diff --git a/.github/matrix.json b/.github/matrix.json
index d09ceee255..911f80b11e 100644
--- a/.github/matrix.json
+++ b/.github/matrix.json
@@ -1,5 +1,5 @@
 {
   "postgresql": ["13"],
-  "ruby": ["3.0"],
+  "ruby": ["3.0", "3.3"],
   "node": ["22"]
 }
diff --git a/.rubocop.yml b/.rubocop.yml
index 9b1850652a..5ccfdfaa26 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -6,7 +6,7 @@ inherit_gem:
 inherit_from: .rubocop_todo.yml
 
 AllCops:
-  TargetRubyVersion: 2.7
+  TargetRubyVersion: 3.0
 
 Bundler/OrderedGems:
   Enabled: false
diff --git a/app/controllers/api/base_controller.rb b/app/controllers/api/base_controller.rb
index 0e4521d03e..bd9256070c 100644
--- a/app/controllers/api/base_controller.rb
+++ b/app/controllers/api/base_controller.rb
@@ -311,7 +311,7 @@ def add_info_headers
     def setup_search_options
       params[:search] ||= ""
       params.each do |param, value|
-        if param =~ /(\w+)_id$/ && value.present?
+        if param.to_s =~ /(\w+)_id$/ && value.present?
           query = " #{Regexp.last_match(1)} = #{value}"
           params[:search] += query unless params[:search].include? query
         end
diff --git a/app/controllers/application_controller.rb b/app/controllers/application_controller.rb
index 7d7701d5e6..92965ccc31 100644
--- a/app/controllers/application_controller.rb
+++ b/app/controllers/application_controller.rb
@@ -196,7 +196,7 @@ def setup_search_options
     @original_search_parameter = params[:search]
     params[:search] ||= ""
     params.each do |param, value|
-      if param =~ /(\w+)_id$/ && value.present?
+      if param.to_s =~ /(\w+)_id$/ && value.present?
         query = "#{Regexp.last_match(1)} = #{value}"
         unless params[:search].include? query
           params[:search] += ' and ' if params[:search].present?
diff --git a/app/lib/foreman/http_proxy.rb b/app/lib/foreman/http_proxy.rb
index 2e798fd109..2548e1172e 100644
--- a/app/lib/foreman/http_proxy.rb
+++ b/app/lib/foreman/http_proxy.rb
@@ -60,7 +60,7 @@ def log_proxied_request(lib, current_proxy, requested_host)
 
     def http_host_excepted_by_wildcard?(host)
       return false if http_proxy_except_list.empty?
-      host =~ Setting.convert_array_to_regexp(http_proxy_except_list)
+      Setting.convert_array_to_regexp(http_proxy_except_list).match?(host)
     end
 
     def http_host_excepted?(host)
diff --git a/app/lib/net/validations.rb b/app/lib/net/validations.rb
index a344c0cf5c..e596d70c10 100644
--- a/app/lib/net/validations.rb
+++ b/app/lib/net/validations.rb
@@ -44,7 +44,7 @@ def self.validate_ip6!(ip)
 
     # validates a network mask
     def self.validate_mask(mask)
-      mask =~ MASK_REGEXP
+      MASK_REGEXP.match?(mask)
     end
 
     # validates a network mask and raises an error
@@ -90,7 +90,7 @@ def self.validate_mac!(mac)
 
     # validates the hostname
     def self.validate_hostname(hostname)
-      hostname =~ HOST_REGEXP
+      HOST_REGEXP.match?(hostname)
     end
 
