diff --git a/CHANGELOG.md b/CHANGELOG.md
index daff7f3a1..083967884 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -37,6 +37,7 @@
 
 ### Fixes
 - Sub-agents: normalize announce delivery origin + queue bucketing by accountId to keep multi-account routing stable. (#1061, #1058) — thanks @adam91holt.
+- Sessions: include deliveryContext in sessions.list and reuse normalized delivery routing for announce/restart fallbacks. (#1058)
 - Gateway: honor explicit delivery targets without implicit accountId fallback; preserve lastAccountId for implicit routing.
 - Gateway: avoid reusing last-to/accountId when the requested channel differs; sync deliveryContext with last route fields.
 - Repo: fix oxlint config filename and move ignore pattern into config. (#1064) — thanks @connorshea.
diff --git a/src/agents/tools/sessions-announce-target.test.ts b/src/agents/tools/sessions-announce-target.test.ts
index bc34eecd0..c405d03a6 100644
--- a/src/agents/tools/sessions-announce-target.test.ts
+++ b/src/agents/tools/sessions-announce-target.test.ts
@@ -26,9 +26,11 @@ describe("resolveAnnounceTarget", () => {
       sessions: [
         {
           key: "agent:main:whatsapp:group:123@g.us",
-          lastChannel: "whatsapp",
-          lastTo: "123@g.us",
-          lastAccountId: "work",
+          deliveryContext: {
+            channel: "whatsapp",
+            to: "123@g.us",
+            accountId: "work",
+          },
         },
       ],
     });
diff --git a/src/agents/tools/sessions-announce-target.ts b/src/agents/tools/sessions-announce-target.ts
index 06cc4965a..ed993788f 100644
--- a/src/agents/tools/sessions-announce-target.ts
+++ b/src/agents/tools/sessions-announce-target.ts
@@ -33,9 +33,19 @@ export async function resolveAnnounceTarget(params: {
       sessions.find((entry) => entry?.key === params.sessionKey) ??
       sessions.find((entry) => entry?.key === params.displayKey);
 
-    const channel = typeof match?.lastChannel === "string" ? match.lastChannel : undefined;
-    const to = typeof match?.lastTo === "string" ? match.lastTo : undefined;
-    const accountId = typeof match?.lastAccountId === "string" ? match.lastAccountId : undefined;
+    const deliveryContext =
+      match?.deliveryContext && typeof match.deliveryContext === "object"
+        ? (match.deliveryContext as Record<string, unknown>)
+        : undefined;
+    const channel =
+      (typeof deliveryContext?.channel === "string" ? deliveryContext.channel : undefined) ??
+      (typeof match?.lastChannel === "string" ? match.lastChannel : undefined);
+    const to =
+      (typeof deliveryContext?.to === "string" ? deliveryContext.to : undefined) ??
+      (typeof match?.lastTo === "string" ? match.lastTo : undefined);
+    const accountId =
+      (typeof deliveryContext?.accountId === "string" ? deliveryContext.accountId : undefined) ??
+      (typeof match?.lastAccountId === "string" ? match.lastAccountId : undefined);
     if (channel && to) return { channel, to, accountId };
   } catch {
     // ignore
diff --git a/src/agents/tools/sessions-list-tool.ts b/src/agents/tools/sessions-list-tool.ts
index dc8bae6de..ad50fc0b0 100644
--- a/src/agents/tools/sessions-list-tool.ts
+++ b/src/agents/tools/sessions-list-tool.ts
@@ -167,9 +167,21 @@ export function createSessionsListTool(opts?: {
         });
 
