diff --git a/CHANGES.md b/CHANGES.md
index 4b7c3021fd..bf95f0277d 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -25,6 +25,7 @@ Core Grammars:
 - enh(json) add json5 support [Kerry Shetline][]
 - fix(css) `unicode-range` parsing, issue #4253 [Kerry Shetline][]
 - fix(csharp) Support digit separators [te-ing][]
+- fix(ruby) support nested content in `%r{}` regex literals outside expression contexts [Jacques Erasmus][]
 
 Documentation:
 
@@ -53,6 +54,7 @@ CONTRIBUTORS
 [Thomas Gorissen]: https://github.com/serrynaimo
 [te-ing]: https://github.com/te-ing
 [Anthony Martin]: https://github.com/anthony-c-martin
+[Jacques Erasmus]: https://github.com/j-erasmus
 
 
 ## Version 11.11.1
diff --git a/src/languages/ruby.js b/src/languages/ruby.js
index 91b2cb527d..ce2ffc18a5 100644
--- a/src/languages/ruby.js
+++ b/src/languages/ruby.js
@@ -227,6 +227,34 @@ export default function(hljs) {
     ]
   };
 
+  const REGEXP = {
+    className: 'regexp',
+    contains: [
+      hljs.BACKSLASH_ESCAPE,
+      SUBST,
+      {
+        begin: /\[/,
+        end: /\]/,
+        contains: [
+          hljs.BACKSLASH_ESCAPE,
+          { begin: /\\./ }
+        ]
+      },
+      {
+        begin: /\{/, end: /\}/,
+        contains: ['self', hljs.BACKSLASH_ESCAPE, SUBST],
+        relevance: 0
+      }
+    ],
+    illegal: /\n/,
+    variants: [
+      { begin: /%r\{/, end: /\}[a-z]*/ },
+      { begin: /%r\(/, end: /\)[a-z]*/ },
+      { begin: /%r!/, end: /![a-z]*/ },
+      { begin: /%r\[/, end: /\][a-z]*/ }
+    ]
+  };
+
   const PARAMS = {
     variants: [
       {
@@ -324,6 +352,7 @@ export default function(hljs) {
     UPPER_CASE_CONSTANT,
     CLASS_REFERENCE,
     METHOD_DEFINITION,
+    REGEXP,
     {
       // swallow namespace qualifiers before symbols
       begin: hljs.IDENT_RE + '::' },
@@ -372,22 +401,6 @@ export default function(hljs) {
             {
               begin: '/',
               end: '/[a-z]*'
-            },
-            {
-              begin: /%r\{/,
-              end: /\}[a-z]*/
-            },
-            {
-              begin: '%r\\(',
-              end: '\\)[a-z]*'
-            },
-            {
-              begin: '%r!',
-              end: '![a-z]*'
-            },
-            {
-              begin: '%r\\[',
-              end: '\\][a-z]*'
             }
           ]
         }
diff --git a/test/markup/ruby/regexes.expect.txt b/test/markup/ruby/regexes.expect.txt
index 0c108383cf..2a9a63d80d 100644
--- a/test/markup/ruby/regexes.expect.txt
+++ b/test/markup/ruby/regexes.expect.txt
@@ -3,3 +3,9 @@ str =~ <span class="hljs-regexp">%r{foo|bar|buz$}</span>
 str =~ <span class="hljs-regexp">%r!foo|bar$!</span>
 str =~ <span class="hljs-regexp">%r[foo|bar$]</span>
 str =~ <span class="hljs-regexp">%r(\(foo|bar\)$)</span>
+str =~ <span class="hljs-regexp">%r{(\.{2}|\A/)}</span>
+str =~ <span class="hljs-regexp">/[{}]/</span>
+str =~ <span class="hljs-regexp">/[\]]/</span>
+str =~ <span class="hljs-regexp">/[a-z]{3}/</span>
+str =~ <span class="hljs-regexp">%r{[{}]+}</span>
+str =~ <span class="hljs-regexp">/<span class="hljs-subst">#{var}</span>[{}]/</span>
diff --git a/test/markup/ruby/regexes.txt b/test/markup/ruby/regexes.txt
index 9d31e03b44..d60c2a24e1 100644
--- a/test/markup/ruby/regexes.txt
+++ b/test/markup/ruby/regexes.txt
@@ -3,3 +3,9 @@ str =~ %r{foo|bar|buz$}
 str =~ %r!foo|bar$!
 str =~ %r[foo|bar$]
 str =~ %r(\(foo|bar\)$)
+str =~ %r{(\.{2}|\A/)}
+str =~ /[{}]/
+str =~ /[\]]/
+str =~ /[a-z]{3}/
+str =~ %r{[{}]+}
+str =~ /#{var}[{}]/