sequel 5.20.0 → 5.49.0

data/lib/sequel/plugins/column_encryption.rb

@@ -0,0 +1,728 @@
+# frozen-string-literal: true
+
+# :nocov:
+raise(Sequel::Error, "Sequel column_encryption plugin requires ruby 2.3 or greater") unless RUBY_VERSION >= '2.3'
+# :nocov:
+
+require 'openssl'
+
+begin
+  # Test cipher actually works
+  cipher = OpenSSL::Cipher.new("aes-256-gcm")
+  cipher.encrypt
+  cipher.key = '1'*32
+  cipher_iv = cipher.random_iv
+  cipher.auth_data = ''
+  cipher_text = cipher.update('2') << cipher.final
+  auth_tag = cipher.auth_tag
+
+  cipher = OpenSSL::Cipher.new("aes-256-gcm")
+  cipher.decrypt
+  cipher.iv = cipher_iv
+  cipher.key = '1'*32
+  cipher.auth_data = ''
+  cipher.auth_tag = auth_tag
+  # :nocov:
+  unless (cipher.update(cipher_text) << cipher.final) == '2'
+    raise OpenSSL::Cipher::CipherError
+  end
+rescue RuntimeError, OpenSSL::Cipher::CipherError
+  raise LoadError, "Sequel column_encryption plugin requires a working aes-256-gcm cipher"
+  # :nocov:
+end
+
+require 'base64'
+require 'securerandom'
+
+module Sequel
+  module Plugins
+    # The column_encryption plugin adds support for encrypting the content of individual
+    # columns in a table.
+    #
+    # Column values are encrypted with AES-256-GCM using a per-value cipher key derived from
+    # a key provided in the configuration using HMAC-SHA256.
+    #
+    # = Usage
+    #
+    # If you would like to support encryption of columns in more than one model, you should
+    # probably load the plugin into the parent class of your models and specify the keys:
+    #
+    #   Sequel::Model.plugin :column_encryption do |enc|
+    #     enc.key 0, ENV["SEQUEL_COLUMN_ENCRYPTION_KEY"]
+    #   end
+    #
+    # This specifies a single master encryption key.  Unless you are actively rotating keys,
+    # it is best to use a single master key.  Rotation of encryption keys will be discussed
+    # in a later section.
+    #
+    # In the above call, <tt>0</tt> is the id of the key, and the
+    # <tt>ENV["SEQUEL_COLUMN_ENCRYPTION_KEY"]</tt> is the content of the key, which must be
+    # a string with exactly 32 bytes. As indicated, this key should not be hardcoded or
+    # otherwise committed to the source control repository.
+    #
+    # For models that need encrypted columns, you load the plugin again, but specify the
+    # columns to encrypt:
+    #
+    #   ConfidentialModel.plugin :column_encryption do |enc|
+    #     enc.column :encrypted_column_name
+    #     enc.column :searchable_column_name, searchable: true
+    #     enc.column :ci_searchable_column_name, searchable: :case_insensitive
+    #   end
+    #
+    # With this, all three specified columns (+encrypted_column_name+, +searchable_column_name+,
+    # and +ci_searchable_column_name+) will be marked as encrypted columns.  When you run the
+    # following code:
+    #
+    #   ConfidentialModel.create(
+    #     encrypted_column_name: 'These',
+    #     searchable_column_name: 'will be',
+    #     ci_searchable_column_name: 'Encrypted'
+    #   )
+    #
+    # It will save encrypted versions to the database.  +encrypted_column_name+ will not be
+    # searchable, +searchable_column_name+ will be searchable with an exact match, and
+    # +ci_searchable_column_name+ will be searchable with a case insensitive match. See section
+    # below for details on searching.