         const entryChannel = typeof entry.channel === "string" ? entry.channel : undefined;
-        const lastChannel = typeof entry.lastChannel === "string" ? entry.lastChannel : undefined;
+        const deliveryContext =
+          entry.deliveryContext && typeof entry.deliveryContext === "object"
+            ? (entry.deliveryContext as Record<string, unknown>)
+            : undefined;
+        const deliveryChannel =
+          typeof deliveryContext?.channel === "string" ? deliveryContext.channel : undefined;
+        const deliveryTo =
+          typeof deliveryContext?.to === "string" ? deliveryContext.to : undefined;
+        const deliveryAccountId =
+          typeof deliveryContext?.accountId === "string" ? deliveryContext.accountId : undefined;
+        const lastChannel =
+          deliveryChannel ?? (typeof entry.lastChannel === "string" ? entry.lastChannel : undefined);
         const lastAccountId =
-          typeof entry.lastAccountId === "string" ? entry.lastAccountId : undefined;
+          deliveryAccountId ??
+          (typeof entry.lastAccountId === "string" ? entry.lastAccountId : undefined);
         const derivedChannel = deriveChannel({
           key,
           kind,
@@ -201,7 +213,7 @@ export function createSessionsListTool(opts?: {
             typeof entry.abortedLastRun === "boolean" ? entry.abortedLastRun : undefined,
           sendPolicy: typeof entry.sendPolicy === "string" ? entry.sendPolicy : undefined,
           lastChannel,
-          lastTo: typeof entry.lastTo === "string" ? entry.lastTo : undefined,
+          lastTo: deliveryTo ?? (typeof entry.lastTo === "string" ? entry.lastTo : undefined),
           lastAccountId,
           transcriptPath,
         };
diff --git a/src/auto-reply/reply/session.ts b/src/auto-reply/reply/session.ts
index 3e6ff9f16..d6751b135 100644
--- a/src/auto-reply/reply/session.ts
+++ b/src/auto-reply/reply/session.ts
@@ -201,9 +201,10 @@ export async function initSessionState(params: {
   const baseEntry = !isNewSession && freshEntry ? entry : undefined;
   // Track the originating channel/to for announce routing (subagent announce-back).
   const lastChannelRaw =
-    (ctx.OriginatingChannel as string | undefined)?.trim() || baseEntry?.lastChannel;
-  const lastToRaw = ctx.OriginatingTo?.trim() || ctx.To?.trim() || baseEntry?.lastTo;
-  const lastAccountIdRaw = ctx.AccountId?.trim() || baseEntry?.lastAccountId;
+    (ctx.OriginatingChannel as string | undefined) || baseEntry?.lastChannel;
+  const lastToRaw = (ctx.OriginatingTo as string | undefined) || ctx.To || baseEntry?.lastTo;
+  const lastAccountIdRaw =
+    (ctx.AccountId as string | undefined) || baseEntry?.lastAccountId;
   const deliveryFields = normalizeSessionDeliveryFields({
     deliveryContext: {
       channel: lastChannelRaw,
diff --git a/src/commands/agent.delivery.test.ts b/src/commands/agent.delivery.test.ts
index 8eabd336a..273fbb984 100644
--- a/src/commands/agent.delivery.test.ts
+++ b/src/commands/agent.delivery.test.ts
@@ -20,9 +20,15 @@ vi.mock("../infra/outbound/deliver.js", () => ({
   deliverOutboundPayloads: mocks.deliverOutboundPayloads,
 }));
 
-vi.mock("../infra/outbound/targets.js", () => ({
-  resolveOutboundTarget: mocks.resolveOutboundTarget,
-}));
+vi.mock("../infra/outbound/targets.js", async () => {
+  const actual = await vi.importActual<typeof import("../infra/outbound/targets.js")>(
+    "../infra/outbound/targets.js",
+  );
+  return {
+    ...actual,
+    resolveOutboundTarget: mocks.resolveOutboundTarget,
+  };
+});
 
