: String = "main"
         var thinking: String = "low"
         var deliver: Bool = true
         var to: String?
+        var channel: String = "last"
     }
 
     @discardableResult
@@ -45,12 +46,15 @@ enum VoiceWakeForwarder {
         options: ForwardOptions = ForwardOptions()) async -> Result<Void, VoiceWakeForwardError>
     {
         let payload = Self.prefixedTranscript(transcript)
+        let channel = options.channel.trimmingCharacters(in: .whitespacesAndNewlines).lowercased()
+        let deliver = options.deliver && channel != "webchat"
         let result = await AgentRPC.shared.send(
             text: payload,
             thinking: options.thinking,
-            session: options.session,
-            deliver: options.deliver,
-            to: options.to)
+            sessionKey: options.sessionKey,
+            deliver: deliver,
+            to: options.to,
+            channel: channel)
 
         if result.ok {
             self.logger.info("voice wake forward ok")
diff --git a/apps/macos/Sources/ClawdisProtocol/GatewayModels.swift b/apps/macos/Sources/ClawdisProtocol/GatewayModels.swift
index e1737d652..6b7c4a475 100644
--- a/apps/macos/Sources/ClawdisProtocol/GatewayModels.swift
+++ b/apps/macos/Sources/ClawdisProtocol/GatewayModels.swift
@@ -28,8 +28,8 @@ public struct Hello: Codable {
         caps: [String]?,
         auth: [String: AnyCodable]?,
         locale: String?,
-        useragent: String?)
-    {
+        useragent: String?
+    ) {
         self.type = type
         self.minprotocol = minprotocol
         self.maxprotocol = maxprotocol
@@ -39,7 +39,6 @@ public struct Hello: Codable {
         self.locale = locale
         self.useragent = useragent
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case minprotocol = "minProtocol"
@@ -66,8 +65,8 @@ public struct HelloOk: Codable {
         server: [String: AnyCodable],
         features: [String: AnyCodable],
         snapshot: Snapshot,
-        policy: [String: AnyCodable])
-    {
+        policy: [String: AnyCodable]
+    ) {
         self.type = type
         self._protocol = _protocol
         self.server = server
@@ -75,7 +74,6 @@ public struct HelloOk: Codable {
         self.snapshot = snapshot
         self.policy = policy
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case _protocol = "protocol"
@@ -96,14 +94,13 @@ public struct HelloError: Codable {
         type: String,
         reason: String,
         expectedprotocol: Int?,
-        minclient: String?)
-    {
+        minclient: String?
+    ) {
         self.type = type
         self.reason = reason
         self.expectedprotocol = expectedprotocol
         self.minclient = minclient
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case reason
@@ -122,14 +119,13 @@ public struct RequestFrame: Codable {
         type: String,
         id: String,
         method: String,
-        params: AnyCodable?)
-    {
+        params: AnyCodable?
+    ) {
         self.type = type
         self.id = id
         self.method = method
         self.params = params
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case id
@@ -150,15 +146,14 @@ public struct ResponseFrame: Codable {
         id: String,
         ok: Bool,
         payload: AnyCodable?,
-        error: [String: AnyCodable]?)
-    {
+        error: [String: AnyCodable]?
+    ) {
         self.type = type
         self.id = id
         self.ok = ok
         self.payload = payload
         self.error = error
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case id
@@ -180,15 +175,14 @@ public struct EventFrame: Codable {
         event: String,
         payload: AnyCodable?,
         seq: Int?,
-        stateversion: [String: AnyCodable]?)
-    {
+        stateversion: [String: AnyCodable]?
+    ) {
         self.type = type
         self.event = event
         self.payload = payload
         self.seq = seq
         self.stateversion = stateversion
     }
-
     private enum CodingKeys: String, CodingKey {
         case type
         case event
@@ -220,8 +214,8 @@ public struct PresenceEntry: Codable {
         tags: [String]?,
         text: String?,
         ts: Int,
-        instanceid: String?)
-    {
+        instanceid: String?
+    ) {
         self.host = host
         self.ip = ip
         self.version = version
@@ -233,7 +227,6 @@ public struct PresenceEntry: Codable {
         self.ts = ts
         self.instanceid = instanceid
     }
-
     private enum CodingKeys: String, CodingKey {
         case host
         case ip
@@ -254,12 +247,11 @@ public struct StateVersion: Codable {
 
