diff --git a/lib/gitlab/untrusted_regexp.rb b/lib/gitlab/untrusted_regexp.rb
index 7ce2e9d636e..75ba0799058 100644
--- a/lib/gitlab/untrusted_regexp.rb
+++ b/lib/gitlab/untrusted_regexp.rb
@@ -11,7 +11,11 @@ module Gitlab
   class UntrustedRegexp
     delegate :===, to: :regexp
 
-    def initialize(pattern)
+    def initialize(pattern, multiline: false)
+      if multiline
+        pattern = "(?m)#{pattern}"
+      end
+
       @regexp = RE2::Regexp.new(pattern, log_errors: false)
 
       raise RegexpError.new(regexp.error) unless regexp.ok?
@@ -31,6 +35,19 @@ module Gitlab
       RE2.Replace(text, regexp, rewrite)
     end
 
+    # Handles regular expressions with the preferred RE2 library where possible
+    # via UntustedRegex. Falls back to Ruby's built-in regular expression library
+    # when the syntax would be invalid in RE2.
+    #
+    # One difference between these is `(?m)` multi-line mode. Ruby regex enables
+    # this by default, but also handles `^` and `$` differently.
+    # See: https://www.regular-expressions.info/modifiers.html
+    def self.with_fallback(pattern, multiline: false)
+      UntrustedRegexp.new(pattern, multiline: multiline)
+    rescue RegexpError
+      Regexp.new(pattern)
+    end
+
     private
 
     attr_reader :regexp
diff --git a/spec/lib/gitlab/untrusted_regexp_spec.rb b/spec/lib/gitlab/untrusted_regexp_spec.rb
index bed58d407ef..0ee7fa1e570 100644
--- a/spec/lib/gitlab/untrusted_regexp_spec.rb
+++ b/spec/lib/gitlab/untrusted_regexp_spec.rb
@@ -39,6 +39,14 @@ describe Gitlab::UntrustedRegexp do
 
       expect(result).to be_falsy
     end
+
+    it 'can handle regular expressions in multiline mode' do
+      regexp = described_class.new('^\d', multiline: true)
+
+      result = regexp === "Header\n\n1. Content"
+
+      expect(result).to be_truthy
+    end
   end
 
   describe '#scan' do