diff --git a/src/markdown/whatsapp.test.ts b/src/markdown/whatsapp.test.ts
new file mode 100644
index 0000000000..e69cfbeaf1
--- /dev/null
+++ b/src/markdown/whatsapp.test.ts
@@ -0,0 +1,62 @@
+import { describe, expect, it } from "vitest";
+import { markdownToWhatsApp } from "./whatsapp.js";
+
+describe("markdownToWhatsApp", () => {
+  it("converts **bold** to *bold*", () => {
+    expect(markdownToWhatsApp("**SOD Blast:**")).toBe("*SOD Blast:*");
+  });
+
+  it("converts __bold__ to *bold*", () => {
+    expect(markdownToWhatsApp("__important__")).toBe("*important*");
+  });
+
+  it("converts ~~strikethrough~~ to ~strikethrough~", () => {
+    expect(markdownToWhatsApp("~~deleted~~")).toBe("~deleted~");
+  });
+
+  it("leaves single *italic* unchanged (already WhatsApp bold)", () => {
+    expect(markdownToWhatsApp("*text*")).toBe("*text*");
+  });
+
+  it("leaves _italic_ unchanged (already WhatsApp italic)", () => {
+    expect(markdownToWhatsApp("_text_")).toBe("_text_");
+  });
+
+  it("preserves fenced code blocks", () => {
+    const input = "```\nconst x = **bold**;\n```";
+    expect(markdownToWhatsApp(input)).toBe(input);
+  });
+
+  it("preserves inline code", () => {
+    expect(markdownToWhatsApp("Use `**not bold**` here")).toBe("Use `**not bold**` here");
+  });
+
+  it("handles mixed formatting", () => {
+    expect(markdownToWhatsApp("**bold** and ~~strike~~ and _italic_")).toBe(
+      "*bold* and ~strike~ and _italic_",
+    );
+  });
+
+  it("handles multiple bold segments", () => {
+    expect(markdownToWhatsApp("**one** then **two**")).toBe("*one* then *two*");
+  });
+
+  it("returns empty string for empty input", () => {
+    expect(markdownToWhatsApp("")).toBe("");
+  });
+
+  it("returns plain text unchanged", () => {
+    expect(markdownToWhatsApp("no formatting here")).toBe("no formatting here");
+  });
+
+  it("handles bold inside a sentence", () => {
+    expect(markdownToWhatsApp("This is **very** important")).toBe("This is *very* important");
+  });
+
+  it("preserves code block with formatting inside", () => {
+    const input = "Before ```**bold** and ~~strike~~``` after **real bold**";
+    expect(markdownToWhatsApp(input)).toBe(
+      "Before ```**bold** and ~~strike~~``` after *real bold*",
+    );
+  });
+});
diff --git a/src/markdown/whatsapp.ts b/src/markdown/whatsapp.ts
new file mode 100644
index 0000000000..9532bc8f7c
--- /dev/null
+++ b/src/markdown/whatsapp.ts
@@ -0,0 +1,77 @@
+import { escapeRegExp } from "../utils.js";
+/**
+ * Convert standard Markdown formatting to WhatsApp-compatible markup.
+ *
+ * WhatsApp uses its own formatting syntax:
+ *   bold:          *text*
+ *   italic:        _text_
+ *   strikethrough: ~text~
+ *   monospace:     ```text```
+ *
+ * Standard Markdown uses:
+ *   bold:          **text** or __text__
+ *   italic:        *text* or _text_
+ *   strikethrough: ~~text~~
+ *   code:          `text` (inline) or ```text``` (block)
+ *
+ * The conversion preserves fenced code blocks and inline code,
+ * then converts bold and strikethrough markers.
+ */
+
+/** Placeholder tokens used during conversion to protect code spans. */
+const FENCE_PLACEHOLDER = "\x00FENCE";
+const INLINE_CODE_PLACEHOLDER = "\x00CODE";
+
+/**
+ * Convert standard Markdown bold/italic/strikethrough to WhatsApp formatting.
+ *
+ * Order of operations matters:
+ * 1. Protect fenced code blocks (```...```) — already WhatsApp-compatible
+ * 2. Protect inline code (`...`) — leave as-is
+ * 3. Convert **bold** → *bold* and __bold__ → *bold*
+ * 4. Convert ~~strike~~ → ~strike~
+ * 5. Restore protected spans
+ *
+ * Italic *text* and _text_ are left alone since WhatsApp uses _text_ for italic
+ * and single * is already WhatsApp bold — no conversion needed for single markers.
