diff --git a/extensions/bluebubbles/src/channel.ts b/extensions/bluebubbles/src/channel.ts
index 126a73131..88b8e5a2a 100644
--- a/extensions/bluebubbles/src/channel.ts
+++ b/extensions/bluebubbles/src/channel.ts
@@ -25,9 +25,11 @@ import { resolveBlueBubblesMessageId } from "./monitor.js";
 import { probeBlueBubbles, type BlueBubblesProbe } from "./probe.js";
 import { sendMessageBlueBubbles } from "./send.js";
 import {
+  extractHandleFromChatGuid,
   looksLikeBlueBubblesTargetId,
   normalizeBlueBubblesHandle,
   normalizeBlueBubblesMessagingTarget,
+  parseBlueBubblesTarget,
 } from "./targets.js";
 import { bluebubblesMessageActions } from "./actions.js";
 import { monitorBlueBubblesProvider, resolveWebhookPathFromConfig } from "./monitor.js";
@@ -148,6 +150,58 @@ export const bluebubblesPlugin: ChannelPlugin<ResolvedBlueBubblesAccount> = {
       looksLikeId: looksLikeBlueBubblesTargetId,
       hint: "<handle|chat_guid:GUID|chat_id:ID|chat_identifier:ID>",
     },
+    formatTargetDisplay: ({ target, display }) => {
+      const shouldParseDisplay = (value: string): boolean => {
+        if (looksLikeBlueBubblesTargetId(value)) return true;
+        return /^(bluebubbles:|chat_guid:|chat_id:|chat_identifier:)/i.test(value);
+      };
+
+      // Helper to extract a clean handle from any BlueBubbles target format
+      const extractCleanDisplay = (value: string | undefined): string | null => {
+        const trimmed = value?.trim();
+        if (!trimmed) return null;
+        try {
+          const parsed = parseBlueBubblesTarget(trimmed);
+          if (parsed.kind === "chat_guid") {
+            const handle = extractHandleFromChatGuid(parsed.chatGuid);
+            if (handle) return handle;
+          }
+          if (parsed.kind === "handle") {
+            return normalizeBlueBubblesHandle(parsed.to);
+          }
+        } catch {
+          // Fall through
+        }
+        // Strip common prefixes and try raw extraction
+        const stripped = trimmed
+          .replace(/^bluebubbles:/i, "")
+          .replace(/^chat_guid:/i, "")
+          .replace(/^chat_id:/i, "")
+          .replace(/^chat_identifier:/i, "");
+        const handle = extractHandleFromChatGuid(stripped);
+        if (handle) return handle;
+        // Don't return raw chat_guid formats - they contain internal routing info
+        if (stripped.includes(";-;") || stripped.includes(";+;")) return null;
+        return stripped;
+      };
+
+      // Try to get a clean display from the display parameter first
+      const trimmedDisplay = display?.trim();
+      if (trimmedDisplay) {
+        if (!shouldParseDisplay(trimmedDisplay)) {
+          return trimmedDisplay;
+        }
+        const cleanDisplay = extractCleanDisplay(trimmedDisplay);
+        if (cleanDisplay) return cleanDisplay;
+      }
+
+      // Fall back to extracting from target
+      const cleanTarget = extractCleanDisplay(target);
+      if (cleanTarget) return cleanTarget;
+
+      // Last resort: return display or target as-is
+      return display?.trim() || target?.trim() || "";
+    },
   },
   setup: {
     resolveAccountId: ({ accountId }) => normalizeAccountId(accountId),
diff --git a/extensions/bluebubbles/src/send.test.ts b/extensions/bluebubbles/src/send.test.ts
index 0b8b77a1f..6509ec3bf 100644
--- a/extensions/bluebubbles/src/send.test.ts
+++ b/extensions/bluebubbles/src/send.test.ts
@@ -187,6 +187,47 @@ describe("send", () => {
       expect(result).toBe("iMessage;-;+15551234567");
     });
 
