diff --git a/src/Tokenizer.ts b/src/Tokenizer.ts
index 443cef4898..66fdccb82f 100644
--- a/src/Tokenizer.ts
+++ b/src/Tokenizer.ts
@@ -629,7 +629,7 @@ export class _Tokenizer {
       endReg.lastIndex = 0;
 
       // Clip maskedSrc to same section of string as src (move to lexer?)
-      maskedSrc = maskedSrc.slice(-1 * src.length + lLength);
+      maskedSrc = maskedSrc.slice(-1 * src.length + match[0].length - 1);
 
       while ((match = endReg.exec(maskedSrc)) != null) {
         rDelim = match[1] || match[2] || match[3] || match[4] || match[5] || match[6];
diff --git a/test/specs/new/emoji_inline.html b/test/specs/new/emoji_inline.html
index d0b19a20a7..17d788c15e 100644
--- a/test/specs/new/emoji_inline.html
+++ b/test/specs/new/emoji_inline.html
@@ -4,8 +4,17 @@
 <p><strong>🤓 test</strong></p>
 <p><strong>🏖️ test</strong></p>
 <p><strong>🏖️🤓💁 test</strong></p>
+<p><strong>💁 test</strong> test</p>
+<p>test <strong>💁 test</strong></p>
+<p>test <strong>💁 test</strong> test</p>
+<p><em><strong>test 💁</strong></em></p>
+<p><em><strong>💁 test</strong></em></p>
+<p><em><strong>💁 test</strong></em> test</p>
+<p>test <em><strong>💁 test</strong></em></p>
+<p>test <em><strong>💁 test</strong></em> test</p>
+<p><strong><strong>💁 test</strong></strong></p>
 <p>Situations where it works:</p>
 <p>**💁 **</p>
 <p><strong>⚠️ test</strong></p>
 <p>Here, the emoji rendering works, but the text doesn't get rendered in italic.</p>
-<p><em>💁 test</em></p>
\ No newline at end of file
+<p><em>💁 test</em></p>
diff --git a/test/specs/new/emoji_inline.md b/test/specs/new/emoji_inline.md
index 36f6385677..5690933d30 100644
--- a/test/specs/new/emoji_inline.md
+++ b/test/specs/new/emoji_inline.md
@@ -10,6 +10,24 @@ Situations where it fails:
 
 **🏖️🤓💁 test**
 
+**💁 test** test
+
+test **💁 test**
+
+test **💁 test** test
+
+***test 💁***
+
+***💁 test***
+
+***💁 test*** test
+
+test ***💁 test***
+
+test ***💁 test*** test
+
+****💁 test****
+
 Situations where it works:
 
 **💁 **
@@ -18,4 +36,4 @@ Situations where it works:
 
 Here, the emoji rendering works, but the text doesn't get rendered in italic.
 
-*💁 test*
\ No newline at end of file
+*💁 test*