+    #
+    # It is possible to have model-specific keys by specifying both the +key+ and +column+ methods
+    # in the model:
+    #
+    #   ConfidentialModel.plugin :column_encryption do |enc|
+    #     enc.key 0, ENV["SEQUEL_MODEL_SPECIFIC_ENCRYPTION_KEY"]
+    #
+    #     enc.column :encrypted_column_name
+    #     enc.column :searchable_column_name, searchable: true
+    #     enc.column :ci_searchable_column_name, searchable: :case_insensitive
+    #   end
+    #
+    # When the +key+ method is called inside the plugin block, previous keys are ignored,
+    # and only the new keys specified will be used.  This approach would allow the
+    # +ConfidentialModel+ to use the model specific encryption keys, and other models
+    # to use the default keys specified in the parent class.
+    #
+    # The +key+ and +column+ methods inside the plugin block support additional options.
+    # The +key+ method supports the following options:
+    #
+    # :auth_data :: The authentication data to use for the AES-256-GCM cipher. Defaults
+    #               to the empty string.
+    # :padding :: The number of padding bytes to use. For security, data is padded so that
+    #             a database administrator cannot determine the exact size of the
+    #             unencrypted data.  By default, this value is 8, which means that
+    #             unencrypted data will be padded to a multiple of 8 bytes. Up to twice as
+    #             much padding as specified will be used, as the number of padding bytes
+    #             is partially randomized.
+    #
+    # The +column+ method supports the following options:
+    #
+    # :searchable :: Whether the column is searchable.  This should not be used unless
+    #                searchability is needed, as it can allow the database administrator
+    #                to determine whether two distinct rows have the same unencrypted
+    #                data (but not what that data is).  This can be set to +true+ to allow
+    #                searching with an exact match, or +:case_insensitive+ for a case
+    #                insensitive match.
+    # :search_both :: This should only be used if you have previously switched the
+    #                 +:searchable+ option from +true+ to +:case_insensitive+ or vice-versa,
+    #                 and would like the search to return values that have not yet been
+    #                 reencrypted.  Note that switching from +true+ to +:case_insensitive+
+    #                 isn't a problem, but switching from +:case_insensitive+ to +true+ and
+    #                 using this option can cause the search to return values that are
+    #                 not an exact match.  You should manually filter those objects
+    #                 after decrypting if you want to ensure an exact match.
+    # :format :: The format of the column, if you want to perform serialization before
+    #            encryption and deserialization after decryption.  Can be either a
+    #            symbol registered with the serialization plugin or an array of two
+    #            callables, the first for serialization and the second for deserialization.
+    #
+    # The +column+ method also supports a block for column-specific keys:
+    #
+    #   ConfidentialModel.plugin :column_encryption do |enc|
+    #     enc.column :encrypted_column_name do |cenc|
+    #       cenc.key 0, ENV["SEQUEL_COLUMN_SPECIFIC_ENCRYPTION_KEY"]
+    #     end
+    #
+    #     enc.column :searchable_column_name, searchable: true
+    #     enc.column :ci_searchable_column_name, searchable: :case_insensitive
+    #   end
+    #
+    # In this case, the <tt>ENV["SEQUEL_COLUMN_SPECIFIC_ENCRYPTION_KEY"]</tt> key will
+    # only be used for the +:encrypted_column_name+ column, and not the other columns.
+    #
+    # Note that there isn't a security reason to prefer either model-specific or
+    # column-specific keys, as the actual cipher key used is unique per column value.
+    #
+    # Note that changing the key_id, key string, or auth_data for an existing key will
+    # break decryption of values encrypted with that key.  If you would like to change
+    # any aspect of the key, add a new key, rotate to the new encryption key, and then
+    # remove the previous key, as described in the section below on key rotation.
+    #
+    # = Searching Encrypted Values
+    #
+    # To search searchable encrypted columns, use +with_encrypted_value+.  This example
+    # code will return the model instance created in the code example in the previous
+    # section:
+    #
+    #   ConfidentialModel.
+    #     with_encrypted_value(:searchable_column_name, "will be")
+    #     with_encrypted_value(:ci_searchable_column_name, "encrypted").
