diff --git a/src/rules.ts b/src/rules.ts
index c9bc07c5d6..b93e0c52cf 100644
--- a/src/rules.ts
+++ b/src/rules.ts
@@ -475,7 +475,7 @@ const inlineGfm: Record<InlineKeys, RegExp> = {
     .getRegex(),
   _backpedal: /(?:[^?!.,:;*_'"~()&]+|\([^)]*\)|&(?![a-zA-Z0-9]+;$)|[?!.,:;*_'"~)]+(?!$))+/,
   del: /^(~~?)(?=[^\s~])((?:\\[\s\S]|[^\\])*?(?:\\[\s\S]|[^\s~\\]))\1(?=[^~]|$)/,
-  text: edit(/^([`~]+|[^`~])(?:(?= {2,}\n)|(?=[a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-]+@)|[\s\S]*?(?:(?=[\\<!\[`*~_]|\b_|protocol:\/\/|www\.|$)|[^ ](?= {2,}\n)|[^a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-](?=[a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-]+@)))/)
+  text: edit(/^(`+|~+|[^`~])(?:(?=[`~])|(?= {2,}\n)|(?=[a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-]+@)|[\s\S]*?(?:(?=[\\<!\[`*~_]|\b_|protocol:\/\/|www\.|$)|[^ ](?= {2,}\n)|[^a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-](?=[a-zA-Z0-9.!#$%&'*+\/=?_`{\|}~-]+@)))/)
     .replace('protocol', _caseInsensitiveProtocol)
     .getRegex(),
 };
diff --git a/test/specs/new/codespan_adjacent_tilde.html b/test/specs/new/codespan_adjacent_tilde.html
new file mode 100644
index 0000000000..e49041d9cc
--- /dev/null
+++ b/test/specs/new/codespan_adjacent_tilde.html
@@ -0,0 +1,5 @@
+<p>~<code>code</code></p>
+<p><code>before</code>~<code>after</code></p>
+<p>`<del>strike</del></p>
+<p>~<code>code ` tick</code></p>
+<p><del><code>deleted code</code></del></p>
diff --git a/test/specs/new/codespan_adjacent_tilde.md b/test/specs/new/codespan_adjacent_tilde.md
new file mode 100644
index 0000000000..c7506a61f1
--- /dev/null
+++ b/test/specs/new/codespan_adjacent_tilde.md
@@ -0,0 +1,9 @@
+~`code`
+
+`before`~`after`
+
+`~strike~
+
+~``code ` tick``
+
+~~`deleted code`~~