diff --git a/app/javascript/dashboard/helper/emailQuoteExtractor.js b/app/javascript/dashboard/helper/emailQuoteExtractor.js
index 965a91f66..0bd68243c 100644
--- a/app/javascript/dashboard/helper/emailQuoteExtractor.js
+++ b/app/javascript/dashboard/helper/emailQuoteExtractor.js
@@ -126,11 +126,12 @@ export class EmailQuoteExtractor {
     return this.findBlocksContainingText(root, HEADER_PATTERNS);
   }
 
-  // ---------- 5. Plain-text RFC `>` tail ----------
-  // For text/plain emails (after sanitizeTextForRender converts \n → <br>),
-  // find the earliest top-level text node whose visible lines all begin with
-  // `>` and strip from there to the end (collapsing leading <br>/whitespace
-  // separators back into the tail).
+  // ---------- 5. Top-level quote tail ----------
+  // For replies that arrive as text + <br> with no block wrapper (text/plain
+  // bodies after sanitizeTextForRender). Find the earliest top-level text
+  // node that begins a quote tail — either every visible line starts with `>`
+  // (RFC quote prefix) or the text contains a header marker — and strip from
+  // there, collapsing leading <br>/whitespace separators into the tail.
 
   static removePlainTextTail(root) {
     const start = this.findPlainTextTailStart(root);
@@ -142,7 +143,7 @@ export class EmailQuoteExtractor {
   static findPlainTextTailStart(root) {
     const children = Array.from(root.childNodes);
     const tailIdx = children.findIndex(node =>
-      this.isQuotePrefixedTextNode(node)
+      this.isQuoteTailStartTextNode(node)
     );
     if (tailIdx === -1) return -1;
     let start = tailIdx;
@@ -152,14 +153,18 @@ export class EmailQuoteExtractor {
     return start;
   }
 
-  static isQuotePrefixedTextNode(node) {
+  static isQuoteTailStartTextNode(node) {
     if (node.nodeType !== Node.TEXT_NODE) return false;
     const text = node.textContent;
     if (!text.trim()) return false;
-    return text
-      .split('\n')
-      .filter(line => line.trim() !== '')
-      .every(line => line.trim().startsWith('>'));
+    const lines = text.split('\n').filter(line => line.trim() !== '');
+    if (lines.length > 0 && lines.every(l => l.trim().startsWith('>'))) {
+      return true;
+    }
+    return (
+      HEADER_PATTERNS.some(p => p.test(text)) ||
+      HARD_HEADER_PATTERNS.some(p => p.test(text))
+    );
   }
 
   static isNeutralNode(node) {
diff --git a/app/javascript/dashboard/helper/specs/emailQuoteExtractor.spec.js b/app/javascript/dashboard/helper/specs/emailQuoteExtractor.spec.js
index f3d338da9..963c83263 100644
--- a/app/javascript/dashboard/helper/specs/emailQuoteExtractor.spec.js
+++ b/app/javascript/dashboard/helper/specs/emailQuoteExtractor.spec.js
@@ -1,4 +1,4 @@
-import { describe, it, expect } from 'vitest';
+import { describe, expect, it } from 'vitest';
 import { EmailQuoteExtractor } from '../emailQuoteExtractor.js';
 
 const SAMPLE_EMAIL_HTML = `
@@ -237,6 +237,38 @@ describe('EmailQuoteExtractor', () => {
       expect(cleaned).toContain('Reply text');
       expect(cleaned).not.toContain('From: Sam');
     });
+
+    // Header markers at the TOP LEVEL — text + <br> shape with no block
+    // wrapper. The marker's nearest block ancestor is root itself.
+    it('detects top-level "On … wrote:" header (no wrapper)', () => {
+      const html =
+        'Reply text<br><br>On Tue, Pat wrote:<br>Original line 1<br>Original line 2';
+      expect(EmailQuoteExtractor.hasQuotes(html)).toBe(true);
+      const c = document.createElement('div');
+      c.innerHTML = EmailQuoteExtractor.extractQuotes(html);
+      expect(c.textContent).toContain('Reply text');
+      expect(c.textContent).not.toContain('On Tue, Pat wrote');
+      expect(c.textContent).not.toContain('Original line 1');
+    });
+
+    it('detects top-level "From:/Sent:" header (no wrapper)', () => {
+      const html =
+        'Reply text<br>From: Sam<br>Sent: Wednesday<br>Original body';
+      expect(EmailQuoteExtractor.hasQuotes(html)).toBe(true);
+      const c = document.createElement('div');
+      c.innerHTML = EmailQuoteExtractor.extractQuotes(html);
+      expect(c.textContent).toContain('Reply text');
+      expect(c.textContent).not.toContain('From: Sam');
+    });
+
+    it('detects top-level "-----Original Message-----" (no wrapper)', () => {
+      const html = 'Reply<br>-----Original Message-----<br>From: Sam<br>Body';
+      expect(EmailQuoteExtractor.hasQuotes(html)).toBe(true);
+      const c = document.createElement('div');
+      c.innerHTML = EmailQuoteExtractor.extractQuotes(html);
+      expect(c.textContent).toContain('Reply');
+      expect(c.textContent).not.toContain('Original Message');
+    });
   });
 
   it('strips RFC-style `>` quoted lines from a plain-text only body (iPhone Mail)', () => {