     # validates the hostname and raises an error
diff --git a/app/models/concerns/audit_extensions.rb b/app/models/concerns/audit_extensions.rb
index 4a7bc221ec..acc2f5ef68 100644
--- a/app/models/concerns/audit_extensions.rb
+++ b/app/models/concerns/audit_extensions.rb
@@ -222,11 +222,11 @@ def ensure_username
 
   def fix_auditable_type
     # STI Host class should use the stub module instead of Host::Base
-    self.auditable_type = "Host::Base" if auditable_type =~ /^(::)?Host::/
-    self.associated_type = "Host::Base" if associated_type =~ /^(::)?Host::/
+    self.auditable_type = "Host::Base" if /^(::)?Host::/.match?(auditable_type)
+    self.associated_type = "Host::Base" if /^(::)?Host::/.match?(associated_type)
     self.auditable_type = auditable.type if ["Taxonomy", "LookupKey"].include?(auditable_type) && auditable
     self.associated_type = associated.type if ["Taxonomy", "LookupKey"].include?(associated_type) && associated
-    self.auditable_type = auditable.type if auditable_type =~ /Nic::/
+    self.auditable_type = auditable.type if /Nic::/.match?(auditable_type)
   end
 
   def ensure_auditable_and_associated_name
diff --git a/app/models/concerns/host_common.rb b/app/models/concerns/host_common.rb
index 076e453621..e3c2d36dcc 100644
--- a/app/models/concerns/host_common.rb
+++ b/app/models/concerns/host_common.rb
@@ -143,7 +143,7 @@ def default_image_file
   def image_file=(file)
     # We only save a value into the image_file field if the value is not the default path, (which was placed in the entry when it was displayed,)
     # and it is not a directory, (ends in /)
-    value = ((default_image_file == file) || (file =~ /\/\Z/) || file == "") ? nil : file
+    value = ((default_image_file == file) || file.blank? || file.end_with?('/')) ? nil : file
     self[:image_file] = value
   end
 
diff --git a/app/models/concerns/hostext/search.rb b/app/models/concerns/hostext/search.rb
index 4ee19858ab..b162120b4f 100644
--- a/app/models/concerns/hostext/search.rb
+++ b/app/models/concerns/hostext/search.rb
@@ -267,7 +267,7 @@ def search_by_os_minor(key, operator, value)
           operator_addition2 = (operator == "=") ? "=" : ""
           operator = '!=' if operator == '<>'
           if operator =~ /ILIKE/
-            match = os.minor =~ /#{value}/
+            match = /#{value}/.match?(os.minor)
             match = !match if operator.start_with?('NOT')
             operatingsystem_ids.append(os.id) if match
           elsif os_y.to_i.public_send(operator + operator_addition1, y.to_i)
diff --git a/app/models/concerns/parameterizable.rb b/app/models/concerns/parameterizable.rb
index ffd130221a..b19d2c63f5 100644
--- a/app/models/concerns/parameterizable.rb
+++ b/app/models/concerns/parameterizable.rb
@@ -27,7 +27,7 @@ def to_param
       end
 
       def self.from_param(id_name)
-        find_by_id(id_name.to_i) if id_name =~ /\A\d+-/
+        find_by_id(id_name.to_i) if /\A\d+-/.match?(id_name)
       end
     end
   end
diff --git a/app/models/concerns/scoped_search_extensions.rb b/app/models/concerns/scoped_search_extensions.rb
index f97ee690d4..574180d49a 100644
--- a/app/models/concerns/scoped_search_extensions.rb
+++ b/app/models/concerns/scoped_search_extensions.rb
@@ -4,7 +4,7 @@ module ScopedSearchExtensions
   module ClassMethods
     def value_to_sql(operator, value)
       return value                 if operator !~ /LIKE/i
-      return value.tr_s('%*', '%') if (value =~ /%|\*/)
+      return value.tr_s('%*', '%') if value.to_s.match?(/%|\*/)
       escape_str_format("%#{value}%")
     end
 
