diff --git a/Gemfile b/Gemfile
index 2ee2a771d..d871d5ef0 100644
--- a/Gemfile
+++ b/Gemfile
@@ -20,7 +20,7 @@ gem 'dotenv-rails', '~> 2.7'
 gem 'aws-sdk-s3', '~> 1.103', require: false
 gem 'fog-core', '<= 2.1.0'
 gem 'fog-openstack', '~> 0.3', require: false
-gem 'paperclip', '~> 6.0'
+gem 'kt-paperclip', '~> 7.0'
 gem 'blurhash', '~> 0.1'
 
 gem 'active_model_serializers', '~> 0.10'
diff --git a/Gemfile.lock b/Gemfile.lock
index e4bbe9ce9..42fe0e8f8 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -316,6 +316,12 @@ GEM
       activerecord
       kaminari-core (= 1.2.1)
     kaminari-core (1.2.1)
+    kt-paperclip (7.0.0)
+      activemodel (>= 4.2.0)
+      activesupport (>= 4.2.0)
+      marcel (~> 1.0.1)
+      mime-types
+      terrapin (~> 0.6.0)
     launchy (2.5.0)
       addressable (~> 2.7)
     letter_opener (1.7.0)
@@ -351,9 +357,6 @@ GEM
     mime-types (3.3.1)
       mime-types-data (~> 3.2015)
     mime-types-data (3.2020.0512)
-    mimemagic (0.3.10)
-      nokogiri (~> 1)
-      rake
     mini_mime (1.1.1)
     mini_portile2 (2.6.1)
     minitest (5.14.4)
@@ -391,12 +394,6 @@ GEM
     openssl-signature_algorithm (0.4.0)
     orm_adapter (0.5.0)
     ox (2.14.5)
-    paperclip (6.0.0)
-      activemodel (>= 4.2.0)
-      activesupport (>= 4.2.0)
-      mime-types
-      mimemagic (~> 0.3.0)
-      terrapin (~> 0.6.0)
     parallel (1.21.0)
     parallel_tests (3.7.3)
       parallel
@@ -720,6 +717,7 @@ DEPENDENCIES
   json-ld
   json-ld-preloaded (~> 3.1)
   kaminari (~> 1.2)
+  kt-paperclip (~> 7.0)
   letter_opener (~> 1.7)
   letter_opener_web (~> 1.4)
   link_header (~> 0.0)
@@ -738,7 +736,6 @@ DEPENDENCIES
   omniauth-rails_csrf_protection (~> 0.1)
   omniauth-saml (~> 1.10)
   ox (~> 2.14)
-  paperclip (~> 6.0)
   parallel (~> 1.21)
   parallel_tests (~> 3.7)
   parslet
diff --git a/app/lib/fast_geometry_parser.rb b/app/lib/fast_geometry_parser.rb
index 5209c2bc5..f3395a833 100644
--- a/app/lib/fast_geometry_parser.rb
+++ b/app/lib/fast_geometry_parser.rb
@@ -2,7 +2,7 @@
 
 class FastGeometryParser
   def self.from_file(file)
-    width, height = FastImage.size(file.path)
+    width, height = FastImage.size(file)
 
     raise Paperclip::Errors::NotIdentifiedByImageMagickError if width.nil?
 
diff --git a/app/models/account.rb b/app/models/account.rb
index 2f2a55b55..291d3e571 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -62,12 +62,12 @@ class Account < ApplicationRecord
   MENTION_RE    = /(?<=^|[^\/[:word:]])@((#{USERNAME_RE})(?:@[[:word:]\.\-]+[[:word:]]+)?)/i
   URL_PREFIX_RE = /\Ahttp(s?):\/\/[^\/]+/
 