     public init(
         presence: Int,
-        health: Int)
-    {
+        health: Int
+    ) {
         self.presence = presence
         self.health = health
     }
-
     private enum CodingKeys: String, CodingKey {
         case presence
         case health
@@ -276,14 +268,13 @@ public struct Snapshot: Codable {
         presence: [PresenceEntry],
         health: AnyCodable,
         stateversion: StateVersion,
-        uptimems: Int)
-    {
+        uptimems: Int
+    ) {
         self.presence = presence
         self.health = health
         self.stateversion = stateversion
         self.uptimems = uptimems
     }
-
     private enum CodingKeys: String, CodingKey {
         case presence
         case health
@@ -304,15 +295,14 @@ public struct ErrorShape: Codable {
         message: String,
         details: AnyCodable?,
         retryable: Bool?,
-        retryafterms: Int?)
-    {
+        retryafterms: Int?
+    ) {
         self.code = code
         self.message = message
         self.details = details
         self.retryable = retryable
         self.retryafterms = retryafterms
     }
-
     private enum CodingKeys: String, CodingKey {
         case code
         case message
@@ -334,15 +324,14 @@ public struct AgentEvent: Codable {
         seq: Int,
         stream: String,
         ts: Int,
-        data: [String: AnyCodable])
-    {
+        data: [String: AnyCodable]
+    ) {
         self.runid = runid
         self.seq = seq
         self.stream = stream
         self.ts = ts
         self.data = data
     }
-
     private enum CodingKeys: String, CodingKey {
         case runid = "runId"
         case seq
@@ -364,15 +353,14 @@ public struct SendParams: Codable {
         message: String,
         mediaurl: String?,
         provider: String?,
-        idempotencykey: String)
-    {
+        idempotencykey: String
+    ) {
         self.to = to
         self.message = message
         self.mediaurl = mediaurl
         self.provider = provider
         self.idempotencykey = idempotencykey
     }
-
     private enum CodingKeys: String, CodingKey {
         case to
         case message
@@ -386,8 +374,10 @@ public struct AgentParams: Codable {
     public let message: String
     public let to: String?
     public let sessionid: String?
+    public let sessionkey: String?
     public let thinking: String?
     public let deliver: Bool?
+    public let channel: String?
     public let timeout: Int?
     public let idempotencykey: String
 
@@ -395,40 +385,135 @@ public struct AgentParams: Codable {
         message: String,
         to: String?,
         sessionid: String?,
+        sessionkey: String?,
         thinking: String?,
         deliver: Bool?,
+        channel: String?,
         timeout: Int?,
-        idempotencykey: String)
-    {
+        idempotencykey: String
+    ) {
         self.message = message
         self.to = to
         self.sessionid = sessionid
+        self.sessionkey = sessionkey
         self.thinking = thinking
         self.deliver = deliver
+        self.channel = channel
         self.timeout = timeout
         self.idempotencykey = idempotencykey
     }
-
     private enum CodingKeys: String, CodingKey {
         case message
         case to
         case sessionid = "sessionId"
+        case sessionkey = "sessionKey"
         case thinking
         case deliver
+        case channel
         case timeout
         case idempotencykey = "idempotencyKey"
     }
 }
 
+public struct ChatHistoryParams: Codable {
+    public let sessionkey: String
+
+    public init(
+        sessionkey: String
+    ) {
+        self.sessionkey = sessionkey
+    }
+    private enum CodingKeys: String, CodingKey {
+        case sessionkey = "sessionKey"
+    }
+}
+
+public struct ChatSendParams: Codable {
+    public let sessionkey: String
+    public let message: String
+    public let thinking: String?
+    public let deliver: Bool?
+    public let attachments: [AnyCodable]?
+    public let timeoutms: Int?
+    public let idempotencykey: String
+
+    public init(
+        sessionkey: String,
+        message: String,
+        thinking: String?,
+        deliver: Bool?,
+        attachments: [AnyCodable]?,
+        timeoutms: Int?,
+        idempotencykey: String
+    ) {
+        self.sessionkey = sessionkey
+        self.message = message
+        self.thinking = thinking
+        self.deliver = deliver
+        self.attachments = attachments
+        self.timeoutms = timeoutms
+        self.idempotencykey = idempotencykey
+    }
+    private enum CodingKeys: String, CodingKey {
+        case sessionkey = "sessionKey"
+        case message
+        case thinking
+        case deliver
+        case attachments
+        case timeoutms = "timeoutMs"
+        case idempotencykey = "idempotencyKey"
+    }
+}
+
+public struct ChatEvent: Codable {
+    public let runid: String
+    public let sessionkey: String
+    public let seq: Int
+    public let state: AnyCodable
+    public let message: AnyCodable?
+    public let errormessage: String?
+    public let usage: AnyCodable?
+    public let stopreason: String?
+
+    public init(
+        runid: String,
+        sessionkey: String,
+        seq: Int,
+        state: AnyCodable,
+        message: AnyCodable?,
+        errormessage: String?,
+        usage: AnyCodable?,
+        stopreason: String?
+    ) {
+        self.runid = runid
+        self.sessionkey = sessionkey
+        self.seq = seq
+        self.state = state
+        self.message = message
+        self.errormessage = errormessage
+        self.usage = usage
+        self.stopreason = stopreason
+    }
+    private enum CodingKeys: String, CodingKey {
+        case runid = "runId"
+        case sessionkey = "sessionKey"
+        case seq
+        case state
+        case message
+        case errormessage = "errorMessage"
+        case usage
+        case stopreason = "stopReason"
+    }
+}
+
 public struct TickEvent: Codable {
     public let ts: Int
 
