diff --git a/lib/flagsmith/engine/segments/models.rb b/lib/flagsmith/engine/segments/models.rb
index c5d8079..73023d8 100644
--- a/lib/flagsmith/engine/segments/models.rb
+++ b/lib/flagsmith/engine/segments/models.rb
@@ -1,5 +1,6 @@
 # frozen_string_literal: true
 
+require 'strscan'
 require_relative 'constants'
 
 module Flagsmith
@@ -45,7 +46,9 @@ class Condition
           CONTAINS => ->(other_value, self_value) { other_value.is_a?(String) && other_value.include?(self_value) },
 
           NOT_CONTAINS => ->(other_value, self_value) { other_value.is_a?(String) && !other_value.include?(self_value) },
-          REGEX => ->(other_value, self_value) { (other_value || false) && other_value.to_s.match?(self_value) }
+          REGEX => lambda { |other_value, self_value|
+            (other_value || false) && !StringScanner.new(other_value.to_s).match?(Regexp.new(self_value)).nil?
+          }
         }.freeze
 
         def initialize(operator:, value:, property: nil)
diff --git a/spec/engine/unit/segments/models_spec.rb b/spec/engine/unit/segments/models_spec.rb
index c534e79..14f0a51 100644
--- a/spec/engine/unit/segments/models_spec.rb
+++ b/spec/engine/unit/segments/models_spec.rb
@@ -75,6 +75,18 @@
   ['REGEX', 'foo', /[a-z]+/, true],
   ['REGEX', 'FOO', /[a-z]+/, false],
   ['REGEX', '1.2.3', /\d/, true],
+  ['REGEX', 'production', 'prod', true],
+  ['REGEX', 'nonproduction', 'prod', false],
+  ['REGEX', 'development', 'prod|dev', true],
+  ['REGEX', 'nondevelopment', 'prod|dev', false],
+  ['REGEX', 'jane@example.com', '@example\.com$', false],
+  ['REGEX', 'jane@example.com', '[a-z]+@example\.com$', true],
+  ['REGEX', 'production-eu', '^production$', false],
+  ['REGEX', 'Production', 'prod', false],
+  ['REGEX', 'Production', '[Pp]rod', true],
+  ['REGEX', 'v1.2', 'v\d', true],
+  ['REGEX', 'release-v1.2', 'v\d', false],
+  ['REGEX', 123, '\d*[13579]$', true],
 
   ['EQUAL', '1.0.0', '1.0.0:semver', true],
   ['EQUAL', '1.0.0', '1.0.1:semver', false],