 describe("deliverAgentCommandResult", () => {
   beforeEach(() => {
@@ -178,4 +184,39 @@ describe("deliverAgentCommandResult", () => {
       expect.objectContaining({ accountId: undefined, channel: "whatsapp" }),
     );
   });
+
+  it("uses session last channel when none is provided", async () => {
+    const cfg = {} as ClawdbotConfig;
+    const deps = {} as CliDeps;
+    const runtime = {
+      log: vi.fn(),
+      error: vi.fn(),
+    } as unknown as RuntimeEnv;
+    const sessionEntry = {
+      lastChannel: "telegram",
+      lastTo: "123",
+    } as SessionEntry;
+    const result = {
+      payloads: [{ text: "hi" }],
+      meta: {},
+    };
+
+    const { deliverAgentCommandResult } = await import("./agent/delivery.js");
+    await deliverAgentCommandResult({
+      cfg,
+      deps,
+      runtime,
+      opts: {
+        message: "hello",
+        deliver: true,
+      },
+      sessionEntry,
+      result,
+      payloads: result.payloads,
+    });
+
+    expect(mocks.resolveOutboundTarget).toHaveBeenCalledWith(
+      expect.objectContaining({ channel: "telegram", to: "123" }),
+    );
+  });
 });
diff --git a/src/commands/agent/delivery.ts b/src/commands/agent/delivery.ts
index 5fb97c3a2..32335c902 100644
--- a/src/commands/agent/delivery.ts
+++ b/src/commands/agent/delivery.ts
@@ -1,6 +1,4 @@
 import { getChannelPlugin, normalizeChannelId } from "../../channels/plugins/index.js";
-import type { ChannelOutboundTargetMode } from "../../channels/plugins/types.js";
-import { DEFAULT_CHAT_CHANNEL } from "../../channels/registry.js";
 import { createOutboundSendDeps, type CliDeps } from "../../cli/outbound-send-deps.js";
 import type { ClawdbotConfig } from "../../config/config.js";
 import type { SessionEntry } from "../../config/sessions.js";
@@ -12,34 +10,16 @@ import {
   normalizeOutboundPayloads,
   normalizeOutboundPayloadsForJson,
 } from "../../infra/outbound/payloads.js";
+import { resolveAgentDeliveryPlan } from "../../infra/outbound/agent-delivery.js";
 import { resolveOutboundTarget } from "../../infra/outbound/targets.js";
 import type { RuntimeEnv } from "../../runtime.js";
-import {
-  isInternalMessageChannel,
-  resolveGatewayMessageChannel,
-} from "../../utils/message-channel.js";
-import { normalizeAccountId } from "../../utils/account-id.js";
-import { deliveryContextFromSession } from "../../utils/delivery-context.js";
+import { isInternalMessageChannel } from "../../utils/message-channel.js";
 import type { AgentCommandOpts } from "./types.js";
 
 type RunResult = Awaited<
   ReturnType<(typeof import("../../agents/pi-embedded.js"))["runEmbeddedPiAgent"]>
 >;
 
-function resolveDeliveryAccountId(params: {
-  opts: AgentCommandOpts;
-  sessionEntry?: SessionEntry;
-  targetMode: ChannelOutboundTargetMode;
-  deliveryChannel?: string;
-}) {
-  const sessionOrigin = deliveryContextFromSession(params.sessionEntry);
-  const explicit = normalizeAccountId(params.opts.accountId);
-  if (explicit || params.targetMode !== "implicit") return explicit;
-  if (!params.deliveryChannel || isInternalMessageChannel(params.deliveryChannel)) return undefined;
-  if (sessionOrigin?.channel !== params.deliveryChannel) return undefined;
-  return normalizeAccountId(sessionOrigin?.accountId);
-}
-
 export async function deliverAgentCommandResult(params: {
   cfg: ClawdbotConfig;
   deps: CliDeps;
@@ -52,7 +32,14 @@ export async function deliverAgentCommandResult(params: {
   const { cfg, deps, runtime, opts, sessionEntry, payloads, result } = params;
   const deliver = opts.deliver === true;
   const bestEffortDeliver = opts.bestEffortDeliver === true;
-  const deliveryChannel = resolveGatewayMessageChannel(opts.channel) ?? DEFAULT_CHAT_CHANNEL;
+  const deliveryPlan = resolveAgentDeliveryPlan({
+    sessionEntry,
+    requestedChannel: opts.channel,
+    explicitTo: opts.to,
+    accountId: opts.accountId,
+    wantsDelivery: deliver,
+  });
+  const deliveryChannel = deliveryPlan.resolvedChannel;
   // Channel docking: delivery channels are resolved via plugin registry.
   const deliveryPlugin = !isInternalMessageChannel(deliveryChannel)
     ? getChannelPlugin(normalizeChannelId(deliveryChannel) ?? deliveryChannel)
@@ -61,19 +48,14 @@ export async function deliverAgentCommandResult(params: {
   const isDeliveryChannelKnown =
     isInternalMessageChannel(deliveryChannel) || Boolean(deliveryPlugin);
 
