diff --git a/.openclaw-sync/source.json b/.openclaw-sync/source.json
index 18201890e..90c5cba0f 100644
--- a/.openclaw-sync/source.json
+++ b/.openclaw-sync/source.json
@@ -1,5 +1,5 @@
 {
   "repository": "openclaw/openclaw",
-  "sha": "f1805ab54d63126e8f83b0837d4f20df2e41f3a0",
-  "syncedAt": "2026-04-21T08:23:24.609Z"
+  "sha": "14506aeca4be0b4cc77448615d76797e679587f7",
+  "syncedAt": "2026-04-21T08:44:03.410Z"
 }
diff --git a/docs/.generated/config-baseline.sha256 b/docs/.generated/config-baseline.sha256
index b04602786..a001cee28 100644
--- a/docs/.generated/config-baseline.sha256
+++ b/docs/.generated/config-baseline.sha256
@@ -1,4 +1,4 @@
-e3a16ceb9e933c5b707b717c18a1d9d50f98e687a98e6c35f4f3a290f7036a62  config-baseline.json
-ae1ab87635e7bf613c84fee04425af901ceeb67fb5dbcf1c74095aa00a59ee88  config-baseline.core.json
-e239cc20f20f8d0172812bc0ad3ee6df52da88e2e2702e3d03a47e01561132ae  config-baseline.channel.json
-8fb3a1cf5fe56ab8fc2cb46341c3403aed32b0d1f0aaeac0e96cd3599db4f06e  config-baseline.plugin.json
+cc473bcd00e63c3d3f351e4de1ceb390aae88dddce8616929e98a9d94412b1b9  config-baseline.json
+7956c319e82d288d496a51cb2ff4485ab72ef4900cb089f99e1df8b9ef3bfb73  config-baseline.core.json
+cd467228990cdbdebde2fa87d8b1384b94c149e791f2e67250bf17b13162d4a1  config-baseline.channel.json
+17a73724e5082b3aa846c220d38115916fb6003887439e6794510a99fc73f7de  config-baseline.plugin.json
diff --git a/docs/channels/bluebubbles.md b/docs/channels/bluebubbles.md
index fc69c542c..e347b9b00 100644
--- a/docs/channels/bluebubbles.md
+++ b/docs/channels/bluebubbles.md
@@ -393,6 +393,103 @@ Use full IDs for durable automations and storage:
 
 See [Configuration](/gateway/configuration) for template variables.
 
+## Coalescing split-send DMs (command + URL in one composition)
+
+When a user types a command and a URL together in iMessage — e.g. `Dump https://example.com/article` — Apple splits the send into **two separate webhook deliveries**:
+
+1. A text message (`"Dump"`).
+2. A URL-preview balloon (`"https://..."`) with OG-preview images as attachments.
+
+The two webhooks arrive at OpenClaw ~0.8-2.0 s apart on most setups. Without coalescing, the agent receives the command alone on turn 1, replies (often "send me the URL"), and only sees the URL on turn 2 — at which point the command context is already lost.
+
+`channels.bluebubbles.coalesceSameSenderDms` opts a DM into merging consecutive same-sender webhooks into a single agent turn. Group chats continue to key per-message so multi-user turn structure is preserved.
+
+### When to enable
+
+Enable when:
+
+- You ship skills that expect `command + payload` in one message (dump, paste, save, queue, etc.).
+- Your users paste URLs, images, or long content alongside commands.
+- You can accept the added DM turn latency (see below).
+
+Leave disabled when:
+
+- You need minimum command latency for single-word DM triggers.
+- All your flows are one-shot commands without payload follow-ups.
+
+### Enabling
+
+```json5
+{
+  channels: {
+    bluebubbles: {
+      coalesceSameSenderDms: true, // opt in (default: false)
+    },
+  },
+}
+```
+
+With the flag on and no explicit `messages.inbound.byChannel.bluebubbles`, the debounce window widens to **2500 ms** (the default for non-coalescing is 500 ms). The wider window is required — Apple's split-send cadence of 0.8-2.0 s does not fit in the tighter default.
+
+To tune the window yourself:
+
+```json5
+{
+  messages: {
+    inbound: {
+      byChannel: {
+        // 2500 ms works for most setups; raise to 4000 ms if your Mac is slow
+        // or under memory pressure (observed gap can stretch past 2 s then).
+        bluebubbles: 2500,
+      },
+    },
+  },
+}
+```
+
+### Trade-offs
+
+- **Added latency for DM control commands.** With the flag on, DM control-command messages (like `Dump`, `Save`, etc.) now wait up to the debounce window before dispatching, in case a payload webhook is coming. Group-chat commands keep instant dispatch.
+- **Merged output is bounded** — merged text caps at 4000 chars with an explicit `…[truncated]` marker; attachments cap at 20; source entries cap at 10 (first-plus-latest retained beyond that). Every source `messageId` still reaches inbound-dedupe so a later MessagePoller replay of any individual event is recognized as a duplicate.
+- **Opt-in, per-channel.** Other channels (Telegram, WhatsApp, Slack, …) are unaffected.
+
+### Scenarios and what the agent sees
+
+| User composes                                                      | Apple delivers            | Flag off (default)                      | Flag on + 2500 ms window                                                |
+| ------------------------------------------------------------------ | ------------------------- | --------------------------------------- | ----------------------------------------------------------------------- |
+| `Dump https://example.com` (one send)                              | 2 webhooks ~1 s apart     | Two agent turns: "Dump" alone, then URL | One turn: merged text `Dump https://example.com`                        |
+| `Save this 📎image.jpg caption` (attachment + text)                | 2 webhooks                | Two turns                               | One turn: text + image                                                  |
+| `/status` (standalone command)                                     | 1 webhook                 | Instant dispatch                        | **Wait up to window, then dispatch**                                    |
+| URL pasted alone                                                   | 1 webhook                 | Instant dispatch                        | Instant dispatch (only one entry in bucket)                             |
+| Text + URL sent as two deliberate separate messages, minutes apart | 2 webhooks outside window | Two turns                               | Two turns (window expires between them)                                 |
+| Rapid flood (>10 small DMs inside window)                          | N webhooks                | N turns                                 | One turn, bounded output (first + latest, text/attachment caps applied) |
+
+### Split-send coalescing troubleshooting
+
+If the flag is on and split-sends still arrive as two turns, check each layer:
+
+1. **Config actually loaded.**
+
+   ```
+   grep coalesceSameSenderDms ~/.openclaw/openclaw.json
+   ```
+
+   Then `openclaw gateway restart` — the flag is read at debouncer-registry creation.
+
+2. **Debounce window wide enough for your setup.** Look at the BlueBubbles server log under `~/Library/Logs/bluebubbles-server/main.log`:
+
+   ```
+   grep -E "Dispatching event to webhook" main.log | tail -20
+   ```
+
+   Measure the gap between the `"Dump"`-style text dispatch and the `"https://..."; Attachments:` dispatch that follows. Raise `messages.inbound.byChannel.bluebubbles` to comfortably cover that gap.
+
+3. **Session JSONL timestamps ≠ webhook arrival.** Session event timestamps (`~/.openclaw/agents/<id>/sessions/*.jsonl`) reflect when the gateway hands a message to the agent, **not** when the webhook arrived. A queued-second message tagged `[Queued messages while agent was busy]` means the first turn was still running when the second webhook arrived — the coalesce bucket had already flushed. Tune the window against the BB server log, not the session log.
+
+4. **Memory pressure slowing reply dispatch.** On smaller machines (8 GB), agent turns can take long enough that the coalesce bucket flushes before the reply completes, and the URL lands as a queued second turn. Check `memory_pressure` and `ps -o rss -p $(pgrep openclaw-gateway)`; if the gateway is over ~500 MB RSS and the compressor is active, close other heavy processes or bump to a larger host.
+
+5. **Reply-quote sends are a different path.** If the user tapped `Dump` as a **reply** to an existing URL-balloon (iMessage shows a "1 Reply" badge on the Dump bubble), the URL lives in `replyToBody`, not in a second webhook. Coalescing does not apply — that's a skill/prompt concern, not a debouncer concern.
+
 ## Block streaming
 
