diff --git a/CHANGELOG.md b/CHANGELOG.md
index dce8595e0..3c1c5fab7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -55,6 +55,7 @@
 ### Fixed
 - Support multiple assistant text replies when using Tau RPC: agents now emit `texts` arrays and command auto-replies deliver each message separately without leaking raw JSON.
 - Normalized agent parsers (pi/claude/opencode/codex/gemini) to the new plural output shape.
+- Enforce outbound text size caps: WhatsApp/Twilio messages chunked at 1600 chars; web replies chunked at 4000 chars.
 
 ### Changes
 - **Heartbeat backpressure:** Web reply heartbeats now check the shared command queue and skip while any command/Claude runs are in flight, preventing concurrent prompts during long-running requests.
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index 06dfa2728..4889887ec 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -28,6 +28,8 @@ import type { GetReplyOptions, ReplyPayload } from "./types.js";
 
 export type { GetReplyOptions, ReplyPayload } from "./types.js";
 
+const TWILIO_TEXT_LIMIT = 1600;
+
 const ABORT_TRIGGERS = new Set(["stop", "esc", "abort", "wait", "exit"]);
 const ABORT_MEMORY = new Map<string, boolean>();
 
@@ -450,37 +452,47 @@ export async function autoReplyIfConfigured(
     };
 
     for (const replyPayload of replies) {
-      if (replyPayload.text) {
-        logVerbose(
-          `Auto-replying via Twilio: from ${replyFrom} to ${replyTo}, body length ${replyPayload.text.length}`,
-        );
-      } else {
-        logVerbose(
-          `Auto-replying via Twilio: from ${replyFrom} to ${replyTo} (media)`,
-        );
-      }
-
       const mediaList = replyPayload.mediaUrls?.length
         ? replyPayload.mediaUrls
         : replyPayload.mediaUrl
           ? [replyPayload.mediaUrl]
           : [];
 
-      if (mediaList.length === 0) {
-        await sendTwilio(replyPayload.text ?? "");
-      } else {
-        await sendTwilio(replyPayload.text ?? "", mediaList[0]);
-        for (const extra of mediaList.slice(1)) {
-          await sendTwilio("", extra);
-        }
-      }
+      const text = replyPayload.text ?? "";
+      const chunks =
+        text.length > 0
+          ? (text.match(new RegExp(`.{1,${TWILIO_TEXT_LIMIT}}`, "g")) ?? [])
+          : [""];
 
-      if (isVerbose()) {
-        console.log(
-          info(
-            `↩️  Auto-replied to ${replyTo} (sid ${message.sid ?? "no-sid"}${replyPayload.mediaUrl ? ", media" : ""})`,
-          ),
-        );
+      for (let i = 0; i < chunks.length; i++) {
+        const body = chunks[i];
+        const attachMedia = i === 0 ? mediaList[0] : undefined;
+
+        if (body) {
+          logVerbose(
+            `Auto-replying via Twilio: from ${replyFrom} to ${replyTo}, body length ${body.length}`,
+          );
+        } else if (attachMedia) {
+          logVerbose(
+            `Auto-replying via Twilio: from ${replyFrom} to ${replyTo} (media only)`,
+          );
+        }
+
+        await sendTwilio(body, attachMedia);
+
+        if (i === 0 && mediaList.length > 1) {
+          for (const extra of mediaList.slice(1)) {
+            await sendTwilio("", extra);
+          }
+        }
+
+        if (isVerbose()) {
+          console.log(
+            info(
+              `↩️  Auto-replied to ${replyTo} (sid ${message.sid ?? "no-sid"}${attachMedia ? ", media" : ""})`,
+            ),
+          );
+        }
       }
     }
   } catch (err) {
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index 2cf9722c8..3677f9843 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -29,6 +29,8 @@ import {
 } from "./reconnect.js";
 import { getWebAuthAgeMs } from "./session.js";
 
+const WEB_TEXT_LIMIT = 4000;
+
 /**
  * Send a message via IPC if relay is running, otherwise fall back to direct.
  * This avoids Signal session corruption from multiple Baileys connections.
@@ -371,14 +373,23 @@ async function deliverWebReply(params: {
     skipLog,
   } = params;
   const replyStarted = Date.now();
+  const textChunks =
+    (replyResult.text || "").length > 0
+      ? ((replyResult.text || "").match(
+          new RegExp(`.{1,${WEB_TEXT_LIMIT}}`, "g"),
+        ) ?? [])
+      : [];
   const mediaList = replyResult.mediaUrls?.length
     ? replyResult.mediaUrls
     : replyResult.mediaUrl
       ? [replyResult.mediaUrl]
       : [];
 
-  if (mediaList.length === 0 && replyResult.text) {
-    await msg.reply(replyResult.text || "");
+  // Text-only replies
+  if (mediaList.length === 0 && textChunks.length) {
+    for (const chunk of textChunks) {
+      await msg.reply(chunk);
+    }
     if (!skipLog) {
       logInfo(
         `✅ Sent web reply to ${msg.from} (${(Date.now() - replyStarted).toFixed(0)}ms)`,
@@ -402,7 +413,9 @@ async function deliverWebReply(params: {
     return;
   }
 
-  const cleanText = replyResult.text ?? undefined;
+  const remainingText = [...textChunks];
+
+  // Media (with optional caption on first item)
   for (const [index, mediaUrl] of mediaList.entries()) {
     try {
       const media = await loadWebMedia(mediaUrl, maxMediaBytes);
@@ -414,7 +427,8 @@ async function deliverWebReply(params: {
           `Web auto-reply media source: ${mediaUrl} (kind ${media.kind})`,
         );
       }
-      const caption = index === 0 ? cleanText || undefined : undefined;
+      const caption =
+        index === 0 ? remainingText.shift() || undefined : undefined;
       if (media.kind === "image") {
         await msg.sendMedia({
           image: media.buffer,
@@ -454,7 +468,7 @@ async function deliverWebReply(params: {
           connectionId: connectionId ?? null,
           to: msg.from,
           from: msg.to,
-          text: index === 0 ? (cleanText ?? null) : null,
+          text: caption ?? null,
           mediaUrl,
           mediaSizeBytes: media.buffer.length,
           mediaKind: media.kind,
@@ -466,12 +480,18 @@ async function deliverWebReply(params: {
       console.error(
         danger(`Failed sending web media to ${msg.from}: ${String(err)}`),
       );
-      if (index === 0 && cleanText) {
+      replyLogger.warn({ err, mediaUrl }, "failed to send web media reply");
+      if (index === 0 && remainingText.length) {
         console.log(`⚠️  Media skipped; sent text-only to ${msg.from}`);
-        await msg.reply(cleanText || "");
+        await msg.reply(remainingText.shift() || "");
       }
     }
   }
+
+  // Remaining text chunks after media
+  for (const chunk of remainingText) {
+    await msg.reply(chunk);
+  }
 }
 
 export async function monitorWebProvider(