The validation of a token needs to load the token_object every time.

app/models/enterprise_token.rb

@@ -80,6 +80,13 @@ class EnterpriseToken < ActiveRecord::Base
     RequestStore.delete :current_ee_token
   end
 
+  def unset_current_token_object
+    # Clear current cache
+    if defined?(@token_object)
+      remove_instance_variable(:@token_object)
+    end
+  end
+
   private
 
   def load_token
@@ -90,6 +97,7 @@ class EnterpriseToken < ActiveRecord::Base
   end
 
   def valid_token_object
-    errors.add(:encoded_token, :unreadable) unless token_object
+    unset_current_token_object
+    errors.add(:encoded_token, :unreadable) unless load_token
   end
 end

spec/models/enterprise_token_spec.rb

@@ -77,6 +77,13 @@ RSpec.describe EnterpriseToken, type: :model do
         expect(EnterpriseToken.show_banners).to eq(true)
       end
     end
+
+    context 'updating it with an invalid token' do
+      it 'will fail validations' do
+        subject.encoded_token = "bar"
+        expect(subject.save).to be_falsey
+      end
+    end
   end
 
   describe 'no token' do