     public init(
-        ts: Int)
-    {
+        ts: Int
+    ) {
         self.ts = ts
     }
-
     private enum CodingKeys: String, CodingKey {
         case ts
     }
@@ -440,12 +525,11 @@ public struct ShutdownEvent: Codable {
 
     public init(
         reason: String,
-        restartexpectedms: Int?)
-    {
+        restartexpectedms: Int?
+    ) {
         self.reason = reason
         self.restartexpectedms = restartexpectedms
     }
-
     private enum CodingKeys: String, CodingKey {
         case reason
         case restartexpectedms = "restartExpectedMs"
@@ -469,17 +553,17 @@ public enum GatewayFrame: Codable {
         }
         switch type {
         case "hello":
-            self = try .hello(Self.decodePayload(Hello.self, from: raw))
+            self = .hello(try Self.decodePayload(Hello.self, from: raw))
         case "hello-ok":
-            self = try .helloOk(Self.decodePayload(HelloOk.self, from: raw))
+            self = .helloOk(try Self.decodePayload(HelloOk.self, from: raw))
         case "hello-error":
-            self = try .helloError(Self.decodePayload(HelloError.self, from: raw))
+            self = .helloError(try Self.decodePayload(HelloError.self, from: raw))
         case "req":
-            self = try .req(Self.decodePayload(RequestFrame.self, from: raw))
+            self = .req(try Self.decodePayload(RequestFrame.self, from: raw))
         case "res":
-            self = try .res(Self.decodePayload(ResponseFrame.self, from: raw))
+            self = .res(try Self.decodePayload(ResponseFrame.self, from: raw))
         case "event":
-            self = try .event(Self.decodePayload(EventFrame.self, from: raw))
+            self = .event(try Self.decodePayload(EventFrame.self, from: raw))
         default:
             self = .unknown(type: type, raw: raw)
         }
@@ -487,26 +571,23 @@ public enum GatewayFrame: Codable {
 
     public func encode(to encoder: Encoder) throws {
         switch self {
-        case let .hello(v): try v.encode(to: encoder)
-        case let .helloOk(v): try v.encode(to: encoder)
-        case let .helloError(v): try v.encode(to: encoder)
-        case let .req(v): try v.encode(to: encoder)
-        case let .res(v): try v.encode(to: encoder)
-        case let .event(v): try v.encode(to: encoder)
-        case let .unknown(_, raw):
+        case .hello(let v): try v.encode(to: encoder)
+        case .helloOk(let v): try v.encode(to: encoder)
+        case .helloError(let v): try v.encode(to: encoder)
+        case .req(let v): try v.encode(to: encoder)
+        case .res(let v): try v.encode(to: encoder)
+        case .event(let v): try v.encode(to: encoder)
+        case .unknown(_, let raw):
             var container = encoder.singleValueContainer()
             try container.encode(raw)
         }
     }
 
+
     private static func decodePayload<T: Decodable>(_ type: T.Type, from raw: [String: AnyCodable]) throws -> T {
-        // Re-encode the already-decoded map using `JSONEncoder` instead of
-        // `JSONSerialization` because `AnyCodable` values are not bridged to
-        // Objective-C types and `JSONSerialization` throws an ObjC exception,
-        // crashing the app (seen on macOS 26.1). `JSONEncoder` understands
-        // `Encodable` values and stays in Swift land.
-        let data = try JSONEncoder().encode(raw)
+        let data = try JSONSerialization.data(withJSONObject: raw)
         let decoder = JSONDecoder()
         return try decoder.decode(T.self, from: data)
     }
+
 }
diff --git a/apps/macos/Sources/ClawdisProtocol/Protocol.swift b/apps/macos/Sources/ClawdisProtocol/Protocol.swift
deleted file mode 100644
index 60841ecd4..000000000
--- a/apps/macos/Sources/ClawdisProtocol/Protocol.swift
+++ /dev/null
@@ -1,6 +0,0 @@
-// Legacy shim: Protocol definitions now live in GatewayModels.swift generated from TypeBox.
-// Kept to satisfy existing project references.
-import Foundation
-
-@available(*, deprecated, message: "Use GatewayModels.swift (GatewayFrame and payload structs)")
-public enum LegacyProtocolShim {}
diff --git a/apps/macos/Tests/ClawdisIPCTests/VoiceWakeForwarderTests.swift b/apps/macos/Tests/ClawdisIPCTests/VoiceWakeForwarderTests.swift
index 13ef28f9e..1307888d5 100644
--- a/apps/macos/Tests/ClawdisIPCTests/VoiceWakeForwarderTests.swift
+++ b/apps/macos/Tests/ClawdisIPCTests/VoiceWakeForwarderTests.swift
@@ -13,9 +13,10 @@ import Testing
 