+    it("returns null when handle only exists in group chat (not DM)", async () => {
+      // This is the critical fix: if a phone number only exists as a participant in a group chat
+      // (no direct DM chat), we should NOT send to that group. Return null instead.
+      mockFetch
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () =>
+            Promise.resolve({
+              data: [
+                {
+                  guid: "iMessage;+;group-the-council",
+                  participants: [
+                    { address: "+12622102921" },
+                    { address: "+15550001111" },
+                    { address: "+15550002222" },
+                  ],
+                },
+              ],
+            }),
+        })
+        // Empty second page to stop pagination
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () => Promise.resolve({ data: [] }),
+        });
+
+      const target: BlueBubblesSendTarget = {
+        kind: "handle",
+        address: "+12622102921",
+        service: "imessage",
+      };
+      const result = await resolveChatGuidForTarget({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        target,
+      });
+
+      // Should return null, NOT the group chat GUID
+      expect(result).toBeNull();
+    });
+
     it("returns null when chat not found", async () => {
       mockFetch.mockResolvedValueOnce({
         ok: true,
diff --git a/extensions/bluebubbles/src/send.ts b/extensions/bluebubbles/src/send.ts
index 675063d6d..bc4bb14bd 100644
--- a/extensions/bluebubbles/src/send.ts
+++ b/extensions/bluebubbles/src/send.ts
@@ -257,11 +257,17 @@ export async function resolveChatGuidForTarget(params: {
           return guid;
         }
         if (!participantMatch && guid) {
-          const participants = extractParticipantAddresses(chat).map((entry) =>
-            normalizeBlueBubblesHandle(entry),
-          );
-          if (participants.includes(normalizedHandle)) {
-            participantMatch = guid;
+          // Only consider DM chats (`;-;` separator) as participant matches.
+          // Group chats (`;+;` separator) should never match when searching by handle/phone.
+          // This prevents routing "send to +1234567890" to a group chat that contains that number.
+          const isDmChat = guid.includes(";-;");
+          if (isDmChat) {
+            const participants = extractParticipantAddresses(chat).map((entry) =>
+              normalizeBlueBubblesHandle(entry),
+            );
+            if (participants.includes(normalizedHandle)) {
+              participantMatch = guid;
+            }
           }
         }
       }
@@ -270,6 +276,55 @@ export async function resolveChatGuidForTarget(params: {
   return participantMatch;
 }
 
+/**
+ * Creates a new chat (DM) and optionally sends an initial message.
+ * Requires Private API to be enabled in BlueBubbles.
+ */
+async function createNewChatWithMessage(params: {
+  baseUrl: string;
+  password: string;
+  address: string;
+  message: string;
+  timeoutMs?: number;
+}): Promise<BlueBubblesSendResult> {
+  const url = buildBlueBubblesApiUrl({
+    baseUrl: params.baseUrl,
+    path: "/api/v1/chat/new",
+    password: params.password,
+  });
+  const payload = {
+    addresses: [params.address],
+    message: params.message,
+  };
+  const res = await blueBubblesFetchWithTimeout(
+    url,
+    {
+      method: "POST",
+      headers: { "Content-Type": "application/json" },
+      body: JSON.stringify(payload),
+    },
+    params.timeoutMs,
+  );
+  if (!res.ok) {
+    const errorText = await res.text();
+    // Check for Private API not enabled error
+    if (res.status === 400 || res.status === 403 || errorText.toLowerCase().includes("private api")) {
+      throw new Error(
+        `BlueBubbles send failed: Cannot create new chat - Private API must be enabled. Original error: ${errorText || res.status}`,
+      );
+    }
+    throw new Error(`BlueBubbles create chat failed (${res.status}): ${errorText || "unknown"}`);
+  }
+  const body = await res.text();
+  if (!body) return { messageId: "ok" };
+  try {
+    const parsed = JSON.parse(body) as unknown;
+    return { messageId: extractMessageId(parsed) };
+  } catch {
+    return { messageId: "ok" };
+  }
+}
+
 export async function sendMessageBlueBubbles(
   to: string,
   text: string,
@@ -297,6 +352,17 @@ export async function sendMessageBlueBubbles(
     target,
   });
   if (!chatGuid) {
+    // If target is a phone number/handle and no existing chat found,
+    // auto-create a new DM chat using the /api/v1/chat/new endpoint
+    if (target.kind === "handle") {
+      return createNewChatWithMessage({
+        baseUrl,
+        password,
+        address: target.address,
+        message: trimmedText,
+        timeoutMs: opts.timeoutMs,
+      });
+    }
     throw new Error(
       "BlueBubbles send failed: chatGuid not found for target. Use a chat_guid target or ensure the chat exists.",
     );
diff --git a/src/agents/tools/message-tool.ts b/src/agents/tools/message-tool.ts
index 6552564e9..eae4356db 100644
--- a/src/agents/tools/message-tool.ts
+++ b/src/agents/tools/message-tool.ts
@@ -333,7 +333,13 @@ export function createMessageTool(options?: MessageToolOptions): AnyAgentTool {
     name: "message",
     description,
     parameters: schema,
-    execute: async (_toolCallId, args) => {
+    execute: async (_toolCallId, args, signal) => {
+      // Check if already aborted before doing any work
+      if (signal?.aborted) {
+        const err = new Error("Message send aborted");
+        err.name = "AbortError";
+        throw err;
+      }
       const params = args as Record<string, unknown>;
       const cfg = options?.config ?? loadConfig();
       const action = readStringParam(params, "action", {
@@ -366,6 +372,9 @@ export function createMessageTool(options?: MessageToolOptions): AnyAgentTool {
               currentThreadTs: options?.currentThreadTs,
               replyToMode: options?.replyToMode,
               hasRepliedRef: options?.hasRepliedRef,
+              // Direct tool invocations should not add cross-context decoration.
+              // The agent is composing a message, not forwarding from another chat.
+              skipCrossContextDecoration: true,
             }
           : undefined;
 