-  const targetMode: ChannelOutboundTargetMode =
-    opts.deliveryTargetMode ?? (opts.to ? "explicit" : "implicit");
-  const resolvedAccountId = resolveDeliveryAccountId({
-    opts,
-    sessionEntry,
-    targetMode,
-    deliveryChannel,
-  });
+  const targetMode =
+    opts.deliveryTargetMode ?? deliveryPlan.deliveryTargetMode ?? (opts.to ? "explicit" : "implicit");
+  const resolvedAccountId = deliveryPlan.resolvedAccountId;
   const resolvedTarget =
     deliver && isDeliveryChannelKnown && deliveryChannel
       ? resolveOutboundTarget({
           channel: deliveryChannel,
-          to: opts.to,
+          to: deliveryPlan.resolvedTo,
           cfg,
           accountId: resolvedAccountId,
           mode: targetMode,
diff --git a/src/config/sessions/store.ts b/src/config/sessions/store.ts
index b2639addf..3544cdcf0 100644
--- a/src/config/sessions/store.ts
+++ b/src/config/sessions/store.ts
@@ -332,24 +332,19 @@ export async function updateLastRoute(params: {
     const store = loadSessionStore(storePath);
     const existing = store[sessionKey];
     const now = Date.now();
-    const trimmedAccountId = accountId?.trim();
-    const resolvedAccountId =
-      trimmedAccountId && trimmedAccountId.length > 0
-        ? trimmedAccountId
-        : existing?.lastAccountId ?? existing?.deliveryContext?.accountId;
     const normalized = normalizeSessionDeliveryFields({
       deliveryContext: {
-        channel: channel ?? existing?.lastChannel,
-        to,
-        accountId: resolvedAccountId,
+        channel: channel ?? existing?.lastChannel ?? existing?.deliveryContext?.channel,
+        to: to ?? existing?.lastTo ?? existing?.deliveryContext?.to,
+        accountId: accountId ?? existing?.lastAccountId ?? existing?.deliveryContext?.accountId,
       },
     });
     const next = mergeSessionEntry(existing, {
       updatedAt: Math.max(existing?.updatedAt ?? 0, now),
       deliveryContext: normalized.deliveryContext,
-      lastChannel: normalized.lastChannel ?? channel,
-      lastTo: normalized.lastTo ?? (to?.trim() ? to.trim() : undefined),
-      lastAccountId: normalized.lastAccountId ?? resolvedAccountId,
+      lastChannel: normalized.lastChannel,
+      lastTo: normalized.lastTo,
+      lastAccountId: normalized.lastAccountId,
     });
     store[sessionKey] = next;
     await saveSessionStoreUnlocked(storePath, store);
diff --git a/src/gateway/server-methods/agent.ts b/src/gateway/server-methods/agent.ts
index 37373a1af..33c2d7b10 100644
--- a/src/gateway/server-methods/agent.ts
+++ b/src/gateway/server-methods/agent.ts
@@ -1,5 +1,4 @@
 import { randomUUID } from "node:crypto";
-import { DEFAULT_CHAT_CHANNEL } from "../../channels/registry.js";
 import { agentCommand } from "../../commands/agent.js";
 import { loadConfig } from "../../config/config.js";
 import {
@@ -9,10 +8,10 @@ import {
   updateSessionStore,
 } from "../../config/sessions.js";
 import { registerAgentRunContext } from "../../infra/agent-events.js";
-import { resolveOutboundTarget, resolveSessionDeliveryTarget } from "../../infra/outbound/targets.js";
+import { resolveAgentDeliveryPlan } from "../../infra/outbound/agent-delivery.js";
+import { resolveOutboundTarget } from "../../infra/outbound/targets.js";
 import { defaultRuntime } from "../../runtime.js";
 import { resolveSendPolicy } from "../../sessions/send-policy.js";
-import { normalizeAccountId } from "../../utils/account-id.js";
 import { normalizeSessionDeliveryFields } from "../../utils/delivery-context.js";
 import {
   INTERNAL_MESSAGE_CHANNEL,
@@ -202,53 +201,21 @@ export const agentHandlers: GatewayRequestHandlers = {
     const runId = idem;
 
