diff --git a/services/gmail.js b/services/gmail.js
index 69189ce..d1d5662 100644
--- a/services/gmail.js
+++ b/services/gmail.js
@@ -274,8 +274,8 @@ async function sendGmailReply(
     `Re: ${subject}`
   ).toString('base64')}?=`;
   const safeUser = escapeHtml(discordUser);
-  const safeReply = escapeHtml(replyText).replace(/\n/g, '<br>');
   const safeLogoUrl = escapeHtml(CONFIG.LOGO_URL || '');
+  const companySignatureText = (CONFIG.SIGNATURE || '').replace(/<br>/g, '\n');
   
   // Get staff signature if userId provided
   let signatureBlocks = { text: '', html: '' };
@@ -283,41 +283,61 @@ async function sendGmailReply(
     signatureBlocks = await getStaffSignatureBlocks(userId);
   }
 
-  const companySignatureHtml = `
-    <table border="0" cellpadding="0" cellspacing="0">
-      <tr>
-        <td style="padding-right: 12px;">
-          ${safeLogoUrl ? `<img src="${safeLogoUrl}" width="65">` : ''}
-        </td>
-        <td style="border-left: 1px solid #ddd; padding-left: 12px;">
-          <p style="margin: 0; font-weight: bold;">${safeUser}</p>
-          <div style="color: #666; font-size: 12px;">${escapeHtml(CONFIG.SIGNATURE || '').replace(/\n/g, '<br>')}</div>
-        </td>
-      </tr>
-    </table>`;
+  const safeStaffSigHtml = signatureBlocks.html ? signatureBlocks.html.replace(/\n/g, '<br>') : '';
+  const safeStaffSigText = signatureBlocks.text;
+  const safeCompanySigHtml = escapeHtml(CONFIG.SIGNATURE || '').replace(/\n/g, '<br>');
 
   const htmlBody = `
     <div style="font-family: sans-serif; font-size: 14px; color: #333;">
-      <p><strong>From:</strong> ${safeUser} on Discord</p>
-      <p>${safeReply}</p>
-      ${signatureBlocks.html ? `<p style="margin: 10px 0;">${signatureBlocks.html.replace(/\n/g, '<br>')}</p>` : ''}
+      <p>${escapeHtml(replyText).replace(/\n/g, '<br>')}</p>
+      ${safeStaffSigHtml ? `<p style="margin: 10px 0;">${safeStaffSigHtml}</p>` : ''}
       <hr style="border:none; border-top:1px solid #ddd; margin:20px 0;">
-      ${companySignatureHtml}
+      <table border="0" cellpadding="0" cellspacing="0">
+         <tr>
+           <td style="padding-right: 12px;">
+             ${safeLogoUrl ? `<img src="${safeLogoUrl}" width="65">` : ''}
+           </td>
+           <td style="border-left: 1px solid #ddd; padding-left: 12px;">
+             <p style="margin: 0; font-weight: bold;">${safeUser}</p>
+             <div style="color: #666; font-size: 12px;">${safeCompanySigHtml}</div>
+           </td>
+         </tr>
+       </table>
     </div>`;
 
-  const headers = [
+  const boundary = `\000000000000${Date.now().toString(16)}`;
+
+  const plainBody = [];
+   plainBody.push(replyText);
+   if (safeStaffSigText) {
+     plainBody.push(safeStaffSigText);
+   }
+   plainBody.push('');
+   plainBody.push('------------------------------');
+   plainBody.push('');
+   plainBody.push(companySignatureText);
+
+  const raw = Buffer.from([
     `From: ${CONFIG.MY_EMAIL}`,
     `To: ${recipientEmail}`,
     `Subject: ${utf8Subject}`,
     messageId ? `In-Reply-To: ${messageId}` : '',
     messageId ? `References: ${messageId}` : '',
     'MIME-Version: 1.0',
+    'Content-Type: multipart/alternative; boundary="' + boundary + '"',
+    '',
+    '--' + boundary,
+    'Content-Type: text/plain; charset="UTF-8"',
+    '',
+    ...plainBody,
+    '',
+    '--' + boundary,
     'Content-Type: text/html; charset="UTF-8"',
     '',
-    htmlBody
-  ].filter(Boolean);
-
-  const raw = Buffer.from(headers.join('\r\n'))
+    htmlBody,
+    '',
+    '--' + boundary + '--'
+  ].join('\r\n'))
     .toString('base64')
     .replace(/\+/g, '-')
     .replace(/\//g, '_')