+    #     first
+    #
+    # = Encryption Key Rotation
+    #
+    # To rotate encryption keys, add a new key above the existing key, with a new key ID:
+    #
+    #   Sequel::Model.plugin :column_encryption do |enc|
+    #     enc.key 1, ENV["SEQUEL_COLUMN_ENCRYPTION_KEY"]
+    #     enc.key 0, ENV["SEQUEL_OLD_COLUMN_ENCRYPTION_KEY"]
+    #   end
+    #
+    # Newly encrypted data will then use the new key.  Records encrypted with the older key
+    # will still be decrypted correctly.
+    #
+    # To force reencryption for existing records that are using the older key, you can use
+    # the +needing_reencryption+ dataset method and the +reencrypt+ instance method. For a
+    # small number of records, you can probably do:
+    #
+    #   ConfidentialModel.needing_reencryption.all(&:reencrypt)
+    #
+    # With more than a small number of records, you'll want to do this in batches.  It's
+    # possible you could use an approach such as:
+    #
+    #   ds = ConfidentialModel.needing_reencryption.limit(100)
+    #   true until ds.all(&:reencrypt).empty?
+    #
+    # After all values have been reencrypted for all models, and no models use the older
+    # encryption key, you can remove it from the configuration:
+    #
+    #   Sequel::Model.plugin :column_encryption do |enc|
+    #     enc.key 1, ENV["SEQUEL_COLUMN_ENCRYPTION_KEY"]
+    #   end
+    #
+    # Once an encryption key has been removed, after no data uses it, it is safe to reuse
+    # the same key id for a new key.  This approach allows for up to 256 concurrent keys
+    # in the same configuration.
+    #
+    # = Encrypting Additional Formats
+    #
+    # By default, the column_encryption plugin assumes that the decrypted data should be
+    # returned as a string, and a string will be passed to encrypt.  However, using the
+    # +:format+ option, you can specify an alternate format.  For example, if you want to
+    # encrypt a JSON representation of the object, so that you can deal with an array/hash
+    # and automatically have it serialized with JSON and then encrypted when saving, and
+    # then deserialized with JSON after decryption when it is retrieved:
+    #
+    #   require 'json'
+    #   ConfidentialModel.plugin :column_encryption do |enc|
+    #     enc.key 0, ENV["SEQUEL_MODEL_SPECIFIC_ENCRYPTION_KEY"]
+    #
+    #     enc.column :encrypted_column_name
+    #     enc.column :searchable_column_name, searchable: true
+    #     enc.column :ci_searchable_column_name, searchable: :case_insensitive
+    #     enc.column :encrypted_json_column_name, format: :json
+    #   end
+    #
+    # The values of the +:format+ are the same values you can pass as the first argument
+    # to +serialize_attributes+ (in the serialization plugin).  You can pass an array
+    # with the serializer and deserializer for custom support.
+    #
+    # You can use both +:searchable+ and +:format+ together for searchable encrypted
+    # serialized columns.  However, note that this allows only exact searches of the
+    # serialized version of the data.  So for JSON, a search for <tt>{'a'=>1, 'b'=>2}</tt>
+    # would not match <tt>{'b'=>2, 'a'=>1}</tt> even though the objects are considered
+    # equal.  If this is an issue, make sure you use a serialization format where all
+    # equal objects are serialized to the same string.
+    #
+    # = Enforcing Uniqueness
+    #
+    # You cannot enforce uniqueness of unencrypted data at the database level
+    # if you also want to support key rotation.  However, absent key rotation, a
+    # unique index on the first 48 characters of the encrypted column can enforce uniqueness,
+    # as long as the column is searchable.  If the encrypted column is case-insensitive
+    # searchable, the uniqueness is case insensitive as well.
