diff --git a/app/services/encryption/encryptors/deprecated_session_encryptor.rb b/app/services/encryption/encryptors/deprecated_session_encryptor.rb
new file mode 100644
index 00000000000..fac387466f2
--- /dev/null
+++ b/app/services/encryption/encryptors/deprecated_session_encryptor.rb
@@ -0,0 +1,28 @@
+module Encryption
+  module Encryptors
+    class DeprecatedSessionEncryptor
+      def encrypt(plaintext)
+        user_access_key = self.class.load_or_init_user_access_key
+        UserAccessKeyEncryptor.new(user_access_key).encrypt(plaintext)
+      end
+
+      def decrypt(ciphertext)
+        user_access_key = self.class.load_or_init_user_access_key
+        UserAccessKeyEncryptor.new(user_access_key).decrypt(ciphertext)
+      end
+
+      def self.load_or_init_user_access_key
+        if @user_access_key_scrypt_hash.present?
+          return UserAccessKey.new(scrypt_hash: @user_access_key_scrypt_hash)
+        end
+
+        key = Figaro.env.session_encryption_key
+        user_access_key = UserAccessKey.new(
+          password: key, salt: OpenSSL::Digest::SHA256.hexdigest(key)
+        )
+        @user_access_key_scrypt_hash = user_access_key.as_scrypt_hash
+        user_access_key
+      end
+    end
+  end
+end
diff --git a/app/services/encryption/encryptors/session_encryptor.rb b/app/services/encryption/encryptors/session_encryptor.rb
index 39e86ceeb56..df9b39b73ec 100644
--- a/app/services/encryption/encryptors/session_encryptor.rb
+++ b/app/services/encryption/encryptors/session_encryptor.rb
@@ -1,27 +1,33 @@
 module Encryption
   module Encryptors
     class SessionEncryptor
-      def encrypt(plaintext)
-        user_access_key = self.class.load_or_init_user_access_key
-        UserAccessKeyEncryptor.new(user_access_key).encrypt(plaintext)
-      end
+      include Encodable
+
+      delegate :encrypt, to: :deprecated_encryptor
 
       def decrypt(ciphertext)
-        user_access_key = self.class.load_or_init_user_access_key
-        UserAccessKeyEncryptor.new(user_access_key).decrypt(ciphertext)
+        return deprecated_encryptor.decrypt(ciphertext) if legacy?(ciphertext)
+
+        aes_ciphertext = KmsClient.new.decrypt(decode(ciphertext))
+        aes_encryptor.decrypt(aes_ciphertext, aes_encryption_key)
+      end
+
+      private
+
+      def legacy?(ciphertext)
+        ciphertext.index('.')
+      end
+
+      def aes_encryptor
+        AesEncryptor.new
+      end
+
+      def aes_encryption_key
+        Figaro.env.session_encryption_key[0...32]
       end
 
-      def self.load_or_init_user_access_key
-        if @user_access_key_scrypt_hash.present?
-          return UserAccessKey.new(scrypt_hash: @user_access_key_scrypt_hash)
-        end
-
-        key = Figaro.env.session_encryption_key
-        user_access_key = UserAccessKey.new(
-          password: key, salt: OpenSSL::Digest::SHA256.hexdigest(key)
-        )
-        @user_access_key_scrypt_hash = user_access_key.as_scrypt_hash
-        user_access_key
+      def deprecated_encryptor
+        DeprecatedSessionEncryptor.new
       end
     end
   end
diff --git a/spec/services/encryption/encryptors/deprecated_session_encryptor.rb b/spec/services/encryption/encryptors/deprecated_session_encryptor.rb
new file mode 100644
index 00000000000..ef88164af91
--- /dev/null
+++ b/spec/services/encryption/encryptors/deprecated_session_encryptor.rb
@@ -0,0 +1,79 @@
+require 'rails_helper'
+
+describe Encryption::Encryptors::DeprecatedSessionEncryptor do
+  let(:plaintext) { '{ "foo": "bar" }' }
+
+  before do
+    described_class.instance_variable_set(:@user_access_key_scrypt_hash, nil)
+  end
+
+  describe '#encrypt' do
+    it 'returns encrypted text' do
+      ciphertext = subject.encrypt(plaintext)
+
+      expect(ciphertext).to_not eq(plaintext)
+    end
+
+    it 'only computes an scrypt hash on the first encryption' do
+      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
+
+      subject.encrypt(plaintext)
+
+      expect(SCrypt::Engine).to_not receive(:hash_secret)
+
+      subject.encrypt(plaintext)
+    end
+  end
+
+  describe '#decrypt' do
+    let(:ciphertext) do
+      result = subject.encrypt(plaintext)
+      described_class.instance_variable_set(:@user_access_key_scrypt_hash, nil)
+      result
+    end
+
+    before do
+      # Memoize the ciphertext and purge memoized key so that encryption does not
+      # affect expected call counts
+      ciphertext
+    end
+
+    it 'returns a decrypted ciphertext' do
+      expect(subject.decrypt(ciphertext)).to eq(plaintext)
+    end
+
+    it 'only computes and scrypt hash on the first decryption' do
+      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
+
+      subject.decrypt(ciphertext)
+
+      expect(SCrypt::Engine).to_not receive(:hash_secret)
+
+      subject.decrypt(ciphertext)
+    end
+  end
+
+  describe '.load_or_init_user_access_key' do
+    it 'does not return the same key object for the same salt and cost' do
+      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
+
+      key1 = described_class.load_or_init_user_access_key
+      key2 = described_class.load_or_init_user_access_key
+
+      expect(key1.as_scrypt_hash).to eq(key2.as_scrypt_hash)
+      expect(key1).to_not eq(key2)
+    end
+  end
+
+  it 'makes a roundtrip across multiple encryptors' do
+    encryptor1 = described_class.new
+    encryptor2 = described_class.new
+
+    # Memoize user access key scrypt hash
+    encryptor1.decrypt(encryptor1.encrypt('asdf'))
+    encryptor2.decrypt(encryptor2.encrypt('1234'))
+
+    encrypted_text = encryptor1.encrypt(plaintext)
+    expect(encryptor2.decrypt(encrypted_text)).to eq(plaintext)
+  end
+end
diff --git a/spec/services/encryption/encryptors/session_encryptor_spec.rb b/spec/services/encryption/encryptors/session_encryptor_spec.rb
index fc1ab152b10..95efbf641aa 100644
--- a/spec/services/encryption/encryptors/session_encryptor_spec.rb
+++ b/spec/services/encryption/encryptors/session_encryptor_spec.rb
@@ -3,77 +3,43 @@
 describe Encryption::Encryptors::SessionEncryptor do
   let(:plaintext) { '{ "foo": "bar" }' }
 
