diff --git a/app/logical/danbooru.rb b/app/logical/danbooru.rb
new file mode 100644
index 000000000..f312afdcd
--- /dev/null
+++ b/app/logical/danbooru.rb
@@ -0,0 +1,32 @@
+# frozen_string_literal: true
+
+# The Danbooru module contains miscellaneous global helper functions.
+module Danbooru
+  module EnumerableMethods
+    extend self
+
+    # Sort a list of strings in natural order, e.g. with "file-2.txt" before "file-10.txt".
+    #
+    # @see https://en.wikipedia.org/wiki/Natural_sort_order
+    # @see https://stackoverflow.com/a/15170063
+    #
+    # @param list [Enumerable<String>] The list to sort.
+    # @return [Array] The sorted list.
+    def natural_sort(list)
+      natural_sort_by(list, &:to_s)
+    end
+
+    # Sort a list of objects in natural order. The block should return a sort key, which is compared in natural order.
+    #
+    # @param list [Enumerable<Object>] The list to sort.
+    # @return [Array] The sorted list.
+    def natural_sort_by(list, &block)
+      list.sort_by do |element|
+        # "file-2022-10-01.txt" => ["file-", 2022, "-", 10, "-", 1, ".txt"]
+        yield(element).to_s.split(/(\d+)/).map { |str| str.match?(/\A\d+\z/) ? str.to_i : str }
+      end
+    end
+  end
+
+  extend EnumerableMethods
+end
diff --git a/app/models/upload.rb b/app/models/upload.rb
index f835ebdbf..d951bfcd3 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -206,7 +206,7 @@ class Upload < ApplicationRecord
         tmpdir, filenames = file.extract!
         tmpdirs << tmpdir
 
-        filenames.map do |filename|
+        Danbooru.natural_sort(filenames).map do |filename|
           name = "file://#{original_filename}/#{Pathname.new(filename).relative_path_from(tmpdir)}" # "file://foo.zip/foo/1.jpg"
           UploadMediaAsset.new(upload: self, file: filename, source_url: name)
         end
diff --git a/config/initializers/core_extensions.rb b/config/initializers/core_extensions.rb
index c98797b73..1dbf8c990 100644
--- a/config/initializers/core_extensions.rb
+++ b/config/initializers/core_extensions.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "danbooru"
+
 module Danbooru
   module Extensions
     module String
diff --git a/test/files/archive/out-of-order.zip b/test/files/archive/out-of-order.zip
new file mode 100644
index 000000000..b5d162673
Binary files /dev/null and b/test/files/archive/out-of-order.zip differ
diff --git a/test/functional/uploads_controller_test.rb b/test/functional/uploads_controller_test.rb
index 7c27de676..85b27eb8e 100644
--- a/test/functional/uploads_controller_test.rb
+++ b/test/functional/uploads_controller_test.rb
@@ -445,6 +445,19 @@ class UploadsControllerTest < ActionDispatch::IntegrationTest
           assert_equal(5, upload.upload_media_assets.size)
           assert_equal("file://ugoira.zip/000000.jpg", upload.upload_media_assets[0].source_url)
         end
+
+        should "upload the files in filename order" do
+          upload = assert_successful_upload("test/files/archive/out-of-order.zip", user: @user)
+
+          assert_equal(6, upload.media_asset_count)
+          assert_equal(6, upload.upload_media_assets.size)
+          assert_equal("file://out-of-order.zip/9/9.gif", upload.upload_media_assets[0].source_url)
+          assert_equal("file://out-of-order.zip/9/10.gif", upload.upload_media_assets[1].source_url)
+          assert_equal("file://out-of-order.zip/9/11.gif", upload.upload_media_assets[2].source_url)
+          assert_equal("file://out-of-order.zip/10/9.gif", upload.upload_media_assets[3].source_url)
+          assert_equal("file://out-of-order.zip/10/10.gif", upload.upload_media_assets[4].source_url)
+          assert_equal("file://out-of-order.zip/10/11.gif", upload.upload_media_assets[5].source_url)
+        end
       end
 
       context "uploading a .rar file from your computer" do