+    #
+    # = Column Value Cryptography/Format
+    #
+    # Column values used by this plugin use the following format (+key+ is specified
+    # in the plugin configuration and must be exactly 32 bytes):
+    #
+    # column_value :: urlsafe_base64(flags + NUL + key_id + NUL + search_data + key_data +
+    #                 cipher_iv + cipher_auth_tag + encrypted_data)
+    # flags :: 1 byte, the type of record (0: not searchable, 1: searchable, 2: lowercase searchable)
+    # NUL :: 1 byte, ASCII NUL
+    # key_id :: 1 byte, the key id, supporting 256 concurrently active keys (0 - 255)
+    # search_data :: 0 bytes if flags is 0, 32 bytes if flags is 1 or 2.
+    #                Format is HMAC-SHA256(key, unencrypted_data).
+    #                Ignored on decryption, only used for searching.
+    # key_data :: 32 bytes random data used to construct cipher key
+    # cipher_iv :: 12 bytes, AES-256-GCM cipher random initialization vector
+    # cipher_auth_tag :: 16 bytes, AES-256-GCM cipher authentication tag
+    # encrypted_data :: AES-256-GCM(HMAC-SHA256(key, key_data),
+    #                   padding_size + padding + unencrypted_data)
+    # padding_size :: 1 byte, with the amount of padding (0-255 bytes of padding allowed)
+    # padding :: number of bytes specified by padding size, ignored on decryption
+    # unencrypted_data :: actual column value
+    #
+    # The reason for <tt>flags + NUL + key_id + NUL</tt> (4 bytes) as the header is to allow for
+    # an easy way to search for values needing reencryption using a database index.  It takes
+    # the first three bytes and converts them to base64, and looks for values less than that value
+    # or greater than that value with 'B' appended. The NUL byte in the fourth byte of the header
+    # ensures that after base64 encoding, the fifth byte in the column will be 'A'.
+    #
+    # The reason for <tt>search_data</tt> (32 bytes) directly after is that for searchable values,
+    # after base64 encoding of the header and search data, it is 48 bytes and can be used directly
+    # as a prefix search on the column, which can be supported by the same database index.  This is
+    # more efficient than a full column value search for large values, and allows for case-insensitive
+    # searching without a separate column, by having the search_data be based on the lowercase value
+    # while the unencrypted data is original case.
+    #
+    # The reason for the padding is so that a database administrator cannot be sure exactly how
+    # many bytes are in the column.  It is stored encrypted because otherwise the database
+    # administrator could calculate it by decoding the base64 data.
+    #
+    # = Unsupported Features
+    #
+    # The following features are delibrately not supported:
+    #
+    # == Compression
+    #
+    # Allowing compression with encryption is inviting security issues later.
+    # While padding can reduce the risk of compression with encryption, it does not
+    # eliminate it entirely.  Users that must have compression with encryption can use
+    # the +:format+ option with a serializer that compresses and a deserializer that
+    # decompresses.
+    #
+    # == Mixing Encrypted/Unencrypted Data
+    #
+    # Mixing encrypted and unencrypted data increases the complexity and security risk, since there
+    # is a chance unencrypted data could look like encrypted data in the pathologic case.
+    # If you have existing unencrypted data that would like to encrypt, create a new column for
+    # the encrypted data, and then migrate the data from the unencrypted column to the encrypted
+    # column.  After all unencrypted values have been migrated, drop the unencrypted column.
+    #
+    # == Arbitrary Encryption Schemes
+    #
+    # Supporting arbitrary encryption schemes increases the complexity risk.
+    # If in the future AES-256-GCM is not considered a secure enough cipher, it is possible to
+    # extend the current format using the reserved values in the first two bytes of the header.
+    #
+    # = Caveats
+    #
+    # As column_encryption is a model plugin, it only works with using model instance methods.