+ */
+export function markdownToWhatsApp(text: string): string {
+  if (!text) {
+    return text;
+  }
+
+  // 1. Extract and protect fenced code blocks
+  const fences: string[] = [];
+  let result = text.replace(/```[\s\S]*?```/g, (match) => {
+    fences.push(match);
+    return `${FENCE_PLACEHOLDER}${fences.length - 1}`;
+  });
+
+  // 2. Extract and protect inline code
+  const inlineCodes: string[] = [];
+  result = result.replace(/`[^`\n]+`/g, (match) => {
+    inlineCodes.push(match);
+    return `${INLINE_CODE_PLACEHOLDER}${inlineCodes.length - 1}`;
+  });
+
+  // 3. Convert **bold** → *bold* and __bold__ → *bold*
+  result = result.replace(/\*\*(.+?)\*\*/g, "*$1*");
+  result = result.replace(/__(.+?)__/g, "*$1*");
+
+  // 4. Convert ~~strikethrough~~ → ~strikethrough~
+  result = result.replace(/~~(.+?)~~/g, "~$1~");
+
+  // 5. Restore inline code
+  result = result.replace(
+    new RegExp(`${escapeRegExp(INLINE_CODE_PLACEHOLDER)}(\\d+)`, "g"),
+    (_, idx) => inlineCodes[Number(idx)] ?? "",
+  );
+
+  // 6. Restore fenced code blocks
+  result = result.replace(
+    new RegExp(`${escapeRegExp(FENCE_PLACEHOLDER)}(\\d+)`, "g"),
+    (_, idx) => fences[Number(idx)] ?? "",
+  );
+
+  return result;
+}
diff --git a/src/web/auto-reply/deliver-reply.ts b/src/web/auto-reply/deliver-reply.ts
index 607b1ac418..cee7e1b79a 100644
--- a/src/web/auto-reply/deliver-reply.ts
+++ b/src/web/auto-reply/deliver-reply.ts
@@ -4,6 +4,7 @@ import type { WebInboundMsg } from "./types.js";
 import { chunkMarkdownTextWithMode, type ChunkMode } from "../../auto-reply/chunk.js";
 import { logVerbose, shouldLogVerbose } from "../../globals.js";
 import { convertMarkdownTables } from "../../markdown/tables.js";
+import { markdownToWhatsApp } from "../../markdown/whatsapp.js";
 import { sleep } from "../../utils.js";
 import { loadWebMedia } from "../media.js";
 import { newConnectionId } from "../reconnect.js";
@@ -29,7 +30,9 @@ export async function deliverWebReply(params: {
   const replyStarted = Date.now();
   const tableMode = params.tableMode ?? "code";
   const chunkMode = params.chunkMode ?? "length";
-  const convertedText = convertMarkdownTables(replyResult.text || "", tableMode);
+  const convertedText = markdownToWhatsApp(
+    convertMarkdownTables(replyResult.text || "", tableMode),
+  );
   const textChunks = chunkMarkdownTextWithMode(convertedText, textLimit, chunkMode);
   const mediaList = replyResult.mediaUrls?.length
     ? replyResult.mediaUrls
diff --git a/src/web/outbound.ts b/src/web/outbound.ts
index 1df9579893..08a0e36341 100644
--- a/src/web/outbound.ts
+++ b/src/web/outbound.ts
@@ -4,6 +4,7 @@ import { resolveMarkdownTableMode } from "../config/markdown-tables.js";
 import { getChildLogger } from "../logging/logger.js";
 import { createSubsystemLogger } from "../logging/subsystem.js";
 import { convertMarkdownTables } from "../markdown/tables.js";
+import { markdownToWhatsApp } from "../markdown/whatsapp.js";
 import { normalizePollInput, type PollInput } from "../polls.js";
 import { toWhatsappJid } from "../utils.js";
 import { type ActiveWebSendOptions, requireActiveWebListener } from "./active-listener.js";
@@ -34,6 +35,7 @@ export async function sendMessageWhatsApp(
     accountId: resolvedAccountId ?? options.accountId,
   });
   text = convertMarkdownTables(text ?? "", tableMode);
+  text = markdownToWhatsApp(text);
   const logger = getChildLogger({
     module: "web-outbound",
     correlationId,