+  include Attachmentable
   include AccountAssociations
   include AccountAvatar
   include AccountFinderConcern
   include AccountHeader
   include AccountInteractions
-  include Attachmentable
   include Paginable
   include AccountCounters
   include DomainNormalizable
diff --git a/app/models/concerns/attachmentable.rb b/app/models/concerns/attachmentable.rb
index c5febb828..01fae4236 100644
--- a/app/models/concerns/attachmentable.rb
+++ b/app/models/concerns/attachmentable.rb
@@ -15,50 +15,47 @@ module Attachmentable
   # those files, it is necessary to use the output of the
   # `file` utility instead
   INCORRECT_CONTENT_TYPES = %w(
+    audio/vorbis
     video/ogg
     video/webm
   ).freeze
 
   included do
-    before_post_process :obfuscate_file_name
-    before_post_process :set_file_extensions
-    before_post_process :check_image_dimensions
-    before_post_process :set_file_content_type
+    def self.has_attached_file(name, options = {}) # rubocop:disable Naming/PredicateName
+      options = { validate_media_type: false }.merge(options)
+      super(name, options)
+      send(:"before_#{name}_post_process") do
+        attachment = send(name)
+        check_image_dimension(attachment)
+        set_file_content_type(attachment)
+        obfuscate_file_name(attachment)
+        set_file_extension(attachment)
+        Paperclip::Validators::MediaTypeSpoofDetectionValidator.new(attributes: [name]).validate(self)
+      end
+    end
   end
 
   private
 
-  def set_file_content_type
-    self.class.attachment_definitions.each_key do |attachment_name|
-      attachment = send(attachment_name)
-
-      next if attachment.blank? || attachment.queued_for_write[:original].blank? || !INCORRECT_CONTENT_TYPES.include?(attachment.instance_read(:content_type))
+  def set_file_content_type(attachment) # rubocop:disable Naming/AccessorMethodName
+    return if attachment.blank? || attachment.queued_for_write[:original].blank? || !INCORRECT_CONTENT_TYPES.include?(attachment.instance_read(:content_type))
 
-      attachment.instance_write :content_type, calculated_content_type(attachment)
-    end
+    attachment.instance_write :content_type, calculated_content_type(attachment)
   end
 
-  def set_file_extensions
-    self.class.attachment_definitions.each_key do |attachment_name|
-      attachment = send(attachment_name)
+  def set_file_extension(attachment) # rubocop:disable Naming/AccessorMethodName
+    return if attachment.blank?
 
-      next if attachment.blank?
-
-      attachment.instance_write :file_name, [Paperclip::Interpolations.basename(attachment, :original), appropriate_extension(attachment)].delete_if(&:blank?).join('.')
-    end
+    attachment.instance_write :file_name, [Paperclip::Interpolations.basename(attachment, :original), appropriate_extension(attachment)].delete_if(&:blank?).join('.')
   end
 
-  def check_image_dimensions
-    self.class.attachment_definitions.each_key do |attachment_name|
-      attachment = send(attachment_name)
+  def check_image_dimension(attachment)
+    return if attachment.blank? || !/image.*/.match?(attachment.content_type) || attachment.queued_for_write[:original].blank?
 
-      next if attachment.blank? || !/image.*/.match?(attachment.content_type) || attachment.queued_for_write[:original].blank?
+    width, height = FastImage.size(attachment.queued_for_write[:original].path)
+    matrix_limit  = attachment.content_type == 'image/gif' ? GIF_MATRIX_LIMIT : MAX_MATRIX_LIMIT
 
-      width, height = FastImage.size(attachment.queued_for_write[:original].path)
-      matrix_limit  = attachment.content_type == 'image/gif' ? GIF_MATRIX_LIMIT : MAX_MATRIX_LIMIT
-
-      raise Mastodon::DimensionsValidationError, "#{width}x#{height} images are not supported" if width.present? && height.present? && (width * height > matrix_limit)
-    end
+    raise Mastodon::DimensionsValidationError, "#{width}x#{height} images are not supported" if width.present? && height.present? && (width * height > matrix_limit)
   end
 
   def appropriate_extension(attachment)
@@ -79,13 +76,9 @@ module Attachmentable
     ''
   end
 
-  def obfuscate_file_name
-    self.class.attachment_definitions.each_key do |attachment_name|
-      attachment = send(attachment_name)
+  def obfuscate_file_name(attachment)
+    return if attachment.blank? || attachment.queued_for_write[:original].blank? || attachment.options[:preserve_files]
 
