diff --git a/CHANGELOG.md b/CHANGELOG.md
index faa93275f..4b86f1696 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@
 - **BREAKING:** `clawdbot message` and message tool now require `target` (dropping `to`/`channelId` for destinations). (#1034) — thanks @tobalsan.
 - **BREAKING:** Drop legacy `chatType: "room"` support; use `chatType: "channel"`.
 - **BREAKING:** remove legacy provider-specific target resolution fallbacks; target resolution is centralized with plugin hints + directory lookups.
+- **BREAKING:** drop legacy target normalization helpers; use outbound target normalization and resolver flows.
 
 ### Changes
 - Tools: improve `web_fetch` extraction using Readability (with fallback).
diff --git a/src/agents/pi-embedded-messaging.ts b/src/agents/pi-embedded-messaging.ts
index d48e0b627..5aae66fd4 100644
--- a/src/agents/pi-embedded-messaging.ts
+++ b/src/agents/pi-embedded-messaging.ts
@@ -31,12 +31,3 @@ export function isMessagingToolSendAction(
   if (!plugin?.actions?.extractToolSend) return false;
   return Boolean(plugin.actions.extractToolSend({ args })?.to);
 }
-
-export function normalizeTargetForProvider(provider: string, raw?: string): string | undefined {
-  if (!raw) return undefined;
-  const providerId = normalizeChannelId(provider);
-  const plugin = providerId ? getChannelPlugin(providerId) : undefined;
-  const normalized =
-    plugin?.messaging?.normalizeTarget?.(raw) ?? (raw.trim().toLowerCase() || undefined);
-  return normalized || undefined;
-}
diff --git a/src/agents/pi-embedded-subscribe.tools.ts b/src/agents/pi-embedded-subscribe.tools.ts
index 5299e1dd4..158138972 100644
--- a/src/agents/pi-embedded-subscribe.tools.ts
+++ b/src/agents/pi-embedded-subscribe.tools.ts
@@ -1,6 +1,7 @@
 import { getChannelPlugin, normalizeChannelId } from "../channels/plugins/index.js";
 import { truncateUtf16Safe } from "../utils.js";
-import { type MessagingToolSend, normalizeTargetForProvider } from "./pi-embedded-messaging.js";
+import { type MessagingToolSend } from "./pi-embedded-messaging.js";
+import { normalizeTargetForProvider } from "../infra/outbound/target-normalization.js";
 
 const TOOL_RESULT_MAX_CHARS = 8000;
 
diff --git a/src/auto-reply/reply/reply-payloads.ts b/src/auto-reply/reply/reply-payloads.ts
index 31303e23a..edfdc1cbc 100644
--- a/src/auto-reply/reply/reply-payloads.ts
+++ b/src/auto-reply/reply/reply-payloads.ts
@@ -1,5 +1,5 @@
 import { isMessagingToolDuplicate } from "../../agents/pi-embedded-helpers.js";
-import { normalizeTargetForProvider } from "../../agents/pi-embedded-messaging.js";
+import { normalizeTargetForProvider } from "../../infra/outbound/target-normalization.js";
 import type { MessagingToolSend } from "../../agents/pi-embedded-runner.js";
 import type { ReplyToMode } from "../../config/types.js";
 import type { OriginatingChannelType } from "../templating.js";
diff --git a/src/infra/outbound/channel-target.ts b/src/infra/outbound/channel-target.ts
index fc53dda34..dae736abf 100644
--- a/src/infra/outbound/channel-target.ts
+++ b/src/infra/outbound/channel-target.ts
@@ -6,10 +6,6 @@ export const CHANNEL_TARGET_DESCRIPTION =
 export const CHANNEL_TARGETS_DESCRIPTION =
   "Recipient/channel targets (same format as --target); accepts ids or names when the directory is available.";
 