-  before do
-    described_class.instance_variable_set(:@user_access_key_scrypt_hash, nil)
-  end
-
   describe '#encrypt' do
-    it 'returns encrypted text' do
-      ciphertext = subject.encrypt(plaintext)
-
-      expect(ciphertext).to_not eq(plaintext)
-    end
-
-    it 'only computes an scrypt hash on the first encryption' do
-      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
+    it 'returns ciphertext created by the deprecated session encryptor' do
+      expected_ciphertext = '123abc'
 
-      subject.encrypt(plaintext)
+      deprecated_encryptor = Encryption::Encryptors::DeprecatedSessionEncryptor.new
+      expect(deprecated_encryptor).to receive(:encrypt).
+        with(plaintext).
+        and_return(expected_ciphertext)
+      expect(Encryption::Encryptors::DeprecatedSessionEncryptor).to receive(:new).
+        and_return(deprecated_encryptor)
 
-      expect(SCrypt::Engine).to_not receive(:hash_secret)
+      ciphertext = subject.encrypt(plaintext)
 
-      subject.encrypt(plaintext)
+      expect(ciphertext).to eq(expected_ciphertext)
     end
   end
 
   describe '#decrypt' do
-    let(:ciphertext) do
-      result = subject.encrypt(plaintext)
-      described_class.instance_variable_set(:@user_access_key_scrypt_hash, nil)
-      result
-    end
-
-    before do
-      # Memoize the ciphertext and purge memoized key so that encryption does not
-      # affect expected call counts
-      ciphertext
-    end
-
-    it 'returns a decrypted ciphertext' do
-      expect(subject.decrypt(ciphertext)).to eq(plaintext)
-    end
-
-    it 'only computes and scrypt hash on the first decryption' do
-      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
-
-      subject.decrypt(ciphertext)
+    context 'with a legacy ciphertext' do
+      let(:ciphertext) { Encryption::Encryptors::DeprecatedSessionEncryptor.new.encrypt(plaintext) }
 
-      expect(SCrypt::Engine).to_not receive(:hash_secret)
-
-      subject.decrypt(ciphertext)
+      it 'decrypts the ciphertext' do
+        expect(subject.decrypt(ciphertext)).to eq(plaintext)
+      end
     end
-  end
-
-  describe '.load_or_init_user_access_key' do
-    it 'does not return the same key object for the same salt and cost' do
-      expect(SCrypt::Engine).to receive(:hash_secret).once.and_call_original
 
-      key1 = described_class.load_or_init_user_access_key
-      key2 = described_class.load_or_init_user_access_key
-
-      expect(key1.as_scrypt_hash).to eq(key2.as_scrypt_hash)
-      expect(key1).to_not eq(key2)
+    context 'with a 2L-KMS ciphertext' do
+      let(:ciphertext) do
+        key = Figaro.env.session_encryption_key[0...32]
+        aes_ciphertext = Encryption::Encryptors::AesEncryptor.new.encrypt(plaintext, key)
+        kms_ciphertext = Encryption::KmsClient.new.encrypt(aes_ciphertext)
+        Base64.strict_encode64(kms_ciphertext)
+      end
+
+      it 'decrypts the ciphertext' do
+        expect(subject.decrypt(ciphertext)).to eq(plaintext)
+      end
     end
   end
-
-  it 'makes a roundtrip across multiple encryptors' do
-    encryptor1 = described_class.new
-    encryptor2 = described_class.new
-
-    # Memoize user access key scrypt hash
-    encryptor1.decrypt(encryptor1.encrypt('asdf'))
-    encryptor2.decrypt(encryptor2.encrypt('1234'))
-
-    encrypted_text = encryptor1.encrypt(plaintext)
-    expect(encryptor2.decrypt(encrypted_text)).to eq(plaintext)
-  end
 end