@@ -379,6 +388,7 @@ export function createMessageTool(options?: MessageToolOptions): AnyAgentTool {
         agentId: options?.agentSessionKey
           ? resolveSessionAgentId({ sessionKey: options.agentSessionKey, config: cfg })
           : undefined,
+        abortSignal: signal,
       });
 
       const toolResult = getToolResult(result);
diff --git a/src/channels/plugins/types.core.ts b/src/channels/plugins/types.core.ts
index 99f847fda..6a76743f2 100644
--- a/src/channels/plugins/types.core.ts
+++ b/src/channels/plugins/types.core.ts
@@ -240,6 +240,12 @@ export type ChannelThreadingToolContext = {
   currentThreadTs?: string;
   replyToMode?: "off" | "first" | "all";
   hasRepliedRef?: { value: boolean };
+  /**
+   * When true, skip cross-context decoration (e.g., "[from X]" prefix).
+   * Use this for direct tool invocations where the agent is composing a new message,
+   * not forwarding/relaying a message from another conversation.
+   */
+  skipCrossContextDecoration?: boolean;
 };
 
 export type ChannelMessagingAdapter = {
diff --git a/src/infra/outbound/message-action-runner.ts b/src/infra/outbound/message-action-runner.ts
index 50ddce227..2fe4cfeb6 100644
--- a/src/infra/outbound/message-action-runner.ts
+++ b/src/infra/outbound/message-action-runner.ts
@@ -64,6 +64,7 @@ export type RunMessageActionParams = {
   sessionKey?: string;
   agentId?: string;
   dryRun?: boolean;
+  abortSignal?: AbortSignal;
 };
 
 export type MessageActionRunResult =
@@ -507,6 +508,7 @@ type ResolvedActionContext = {
   input: RunMessageActionParams;
   agentId?: string;
   resolvedTarget?: ResolvedMessagingTarget;
+  abortSignal?: AbortSignal;
 };
 function resolveGateway(input: RunMessageActionParams): MessageActionRunnerGateway | undefined {
   if (!input.gateway) return undefined;
@@ -592,8 +594,28 @@ async function handleBroadcastAction(
   };
 }
 