@@ -13,12 +13,8 @@ def escape_str_format(str)
     end
 
     def cast_facts(table, key, operator, value)
-      is_int = (value =~ /\A[-+]?\d+\z/) || value.is_a?(Integer)
-      is_pg = ActiveRecord::Base.connection.adapter_name.downcase.starts_with? 'postgresql'
-      # Once Postgresql 8 support is removed (used in CentOS 6), this could be replaced to only keep the first form (working well with PG 9)
-      if (is_int && !is_pg)
-        casted = "CAST(#{table}.value AS DECIMAL) #{operator} #{value}"
-      elsif (is_int && is_pg && operator !~ /LIKE/i)
+      is_int = value.to_s.match?(/\A[-+]?\d+\z/)
+      if is_int && operator !~ /LIKE/i
         casted = "#{table}.value ~ E'^\\\\d+$' AND CAST(#{table}.value AS DECIMAL) #{operator} #{value}"
       else
         # Escape string formatting with %, as conditions will be re-sanitized through scoped_search
diff --git a/app/models/fact_value.rb b/app/models/fact_value.rb
index 8a60895f31..f0df424307 100644
--- a/app/models/fact_value.rb
+++ b/app/models/fact_value.rb
@@ -49,7 +49,7 @@ class FactValue < ApplicationRecord
 
   def self.search_by_host_or_hostgroup(key, operator, value)
     host_or_hg = (key == 'host.hostgroup') ? 'hostgroup' : 'host'
-    search_term = (value =~ /\A\d+\Z/) ? 'id' : 'name'
+    search_term = /\A\d+\Z/.match?(value) ? 'id' : 'name'
     conditions = sanitize_sql_for_conditions(["#{host_or_hg.pluralize}.#{search_term} #{operator} ?", value_to_sql(operator, value)])
     { :joins => host_or_hg.to_sym, :conditions => conditions }
   end
diff --git a/app/models/medium.rb b/app/models/medium.rb
index 5cb5faf650..441887f233 100644
--- a/app/models/medium.rb
+++ b/app/models/medium.rb
@@ -56,7 +56,7 @@ def jumpstart_dir
 
   # Write the image path, with a trailing "/" if required
   def image_path=(path)
-    self[:image_path] = "#{path}#{'/' unless path =~ /\/$|^$/}"
+    self[:image_path] = "#{path}#{'/' unless /\/$|^$/.match?(path)}"
   end
 
   def ensure_hosts_not_in_build
diff --git a/app/models/operatingsystem.rb b/app/models/operatingsystem.rb
index a2b61924b6..468e1a30a2 100644
--- a/app/models/operatingsystem.rb
+++ b/app/models/operatingsystem.rb
@@ -299,7 +299,7 @@ def shorten_description(description)
 
   def self.deduce_family(name)
     families.find do |f|
-      name =~ FAMILIES[f]
+      FAMILIES[f].match?(name)
     end
   end
 
diff --git a/app/models/setting.rb b/app/models/setting.rb
index 2b9c3c415a..bf4e8144a6 100644
--- a/app/models/setting.rb
+++ b/app/models/setting.rb
@@ -133,7 +133,7 @@ def parse_string_value(val)
       end
 
     when "array"
-      if val =~ /\A\[.*\]\Z/
+      if /\A\[.*\]\Z/.match?(val)
         begin
           self.value = YAML.safe_load(val.gsub(/(,)(\S)/, "\\1 \\2"))
         rescue => e
diff --git a/app/models/user.rb b/app/models/user.rb
index bbf2c60dd3..dd70668532 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -464,22 +464,22 @@ def can_change_admin_flag?
 
   def editing_self?(options = {})
     options[:controller].to_s == 'users' &&
-      options[:action] =~ /edit|update|invalidate_jwt/ &&
+      /edit|update|invalidate_jwt/.match?(options[:action]) &&
       options[:id].to_i == id ||
-    options[:controller].to_s =~ /\Aapi\/v\d+\/users\Z/ &&
-      options[:action] =~ /show|update/ &&
+    /\Aapi\/v\d+\/users\Z/.match?(options[:controller]) &&
+      /show|update/.match?(options[:action]) &&
       (options[:id].to_i == id || options[:id] == login) ||
     options[:controller].to_s == 'ssh_keys' &&
       options[:user_id].to_i == id &&
-      options[:action] =~ /new|create|destroy/ ||
+      /new|create|destroy/.match?(options[:action]) ||
     options[:controller].to_s == 'api/v2/ssh_keys' &&
-      options[:action] =~ /show|destroy|index|create/ &&
+      /show|destroy|index|create/.match?(options[:action]) &&
       options[:user_id].to_i == id ||
     options[:controller].to_s == 'api/v2/personal_access_tokens' &&
-      options[:action] =~ /show|destroy|index|create/ &&
+      /show|destroy|index|create/.match?(options[:action]) &&
       options[:user_id].to_i == id ||
     options[:controller].to_s == 'api/v2/registration_tokens' &&
-      options[:action] =~ /invalidate_jwt/ &&
+      /invalidate_jwt/.match?(options[:action]) &&
       options[:id].to_i == id
   end
 