+    # If you directly modify the database using a dataset or an external program that modifies
+    # the contents of the encrypted columns, you will probably corrupt the data. To make data
+    # corruption less likely, it is best to have a CHECK constraints on the encrypted column
+    # with a basic format and length check:
+    #
+    #   DB.alter_table(:table_name) do
+    #     c = Sequel[:encrypted_column_name]
+    #     add_constraint(:encrypted_column_name_format,
+    #                    c.like('AA__A%') | c.like('Ag__A%') | c.like('AQ__A%'))
+    #     add_constraint(:encrypted_column_name_length, Sequel.char_length(c) >= 88)
+    #   end
+    #
+    # If possible, it's also best to check that the column is valid urlsafe base64 data of
+    # sufficient length. This can be done on PostgreSQL using a combination of octet_length,
+    # decode, and regexp_replace:
+    #
+    #   DB.alter_table(:ce_test) do
+    #     c = Sequel[:encrypted_column_name]
+    #     add_constraint(:enc_base64) do
+    #       octet_length(decode(regexp_replace(regexp_replace(c, '_', '/', 'g'), '-', '+', 'g'), 'base64')) >= 65}
+    #     end
+    #   end
+    #
+    # Such constraints will probably be sufficient to protect against most unintentional corruption of
+    # encrypted columns.
+    #
+    # If the database supports transparent data encryption and you trust the database administrator,
+    # using the database support is probably a better approach.
+    #
+    # The column_encryption plugin is only supported on Ruby 2.3+ and when the Ruby openssl standard
+    # library supports the AES-256-GCM cipher.
+    module ColumnEncryption
+      # Cryptor handles the encryption and decryption of rows for a key set.
+      # It also provides methods that return search prefixes, which datasets
+      # use in queries.
+      #
+      # The same cryptor can support non-searchable, searchable, and case-insensitive
+      # searchable columns.
+      class Cryptor # :nodoc:
+        # Flags
+        NOT_SEARCHABLE = 0
+        SEARCHABLE = 1
+        LOWERCASE_SEARCHABLE = 2
+
+        # This is the default padding, but up to 2x the padding can be used for a record.
+        DEFAULT_PADDING = 8
+
+        # Keys should be an array of arrays containing key_id, key string, auth_data, and padding.
+        def initialize(keys)
+          if keys.empty?
+            raise Error, "Cannot initialize encryptor without encryption key"
+          end
+
+          # First key is used for encryption
+          @key_id, @key, @auth_data, @padding = keys[0]
+
+          # All keys are candidates for decryption
+          @key_map = {}
+          keys.each do |key_id, key, auth_data, padding|
+            @key_map[key_id] = [key, auth_data, padding].freeze
+          end
+
+          freeze
+        end
+
+        # Decrypt using any supported format and any available key.
+        def decrypt(data)
+          begin
+            data = Base64.urlsafe_decode64(data)
+          rescue ArgumentError
+            raise Error, "Unable to decode encrypted column: invalid base64"
+          end
+
+          unless data.getbyte(1) == 0 && data.getbyte(3) == 0
+            raise Error, "Unable to decode encrypted column: invalid format"
+          end
+
+          flags = data.getbyte(0)
+
+          key, auth_data = @key_map[data.getbyte(2)]
+          unless key
+            raise Error, "Unable to decode encrypted column: invalid key id"
+          end
+
+          case flags
+          when NOT_SEARCHABLE
+            if data.bytesize < 65
+              raise Error, "Decoded encrypted column smaller than minimum size"
+            end
+
+            data.slice!(0, 4)
+          when SEARCHABLE, LOWERCASE_SEARCHABLE
+            if data.bytesize < 97
+              raise Error, "Decoded encrypted column smaller than minimum size"
+            end
+
+            data.slice!(0, 36)
+          else
+            raise Error, "Unable to decode encrypted column: invalid flags"
+          end
+
+          key_part = data.slice!(0, 32)
+          cipher_iv = data.slice!(0, 12)
+          auth_tag = data.slice!(0, 16)
+
+          cipher = OpenSSL::Cipher.new("aes-256-gcm")
+          cipher.decrypt
+          cipher.iv = cipher_iv
+          cipher.key = OpenSSL::HMAC.digest(OpenSSL::Digest::SHA256.new, key, key_part)
+          cipher.auth_data = auth_data
+          cipher.auth_tag = auth_tag
+          begin
+            decrypted_data = cipher.update(data) << cipher.final
+          rescue OpenSSL::Cipher::CipherError => e
+            raise Error, "Unable to decrypt encrypted column: #{e.class} (probably due to encryption key or auth data mismatch or corrupt data)"
+          end
+
+          # Remove padding
+          decrypted_data.slice!(0, decrypted_data.getbyte(0) + 1)
+
+          decrypted_data
+        end
+
+        # Encrypt in not searchable format with the first configured encryption key.