     @Test func forwardOptionsDefaults() {
         let opts = VoiceWakeForwarder.ForwardOptions()
-        #expect(opts.session == "main")
+        #expect(opts.sessionKey == "main")
         #expect(opts.thinking == "low")
         #expect(opts.deliver == true)
         #expect(opts.to == nil)
+        #expect(opts.channel == "last")
     }
 }
diff --git a/dist/protocol.schema.json b/dist/protocol.schema.json
index a1e1b542f..f22d0d7a9 100644
--- a/dist/protocol.schema.json
+++ b/dist/protocol.schema.json
@@ -1108,12 +1108,18 @@
         "sessionId": {
           "type": "string"
         },
+        "sessionKey": {
+          "type": "string"
+        },
         "thinking": {
           "type": "string"
         },
         "deliver": {
           "type": "boolean"
         },
+        "channel": {
+          "type": "string"
+        },
         "timeout": {
           "minimum": 0,
           "type": "integer"
@@ -1128,6 +1134,104 @@
         "idempotencyKey"
       ]
     },
+    "ChatHistoryParams": {
+      "additionalProperties": false,
+      "type": "object",
+      "properties": {
+        "sessionKey": {
+          "minLength": 1,
+          "type": "string"
+        }
+      },
+      "required": [
+        "sessionKey"
+      ]
+    },
+    "ChatSendParams": {
+      "additionalProperties": false,
+      "type": "object",
+      "properties": {
+        "sessionKey": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "message": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "thinking": {
+          "type": "string"
+        },
+        "deliver": {
+          "type": "boolean"
+        },
+        "attachments": {
+          "type": "array",
+          "items": {}
+        },
+        "timeoutMs": {
+          "minimum": 0,
+          "type": "integer"
+        },
+        "idempotencyKey": {
+          "minLength": 1,
+          "type": "string"
+        }
+      },
+      "required": [
+        "sessionKey",
+        "message",
+        "idempotencyKey"
+      ]
+    },
+    "ChatEvent": {
+      "additionalProperties": false,
+      "type": "object",
+      "properties": {
+        "runId": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "sessionKey": {
+          "minLength": 1,
+          "type": "string"
+        },
+        "seq": {
+          "minimum": 0,
+          "type": "integer"
+        },
+        "state": {
+          "anyOf": [
+            {
+              "const": "delta",
+              "type": "string"
+            },
+            {
+              "const": "final",
+              "type": "string"
+            },
+            {
+              "const": "error",
+              "type": "string"
+            }
+          ]
+        },
+        "message": {},
+        "errorMessage": {
+          "type": "string"
+        },
+        "usage": {},
+        "stopReason": {
+          "type": "string"
+        }
+      },
+      "required": [
+        "runId",
+        "sessionKey",
+        "seq",
+        "state"
+      ]
+    },
     "TickEvent": {
       "additionalProperties": false,
       "type": "object",
diff --git a/scripts/protocol-gen.ts b/scripts/protocol-gen.ts
index f0629ae37..a915791a9 100644
--- a/scripts/protocol-gen.ts
+++ b/scripts/protocol-gen.ts
@@ -2,12 +2,6 @@ import { promises as fs } from "node:fs";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 import { ProtocolSchemas } from "../src/gateway/protocol/schema.js";
-import {
-  InputData,
-  JSONSchemaInput,
-  JSONSchemaStore,
-  quicktype,
-} from "quicktype-core";
 
 const __dirname = path.dirname(fileURLToPath(import.meta.url));
 const repoRoot = path.resolve(__dirname, "..");
@@ -53,40 +47,8 @@ async function writeJsonSchema() {
   return { jsonSchemaPath, schemaString: JSON.stringify(rootSchema) };
 }
 
