diff --git a/__tests__/ExpensiMark-HTML-test.js b/__tests__/ExpensiMark-HTML-test.js
index 0051dd4c..df53ba14 100644
--- a/__tests__/ExpensiMark-HTML-test.js
+++ b/__tests__/ExpensiMark-HTML-test.js
@@ -26,6 +26,24 @@ test('Test bold within code blocks is skipped', () => {
     expect(parser.replace(testString)).toBe(replacedString);
 });
 
+test('Test special character plus _ ahead asterisk still result in bold', () => {
+    const testString = 'This is a !_*bold*';
+    const replacedString = 'This is a !_<strong>bold</strong>';
+    expect(parser.replace(testString)).toBe(replacedString);
+});
+
+test('Test a word plus _ ahead asterisk not result in bold', () => {
+    const testString = 'This is not a_*bold*';
+    const replacedString = 'This is not a_*bold*';
+    expect(parser.replace(testString)).toBe(replacedString);
+});
+
+test('Test _ ahead asterisk still result in bold', () => {
+    const testString = 'This is a ~_*bold*';
+    const replacedString = 'This is a ~_<strong>bold</strong>';
+    expect(parser.replace(testString)).toBe(replacedString);
+});
+
 test('Test heading markdown replacement', () => {
     let testString = '# Heading should not have new line after it.\n';
     expect(parser.replace(testString)).toBe('<h1>Heading should not have new line after it.</h1>');
diff --git a/lib/ExpensiMark.ts b/lib/ExpensiMark.ts
index 0ffd3758..596af552 100644
--- a/lib/ExpensiMark.ts
+++ b/lib/ExpensiMark.ts
@@ -468,8 +468,14 @@ export default class ExpensiMark {
                 // \B will match everything that \b doesn't, so it works
                 // for * and ~: https://www.rexegg.com/regex-boundaries.html#notb
                 name: 'bold',
-                regex: /(?<!<[^>]*)\B\*(?![^<]*(?:<\/pre>|<\/code>|<\/a>))((?![\s*])[\s\S]*?[^\s*](?<!\s))\*\B(?![^<]*>)(?![^<]*(<\/pre>|<\/code>|<\/a>))/g,
-                replacement: (_extras, match, g1) => (g1.includes('</pre>') || this.containsNonPairTag(g1) ? match : `<strong>${g1}</strong>`),
+                regex: /(?<!<[^>]*)(\b_|\B)\*(?![^<]*(?:<\/pre>|<\/code>|<\/a>))((?![\s*])[\s\S]*?[^\s*](?<!\s))\*\B(?![^<]*>)(?![^<]*(<\/pre>|<\/code>|<\/a>))/g,
+                replacement: (_extras, match, g1, g2) => {
+                    if (g1.includes('_')) {
+                        return `${g1}<strong>${g2}</strong>`;
+                    }
+
+                    return g2.includes('</pre>') || this.containsNonPairTag(g2) ? match : `<strong>${g2}</strong>`;
+                },
             },
             {
                 name: 'strikethrough',