     const wantsDelivery = request.deliver === true;
-    const requestedChannel = normalizeMessageChannel(request.channel) ?? "last";
     const explicitTo =
       typeof request.to === "string" && request.to.trim() ? request.to.trim() : undefined;
-
-    const baseDelivery = resolveSessionDeliveryTarget({
-      entry: sessionEntry,
-      requestedChannel: requestedChannel === INTERNAL_MESSAGE_CHANNEL ? "last" : requestedChannel,
+    const deliveryPlan = resolveAgentDeliveryPlan({
+      sessionEntry,
+      requestedChannel: request.channel,
       explicitTo,
+      accountId: request.accountId,
+      wantsDelivery,
     });
 
-    const resolvedChannel = (() => {
-      if (requestedChannel === INTERNAL_MESSAGE_CHANNEL) return INTERNAL_MESSAGE_CHANNEL;
-      if (requestedChannel === "last") {
-        // WebChat is not a deliverable surface. Treat it as "unset" for routing,
-        // so VoiceWake and CLI callers don't get stuck with deliver=false.
-        if (baseDelivery.channel && baseDelivery.channel !== INTERNAL_MESSAGE_CHANNEL) {
-          return baseDelivery.channel;
-        }
-        return wantsDelivery ? DEFAULT_CHAT_CHANNEL : INTERNAL_MESSAGE_CHANNEL;
-      }
+    const resolvedChannel = deliveryPlan.resolvedChannel;
+    const deliveryTargetMode = deliveryPlan.deliveryTargetMode;
+    const resolvedAccountId = deliveryPlan.resolvedAccountId;
+    let resolvedTo = deliveryPlan.resolvedTo;
 
-      if (isGatewayMessageChannel(requestedChannel)) return requestedChannel;
-
-      if (baseDelivery.channel && baseDelivery.channel !== INTERNAL_MESSAGE_CHANNEL) {
-        return baseDelivery.channel;
-      }
-      return wantsDelivery ? DEFAULT_CHAT_CHANNEL : INTERNAL_MESSAGE_CHANNEL;
-    })();
-
-    const deliveryTargetMode = explicitTo
-      ? "explicit"
-      : isDeliverableMessageChannel(resolvedChannel)
-        ? "implicit"
-        : undefined;
-    const resolvedAccountId =
-      normalizeAccountId(request.accountId) ??
-      (deliveryTargetMode === "implicit" && resolvedChannel === baseDelivery.lastChannel
-        ? baseDelivery.lastAccountId
-        : undefined);
-    let resolvedTo = explicitTo;
-    if (
-      !resolvedTo &&
-      isDeliverableMessageChannel(resolvedChannel) &&
-      resolvedChannel === baseDelivery.lastChannel
-    ) {
-      resolvedTo = baseDelivery.lastTo;
-    }
     if (!resolvedTo && isDeliverableMessageChannel(resolvedChannel)) {
       const cfg = cfgForAgent ?? loadConfig();
       const fallback = resolveOutboundTarget({
diff --git a/src/gateway/server-restart-sentinel.ts b/src/gateway/server-restart-sentinel.ts
index 723cad067..d0661c063 100644
--- a/src/gateway/server-restart-sentinel.ts
+++ b/src/gateway/server-restart-sentinel.ts
@@ -11,6 +11,7 @@ import {
 } from "../infra/restart-sentinel.js";
 import { enqueueSystemEvent } from "../infra/system-events.js";
 import { defaultRuntime } from "../runtime.js";
+import { deliveryContextFromSession, mergeDeliveryContext } from "../utils/delivery-context.js";
 import { loadSessionEntry } from "./session-utils.js";
 
 export async function scheduleRestartSentinelWake(params: { deps: CliDeps }) {
@@ -28,12 +29,11 @@ export async function scheduleRestartSentinelWake(params: { deps: CliDeps }) {
   }
 