-async function writeSwiftModels(schemaString: string) {
-  const schemaInput = new JSONSchemaInput(new JSONSchemaStore());
-  await schemaInput.addSource({ name: "ClawdisGateway", schema: schemaString });
-
-  const inputData = new InputData();
-  inputData.addInput(schemaInput);
-
-  const qtResult = await quicktype({
-    inputData,
-    lang: "swift",
-    topLevel: "GatewayFrame",
-    rendererOptions: {
-      "struct-or-class": "struct",
-      "immutable-types": "true",
-      "accessLevel": "public",
-    },
-  });
-
-  const swiftDir = path.join(
-    repoRoot,
-    "apps",
-    "macos",
-    "Sources",
-    "ClawdisProtocol",
-  );
-  await fs.mkdir(swiftDir, { recursive: true });
-  const swiftPath = path.join(swiftDir, "Protocol.swift");
-  await fs.writeFile(swiftPath, qtResult.lines.join("\n"));
-  console.log(`wrote ${swiftPath}`);
-}
-
 async function main() {
-  const { schemaString } = await writeJsonSchema();
-  await writeSwiftModels(schemaString);
+  await writeJsonSchema();
 }
 
 main().catch((err) => {
diff --git a/src/commands/agent.ts b/src/commands/agent.ts
index aad1b3d46..9a709397b 100644
--- a/src/commands/agent.ts
+++ b/src/commands/agent.ts
@@ -1,4 +1,5 @@
 import crypto from "node:crypto";
+import { chunkText } from "../auto-reply/chunk.js";
 import { runCommandReply } from "../auto-reply/command-reply.js";
 import {
   applyTemplate,
@@ -36,6 +37,8 @@ type AgentCommandOpts = {
   timeout?: string;
   deliver?: boolean;
   surface?: string;
+  provider?: string;
+  bestEffortDeliver?: boolean;
 };
 
 type SessionResolution = {
@@ -369,11 +372,47 @@ export async function agentCommand(
 
   const payloads = result.payloads ?? [];
   const deliver = opts.deliver === true;
-  const targetTo = opts.to ? normalizeE164(opts.to) : allowFrom[0];
-  if (deliver && !targetTo) {
-    throw new Error(
-      "Delivering to WhatsApp requires --to <E.164> or inbound.allowFrom[0]",
-    );
+  const bestEffortDeliver = opts.bestEffortDeliver === true;
+  const provider = (opts.provider ?? "whatsapp").toLowerCase();
+
+  const whatsappTarget = opts.to ? normalizeE164(opts.to) : allowFrom[0];
+  const telegramTarget = opts.to?.trim() || undefined;
+
+  const logDeliveryError = (err: unknown) => {
+    const message = `Delivery failed (${provider}): ${String(err)}`;
+    runtime.error?.(message);
+    if (!runtime.error) runtime.log(message);
+  };
+
+  if (deliver) {
+    if (provider === "whatsapp" && !whatsappTarget) {
+      const err = new Error(
+        "Delivering to WhatsApp requires --to <E.164> or inbound.allowFrom[0]",
+      );
+      if (!bestEffortDeliver) throw err;
+      logDeliveryError(err);
+    }
+    if (provider === "telegram" && !telegramTarget) {
+      const err = new Error("Delivering to Telegram requires --to <chatId>");
+      if (!bestEffortDeliver) throw err;
+      logDeliveryError(err);
+    }
+    if (provider === "webchat") {
+      const err = new Error(
+        "Delivering to WebChat is not supported via `clawdis agent`; use WebChat RPC instead.",
+      );
+      if (!bestEffortDeliver) throw err;
+      logDeliveryError(err);
+    }
+    if (
+      provider !== "whatsapp" &&
+      provider !== "telegram" &&
+      provider !== "webchat"
+    ) {
+      const err = new Error(`Unknown provider: ${provider}`);
+      if (!bestEffortDeliver) throw err;
+      logDeliveryError(err);
+    }
   }
 
   if (opts.json) {
@@ -414,22 +453,55 @@ export async function agentCommand(
       runtime.log(lines.join("\n"));
     }
 
-    if (deliver && targetTo) {
-      const text = payload.text ?? "";
-      const media = mediaList;
-      if (!text && media.length === 0) continue;
+    if (!deliver) continue;
 
-      const primaryMedia = media[0];
-      await deps.sendMessageWhatsApp(targetTo, text, {
-        verbose: false,
-        mediaUrl: primaryMedia,
-      });
+    const text = payload.text ?? "";
+    const media = mediaList;
+    if (!text && media.length === 0) continue;
 