-export function normalizeChannelTargetInput(raw: string): string {
-  return raw.trim();
-}
-
 export function applyTargetToParams(params: {
   action: string;
   args: Record<string, unknown>;
diff --git a/src/infra/outbound/directory-cache.ts b/src/infra/outbound/directory-cache.ts
index f2dd4f1f0..f1b6c43c2 100644
--- a/src/infra/outbound/directory-cache.ts
+++ b/src/infra/outbound/directory-cache.ts
@@ -11,10 +11,12 @@ export type DirectoryCacheKey = {
   accountId?: string | null;
   kind: ChannelDirectoryEntryKind;
   source: "cache" | "live";
+  signature?: string | null;
 };
 
 export function buildDirectoryCacheKey(key: DirectoryCacheKey): string {
-  return `${key.channel}:${key.accountId ?? "default"}:${key.kind}:${key.source}`;
+  const signature = key.signature ?? "default";
+  return `${key.channel}:${key.accountId ?? "default"}:${key.kind}:${key.source}:${signature}`;
 }
 
 export class DirectoryCache<T> {
diff --git a/src/infra/outbound/outbound-policy.ts b/src/infra/outbound/outbound-policy.ts
index 19961729f..9c0ecb027 100644
--- a/src/infra/outbound/outbound-policy.ts
+++ b/src/infra/outbound/outbound-policy.ts
@@ -1,4 +1,4 @@
-import { normalizeTargetForProvider } from "../../agents/pi-embedded-messaging.js";
+import { normalizeTargetForProvider } from "./target-normalization.js";
 import type {
   ChannelId,
   ChannelMessageActionName,
diff --git a/src/infra/outbound/target-errors.ts b/src/infra/outbound/target-errors.ts
index 5064b0967..14caf79c3 100644
--- a/src/infra/outbound/target-errors.ts
+++ b/src/infra/outbound/target-errors.ts
@@ -1,8 +1,28 @@
 export function missingTargetMessage(provider: string, hint?: string): string {
-  const suffix = hint ? ` ${hint}` : "";
-  return `Delivering to ${provider} requires target${suffix}`;
+  return `Delivering to ${provider} requires target${formatHint(hint)}`;
 }
 