 Control whether responses are sent as a single message or streamed in blocks:
@@ -436,6 +533,7 @@ Provider options:
 - `channels.bluebubbles.chunkMode`: `length` (default) splits only when exceeding `textChunkLimit`; `newline` splits on blank lines (paragraph boundaries) before length chunking.
 - `channels.bluebubbles.mediaMaxMb`: Inbound/outbound media cap in MB (default: 8).
 - `channels.bluebubbles.mediaLocalRoots`: Explicit allowlist of absolute local directories permitted for outbound local media paths. Local path sends are denied by default unless this is configured. Per-account override: `channels.bluebubbles.accounts.<accountId>.mediaLocalRoots`.
+- `channels.bluebubbles.coalesceSameSenderDms`: Merge consecutive same-sender DM webhooks into one agent turn so Apple's text+URL split-send arrives as a single message (default: `false`). See [Coalescing split-send DMs](#coalescing-split-send-dms-command--url-in-one-composition) for scenarios, window tuning, and trade-offs. Widens the default inbound debounce window from 500 ms to 2500 ms when enabled without an explicit `messages.inbound.byChannel.bluebubbles`.
 - `channels.bluebubbles.historyLimit`: Max group messages for context (0 disables).
 - `channels.bluebubbles.dmHistoryLimit`: DM history limit.
 - `channels.bluebubbles.actions`: Enable/disable specific actions.
@@ -471,6 +569,7 @@ Prefer `chat_guid` for stable routing:
 - Edit/unsend require macOS 13+ and a compatible BlueBubbles server version. On macOS 26 (Tahoe), edit is currently broken due to private API changes.
 - Group icon updates can be flaky on macOS 26 (Tahoe): the API may return success but the new icon does not sync.
 - OpenClaw auto-hides known-broken actions based on the BlueBubbles server's macOS version. If edit still appears on macOS 26 (Tahoe), disable it manually with `channels.bluebubbles.actions.edit=false`.
+- `coalesceSameSenderDms` enabled but split-sends (e.g. `Dump` + URL) still arrive as two turns: see the [split-send coalescing troubleshooting](#split-send-coalescing-troubleshooting) checklist — common causes are too-tight debounce window, session-log timestamps misread as webhook arrival, or a reply-quote send (which uses `replyToBody`, not a second webhook).
 - For status/health info: `openclaw status --all` or `openclaw status --deep`.
 
 For general channel workflow reference, see [Channels](/channels) and the [Plugins](/tools/plugin) guide.
diff --git a/docs/concepts/messages.md b/docs/concepts/messages.md
index 4e9240c0c..6490faf51 100644
--- a/docs/concepts/messages.md
+++ b/docs/concepts/messages.md
@@ -62,7 +62,7 @@ Config (global default + per-channel overrides):
 Notes:
 
 - Debounce applies to **text-only** messages; media/attachments flush immediately.
-- Control commands bypass debouncing so they remain standalone.
+- Control commands bypass debouncing so they remain standalone — **except** when a channel explicitly opts in to same-sender DM coalescing (e.g. [BlueBubbles `coalesceSameSenderDms`](/channels/bluebubbles#coalescing-split-send-dms-command--url-in-one-composition)), where DM commands wait inside the debounce window so a split-send payload can join the same agent turn.
 
 ## Sessions and devices