+        def encrypt(data)
+          _encrypt(data, "#{NOT_SEARCHABLE.chr}\0#{@key_id.chr}\0")
+        end
+
+        # Encrypt in searchable format with the first configured encryption key.
+        def searchable_encrypt(data)
+          _encrypt(data, _search_prefix(data, SEARCHABLE, @key_id, @key))
+        end
+
+        # Encrypt in case insensitive searchable format with the first configured encryption key.
+        def case_insensitive_searchable_encrypt(data)
+          _encrypt(data, _search_prefix(data.downcase, LOWERCASE_SEARCHABLE, @key_id, @key))
+        end
+
+        # The prefix string of columns for the given search type and the first configured encryption key.
+        # Used to find values that do not use this prefix in order to perform reencryption.
+        def current_key_prefix(search_type)
+          Base64.urlsafe_encode64("#{search_type.chr}\0#{@key_id.chr}")
+        end
+
+        # The prefix values to search for the given data (an array of strings), assuming the column uses
+        # the searchable format.
+        def search_prefixes(data)
+          _search_prefixes(data, SEARCHABLE)
+        end
+
+        # The prefix values to search for the given data (an array of strings), assuming the column uses
+        # the case insensitive searchable format.
+        def lowercase_search_prefixes(data)
+          _search_prefixes(data.downcase, LOWERCASE_SEARCHABLE)
+        end
+
+        # The prefix values to search for the given data (an array of strings), assuming the column uses
+        # either the searchable or the case insensitive searchable format.  Should be used only when
+        # transitioning between formats (used by the :search_both option when encrypting columns).
+        def regular_and_lowercase_search_prefixes(data)
+          search_prefixes(data) + lowercase_search_prefixes(data)
+        end
+
+        private
+
+        # An array of strings, one for each configured encryption key, to find encypted values matching
+        # the given data and search format.
+        def _search_prefixes(data, search_type)
+          @key_map.map do |key_id, (key, _)|
+            Base64.urlsafe_encode64(_search_prefix(data, search_type, key_id, key))
+          end
+        end
+
+        # The prefix to use for searchable data, including the HMAC-SHA256(key, data).
+        def _search_prefix(data, search_type, key_id, key)
+          "#{search_type.chr}\0#{key_id.chr}\0#{OpenSSL::HMAC.digest(OpenSSL::Digest::SHA256.new, key, data)}"
+        end
+
+        # Encrypt the data using AES-256-GCM, with the given prefix.
+        def _encrypt(data, prefix)
+          padding = @padding
+          random_data = SecureRandom.random_bytes(32)
+          cipher = OpenSSL::Cipher.new("aes-256-gcm")
+          cipher.encrypt
+          cipher.key = OpenSSL::HMAC.digest(OpenSSL::Digest::SHA256.new, @key, random_data)
+          cipher_iv = cipher.random_iv
+          cipher.auth_data = @auth_data
+
+          cipher_text = String.new
+          data_size = data.bytesize
+
+          padding_size = if padding
+            (padding * rand(1)) + padding - (data.bytesize % padding)
+          else
+            0
+          end
+
+          cipher_text << cipher.update(padding_size.chr)
+          cipher_text << cipher.update(SecureRandom.random_bytes(padding_size)) if padding_size > 0
+          cipher_text << cipher.update(data) if data_size > 0
+          cipher_text << cipher.final
+
+          Base64.urlsafe_encode64("#{prefix}#{random_data}#{cipher_iv}#{cipher.auth_tag}#{cipher_text}")
+        end
+      end
+
+      # The object type yielded to blocks passed to the +column+ method inside
+      # <tt>plugin :column_encryption</tt> blocks.  This is used to configure custom
+      # per-column keys.
