fix: harden message aborts + bluebubbles dm create (#1751) (thanks @tyler6204)

Two fixes:

1. Cross-context decoration (e.g., '[from +19257864429]' prefix) was being
   added to ALL messages sent to a different target, even when the agent
   was just composing a new message via the message tool. This decoration
   should only be applied when forwarding/relaying messages between chats.

   Fix: Added skipCrossContextDecoration flag to ChannelThreadingToolContext.
   The message tool now sets this flag to true, so direct sends don't get
   decorated. The buildCrossContextDecoration function checks this flag
   and returns null when set.

2. Aborted requests were still completing because the abort signal wasn't
   being passed through the message tool execution chain.

   Fix: Added abortSignal propagation from message tool → runMessageAction →
   executeSendAction → sendMessage → deliverOutboundPayloads. Added abort
   checks at key points in the chain to fail fast when aborted.

Files changed:
- src/channels/plugins/types.core.ts: Added skipCrossContextDecoration field
- src/infra/outbound/outbound-policy.ts: Check skip flag before decorating
- src/agents/tools/message-tool.ts: Set skip flag, accept and pass abort signal
- src/infra/outbound/message-action-runner.ts: Pass abort signal through
- src/infra/outbound/outbound-send-service.ts: Check and pass abort signal
- src/infra/outbound/message.ts: Pass abort signal to delivery

CHANGELOG.md

@@ -24,6 +24,7 @@ Docs: https://docs.clawd.bot
 - Telegram: add verbose raw-update logging for inbound Telegram updates. (#1597) Thanks @rohannagpal.
 
 ### Fixes
+- BlueBubbles: route phone-number targets to DMs, avoid leaking routing IDs, and auto-create missing DMs (Private API required). (#1751) Thanks @tyler6204. https://docs.clawd.bot/channels/bluebubbles
 - BlueBubbles: keep part-index GUIDs in reply tags when short IDs are missing.
 - Web UI: hide internal `message_id` hints in chat bubbles.
 - Web UI: show Stop button during active runs, swap back to New session when idle. (#1664) Thanks @ndbroadbent.

docs/channels/bluebubbles.md

@@ -213,6 +213,7 @@ Prefer `chat_guid` for stable routing:
 - `chat_id:123`
 - `chat_identifier:...`
 - Direct handles: `+15555550123`, `user@example.com`
+  - If a direct handle does not have an existing DM chat, Clawdbot will create one via `POST /api/v1/chat/new`. This requires the BlueBubbles Private API to be enabled.
 
 ## Security
 - Webhook requests are authenticated by comparing `guid`/`password` query params or headers against `channels.bluebubbles.password`. Requests from `localhost` are also accepted.

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),

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,
@@ -344,14 +385,14 @@ describe("send", () => {
       ).rejects.toThrow("password is required");
     });
 
-    it("throws when chatGuid cannot be resolved", async () => {
+    it("throws when chatGuid cannot be resolved for non-handle targets", async () => {
       mockFetch.mockResolvedValue({
         ok: true,
         json: () => Promise.resolve({ data: [] }),
       });
 
       await expect(
-        sendMessageBlueBubbles("+15559999999", "Hello", {
+        sendMessageBlueBubbles("chat_id:999", "Hello", {
           serverUrl: "http://localhost:1234",
           password: "test",
         }),
@@ -398,6 +439,57 @@ describe("send", () => {
       expect(body.method).toBeUndefined();
     });
 
+    it("creates a new chat when handle target is missing", async () => {
+      mockFetch
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () => Promise.resolve({ data: [] }),
+        })
+        .mockResolvedValueOnce({
+          ok: true,
+          text: () =>
+            Promise.resolve(
+              JSON.stringify({
+                data: { guid: "new-msg-guid" },
+              }),
+            ),
+        });
+
+      const result = await sendMessageBlueBubbles("+15550009999", "Hello new chat", {
+        serverUrl: "http://localhost:1234",
+        password: "test",
+      });
+
+      expect(result.messageId).toBe("new-msg-guid");
+      expect(mockFetch).toHaveBeenCalledTimes(2);
+
+      const createCall = mockFetch.mock.calls[1];
+      expect(createCall[0]).toContain("/api/v1/chat/new");
+      const body = JSON.parse(createCall[1].body);
+      expect(body.addresses).toEqual(["+15550009999"]);
+      expect(body.message).toBe("Hello new chat");
+    });
+
+    it("throws when creating a new chat requires Private API", async () => {
+      mockFetch
+        .mockResolvedValueOnce({
+          ok: true,
+          json: () => Promise.resolve({ data: [] }),
+        })
+        .mockResolvedValueOnce({
+          ok: false,
+          status: 403,
+          text: () => Promise.resolve("Private API not enabled"),
+        });
+
+      await expect(
+        sendMessageBlueBubbles("+15550008888", "Hello", {
+          serverUrl: "http://localhost:1234",
+          password: "test",
+        }),
+      ).rejects.toThrow("Private API must be enabled");
+    });
+
     it("uses private-api when reply metadata is present", async () => {
       mockFetch
         .mockResolvedValueOnce({

