diff --git a/app/javascript/dashboard/helper/editorHelper.js b/app/javascript/dashboard/helper/editorHelper.js
index 9839a04e0..491dd9d44 100644
--- a/app/javascript/dashboard/helper/editorHelper.js
+++ b/app/javascript/dashboard/helper/editorHelper.js
@@ -123,6 +123,13 @@ export function cleanSignature(signature) {
   }
 }
 
+// Strip `\<newline>` hardbreak markers trailing `--` after a signature slice
+const stripDelimiterHardbreaks = body =>
+  body.replace(/(--)\s*(?:\\\s*)+$/, '$1');
+
+// Strip standalone blank-paragraph markers (`\` on their own lines).
+const stripTrailingBlankLine = body => body.replace(/\n(?:\s*\\\n)+$/, '');
+
 /**
  * Adds the signature delimiter to the beginning of the signature.
  *
@@ -227,13 +234,19 @@ export function removeSignature(body, signature, channelType) {
   // trimming will ensure any spaces or new lines before the signature are removed
   // This means we will have the delimiter at the end
   if (signatureIndex > -1) {
-    newBody = newBody.substring(0, signatureIndex).trimEnd();
+    newBody = stripDelimiterHardbreaks(
+      newBody.substring(0, signatureIndex)
+    ).trimEnd();
   }
 
   // Remove delimiter if it's at the end
   if (newBody.endsWith(SIGNATURE_DELIMITER)) {
     // if the delimiter is at the end, remove it
     newBody = newBody.slice(0, -SIGNATURE_DELIMITER.length);
+    // strip any trailing blank-line markers
+    if (signatureIndex > -1) {
+      newBody = stripTrailingBlankLine(newBody);
+    }
   }
 
   return newBody;
diff --git a/app/javascript/dashboard/helper/specs/editorHelper.spec.js b/app/javascript/dashboard/helper/specs/editorHelper.spec.js
index b06c36d42..c7822bde7 100644
--- a/app/javascript/dashboard/helper/specs/editorHelper.spec.js
+++ b/app/javascript/dashboard/helper/specs/editorHelper.spec.js
@@ -336,6 +336,38 @@ describe('removeSignature', () => {
       'This is a test\n\n'
     );
   });
+  it('strips blank-paragraph marker before the delimiter', () => {
+    expect(removeSignature('hey\n\n\\\n--\n\nHello there', 'Hello there')).toBe(
+      'hey'
+    );
+  });
+  it('strips multiple consecutive blank-paragraph markers before the delimiter', () => {
+    expect(
+      removeSignature('wewe\n\n\\\n\\\n\\\n--\n\nHello there', 'Hello there')
+    ).toBe('wewe');
+  });
+  it('strips dangling hardbreak when signature shared a paragraph with "--"', () => {
+    expect(removeSignature('hey\n\n--\\\nHello there', 'Hello there')).toBe(
+      'hey\n\n'
+    );
+  });
+  it('preserves trailing backslash in user text when appending', () => {
+    expect(appendSignature('The path is C:\\', 'Best\nAgent')).toContain(
+      'C:\\'
+    );
+    expect(appendSignature('C:\\\n', 'Best\nAgent')).toContain('C:\\');
+    expect(appendSignature('C:\\\n\n', 'Best\nAgent')).toContain('C:\\');
+  });
+  it('preserves trailing backslash in user text when removing', () => {
+    expect(removeSignature('C:\\\n--\n\nBest\nAgent', 'Best\nAgent')).toContain(
+      'C:\\'
+    );
+    expect(removeSignature('C:\\\n--', 'no matching sig')).toContain('C:\\');
+    expect(removeSignature('C:\\\nBest\\\nAgent', 'Best\nAgent')).toContain(
+      'C:\\'
+    );
+    expect(removeSignature('notes\n\\\n--', 'no matching sig')).toContain('\\');
+  });
 });
 
 describe('removeSignature with stripped signature', () => {
diff --git a/app/javascript/shared/helpers/MessageFormatter.js b/app/javascript/shared/helpers/MessageFormatter.js
index c87209fd4..825132e13 100644
--- a/app/javascript/shared/helpers/MessageFormatter.js
+++ b/app/javascript/shared/helpers/MessageFormatter.js
@@ -42,6 +42,7 @@ const createMarkdownInstance = (linkify = true) => {
     quotes: '\u201c\u201d\u2018\u2019',
     maxNesting: 20,
   })
+    .disable(['lheading'])
     .use(mentionPlugin)
     .use(imgResizeManager)
     .use(mila, {
diff --git a/app/javascript/shared/helpers/specs/MessageFormatter.spec.js b/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
index a685cb0da..12b84085c 100644
--- a/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
+++ b/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
@@ -33,6 +33,13 @@ describe('#MessageFormatter', () => {
 <h2>tool</h2>`
       );
     });
+
+    it('should not render a setext heading when text is followed by "--"', () => {
+      const message = 'hy\n\n\\\n\\-\\-\n\nHello there';
+      const result = new MessageFormatter(message).formattedMessage;
+      expect(result).not.toMatch('<h2>');
+      expect(result).not.toMatch('<h1>');
+    });
   });
 
   describe('content with image and has "cw_image_height" query at the end of URL', () => {