diff --git a/app/interactions/actions/contact_update.rb b/app/interactions/actions/contact_update.rb
index 81b7e74090..bfa3f3b7c2 100644
--- a/app/interactions/actions/contact_update.rb
+++ b/app/interactions/actions/contact_update.rb
@@ -115,8 +115,9 @@ def commit
       contact.email_history = old_email
       updated = contact.save
 
-      if updated && email_changed && contact.registrant?
-        ContactMailer.email_changed(contact: contact, old_email: old_email).deliver_now
+      if updated && email_changed
+        contact.validation_events.where('event_data @> ?', { 'email': old_email }.to_json).destroy_all
+        ContactMailer.email_changed(contact: contact, old_email: old_email).deliver_now if contact.registrant?
       end
 
       updated
diff --git a/test/integration/epp/contact/update/base_test.rb b/test/integration/epp/contact/update/base_test.rb
index 364741f0c1..0c55c52237 100644
--- a/test/integration/epp/contact/update/base_test.rb
+++ b/test/integration/epp/contact/update/base_test.rb
@@ -80,6 +80,35 @@ def test_notifies_contact_by_email_when_email_is_changed
     assert_emails 1
   end
 
+  def test_destroy_old_validation_when_email_is_changed
+    @contact.verify_email
+    old_validation_event = @contact.validation_events.first
+    @contact.update_columns(code: @contact.code.upcase)
+
+    request_xml = <<-XML
+      <?xml version="1.0" encoding="UTF-8" standalone="no"?>
+      <epp xmlns="#{Xsd::Schema.filename(for_prefix: 'epp-ee', for_version: '1.0')}">
+        <command>
+          <update>
+            <contact:update xmlns:contact="#{Xsd::Schema.filename(for_prefix: 'contact-ee', for_version: '1.1')}">
+              <contact:id>john-001</contact:id>
+              <contact:chg>
+                <contact:email>john-new@inbox.test</contact:email>
+              </contact:chg>
+            </contact:update>
+          </update>
+        </command>
+      </epp>
+    XML
+
+    post epp_update_path, params: { frame: request_xml },
+         headers: { 'HTTP_COOKIE' => 'session=api_bestnames' }
+
+    assert_raises(ActiveRecord::RecordNotFound) do
+      ValidationEvent.find(old_validation_event.id)
+    end
+  end
+
   def test_skips_notifying_contact_when_email_is_not_changed
     assert_equal 'john-001', @contact.code
     assert_equal 'john@inbox.test', @contact.email