-      next if attachment.blank? || attachment.queued_for_write[:original].blank? || attachment.options[:preserve_files]
-
-      attachment.instance_write :file_name, SecureRandom.hex(8) + File.extname(attachment.instance_read(:file_name))
-    end
+    attachment.instance_write :file_name, SecureRandom.hex(8) + File.extname(attachment.instance_read(:file_name))
   end
 end
diff --git a/app/models/custom_emoji.rb b/app/models/custom_emoji.rb
index 7cb03b819..a85feb73a 100644
--- a/app/models/custom_emoji.rb
+++ b/app/models/custom_emoji.rb
@@ -21,6 +21,8 @@
 #
 
 class CustomEmoji < ApplicationRecord
+  include Attachmentable
+
   LIMIT = 50.kilobytes
 
   SHORTCODE_RE_FRAGMENT = '[a-zA-Z0-9_]{2,}'
@@ -34,7 +36,7 @@ class CustomEmoji < ApplicationRecord
   belongs_to :category, class_name: 'CustomEmojiCategory', optional: true
   has_one :local_counterpart, -> { where(domain: nil) }, class_name: 'CustomEmoji', primary_key: :shortcode, foreign_key: :shortcode
 
-  has_attached_file :image, styles: { static: { format: 'png', convert_options: '-coalesce -strip' } }
+  has_attached_file :image, styles: { static: { format: 'png', convert_options: '-coalesce -strip' } }, validate_media_type: false
 
   before_validation :downcase_domain
 
@@ -49,8 +51,6 @@ class CustomEmoji < ApplicationRecord
 
   remotable_attachment :image, LIMIT
 
-  include Attachmentable
-
   after_commit :remove_entity_cache
 
   def local?
diff --git a/app/models/media_attachment.rb b/app/models/media_attachment.rb
index 66d800b7b..cc48f65ed 100644
--- a/app/models/media_attachment.rb
+++ b/app/models/media_attachment.rb
@@ -31,6 +31,8 @@
 class MediaAttachment < ApplicationRecord
   self.inheritance_column = nil
 
+  include Attachmentable
+
   enum type: [:image, :gifv, :video, :unknown, :audio]
   enum processing: [:queued, :in_progress, :complete, :failed], _prefix: true
 
@@ -50,7 +52,7 @@ class MediaAttachment < ApplicationRecord
   IMAGE_MIME_TYPES             = %w(image/jpeg image/png image/gif).freeze
   VIDEO_MIME_TYPES             = %w(video/webm video/mp4 video/quicktime video/ogg).freeze
   VIDEO_CONVERTIBLE_MIME_TYPES = %w(video/webm video/quicktime).freeze
-  AUDIO_MIME_TYPES             = %w(audio/wave audio/wav audio/x-wav audio/x-pn-wave audio/ogg audio/mpeg audio/mp3 audio/webm audio/flac audio/aac audio/m4a audio/x-m4a audio/mp4 audio/3gpp video/x-ms-asf).freeze
+  AUDIO_MIME_TYPES             = %w(audio/wave audio/wav audio/x-wav audio/x-pn-wave audio/ogg audio/vorbis audio/mpeg audio/mp3 audio/webm audio/flac audio/aac audio/m4a audio/x-m4a audio/mp4 audio/3gpp video/x-ms-asf).freeze
 
   BLURHASH_OPTIONS = {
     x_comp: 4,
@@ -182,8 +184,6 @@ class MediaAttachment < ApplicationRecord
   validates_attachment_size :thumbnail, less_than: IMAGE_LIMIT
   remotable_attachment :thumbnail, IMAGE_LIMIT, suppress_errors: true, download_on_assign: false
 
