diff --git a/app/services/encryption_service.rb b/app/services/encryption_service.rb
index 8949d54a7..3d0dbb92e 100644
--- a/app/services/encryption_service.rb
+++ b/app/services/encryption_service.rb
@@ -7,6 +7,10 @@ class EncryptionService
     password   = Rails.application.secrets.secret_key_base
     key        = ActiveSupport::KeyGenerator.new(password).generate_key(salt, len)
     @encryptor = ActiveSupport::MessageEncryptor.new(key)
+
+    # Remove after all encrypted attributes have been rotated.
+    legacy_key = ActiveSupport::KeyGenerator.new(password, hash_digest_class: OpenSSL::Digest::SHA1).generate_key(salt, len)
+    @encryptor.rotate legacy_key
   end
 
   def encrypt(value)
diff --git a/spec/services/encryption_service_spec.rb b/spec/services/encryption_service_spec.rb
index 91540cc43..051c48cb1 100644
--- a/spec/services/encryption_service_spec.rb
+++ b/spec/services/encryption_service_spec.rb
@@ -41,4 +41,89 @@ describe EncryptionService do
       it { expect { subject }.to raise_exception StandardError }
     end
   end
+
+  describe "key rotation" do
+    let(:password) { Rails.application.secrets.secret_key_base }
+    let(:salt) { Rails.application.secrets.encryption_service_salt }
+    let(:len) { ActiveSupport::MessageEncryptor.key_len }
+    let(:value) { "Sensitive information" }
+
+    let(:legacy_key) do
+      ActiveSupport::KeyGenerator.new(password, hash_digest_class: OpenSSL::Digest::SHA1)
+        .generate_key(salt, len)
+    end
+
+    let(:new_key) do
+      ActiveSupport::KeyGenerator.new(password)
+        .generate_key(salt, len)
+    end
+
+    let(:legacy_encryptor) { ActiveSupport::MessageEncryptor.new(legacy_key) }
+    let(:new_encryptor) { ActiveSupport::MessageEncryptor.new(new_key) }
+
+    describe "#decrypt" do
+      subject { EncryptionService.new.decrypt(encrypted_value) }
+
+      context "with a value encrypted using the legacy SHA1-based key" do
+        let(:encrypted_value) { legacy_encryptor.encrypt_and_sign(value) }
+
+        it "successfully decrypts the value" do
+          expect(subject).to eq(value)
+        end
+      end
+
+      context "with a value encrypted using the new SHA256-based key" do
+        let(:encrypted_value) { new_encryptor.encrypt_and_sign(value) }
+
+        it "successfully decrypts the value" do
+          expect(subject).to eq(value)
+        end
+      end
+    end
+
+    describe "transition from legacy to new encryption" do
+      let(:legacy_service) do
+        legacy_encryption_service = EncryptionService.new
+        legacy_encryption_service.instance_variable_set(:@encryptor, legacy_encryptor)
+        legacy_encryption_service
+      end
+
+      let(:new_service) { EncryptionService.new }
+
+      it "can decrypt values encrypted with the legacy key" do
+        legacy_encrypted = legacy_service.encrypt(value)
+        expect(new_service.decrypt(legacy_encrypted)).to eq(value)
+      end
+
+      it "uses the new key for new encryptions" do
+        new_encrypted = new_service.encrypt(value)
+        expect { legacy_encryptor.decrypt_and_verify(new_encrypted) }
+          .to raise_error(ActiveSupport::MessageEncryptor::InvalidMessage)
+        expect(new_encryptor.decrypt_and_verify(new_encrypted)).to eq(value)
+      end
+    end
+
+    describe "backwards compatibility" do
+      let(:value) { "Important data" }
+      let(:old_service) do # Test with a service encrypting data without rotation mechanism
+        Class.new do
+          def initialize(key)
+            @encryptor = ActiveSupport::MessageEncryptor.new(key)
+          end
+
+          def encrypt(value)
+            @encryptor.encrypt_and_sign(value)
+          end
+        end
+      end
+
+      it "can decrypt values from a hypothetical old version without rotation" do
+        old_key = ActiveSupport::KeyGenerator.new(password, hash_digest_class: OpenSSL::Digest::SHA1)
+          .generate_key(salt, len)
+        old_encrypted = old_service.new(old_key).encrypt(value)
+
+        expect(EncryptionService.new.decrypt(old_encrypted)).to eq(value)
+      end
+    end
+  end
 end