   const { cfg, entry } = loadSessionEntry(sessionKey);
-  const lastChannel = entry?.lastChannel;
-  const lastTo = entry?.lastTo?.trim();
   const parsedTarget = resolveAnnounceTargetFromKey(sessionKey);
-  const channelRaw = lastChannel ?? parsedTarget?.channel;
+  const origin = mergeDeliveryContext(deliveryContextFromSession(entry), parsedTarget ?? undefined);
+  const channelRaw = origin?.channel;
   const channel = channelRaw ? normalizeChannelId(channelRaw) : null;
-  const to = lastTo || parsedTarget?.to;
+  const to = origin?.to;
   if (!channel || !to) {
     enqueueSystemEvent(message, { sessionKey });
     return;
@@ -43,7 +43,7 @@ export async function scheduleRestartSentinelWake(params: { deps: CliDeps }) {
     channel,
     to,
     cfg,
-    accountId: parsedTarget?.accountId ?? entry?.lastAccountId,
+    accountId: origin?.accountId,
     mode: "implicit",
   });
   if (!resolved.ok) {
diff --git a/src/gateway/server.sessions.gateway-server-sessions-a.test.ts b/src/gateway/server.sessions.gateway-server-sessions-a.test.ts
index 9396c50fd..83f1c136b 100644
--- a/src/gateway/server.sessions.gateway-server-sessions-a.test.ts
+++ b/src/gateway/server.sessions.gateway-server-sessions-a.test.ts
@@ -128,6 +128,7 @@ describe("gateway server sessions", () => {
         thinkingLevel?: string;
         verboseLevel?: string;
         lastAccountId?: string;
+        deliveryContext?: { channel?: string; to?: string; accountId?: string };
       }>;
     }>(ws, "sessions.list", { includeGlobal: false, includeUnknown: false });
 
@@ -140,6 +141,11 @@ describe("gateway server sessions", () => {
     expect(main?.thinkingLevel).toBe("low");
     expect(main?.verboseLevel).toBe("on");
     expect(main?.lastAccountId).toBe("work");
+    expect(main?.deliveryContext).toEqual({
+      channel: "whatsapp",
+      to: "+1555",
+      accountId: "work",
+    });
 
     const active = await rpcReq<{
       sessions: Array<{ key: string }>;
diff --git a/src/gateway/session-utils.ts b/src/gateway/session-utils.ts
index 099de7eeb..9382edc05 100644
--- a/src/gateway/session-utils.ts
+++ b/src/gateway/session-utils.ts
@@ -21,6 +21,7 @@ import {
   normalizeMainKey,
   parseAgentSessionKey,
 } from "../routing/session-key.js";
+import { normalizeSessionDeliveryFields } from "../utils/delivery-context.js";
 import type {
   GatewayAgentRow,
   GatewaySessionRow,
@@ -401,6 +402,7 @@ export function listSessionsFromStore(params: {
               key,
             })
           : undefined);
+      const deliveryFields = normalizeSessionDeliveryFields(entry);
       return {
         key,
         kind: classifySessionKey(key, entry),
@@ -427,9 +429,10 @@ export function listSessionsFromStore(params: {
         modelProvider: entry?.modelProvider,
         model: entry?.model,
         contextTokens: entry?.contextTokens,
-        lastChannel: entry?.lastChannel,
-        lastTo: entry?.lastTo,
-        lastAccountId: entry?.lastAccountId,
+        deliveryContext: deliveryFields.deliveryContext,
+        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));
diff --git a/src/gateway/session-utils.types.ts b/src/gateway/session-utils.types.ts
index d69c7b342..cb11db95a 100644
--- a/src/gateway/session-utils.types.ts
+++ b/src/gateway/session-utils.types.ts
@@ -1,4 +1,5 @@
 import type { SessionEntry } from "../config/sessions.js";
+import type { DeliveryContext } from "../utils/delivery-context.js";
 
