diff --git a/app/controllers/tags_controller.rb b/app/controllers/tags_controller.rb
index 1c286290788..e41ec729a8d 100644
--- a/app/controllers/tags_controller.rb
+++ b/app/controllers/tags_controller.rb
@@ -2,8 +2,7 @@ class TagsController < ApplicationController
   before_action :set_tag, only: %i[edit update destroy]
 
   def index
-    @tags = Current.family.tags.alphabetically
-
+    @tags = Current.family.tags.sorted_naturally
     render layout: "settings"
   end
 
diff --git a/app/models/rule/action_executor/set_transaction_category.rb b/app/models/rule/action_executor/set_transaction_category.rb
index 6360e45a287..1b4dbaf68ce 100644
--- a/app/models/rule/action_executor/set_transaction_category.rb
+++ b/app/models/rule/action_executor/set_transaction_category.rb
@@ -4,7 +4,7 @@ def type
   end
 
   def options
-    family.categories.pluck(:name, :id)
+    family.categories.order(:name).pluck(:name, :id)
   end
 
   def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
diff --git a/app/models/rule/action_executor/set_transaction_tags.rb b/app/models/rule/action_executor/set_transaction_tags.rb
index d74029ca1ed..ff92872b1e5 100644
--- a/app/models/rule/action_executor/set_transaction_tags.rb
+++ b/app/models/rule/action_executor/set_transaction_tags.rb
@@ -4,7 +4,7 @@ def type
   end
 
   def options
-    family.tags.pluck(:name, :id)
+    family.tags.order(:name).pluck(:name, :id)
   end
 
   def execute(transaction_scope, value: nil, ignore_attribute_locks: false)
diff --git a/app/models/rule/registry/transaction_resource.rb b/app/models/rule/registry/transaction_resource.rb
index d00f2b1ea8b..af0c1c03dc9 100644
--- a/app/models/rule/registry/transaction_resource.rb
+++ b/app/models/rule/registry/transaction_resource.rb
@@ -8,7 +8,7 @@ def condition_filters
       Rule::ConditionFilter::TransactionName.new(rule),
       Rule::ConditionFilter::TransactionAmount.new(rule),
       Rule::ConditionFilter::TransactionMerchant.new(rule)
-    ]
+    ].sort_by { |filter| filter.label.downcase }
   end
 
   def action_executors
@@ -24,7 +24,7 @@ def action_executors
       enabled_executors << Rule::ActionExecutor::AutoDetectMerchants.new(rule)
     end
 
-    enabled_executors
+    enabled_executors.sort_by { |executor| executor.label.downcase }
   end
 
   private
diff --git a/app/models/tag.rb b/app/models/tag.rb
index c5bdc0bc244..a86490fc5e4 100644
--- a/app/models/tag.rb
+++ b/app/models/tag.rb
@@ -8,6 +8,15 @@ class Tag < ApplicationRecord
 
   scope :alphabetically, -> { order(:name) }
 
+  scope :sorted_naturally_db, -> {
+    order(
+      Arel.sql(
+        "REGEXP_REPLACE(name, '\\d+$', '') ASC, " \
+        "CAST(REGEXP_REPLACE(name, '\\D+', '') AS INTEGER) ASC"
+      )
+    )
+  }
+
   COLORS = %w[#e99537 #4da568 #6471eb #db5a54 #df4e92 #c44fe9 #eb5429 #61c9ea #805dee #6ad28a]
 
   UNCATEGORIZED_COLOR = "#737373"
@@ -23,4 +32,10 @@ def replace_and_destroy!(replacement)
       destroy!
     end
   end
+
+  def self.sorted_naturally
+    all.to_a.sort_by do |tag|
+      tag.name.to_s.scan(/\d+|\D+/).map { |s| s =~ /\d+/ ? s.to_i : s.downcase }
+    end
+  end
 end
diff --git a/app/views/transactions/_form.html.erb b/app/views/transactions/_form.html.erb
index 3760f7dd0a9..00f17b3c464 100644
--- a/app/views/transactions/_form.html.erb
+++ b/app/views/transactions/_form.html.erb
@@ -32,7 +32,7 @@
   <%= render DS::Disclosure.new(title: t(".details")) do %>
     <%= f.fields_for :entryable do |ef| %>
       <%= ef.select :tag_ids,
-                    Current.family.tags.alphabetically.pluck(:name, :id),
+                    Current.family.tags.sorted_naturally.pluck(:name, :id),
                     {
                       include_blank: t(".none"),
                       multiple: true,
diff --git a/app/views/transactions/show.html.erb b/app/views/transactions/show.html.erb
index 4111cd437cb..394ac0f9b20 100644
--- a/app/views/transactions/show.html.erb
+++ b/app/views/transactions/show.html.erb
@@ -77,7 +77,7 @@
                     "data-auto-submit-form-target": "auto" %>
 
               <%= ef.select :tag_ids,
-                    Current.family.tags.alphabetically.pluck(:name, :id),
+                    Current.family.tags.sorted_naturally.pluck(:name, :id),
                     {
                       include_blank: t(".none"),
                       multiple: true,