 export function missingTargetError(provider: string, hint?: string): Error {
   return new Error(missingTargetMessage(provider, hint));
 }
+
+export function ambiguousTargetMessage(provider: string, raw: string, hint?: string): string {
+  return `Ambiguous target "${raw}" for ${provider}. Provide a unique name or an explicit id.${formatHint(hint, true)}`;
+}
+
+export function ambiguousTargetError(provider: string, raw: string, hint?: string): Error {
+  return new Error(ambiguousTargetMessage(provider, raw, hint));
+}
+
+export function unknownTargetMessage(provider: string, raw: string, hint?: string): string {
+  return `Unknown target "${raw}" for ${provider}.${formatHint(hint, true)}`;
+}
+
+export function unknownTargetError(provider: string, raw: string, hint?: string): Error {
+  return new Error(unknownTargetMessage(provider, raw, hint));
+}
+
+function formatHint(hint?: string, withLabel = false): string {
+  if (!hint) return "";
+  return withLabel ? ` Hint: ${hint}` : ` ${hint}`;
+}
diff --git a/src/infra/outbound/target-normalization.ts b/src/infra/outbound/target-normalization.ts
new file mode 100644
index 000000000..93bd79dba
--- /dev/null
+++ b/src/infra/outbound/target-normalization.ts
@@ -0,0 +1,31 @@
+import { getChannelPlugin, normalizeChannelId } from "../../channels/plugins/index.js";
+import type { ChannelId } from "../../channels/plugins/types.js";
+
+export function normalizeChannelTargetInput(raw: string): string {
+  return raw.trim();
+}
+
+export function normalizeTargetForProvider(provider: string, raw?: string): string | undefined {
+  if (!raw) return undefined;
+  const providerId = normalizeChannelId(provider);
+  const plugin = providerId ? getChannelPlugin(providerId) : undefined;
+  const normalized =
+    plugin?.messaging?.normalizeTarget?.(raw) ?? (raw.trim().toLowerCase() || undefined);
+  return normalized || undefined;
+}
+
+export function buildTargetResolverSignature(channel: ChannelId): string {
+  const plugin = getChannelPlugin(channel);
+  const hint = plugin?.messaging?.targetHint ?? "";
+  const looksLike = plugin?.messaging?.looksLikeTargetId;
+  const source = looksLike ? looksLike.toString() : "";
+  return hashSignature(`${hint}|${source}`);
+}
+
+function hashSignature(value: string): string {
+  let hash = 5381;
+  for (let i = 0; i < value.length; i += 1) {
+    hash = ((hash << 5) + hash) ^ value.charCodeAt(i);
+  }
+  return (hash >>> 0).toString(36);
+}
diff --git a/src/infra/outbound/target-resolver.ts b/src/infra/outbound/target-resolver.ts
index 760e64791..14df9dd4c 100644
--- a/src/infra/outbound/target-resolver.ts
+++ b/src/infra/outbound/target-resolver.ts
@@ -1,4 +1,3 @@
-import { normalizeTargetForProvider } from "../../agents/pi-embedded-messaging.js";
 import { getChannelPlugin } from "../../channels/plugins/index.js";
 import type {
   ChannelDirectoryEntry,
@@ -7,8 +6,13 @@ import type {
 } from "../../channels/plugins/types.js";
 import type { ClawdbotConfig } from "../../config/config.js";
 import { defaultRuntime, type RuntimeEnv } from "../../runtime.js";
-import { normalizeChannelTargetInput } from "./channel-target.js";
 import { buildDirectoryCacheKey, DirectoryCache } from "./directory-cache.js";
+import {
+  buildTargetResolverSignature,
+  normalizeChannelTargetInput,
+  normalizeTargetForProvider,
+} from "./target-normalization.js";
+import { ambiguousTargetError, unknownTargetError } from "./target-errors.js";
 
 export type TargetResolveKind = ChannelDirectoryEntryKind | "channel";
 
@@ -223,11 +227,13 @@ async function getDirectoryEntries(params: {
   runtime?: RuntimeEnv;
   preferLiveOnMiss?: boolean;
 }): Promise<ChannelDirectoryEntry[]> {
+  const signature = buildTargetResolverSignature(params.channel);
   const cacheKey = buildDirectoryCacheKey({
     channel: params.channel,
     accountId: params.accountId,
     kind: params.kind,
     source: "cache",
+    signature,
   });
   const cached = directoryCache.get(cacheKey, params.cfg);
   if (cached) return cached;
@@ -249,6 +255,7 @@ async function getDirectoryEntries(params: {
     accountId: params.accountId,
     kind: params.kind,
     source: "live",
+    signature,
   });
   const liveEntries = await listDirectoryEntries({
     cfg: params.cfg,
@@ -276,6 +283,9 @@ export async function resolveMessagingTarget(params: {
   if (!raw) {
     return { ok: false, error: new Error("Target is required") };
   }
+  const plugin = getChannelPlugin(params.channel);
+  const providerLabel = plugin?.meta?.label ?? params.channel;
+  const hint = plugin?.messaging?.targetHint;
   const kind = detectTargetKind(raw, params.preferredKind);
   const normalized = normalizeTargetForProvider(params.channel, raw) ?? raw;
   if (looksLikeTargetId({ channel: params.channel, raw, normalized })) {
@@ -316,13 +326,13 @@ export async function resolveMessagingTarget(params: {
   if (match.kind === "ambiguous") {
     return {
       ok: false,
-      error: new Error(`Ambiguous target "${raw}". Provide a unique name or an explicit id.`),
+      error: ambiguousTargetError(providerLabel, raw, hint),
       candidates: match.entries,
     };
   }
   return {
     ok: false,
-    error: new Error(`Unknown target "${raw}" for ${params.channel}.`),
+    error: unknownTargetError(providerLabel, raw, hint),
   };
 }