diff --git a/app/registries/setting_registry.rb b/app/registries/setting_registry.rb
index 6bb201dbc9..9a4059aa67 100644
--- a/app/registries/setting_registry.rb
+++ b/app/registries/setting_registry.rb
@@ -36,7 +36,7 @@ def complete_value_from_db(field, val)
       count = 20
       case field.field
       when :name
-        results = @registry.filter_map { |set| ((set.full_name =~ /\s/) ? "\"#{set.full_name.gsub('"', '\"')}\"" : set.full_name) if set.name.include?(val) || set.full_name&.include?(val) }
+        results = @registry.filter_map { |set| (/\s/.match?(set.full_name) ? "\"#{set.full_name.gsub('"', '\"')}\"" : set.full_name) if set.name.include?(val) || set.full_name&.include?(val) }
         results.first(count)
       when :description
         []
diff --git a/app/services/fact_parser.rb b/app/services/fact_parser.rb
index 8954d2e1d4..454a658947 100644
--- a/app/services/fact_parser.rb
+++ b/app/services/fact_parser.rb
@@ -218,17 +218,17 @@ def find_virtual_interface(interfaces)
 
   # adds attributes like virtual
   def set_additional_attributes(attributes, name)
-    if name =~ VIRTUAL_NAMES
+    if name.to_s =~ VIRTUAL_NAMES
       attributes[:virtual] = true
-      if Regexp.last_match(1).nil? && name =~ BRIDGES
+      if Regexp.last_match(1).nil? && name.to_s =~ BRIDGES
         attributes[:bridge] = true
-      elsif name =~ ALIASES
+      elsif name.to_s =~ ALIASES
         attributes[:attached_to] = Regexp.last_match(1)
         attributes[:tag] = ''
-      elsif name =~ VLANS
+      elsif name.to_s =~ VLANS
         attributes[:attached_to] = Regexp.last_match(1)
         attributes[:tag] = Regexp.last_match(2)
-      elsif name =~ VIRTUAL
+      elsif name.to_s =~ VIRTUAL
         # Legacy: facter < v3.0
         # vlans fact has been removed in facter 3.0
         attributes[:attached_to] = Regexp.last_match(1)
diff --git a/app/services/foreman/parameters/validator.rb b/app/services/foreman/parameters/validator.rb
index fb4d00b094..113a2679c0 100644
--- a/app/services/foreman/parameters/validator.rb
+++ b/app/services/foreman/parameters/validator.rb
@@ -25,7 +25,7 @@ def value
       def validate_regexp
         return true if value.contains_erb? && Setting[:interpolate_erb_in_parameters]
 
-        unless value =~ /#{@options[:validate_with]}/
+        unless /#{@options[:validate_with]}/.match?(value)
           add_error(_("is invalid"))
           return false
         end
diff --git a/app/services/name_generator.rb b/app/services/name_generator.rb
index 777b686000..e3264bc09f 100644
--- a/app/services/name_generator.rb
+++ b/app/services/name_generator.rb
@@ -6,12 +6,12 @@ class NameGenerator
   }.freeze
 
   def self.random_based?
-    Setting[:name_generator_type] =~ /^Random/i
+    /^Random/i.match?(Setting[:name_generator_type])
   end
   delegate :random_based?, :to => :class
 
   def self.mac_based?
-    Setting[:name_generator_type] =~ /^MAC/i
+    /^MAC/i.match?(Setting[:name_generator_type])
   end
   delegate :mac_based?, :to => :class
 
diff --git a/app/services/puppet_fact_parser.rb b/app/services/puppet_fact_parser.rb
index 0c5afaf735..e7024aa35f 100644
--- a/app/services/puppet_fact_parser.rb
+++ b/app/services/puppet_fact_parser.rb
@@ -7,7 +7,7 @@ def operatingsystem
     args = { :name => os_name }
 