-  include Attachmentable
-
   validates :account, presence: true
   validates :description, length: { maximum: MAX_DESCRIPTION_LENGTH }, if: :local?
   validates :file, presence: true, if: :local?
diff --git a/app/models/preview_card.rb b/app/models/preview_card.rb
index a6ec839f8..bca3a3ce8 100644
--- a/app/models/preview_card.rb
+++ b/app/models/preview_card.rb
@@ -27,6 +27,8 @@
 #
 
 class PreviewCard < ApplicationRecord
+  include Attachmentable
+
   IMAGE_MIME_TYPES = ['image/jpeg', 'image/png', 'image/gif'].freeze
   LIMIT = 1.megabytes
 
@@ -41,9 +43,7 @@ class PreviewCard < ApplicationRecord
 
   has_and_belongs_to_many :statuses
 
-  has_attached_file :image, processors: [:thumbnail, :blurhash_transcoder], styles: ->(f) { image_styles(f) }, convert_options: { all: '-quality 80 -strip' }
-
-  include Attachmentable
+  has_attached_file :image, processors: [:thumbnail, :blurhash_transcoder], styles: ->(f) { image_styles(f) }, convert_options: { all: '-quality 80 -strip' }, validate_media_type: false
 
   validates :url, presence: true, uniqueness: true
   validates_attachment_content_type :image, content_type: IMAGE_MIME_TYPES
diff --git a/config/application.rb b/config/application.rb
index 1761bdc2e..68855a567 100644
--- a/config/application.rb
+++ b/config/application.rb
@@ -25,11 +25,8 @@ require_relative '../lib/exceptions'
 require_relative '../lib/enumerable'
 require_relative '../lib/sanitize_ext/sanitize_config'
 require_relative '../lib/redis/namespace_extensions'
-require_relative '../lib/paperclip/schema_extensions'
-require_relative '../lib/paperclip/validation_extensions'
 require_relative '../lib/paperclip/url_generator_extensions'
 require_relative '../lib/paperclip/attachment_extensions'
-require_relative '../lib/paperclip/media_type_spoof_detector_extensions'
 require_relative '../lib/paperclip/lazy_thumbnail'
 require_relative '../lib/paperclip/gif_transcoder'
 require_relative '../lib/paperclip/transcoder'
diff --git a/lib/paperclip/attachment_extensions.rb b/lib/paperclip/attachment_extensions.rb
index 271f8b603..786f558e9 100644
--- a/lib/paperclip/attachment_extensions.rb
+++ b/lib/paperclip/attachment_extensions.rb
@@ -6,6 +6,35 @@ module Paperclip
       instance_read(:meta)
     end
 