-      for (const extra of media.slice(1)) {
-        await deps.sendMessageWhatsApp(targetTo, "", {
+    if (provider === "whatsapp" && whatsappTarget) {
+      try {
+        const primaryMedia = media[0];
+        await deps.sendMessageWhatsApp(whatsappTarget, text, {
           verbose: false,
-          mediaUrl: extra,
+          mediaUrl: primaryMedia,
         });
+
+        for (const extra of media.slice(1)) {
+          await deps.sendMessageWhatsApp(whatsappTarget, "", {
+            verbose: false,
+            mediaUrl: extra,
+          });
+        }
+      } catch (err) {
+        if (!bestEffortDeliver) throw err;
+        logDeliveryError(err);
+      }
+      continue;
+    }
+
+    if (provider === "telegram" && telegramTarget) {
+      try {
+        if (media.length === 0) {
+          for (const chunk of chunkText(text, 4000)) {
+            await deps.sendMessageTelegram(telegramTarget, chunk, {
+              verbose: false,
+            });
+          }
+        } else {
+          let first = true;
+          for (const url of media) {
+            const caption = first ? text : "";
+            first = false;
+            await deps.sendMessageTelegram(telegramTarget, caption, {
+              verbose: false,
+              mediaUrl: url,
+            });
+          }
+        }
+      } catch (err) {
+        if (!bestEffortDeliver) throw err;
+        logDeliveryError(err);
       }
     }
   }
diff --git a/src/config/sessions.ts b/src/config/sessions.ts
index e5f16b754..e5223bdbf 100644
--- a/src/config/sessions.ts
+++ b/src/config/sessions.ts
@@ -1,3 +1,4 @@
+import crypto from "node:crypto";
 import fs from "node:fs";
 import os from "node:os";
 import path from "node:path";
@@ -20,6 +21,8 @@ export type SessionEntry = {
   totalTokens?: number;
   model?: string;
   contextTokens?: number;
+  lastChannel?: "whatsapp" | "telegram" | "webchat";
+  lastTo?: string;
   // Optional flag to mirror Mac app UI and future sync states.
   syncing?: boolean | string;
 };
@@ -66,6 +69,37 @@ export async function saveSessionStore(
   );
 }
 
+export async function updateLastRoute(params: {
+  storePath: string;
+  sessionKey: string;
+  channel: SessionEntry["lastChannel"];
+  to?: string;
+}) {
+  const { storePath, sessionKey, channel, to } = params;
+  const store = loadSessionStore(storePath);
+  const existing = store[sessionKey];
+  const now = Date.now();
+  const next: SessionEntry = {
+    sessionId: existing?.sessionId ?? crypto.randomUUID(),
+    updatedAt: Math.max(existing?.updatedAt ?? 0, now),
+    systemSent: existing?.systemSent,
+    abortedLastRun: existing?.abortedLastRun,
+    thinkingLevel: existing?.thinkingLevel,
+    verboseLevel: existing?.verboseLevel,
+    inputTokens: existing?.inputTokens,
+    outputTokens: existing?.outputTokens,
+    totalTokens: existing?.totalTokens,
+    model: existing?.model,
+    contextTokens: existing?.contextTokens,
+    syncing: existing?.syncing,
+    lastChannel: channel,
+    lastTo: to?.trim() ? to.trim() : undefined,
+  };
+  store[sessionKey] = next;
+  await saveSessionStore(storePath, store);
+  return next;
+}
+
 // Decide which session bucket to use (per-sender vs global).
 export function deriveSessionKey(scope: SessionScope, ctx: MsgContext) {
   if (scope === "global") return "global";
diff --git a/src/gateway/protocol/schema.ts b/src/gateway/protocol/schema.ts
index f4fddd402..e998ada14 100644
--- a/src/gateway/protocol/schema.ts
+++ b/src/gateway/protocol/schema.ts
@@ -211,8 +211,10 @@ export const AgentParamsSchema = Type.Object(
     message: NonEmptyString,
     to: Type.Optional(Type.String()),
     sessionId: Type.Optional(Type.String()),
+    sessionKey: Type.Optional(Type.String()),
     thinking: Type.Optional(Type.String()),
     deliver: Type.Optional(Type.Boolean()),
+    channel: Type.Optional(Type.String()),
     timeout: Type.Optional(Type.Integer({ minimum: 0 })),
     idempotencyKey: NonEmptyString,
   },
diff --git a/src/gateway/server.test.ts b/src/gateway/server.test.ts
index 3551d6784..9407a67fe 100644
--- a/src/gateway/server.test.ts
+++ b/src/gateway/server.test.ts
@@ -2,8 +2,8 @@ import { type AddressInfo, createServer } from "node:net";
 import { describe, expect, test, vi } from "vitest";
 import { WebSocket } from "ws";
 import { emitAgentEvent } from "../infra/agent-events.js";
-import { startGatewayServer } from "./server.js";
 import { GatewayLockError } from "../infra/gateway-lock.js";
+import { startGatewayServer } from "./server.js";
 
 vi.mock("../commands/health.js", () => ({
   getHealthSnapshot: vi.fn().mockResolvedValue({ ok: true, stub: true }),
@@ -35,7 +35,10 @@ async function getFreePort(): Promise<number> {
   });
 }
 