+function throwIfAborted(abortSignal?: AbortSignal): void {
+  if (abortSignal?.aborted) {
+    const err = new Error("Message send aborted");
+    err.name = "AbortError";
+    throw err;
+  }
+}
+
 async function handleSendAction(ctx: ResolvedActionContext): Promise<MessageActionRunResult> {
-  const { cfg, params, channel, accountId, dryRun, gateway, input, agentId, resolvedTarget } = ctx;
+  const {
+    cfg,
+    params,
+    channel,
+    accountId,
+    dryRun,
+    gateway,
+    input,
+    agentId,
+    resolvedTarget,
+    abortSignal,
+  } = ctx;
+  throwIfAborted(abortSignal);
   const action: ChannelMessageActionName = "send";
   const to = readStringParam(params, "to", { required: true });
   // Support media, path, and filePath parameters for attachments
@@ -676,6 +698,7 @@ async function handleSendAction(ctx: ResolvedActionContext): Promise<MessageActi
   }
   const mirrorMediaUrls =
     mergedMediaUrls.length > 0 ? mergedMediaUrls : mediaUrl ? [mediaUrl] : undefined;
+  throwIfAborted(abortSignal);
   const send = await executeSendAction({
     ctx: {
       cfg,
@@ -695,6 +718,7 @@ async function handleSendAction(ctx: ResolvedActionContext): Promise<MessageActi
               mediaUrls: mirrorMediaUrls,
             }
           : undefined,
+      abortSignal,
     },
     to,
     message,
@@ -718,7 +742,8 @@ async function handleSendAction(ctx: ResolvedActionContext): Promise<MessageActi
 }
 
 async function handlePollAction(ctx: ResolvedActionContext): Promise<MessageActionRunResult> {
-  const { cfg, params, channel, accountId, dryRun, gateway, input } = ctx;
+  const { cfg, params, channel, accountId, dryRun, gateway, input, abortSignal } = ctx;
+  throwIfAborted(abortSignal);
   const action: ChannelMessageActionName = "poll";
   const to = readStringParam(params, "to", { required: true });
   const question = readStringParam(params, "pollQuestion", {
@@ -777,7 +802,8 @@ async function handlePollAction(ctx: ResolvedActionContext): Promise<MessageActi
 }
 
 async function handlePluginAction(ctx: ResolvedActionContext): Promise<MessageActionRunResult> {
-  const { cfg, params, channel, accountId, dryRun, gateway, input } = ctx;
+  const { cfg, params, channel, accountId, dryRun, gateway, input, abortSignal } = ctx;
+  throwIfAborted(abortSignal);
   const action = input.action as Exclude<ChannelMessageActionName, "send" | "poll" | "broadcast">;
   if (dryRun) {
     return {
@@ -930,6 +956,7 @@ export async function runMessageAction(
       input,
       agentId: resolvedAgentId,
       resolvedTarget,
+      abortSignal: input.abortSignal,
     });
   }
 
@@ -942,6 +969,7 @@ export async function runMessageAction(
       dryRun,
       gateway,
       input,
+      abortSignal: input.abortSignal,
     });
   }
 
@@ -953,5 +981,6 @@ export async function runMessageAction(
     dryRun,
     gateway,
     input,
+    abortSignal: input.abortSignal,
   });
 }
diff --git a/src/infra/outbound/message.ts b/src/infra/outbound/message.ts
index fcb90c295..6f5f88bd2 100644
--- a/src/infra/outbound/message.ts
+++ b/src/infra/outbound/message.ts
@@ -50,6 +50,7 @@ type MessageSendParams = {
     text?: string;
     mediaUrls?: string[];
   };
+  abortSignal?: AbortSignal;
 };
 
 export type MessageSendResult = {
@@ -167,6 +168,7 @@ export async function sendMessage(params: MessageSendParams): Promise<MessageSen
       gifPlayback: params.gifPlayback,
       deps: params.deps,
       bestEffort: params.bestEffort,
+      abortSignal: params.abortSignal,
       mirror: params.mirror
         ? {
             ...params.mirror,
diff --git a/src/infra/outbound/outbound-policy.ts b/src/infra/outbound/outbound-policy.ts
index e1f654109..173e8314b 100644
--- a/src/infra/outbound/outbound-policy.ts
+++ b/src/infra/outbound/outbound-policy.ts
@@ -119,6 +119,8 @@ export async function buildCrossContextDecoration(params: {
   accountId?: string | null;
 }): Promise<CrossContextDecoration | null> {
   if (!params.toolContext?.currentChannelId) return null;
+  // Skip decoration for direct tool sends (agent composing, not forwarding)
+  if (params.toolContext.skipCrossContextDecoration) return null;
   if (!isCrossContextTarget(params)) return null;
 