+      class ColumnDSL # :nodoc:
+        # An array of arrays for the data for the keys configured inside the block.
+        attr_reader :keys
+
+        def initialize
+          @keys = []
+        end
+
+        # Verify that the key_id, key, and options are value.
+        def key(key_id, key, opts=OPTS)
+          unless key_id.is_a?(Integer) && key_id >= 0 && key_id <= 255
+            raise Error, "invalid key_id argument, must be integer between 0 and 255"
+          end
+
+          unless key.is_a?(String) && key.bytesize == 32
+            raise Error, "invalid key argument, must be string with exactly 32 bytes"
+          end
+
+          if opts.has_key?(:padding)
+            if padding = opts[:padding]
+              unless padding.is_a?(Integer) && padding >= 1 && padding <= 120
+                raise Error, "invalid :padding option, must be between 1 and 120"
+              end
+            end
+          else
+            padding = Cryptor::DEFAULT_PADDING
+          end
+
+          @keys << [key_id, key, opts[:auth_data].to_s, padding].freeze
+        end
+      end
+
+      # The object type yielded to <tt>plugin :column_encryption</tt> blocks,
+      # used to configure encryption keys and encrypted columns.
+      class DSL < ColumnDSL # :nodoc:
+        # An array of arrays of data for the columns configured inside the block.
+        attr_reader :columns
+
+        def initialize
+          super
+          @columns = []
+        end
+
+        # Store the column information.
+        def column(column, opts=OPTS, &block)
+          @columns << [column, opts, block].freeze
+        end
+      end
+
+      def self.apply(model, opts=OPTS)
+        model.plugin :serialization
+      end
+
+      def self.configure(model)
+        dsl = DSL.new
+        yield dsl
+
+        model.instance_exec do
+          unless dsl.keys.empty?
+            @column_encryption_keys = dsl.keys.freeze
+            @column_encryption_cryptor = nil
+          end
+
+          @column_encryption_metadata = Hash[@column_encryption_metadata || {}]
+
+          dsl.columns.each do |column, opts, block|
+            _encrypt_column(column, opts, &block)
+          end
+
+          @column_encryption_metadata.freeze
+        end
+      end
+
+      # This stores four callables for handling encyption, decryption, data searching,
+      # and key searching.  One of these is created for each encrypted column.
+      ColumnEncryptionMetadata = Struct.new(:encryptor, :decryptor, :data_searcher, :key_searcher) # :nodoc:
+
+      module ClassMethods
+        private
+
+        # A hash with column symbol keys and ColumnEncryptionMetadata values for each
+        # encrypted column.
+        attr_reader :column_encryption_metadata
+
+        # The default Cryptor to use for encrypted columns.  This is only overridden if
+        # per-column keys are used.
+        def column_encryption_cryptor
+          @column_encryption_cryptor ||= Cryptor.new(@column_encryption_keys)
+        end
+
+        # Setup encryption for the given column.
+        def _encrypt_column(column, opts)
+          cryptor ||= if defined?(yield)
+            dsl = ColumnDSL.new
+            yield dsl
+            Cryptor.new(dsl.keys)
+          else
+            column_encryption_cryptor
+          end
+
+          encrypt_method, search_prefixes_method, search_type = case searchable = opts[:searchable]
+          when nil, false
+            [:encrypt, nil, Cryptor::NOT_SEARCHABLE] 
+          when true
+            [:searchable_encrypt, :search_prefixes, Cryptor::SEARCHABLE] 
+          when :case_insensitive
+            [:case_insensitive_searchable_encrypt, :lowercase_search_prefixes, Cryptor::LOWERCASE_SEARCHABLE] 
+          else
+            raise Error, "invalid :searchable option for encrypted column: #{searchable.inspect}"
+          end
+
+          if searchable && opts[:search_both]
+            search_prefixes_method = :regular_and_lowercase_search_prefixes
+          end
+
+          # Setup the callables used in the metadata.