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.",
     );

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);

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 = {

src/infra/outbound/message-action-runner.test.ts

@@ -321,6 +321,44 @@ describe("runMessageAction context isolation", () => {
       }),
     ).rejects.toThrow(/Cross-context messaging denied/);
   });
+
+  it("aborts send when abortSignal is already aborted", async () => {
+    const controller = new AbortController();
+    controller.abort();
+
+    await expect(
+      runMessageAction({
+        cfg: slackConfig,
+        action: "send",
+        params: {
+          channel: "slack",
+          target: "#C12345678",
+          message: "hi",
+        },
+        dryRun: true,
+        abortSignal: controller.signal,
+      }),
+    ).rejects.toMatchObject({ name: "AbortError" });
+  });
+
+  it("aborts broadcast when abortSignal is already aborted", async () => {
+    const controller = new AbortController();
+    controller.abort();
+
+    await expect(
+      runMessageAction({
+        cfg: slackConfig,
+        action: "broadcast",
+        params: {
+          targets: ["channel:C12345678"],
+          channel: "slack",
+          message: "hi",
+        },
+        dryRun: true,
+        abortSignal: controller.signal,
+      }),
+    ).rejects.toMatchObject({ name: "AbortError" });
+  });
 });
 
 describe("runMessageAction sendAttachment hydration", () => {

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;
@@ -524,6 +526,7 @@ async function handleBroadcastAction(
   input: RunMessageActionParams,
   params: Record<string, unknown>,
 ): Promise<MessageActionRunResult> {
+  throwIfAborted(input.abortSignal);
   const broadcastEnabled = input.cfg.tools?.message?.broadcast?.enabled !== false;
   if (!broadcastEnabled) {
     throw new Error("Broadcast is disabled. Set tools.message.broadcast.enabled to true.");
@@ -548,8 +551,11 @@ async function handleBroadcastAction(
     error?: string;
     result?: MessageSendResult;
   }> = [];
+  const isAbortError = (err: unknown): boolean => err instanceof Error && err.name === "AbortError";
   for (const targetChannel of targetChannels) {
+    throwIfAborted(input.abortSignal);
     for (const target of rawTargets) {
+      throwIfAborted(input.abortSignal);
       try {
         const resolved = await resolveChannelTarget({
           cfg: input.cfg,
@@ -573,6 +579,7 @@ async function handleBroadcastAction(
           result: sendResult.kind === "send" ? sendResult.sendResult : undefined,
         });
       } catch (err) {
+        if (isAbortError(err)) throw err;
         results.push({
           channel: targetChannel,
           to: target,
@@ -592,8 +599,28 @@ 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 +703,7 @@ 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 +723,7 @@ async function handleSendAction(ctx: ResolvedActionContext): Promise<MessageActi
               mediaUrls: mirrorMediaUrls,
             }
           : undefined,
+      abortSignal,
     },
     to,
     message,
@@ -718,7 +747,8 @@ 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 +807,8 @@ 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 +961,7 @@ export async function runMessageAction(
       input,
       agentId: resolvedAgentId,
       resolvedTarget,
+      abortSignal: input.abortSignal,
     });
   }
 
@@ -942,6 +974,7 @@ export async function runMessageAction(
       dryRun,
       gateway,
       input,
+      abortSignal: input.abortSignal,
     });
   }
 
@@ -953,5 +986,6 @@ export async function runMessageAction(
     dryRun,
     gateway,
     input,
+    abortSignal: input.abortSignal,
   });
 }

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,

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 ?? "";

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 {

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;
 }