   const markerConfig = params.cfg.tools?.message?.crossContext?.marker;
@@ -131,11 +133,11 @@ export async function buildCrossContextDecoration(params: {
       targetId: params.toolContext.currentChannelId,
       accountId: params.accountId ?? undefined,
     })) ?? params.toolContext.currentChannelId;
+  // Don't force group formatting here; currentChannelId can be a DM or a group.
   const originLabel = formatTargetDisplay({
     channel: params.channel,
     target: params.toolContext.currentChannelId,
     display: currentName,
-    kind: "group",
   });
   const prefixTemplate = markerConfig?.prefix ?? "[from {channel}] ";
   const suffixTemplate = markerConfig?.suffix ?? "";
diff --git a/src/infra/outbound/outbound-send-service.ts b/src/infra/outbound/outbound-send-service.ts
index dd5dfd5e6..88a64d251 100644
--- a/src/infra/outbound/outbound-send-service.ts
+++ b/src/infra/outbound/outbound-send-service.ts
@@ -32,6 +32,7 @@ export type OutboundSendContext = {
     text?: string;
     mediaUrls?: string[];
   };
+  abortSignal?: AbortSignal;
 };
 
 function extractToolPayload(result: AgentToolResult<unknown>): unknown {
@@ -56,6 +57,14 @@ function extractToolPayload(result: AgentToolResult<unknown>): unknown {
   return result.content ?? result;
 }
 
+function throwIfAborted(abortSignal?: AbortSignal): void {
+  if (abortSignal?.aborted) {
+    const err = new Error("Message send aborted");
+    err.name = "AbortError";
+    throw err;
+  }
+}
+
 export async function executeSendAction(params: {
   ctx: OutboundSendContext;
   to: string;
@@ -70,6 +79,7 @@ export async function executeSendAction(params: {
   toolResult?: AgentToolResult<unknown>;
   sendResult?: MessageSendResult;
 }> {
+  throwIfAborted(params.ctx.abortSignal);
   if (!params.ctx.dryRun) {
     const handled = await dispatchChannelMessageAction({
       channel: params.ctx.channel,
@@ -103,6 +113,7 @@ export async function executeSendAction(params: {
     }
   }
 
+  throwIfAborted(params.ctx.abortSignal);
   const result: MessageSendResult = await sendMessage({
     cfg: params.ctx.cfg,
     to: params.to,
@@ -117,6 +128,7 @@ export async function executeSendAction(params: {
     deps: params.ctx.deps,
     gateway: params.ctx.gateway,
     mirror: params.ctx.mirror,
+    abortSignal: params.ctx.abortSignal,
   });
 
   return {
diff --git a/src/infra/outbound/target-resolver.ts b/src/infra/outbound/target-resolver.ts
index d21685a93..9f9d2f8d2 100644
--- a/src/infra/outbound/target-resolver.ts
+++ b/src/infra/outbound/target-resolver.ts
@@ -100,7 +100,12 @@ export function formatTargetDisplay(params: {
   if (!trimmedTarget) return trimmedTarget;
   if (trimmedTarget.startsWith("#") || trimmedTarget.startsWith("@")) return trimmedTarget;
 
-  const withoutPrefix = trimmedTarget.replace(/^telegram:/i, "");
+  const channelPrefix = `${params.channel}:`;
+  const withoutProvider = trimmedTarget.toLowerCase().startsWith(channelPrefix)
+    ? trimmedTarget.slice(channelPrefix.length)
+    : trimmedTarget;
+
+  const withoutPrefix = withoutProvider.replace(/^telegram:/i, "");
   if (/^channel:/i.test(withoutPrefix)) {
     return `#${withoutPrefix.replace(/^channel:/i, "")}`;
   }
@@ -119,14 +124,23 @@ function preserveTargetCase(channel: ChannelId, raw: string, normalized: string)
   return trimmed;
 }
 
-function detectTargetKind(raw: string, preferred?: TargetResolveKind): TargetResolveKind {
+function detectTargetKind(
+  channel: ChannelId,
+  raw: string,
+  preferred?: TargetResolveKind,
+): TargetResolveKind {
   if (preferred) return preferred;
   const trimmed = raw.trim();
   if (!trimmed) return "group";
+
   if (trimmed.startsWith("@") || /^<@!?/.test(trimmed) || /^user:/i.test(trimmed)) return "user";
-  if (trimmed.startsWith("#") || /^channel:/i.test(trimmed)) {
-    return "group";
+  if (trimmed.startsWith("#") || /^channel:/i.test(trimmed)) return "group";
+
+  // For some channels (e.g., BlueBubbles/iMessage), bare phone numbers are almost always DM targets.
+  if ((channel === "bluebubbles" || channel === "imessage") && /^\+?\d{6,}$/.test(trimmed)) {
+    return "user";
   }
+
   return "group";
 }
 