+    # monkey-patch to avoid unlinking too avoid unlinking source file too early
+    # see https://github.com/kreeti/kt-paperclip/issues/64
+    def post_process_style(name, style) #:nodoc:
+      raise "Style #{name} has no processors defined." if style.processors.blank?
+
+      intermediate_files = []
+      original = @queued_for_write[:original]
+      # if we're processing the original, close + unlink the source tempfile
+      intermediate_files << original if name == :original
+
+      @queued_for_write[name] = style.processors.
+                                inject(original) do |file, processor|
+        file = Paperclip.processor(processor).make(file, style.processor_options, self)
+        intermediate_files << file unless file == original
+        file
+      end
+
+      unadapted_file = @queued_for_write[name]
+      @queued_for_write[name] = Paperclip.io_adapters.
+                                for(@queued_for_write[name], @options[:adapter_options])
+      unadapted_file.close if unadapted_file.respond_to?(:close)
+      @queued_for_write[name]
+    rescue Paperclip::Errors::NotIdentifiedByImageMagickError => e
+      log("An error was received while processing: #{e.inspect}")
+      (@errors[:processing] ||= []) << e.message if @options[:whiny]
+    ensure
+      unlink_files(intermediate_files)
+    end
+
     # We overwrite this method to support delayed processing in
     # Sidekiq. Since we process the original file to reduce disk
     # usage, and we still want to generate thumbnails straight
diff --git a/lib/paperclip/media_type_spoof_detector_extensions.rb b/lib/paperclip/media_type_spoof_detector_extensions.rb
deleted file mode 100644
index 43337cc68..000000000
--- a/lib/paperclip/media_type_spoof_detector_extensions.rb
+++ /dev/null
@@ -1,35 +0,0 @@
-# frozen_string_literal: true
-
-module Paperclip
-  module MediaTypeSpoofDetectorExtensions
-    def mapping_override_mismatch?
-      !Array(mapped_content_type).include?(calculated_content_type) && !Array(mapped_content_type).include?(type_from_mime_magic)
-    end
-
-    def calculated_media_type_from_mime_magic
-      @calculated_media_type_from_mime_magic ||= type_from_mime_magic.split('/').first
-    end
-
-    def calculated_type_mismatch?
-      !media_types_from_name.include?(calculated_media_type) && !media_types_from_name.include?(calculated_media_type_from_mime_magic)
-    end
-
-    def type_from_mime_magic
-      @type_from_mime_magic ||= begin
-        begin
-          File.open(@file.path) do |file|
-            MimeMagic.by_magic(file)&.type || ''
-          end
-        rescue Errno::ENOENT
-          ''
-        end
-      end
-    end
-
-    def type_from_file_command
-      @type_from_file_command ||= FileCommandContentTypeDetector.new(@file.path).detect
-    end
-  end
-end
-
-Paperclip::MediaTypeSpoofDetector.prepend(Paperclip::MediaTypeSpoofDetectorExtensions)
diff --git a/lib/paperclip/schema_extensions.rb b/lib/paperclip/schema_extensions.rb
deleted file mode 100644
index 8d065676a..000000000
--- a/lib/paperclip/schema_extensions.rb
+++ /dev/null
@@ -1,37 +0,0 @@
-# frozen_string_literal: true
-
-# Monkey-patch various Paperclip methods for Ruby 3.0 compatibility
-
-module Paperclip
-  module Schema
-    module StatementsExtensions
-      def add_attachment(table_name, *attachment_names)
-        raise ArgumentError, 'Please specify attachment name in your add_attachment call in your migration.' if attachment_names.empty?
-
-        options = attachment_names.extract_options!
-
-        attachment_names.each do |attachment_name|
-          COLUMNS.each_pair do |column_name, column_type|
-            column_options = options.merge(options[column_name.to_sym] || {})
-            add_column(table_name, "#{attachment_name}_#{column_name}", column_type, **column_options)
-          end
-        end
-      end
-    end
-
-    module TableDefinitionExtensions
-      def attachment(*attachment_names)
-        options = attachment_names.extract_options!
-        attachment_names.each do |attachment_name|
-          COLUMNS.each_pair do |column_name, column_type|
-            column_options = options.merge(options[column_name.to_sym] || {})
-            column("#{attachment_name}_#{column_name}", column_type, **column_options)
-          end
-        end
-      end
-    end
-  end
-end
-
-Paperclip::Schema::Statements.prepend(Paperclip::Schema::StatementsExtensions)
-Paperclip::Schema::TableDefinition.prepend(Paperclip::Schema::TableDefinitionExtensions)
diff --git a/lib/paperclip/url_generator_extensions.rb b/lib/paperclip/url_generator_extensions.rb
index e1d6df2c2..a2cf5929a 100644
--- a/lib/paperclip/url_generator_extensions.rb
+++ b/lib/paperclip/url_generator_extensions.rb
@@ -2,16 +2,6 @@
 