     if orel.present?
-      if os_name =~ /ubuntu/i
+      if /ubuntu/i.match?(os_name)
         major = os_major_version.to_s
         minor = os_minor_version.to_s
       else
@@ -79,7 +79,7 @@ def domain
 
   def ipmi_interface
     # ipmi_ facts are custom facts in foreman-discovery-image
-    ipmi = facts.select { |name, _| name =~ /\Aipmi_(.*)\Z/ }.map { |name, value| [name.sub(/\Aipmi_/, ''), value] }
+    ipmi = facts.select { |name, _| name.to_s =~ /\Aipmi_(.*)\Z/ }.map { |name, value| [name.to_s.sub(/\Aipmi_/, ''), value] }
     Hash[ipmi].with_indifferent_access
   end
 
diff --git a/app/services/sso/oauth.rb b/app/services/sso/oauth.rb
index 7e6c161221..4b56d4bb9c 100644
--- a/app/services/sso/oauth.rb
+++ b/app/services/sso/oauth.rb
@@ -3,7 +3,7 @@
 module SSO
   class Oauth < Base
     def available?
-      controller.api_request? && !!(request.authorization =~ /^OAuth/)
+      controller.api_request? && /^OAuth/.match?(request.authorization)
     end
 
     def authenticate!
diff --git a/app/validators/alphanumeric_validator.rb b/app/validators/alphanumeric_validator.rb
index d175bd1253..6ccd1e1f66 100644
--- a/app/validators/alphanumeric_validator.rb
+++ b/app/validators/alphanumeric_validator.rb
@@ -1,5 +1,5 @@
 class AlphanumericValidator < ActiveModel::EachValidator
   def validate_each(record, attribute, value)
-    record.errors.add(attribute, _("must only contain alphanumeric or underscore characters")) unless value =~ /\A\w+\Z/
+    record.errors.add(attribute, _("must only contain alphanumeric or underscore characters")) unless /\A\w+\Z/.match?(value)
   end
 end
diff --git a/app/validators/no_whitespace_validator.rb b/app/validators/no_whitespace_validator.rb
index 0f5b7fd7a8..a2a1d4de34 100644
--- a/app/validators/no_whitespace_validator.rb
+++ b/app/validators/no_whitespace_validator.rb
@@ -1,5 +1,5 @@
 class NoWhitespaceValidator < ActiveModel::EachValidator
   def validate_each(record, attribute, value)
-    record.errors.add(attribute, _("can't contain spaces.")) if value =~ /\s/
+    record.errors.add(attribute, _("can't contain spaces.")) if /\s/.match?(value)
   end
 end
diff --git a/app/validators/url_schema_validator.rb b/app/validators/url_schema_validator.rb
index 2d612a8b74..2a65618e77 100644
--- a/app/validators/url_schema_validator.rb
+++ b/app/validators/url_schema_validator.rb
@@ -5,7 +5,7 @@ def initialize(args)
   end
 
   def validate_each(record, attribute, value)
-    unless value =~ /\A#{URI.regexp(@schemas)}\z/
+    unless /\A#{URI.regexp(@schemas)}\z/.match?(value)
       error_message = _('URL must be valid and schema must be one of %s') %
         @schemas.to_sentence
       record.errors.add(attribute, error_message)
diff --git a/lib/foreman/logging.rb b/lib/foreman/logging.rb
index 0be65dbd67..64c40954f0 100644
--- a/lib/foreman/logging.rb
+++ b/lib/foreman/logging.rb
@@ -222,7 +222,7 @@ def build_file_appender(name, options)
 
     def build_layout(enable_colors = true)
       pattern, colorize = @config[:pattern], @config[:colorize]
-      pattern = @config[:sys_pattern] if @config[:type] =~ /^(journald?|syslog)$/i
+      pattern = @config[:sys_pattern] if /^(journald?|syslog)$/i.match?(@config[:type])
       colorize = nil unless enable_colors
       case @config[:layout]
       when 'json'