@@ -282,7 +296,7 @@ export async function resolveMessagingTarget(params: {
   const plugin = getChannelPlugin(params.channel);
   const providerLabel = plugin?.meta?.label ?? params.channel;
   const hint = plugin?.messaging?.targetResolver?.hint;
-  const kind = detectTargetKind(raw, params.preferredKind);
+  const kind = detectTargetKind(params.channel, raw, params.preferredKind);
   const normalized = normalizeTargetForProvider(params.channel, raw) ?? raw;
   const looksLikeTargetId = (): boolean => {
     const trimmed = raw.trim();
@@ -291,7 +305,12 @@ export async function resolveMessagingTarget(params: {
     if (lookup) return lookup(trimmed, normalized);
     if (/^(channel|group|user):/i.test(trimmed)) return true;
     if (/^[@#]/.test(trimmed)) return true;
-    if (/^\+?\d{6,}$/.test(trimmed)) return true;
+    if (/^\+?\d{6,}$/.test(trimmed)) {
+      // BlueBubbles/iMessage phone numbers should usually resolve via the directory to a DM chat,
+      // otherwise the provider may pick an existing group containing that handle.
+      if (params.channel === "bluebubbles" || params.channel === "imessage") return false;
+      return true;
+    }
     if (trimmed.includes("@thread")) return true;
     if (/^(conversation|user):/i.test(trimmed)) return true;
     return false;
@@ -353,6 +372,24 @@ export async function resolveMessagingTarget(params: {
       candidates: match.entries,
     };
   }
+  // For iMessage-style channels, allow sending directly to the normalized handle
+  // even if the directory doesn't contain an entry yet.
+  if (
+    (params.channel === "bluebubbles" || params.channel === "imessage") &&
+    /^\+?\d{6,}$/.test(query)
+  ) {
+    const directTarget = preserveTargetCase(params.channel, raw, normalized);
+    return {
+      ok: true,
+      target: {
+        to: directTarget,
+        kind,
+        display: stripTargetPrefixes(raw),
+        source: "normalized",
+      },
+    };
+  }
+
   return {
     ok: false,
     error: unknownTargetError(providerLabel, raw, hint),
@@ -367,16 +404,32 @@ export async function lookupDirectoryDisplay(params: {
   runtime?: RuntimeEnv;
 }): Promise<string | undefined> {
   const normalized = normalizeTargetForProvider(params.channel, params.targetId) ?? params.targetId;
-  const candidates = await getDirectoryEntries({
-    cfg: params.cfg,
-    channel: params.channel,
-    accountId: params.accountId,
-    kind: "group",
-    runtime: params.runtime,
-    preferLiveOnMiss: false,
-  });
-  const entry = candidates.find(
-    (candidate) => normalizeDirectoryEntryId(params.channel, candidate) === normalized,
-  );
+
+  // Targets can resolve to either peers (DMs) or groups. Try both.
+  const [groups, users] = await Promise.all([
+    getDirectoryEntries({
+      cfg: params.cfg,
+      channel: params.channel,
+      accountId: params.accountId,
+      kind: "group",
+      runtime: params.runtime,
+      preferLiveOnMiss: false,
+    }),
+    getDirectoryEntries({
+      cfg: params.cfg,
+      channel: params.channel,
+      accountId: params.accountId,
+      kind: "user",
+      runtime: params.runtime,
+      preferLiveOnMiss: false,
+    }),
+  ]);
+
+  const findMatch = (candidates: ChannelDirectoryEntry[]) =>
+    candidates.find(
+      (candidate) => normalizeDirectoryEntryId(params.channel, candidate) === normalized,
+    );
+
+  const entry = findMatch(groups) ?? findMatch(users);
   return entry?.name ?? entry?.handle ?? undefined;
 }