 module Paperclip
   module UrlGeneratorExtensions
-    # Monkey-patch Paperclip to use Addressable::URI's normalization instead
-    # of the long-deprecated URI.esacpe
-    def escape_url(url)
-      if url.respond_to?(:escape)
-        url.escape
-      else
-        Addressable::URI.parse(url).normalize.to_str.gsub(escape_regex) { |m| "%#{m.ord.to_s(16).upcase}" }
-      end
-    end
-
     def for_as_default(style_name)
       attachment_options[:interpolator].interpolate(default_url, @attachment, style_name)
     end
diff --git a/lib/paperclip/validation_extensions.rb b/lib/paperclip/validation_extensions.rb
deleted file mode 100644
index 0df0434f6..000000000
--- a/lib/paperclip/validation_extensions.rb
+++ /dev/null
@@ -1,58 +0,0 @@
-# frozen_string_literal: true
-
-# Monkey-patch various Paperclip validators for Ruby 3.0 compatibility
-
-module Paperclip
-  module Validators
-    module AttachmentSizeValidatorExtensions
-      def validate_each(record, attr_name, _value)
-        base_attr_name = attr_name
-        attr_name = "#{attr_name}_file_size".to_sym
-        value = record.send(:read_attribute_for_validation, attr_name)
-
-        if value.present?
-          options.slice(*Paperclip::Validators::AttachmentSizeValidator::AVAILABLE_CHECKS).each do |option, option_value|
-            option_value = option_value.call(record) if option_value.is_a?(Proc)
-            option_value = extract_option_value(option, option_value)
-
-            next if value.send(Paperclip::Validators::AttachmentSizeValidator::CHECKS[option], option_value)
-
-            error_message_key = options[:in] ? :in_between : option
-            [attr_name, base_attr_name].each do |error_attr_name|
-              record.errors.add(error_attr_name, error_message_key, **filtered_options(value).merge(
-                min: min_value_in_human_size(record),
-                max: max_value_in_human_size(record),
-                count: human_size(option_value)
-              ))
-            end
-          end
-        end
-      end
-    end
-
-    module AttachmentContentTypeValidatorExtensions
-      def mark_invalid(record, attribute, types)
-        record.errors.add attribute, :invalid, **options.merge({ types: types.join(', ') })
-      end
-    end
-
-    module AttachmentPresenceValidatorExtensions
-      def validate_each(record, attribute, _value)
-        if record.send("#{attribute}_file_name").blank?
-          record.errors.add(attribute, :blank, **options)
-        end
-      end
-    end
-
-    module AttachmentFileNameValidatorExtensions
-      def mark_invalid(record, attribute, patterns)
-        record.errors.add attribute, :invalid, options.merge({ names: patterns.join(', ') })
-      end
-    end
-  end
-end
-
-Paperclip::Validators::AttachmentSizeValidator.prepend(Paperclip::Validators::AttachmentSizeValidatorExtensions)
-Paperclip::Validators::AttachmentContentTypeValidator.prepend(Paperclip::Validators::AttachmentContentTypeValidatorExtensions)
-Paperclip::Validators::AttachmentPresenceValidator.prepend(Paperclip::Validators::AttachmentPresenceValidatorExtensions)
-Paperclip::Validators::AttachmentFileNameValidator.prepend(Paperclip::Validators::AttachmentFileNameValidatorExtensions)
diff --git a/spec/fixtures/files/boop.ogg b/spec/fixtures/files/boop.ogg
new file mode 100644
index 000000000..23cbbedb1
Binary files /dev/null and b/spec/fixtures/files/boop.ogg differ
diff --git a/spec/models/media_attachment_spec.rb b/spec/models/media_attachment_spec.rb
index 456bc4216..edab67d47 100644
--- a/spec/models/media_attachment_spec.rb
+++ b/spec/models/media_attachment_spec.rb
@@ -114,6 +114,30 @@ RSpec.describe MediaAttachment, type: :model do
     end
   end
 
+  describe 'ogg with cover art' do
+    let(:media) { MediaAttachment.create(account: Fabricate(:account), file: attachment_fixture('boop.ogg')) }
+
+    it 'detects it as an audio file' do
+      expect(media.type).to eq 'audio'
+    end
+
+    it 'sets meta for the duration' do
+      expect(media.file.meta['original']['duration']).to be_within(0.05).of(0.235102)
+    end
+
+    it 'extracts thumbnail' do
+      expect(media.thumbnail.present?).to eq true
+    end
+
+    it 'extracts colors from thumbnail' do
+      expect(media.file.meta['colors']['background']).to eq '#3088d4'
+    end
+
+    it 'gives the file a random name' do
+      expect(media.file_file_name).to_not eq 'boop.ogg'
+    end
+  end
+
   describe 'jpeg' do
     let(:media) { MediaAttachment.create(account: Fabricate(:account), file: attachment_fixture('attachment.jpg')) }