diff --git a/src/apps/chatwoot/messages/to/chatwoot/PixMessage.test.ts b/src/apps/chatwoot/messages/to/chatwoot/PixMessage.test.ts
index aa760e42..d8472808 100644
--- a/src/apps/chatwoot/messages/to/chatwoot/PixMessage.test.ts
+++ b/src/apps/chatwoot/messages/to/chatwoot/PixMessage.test.ts
@@ -108,15 +108,15 @@ describe('PixMessage - pt-BR', () => {
     const result = converter.convert(payload, protoMessage);
 
     // Assert
-    const expected = `💳 ****PIX - Copia e Cola****
+    const expected = `💳 **PIX - Copia e Cola**
 
-****Merchant Name Here****
+**Merchant Name Here**
 
-****Chave PIX:**** +5000000000000
-****Tipo:**** PHONE
-****Referência:**** 4TB11111111
+**Chave PIX:** +5000000000000
+**Tipo:** PHONE
+**Referência:** 4TB11111111
 
-💳 ****PIX Copia e Cola enviado****`;
+💳 **PIX Copia e Cola enviado**`;
 
     expect(protoMessage).not.toBeNull();
     expect(result).not.toBeNull();
@@ -227,16 +227,16 @@ describe('PixMessage - pt-BR', () => {
     const result = converter.convert(payload, protoMessage);
 
     // Assert
-    const expected = `💳 ****PIX - Copia e Cola****
+    const expected = `💳 **PIX - Copia e Cola**
 
-****Merchant Name Here****
+**Merchant Name Here**
 
-****Chave PIX:**** +5000000000000
-****Tipo:**** PHONE
-****Valor:**** R$\u00A025,12
-****Referência:**** 4TB11111111
+**Chave PIX:** +5000000000000
+**Tipo:** PHONE
+**Valor:** R$\u00A025,12
+**Referência:** 4TB11111111
 
-💳 ****PIX Copia e Cola enviado****`;
+💳 **PIX Copia e Cola enviado**`;
 
     expect(protoMessage).not.toBeNull();
     expect(result).not.toBeNull();
diff --git a/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.test.ts b/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.test.ts
index 9f63c562..b6c90352 100644
--- a/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.test.ts
+++ b/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.test.ts
@@ -53,4 +53,40 @@ describe('WhatsappToMarkdown', () => {
     const expected = 'URL: https://example.com/test_page e texto *em itálico*';
     expect(WhatsappToMarkdown(input)).toBe(expected);
   });
+
+  it('keeps already bold markdown intact', () => {
+    const input = '**PIX - Copia e Cola**';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
+
+  it('keeps already strikethrough markdown intact', () => {
+    const input = '~~removed~~';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
+
+  it('keeps underscores inside identifiers intact', () => {
+    const input = 'api key: abc_test_key';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
+
+  it('does not convert underscores inside words', () => {
+    const input = 'Instance name: customer_prod_instance';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
+
+  it('does not convert when markers are stuck to word characters', () => {
+    const input = 'My name is*Rafael* and email is test_user@example.com';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
+
+  it('keeps formatting when markers touch punctuation boundaries', () => {
+    const input = 'Hello *Rafael*, welcome to _WAHA_!';
+    const expected = 'Hello **Rafael**, welcome to *WAHA*!';
+    expect(WhatsappToMarkdown(input)).toBe(expected);
+  });
+
+  it('ignores markers with inner spaces next to the marker', () => {
+    const input = '* text* and _ text_ should stay the same';
+    expect(WhatsappToMarkdown(input)).toBe(input);
+  });
 });
diff --git a/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.ts b/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.ts
index a59cafed..0f1beafb 100644
--- a/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.ts
+++ b/src/apps/chatwoot/messages/to/chatwoot/utils/markdown.ts
@@ -1,5 +1,18 @@
 import { UrlProtection } from '@waha/apps/chatwoot/messages/to/markdown';
 
+const boldPattern = new RegExp(
+  `(?<![\\p{L}\\p{N}_*])\\*(?!\\*)(?=\\S)(.+?)(?<=\\S)\\*(?![\\p{L}\\p{N}_*])`,
+  'gu',
+);
+const italicPattern = new RegExp(
+  `(?<![\\p{L}\\p{N}_])_(?!_)(?=\\S)(.+?)(?<=\\S)_(?![\\p{L}\\p{N}_])`,
+  'gu',
+);
+const strikePattern = new RegExp(
+  `(?<![\\p{L}\\p{N}_~])~(?!~)(?=\\S)(.+?)(?<=\\S)~(?![\\p{L}\\p{N}_~])`,
+  'gu',
+);
+
 export function WhatsappToMarkdown(text: string): string {
   if (!text) {
     return text;
@@ -16,11 +29,11 @@ export function WhatsappToMarkdown(text: string): string {
   // Apply markdown transformations to "clean" text
   let result = text
     // Bold: *bold* → **bold**
-    .replace(/\*(.*?)\*/g, '**$1**')
+    .replace(boldPattern, '**$1**')
     // Strikethrough: ~strike~ → ~~strike~~
-    .replace(/~(.*?)~/g, '~~$1~~')
+    .replace(strikePattern, '~~$1~~')
     // Italic: _italic_ → *italic*
-    .replace(/_(.*?)_/g, '*$1*');
+    .replace(italicPattern, '*$1*');
 
   // Restore original URLs after all transformations
   result = urls.restore(result);