-async function occupyPort(): Promise<{ server: ReturnType<typeof createServer>; port: number }> {
+async function occupyPort(): Promise<{
+  server: ReturnType<typeof createServer>;
+  port: number;
+}> {
   return await new Promise((resolve, reject) => {
     const server = createServer();
     server.once("error", reject);
diff --git a/src/gateway/server.ts b/src/gateway/server.ts
index 49f8b409f..43b3ca613 100644
--- a/src/gateway/server.ts
+++ b/src/gateway/server.ts
@@ -1,8 +1,11 @@
 import { randomUUID } from "node:crypto";
 import fs from "node:fs";
+import {
+  createServer as createHttpServer,
+  type Server as HttpServer,
+} from "node:http";
 import os from "node:os";
 import path from "node:path";
-import { createServer as createHttpServer, type Server as HttpServer } from "node:http";
 import chalk from "chalk";
 import { type WebSocket, WebSocketServer } from "ws";
 import { createDefaultDeps } from "../cli/deps.js";
@@ -850,7 +853,9 @@ export async function startGatewayServer(
                 break;
               }
             }
-            const { storePath, store, entry } = loadSessionEntry(p.sessionKey);
+            const { cfg, storePath, store, entry } = loadSessionEntry(
+              p.sessionKey,
+            );
             const now = Date.now();
             const sessionId = entry?.sessionId ?? randomUUID();
             const sessionEntry: SessionEntry = {
@@ -859,7 +864,15 @@ export async function startGatewayServer(
               thinkingLevel: entry?.thinkingLevel,
               verboseLevel: entry?.verboseLevel,
               systemSent: entry?.systemSent,
+              lastChannel: entry?.lastChannel,
+              lastTo: entry?.lastTo,
             };
+            const mainKey =
+              (cfg.inbound?.reply?.session?.mainKey ?? "main").trim() || "main";
+            if (p.sessionKey === mainKey) {
+              sessionEntry.lastChannel = "webchat";
+              delete sessionEntry.lastTo;
+            }
             if (store) {
               store[p.sessionKey] = sessionEntry;
               if (storePath) {
@@ -1081,8 +1094,10 @@ export async function startGatewayServer(
               message: string;
               to?: string;
               sessionId?: string;
+              sessionKey?: string;
               thinking?: string;
               deliver?: boolean;
+              channel?: string;
               idempotencyKey: string;
               timeout?: number;
             };
@@ -1095,7 +1110,90 @@ export async function startGatewayServer(
               break;
             }
             const message = params.message.trim();
-            const runId = params.sessionId || randomUUID();
+
+            const requestedSessionKey =
+              typeof params.sessionKey === "string" && params.sessionKey.trim()
+                ? params.sessionKey.trim()
+                : undefined;
+            let resolvedSessionId = params.sessionId?.trim() || undefined;
+            let sessionEntry: SessionEntry | undefined;
+            let bestEffortDeliver = false;
+
+            if (requestedSessionKey) {
+              const { cfg, storePath, store, entry } =
+                loadSessionEntry(requestedSessionKey);
+              const now = Date.now();
+              const sessionId = entry?.sessionId ?? randomUUID();
+              sessionEntry = {
+                sessionId,
+                updatedAt: now,
+                thinkingLevel: entry?.thinkingLevel,
+                verboseLevel: entry?.verboseLevel,
+                systemSent: entry?.systemSent,
+                lastChannel: entry?.lastChannel,
+                lastTo: entry?.lastTo,
+              };
+              if (store) {
+                store[requestedSessionKey] = sessionEntry;
+                if (storePath) {
+                  await saveSessionStore(storePath, store);
+                }
+              }
+              resolvedSessionId = sessionId;
+              const mainKey =
+                (cfg.inbound?.reply?.session?.mainKey ?? "main").trim() ||
+                "main";
+              if (requestedSessionKey === mainKey) {
+                chatRunSessions.set(sessionId, requestedSessionKey);
+                bestEffortDeliver = true;
+              }
+            }
+
+            const runId = resolvedSessionId || randomUUID();
+
+            const requestedChannelRaw =
+              typeof params.channel === "string" ? params.channel.trim() : "";
+            const requestedChannel = requestedChannelRaw
+              ? requestedChannelRaw.toLowerCase()
+              : "last";
+
+            const lastChannel = sessionEntry?.lastChannel;
+            const lastTo =
+              typeof sessionEntry?.lastTo === "string"
+                ? sessionEntry.lastTo.trim()
+                : "";
+
+            const resolvedChannel = (() => {
+              if (requestedChannel === "last") {
+                return lastChannel ?? "whatsapp";
+              }
+              if (
+                requestedChannel === "whatsapp" ||
+                requestedChannel === "telegram" ||
+                requestedChannel === "webchat"
+              ) {
+                return requestedChannel;
+              }
+              return lastChannel ?? "whatsapp";
+            })();
+
+            const resolvedTo = (() => {
+              const explicit =
+                typeof params.to === "string" && params.to.trim()
+                  ? params.to.trim()
+                  : undefined;
+              if (explicit) return explicit;
+              if (
+                resolvedChannel === "whatsapp" ||
+                resolvedChannel === "telegram"
+              ) {
+                return lastTo || undefined;
+              }
+              return undefined;
+            })();
+
+            const deliver =
+              params.deliver === true && resolvedChannel !== "webchat";
             // Acknowledge via event to avoid double res frames
             const ackEvent = {
               type: "event",
@@ -1114,11 +1212,14 @@ export async function startGatewayServer(
               await agentCommand(
                 {
                   message,
-                  to: params.to,
-                  sessionId: params.sessionId,
+                  to: resolvedTo,
+                  sessionId: resolvedSessionId,
                   thinking: params.thinking,
-                  deliver: params.deliver,
+                  deliver,
+                  provider: resolvedChannel,
                   timeout: params.timeout?.toString(),
+                  bestEffortDeliver,
+                  surface: "VoiceWake",
                 },
                 defaultRuntime,
                 deps,
diff --git a/src/telegram/bot.ts b/src/telegram/bot.ts
index 5a42beedd..fadf2708e 100644
--- a/src/telegram/bot.ts
+++ b/src/telegram/bot.ts
@@ -10,6 +10,7 @@ import { formatAgentEnvelope } from "../auto-reply/envelope.js";
 import { getReplyFromConfig } from "../auto-reply/reply.js";
 import type { ReplyPayload } from "../auto-reply/types.js";
 import { loadConfig } from "../config/config.js";
+import { resolveStorePath, updateLastRoute } from "../config/sessions.js";
 import { danger, logVerbose } from "../globals.js";
 import { getChildLogger } from "../logging.js";
 import { mediaKindFromMime } from "../media/constants.js";
@@ -145,6 +146,18 @@ export function createTelegramBot(opts: TelegramBotOptions) {
         MediaUrl: media?.path,
       };
 