+          encryptor = cryptor.method(encrypt_method)
+          decryptor = cryptor.method(:decrypt)
+          data_searcher = cryptor.method(search_prefixes_method) if search_prefixes_method
+          key_searcher = lambda{cryptor.current_key_prefix(search_type)}
+
+          if format = opts[:format]
+            if format.is_a?(Symbol)
+              unless format = Sequel.synchronize{Serialization::REGISTERED_FORMATS[format]}
+                raise(Error, "Unsupported serialization format: #{format} (valid formats: #{Sequel.synchronize{Serialization::REGISTERED_FORMATS.keys}.inspect})")
+              end
+            end
+
+            # If a custom serialization format is used, override the
+            # callables to handle serialization and deserialization.
+            serializer, deserializer = format
+            enc, dec, data_s = encryptor, decryptor, data_searcher
+            encryptor = lambda do |data|
+              enc.call(serializer.call(data))
+            end
+            decryptor = lambda do |data|
+              deserializer.call(dec.call(data))
+            end
+            data_searcher = lambda do |data|
+              data_s.call(serializer.call(data))
+            end
+          end
+
+          # Setup the setter and getter methods to do encryption and decryption using
+          # the serialization plugin.
+          serialize_attributes([encryptor, decryptor], column)
+
+          column_encryption_metadata[column] = ColumnEncryptionMetadata.new(encryptor, decryptor, data_searcher, key_searcher).freeze
+
+          nil
+        end
+      end
+
+      module ClassMethods
+        Plugins.def_dataset_methods(self, [:with_encrypted_value, :needing_reencryption])
+
+        Plugins.inherited_instance_variables(self,
+          :@column_encryption_cryptor=>nil,
+          :@column_encryption_keys=>nil,
+          :@column_encryption_metadata=>nil,
+        )
+      end
+
+      module InstanceMethods
+        # Reencrypt the model if needed.  Looks at all of the models encrypted columns
+        # and if any were encypted with older keys or a different format, reencrypt
+        # with the current key and format and save the object.  Returns the object
+        # if reencryption was needed, or nil if reencryption was not needed.
+        def reencrypt
+          do_save = false
+
+          model.send(:column_encryption_metadata).each do |column, metadata|
+            if (value = values[column]) && !value.start_with?(metadata.key_searcher.call)
+              do_save = true
+              values[column] = metadata.encryptor.call(metadata.decryptor.call(value))
+            end
+          end
+
+          save if do_save
+        end
+      end
+
+      module DatasetMethods
+        # Filter the dataset to only match rows where the column contains an encrypted version
+        # of value.  Only works on searchable encrypted columns.
+        def with_encrypted_value(column, value)
+          metadata = model.send(:column_encryption_metadata)[column]
+          
+          unless metadata && metadata.data_searcher
+            raise Error, "lookup for encrypted column #{column.inspect} is not supported"
+          end
+
+          prefixes = metadata.data_searcher.call(value)
+          where(Sequel.|(*prefixes.map{|v| Sequel.like(column, "#{escape_like(v)}%")}))
+        end
+
+        # Filter the dataset to exclude rows where all encrypted columns are already encrypted
+        # with the current key and format.
+        def needing_reencryption
+          incorrect_column_prefixes = model.send(:column_encryption_metadata).map do |column, metadata|
+            prefix = metadata.key_searcher.call
+            (Sequel[column] < prefix) | (Sequel[column] > prefix + 'B')
+          end
+
+          where(Sequel.|(*incorrect_column_prefixes))
+        end
+      end
+    end
+  end
+end