 export type GatewaySessionsDefaults = {
   modelProvider: string | null;
@@ -32,6 +33,7 @@ export type GatewaySessionRow = {
   modelProvider?: string;
   model?: string;
   contextTokens?: number;
+  deliveryContext?: DeliveryContext;
   lastChannel?: SessionEntry["lastChannel"];
   lastTo?: string;
   lastAccountId?: string;
diff --git a/src/infra/outbound/agent-delivery.ts b/src/infra/outbound/agent-delivery.ts
new file mode 100644
index 000000000..adde8ee24
--- /dev/null
+++ b/src/infra/outbound/agent-delivery.ts
@@ -0,0 +1,88 @@
+import { DEFAULT_CHAT_CHANNEL } from "../../channels/registry.js";
+import type { ChannelOutboundTargetMode } from "../../channels/plugins/types.js";
+import type { SessionEntry } from "../../config/sessions.js";
+import { normalizeAccountId } from "../../utils/account-id.js";
+import {
+  INTERNAL_MESSAGE_CHANNEL,
+  isDeliverableMessageChannel,
+  isGatewayMessageChannel,
+  normalizeMessageChannel,
+  type GatewayMessageChannel,
+} from "../../utils/message-channel.js";
+import { resolveSessionDeliveryTarget, type SessionDeliveryTarget } from "./targets.js";
+
+export type AgentDeliveryPlan = {
+  baseDelivery: SessionDeliveryTarget;
+  resolvedChannel: GatewayMessageChannel;
+  resolvedTo?: string;
+  resolvedAccountId?: string;
+  deliveryTargetMode?: ChannelOutboundTargetMode;
+};
+
+export function resolveAgentDeliveryPlan(params: {
+  sessionEntry?: SessionEntry;
+  requestedChannel?: string;
+  explicitTo?: string;
+  accountId?: string;
+  wantsDelivery: boolean;
+}): AgentDeliveryPlan {
+  const requestedRaw =
+    typeof params.requestedChannel === "string" ? params.requestedChannel.trim() : "";
+  const normalizedRequested = requestedRaw ? normalizeMessageChannel(requestedRaw) : undefined;
+  const requestedChannel = normalizedRequested || "last";
+
+  const explicitTo =
+    typeof params.explicitTo === "string" && params.explicitTo.trim()
+      ? params.explicitTo.trim()
+      : undefined;
+
+  const baseDelivery = resolveSessionDeliveryTarget({
+    entry: params.sessionEntry,
+    requestedChannel: requestedChannel === INTERNAL_MESSAGE_CHANNEL ? "last" : requestedChannel,
+    explicitTo,
+  });
+
+  const resolvedChannel = (() => {
+    if (requestedChannel === INTERNAL_MESSAGE_CHANNEL) return INTERNAL_MESSAGE_CHANNEL;
+    if (requestedChannel === "last") {
+      if (baseDelivery.channel && baseDelivery.channel !== INTERNAL_MESSAGE_CHANNEL) {
+        return baseDelivery.channel;
+      }
+      return params.wantsDelivery ? DEFAULT_CHAT_CHANNEL : INTERNAL_MESSAGE_CHANNEL;
+    }
+
+    if (isGatewayMessageChannel(requestedChannel)) return requestedChannel;
+
+    if (baseDelivery.channel && baseDelivery.channel !== INTERNAL_MESSAGE_CHANNEL) {
+      return baseDelivery.channel;
+    }
+    return params.wantsDelivery ? DEFAULT_CHAT_CHANNEL : INTERNAL_MESSAGE_CHANNEL;
+  })();
+
+  const deliveryTargetMode = explicitTo
+    ? "explicit"
+    : isDeliverableMessageChannel(resolvedChannel)
+      ? "implicit"
+      : undefined;
+
+  const resolvedAccountId =
+    normalizeAccountId(params.accountId) ??
+    (deliveryTargetMode === "implicit" ? baseDelivery.accountId : undefined);
+
+  let resolvedTo = explicitTo;
+  if (
+    !resolvedTo &&
+    isDeliverableMessageChannel(resolvedChannel) &&
+    resolvedChannel === baseDelivery.lastChannel
+  ) {
+    resolvedTo = baseDelivery.lastTo;
+  }
+
+  return {
+    baseDelivery,
+    resolvedChannel,
+    resolvedTo,
+    resolvedAccountId,
+    deliveryTargetMode,
+  };
+}