+      if (!isGroup) {
+        const sessionCfg = cfg.inbound?.reply?.session;
+        const mainKey = (sessionCfg?.mainKey ?? "main").trim() || "main";
+        const storePath = resolveStorePath(sessionCfg?.store);
+        await updateLastRoute({
+          storePath,
+          sessionKey: mainKey,
+          channel: "telegram",
+          to: String(chatId),
+        });
+      }
+
       if (logVerbose()) {
         const preview = body.slice(0, 200).replace(/\n/g, "\\n");
         logVerbose(
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index c12ffdb88..aa84f1071 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -10,6 +10,7 @@ import {
   resolveSessionKey,
   resolveStorePath,
   saveSessionStore,
+  updateLastRoute,
 } from "../config/sessions.js";
 import { danger, isVerbose, logVerbose, success } from "../globals.js";
 import { emitHeartbeatEvent } from "../infra/heartbeat-events.js";
@@ -849,6 +850,23 @@ export async function monitorWebProvider(
         `\n[${tsDisplay}] ${fromDisplay} -> ${latest.to}: ${combinedBody}`,
       );
 
+      if (latest.chatType !== "group") {
+        const sessionCfg = cfg.inbound?.reply?.session;
+        const mainKey = (sessionCfg?.mainKey ?? "main").trim() || "main";
+        const storePath = resolveStorePath(sessionCfg?.store);
+        const to = latest.senderE164
+          ? normalizeE164(latest.senderE164)
+          : jidToE164(latest.from);
+        if (to) {
+          await updateLastRoute({
+            storePath,
+            sessionKey: mainKey,
+            channel: "whatsapp",
+            to,
+          });
+        }
+      }
+
       const replyResult = await (replyResolver ?? getReplyFromConfig)(
         {
           Body: combinedBody,