diff --git a/Gemfile b/Gemfile
index 5e80a7497..e8c7dd32a 100644
--- a/Gemfile
+++ b/Gemfile
@@ -113,8 +113,8 @@ end
 
 group :test do
   gem 'test-unit', '~> 3.0'
-  gem 'shoulda', '~> 3.5'
-  gem 'shoulda-matchers', '~> 2.0'
+  gem 'shoulda', '~> 4.0.0'
+  gem 'shoulda-matchers', '~> 4.4.0'
   gem 'minitest-reporters'
   gem 'valid_attribute'
   gem 'factory_bot_rails'
diff --git a/Gemfile.lock b/Gemfile.lock
index e5b8607c7..8aec52905 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -361,12 +361,12 @@ GEM
       ruby_http_client (~> 3.4)
     sexp_processor (4.15.0)
     shellany (0.0.1)
-    shoulda (3.5.0)
-      shoulda-context (~> 1.0, >= 1.0.1)
-      shoulda-matchers (>= 1.4.1, < 3.0)
-    shoulda-context (1.2.2)
-    shoulda-matchers (2.8.0)
-      activesupport (>= 3.0.0)
+    shoulda (4.0.0)
+      shoulda-context (~> 2.0)
+      shoulda-matchers (~> 4.0)
+    shoulda-context (2.0.0)
+    shoulda-matchers (4.4.1)
+      activesupport (>= 4.2.0)
     sidekiq (6.0.7)
       connection_pool (>= 2.2.2)
       rack (~> 2.0)
@@ -408,7 +408,7 @@ GEM
     turbolinks (5.2.1)
       turbolinks-source (~> 5.2)
     turbolinks-source (5.2.0)
-    tzinfo (1.2.8)
+    tzinfo (1.2.9)
       thread_safe (~> 0.1)
     uglifier (4.2.0)
       execjs (>= 0.3.0, < 3)
@@ -487,8 +487,8 @@ DEPENDENCIES
   selectize-rails
   selenium-webdriver
   sendgrid-actionmailer
-  shoulda (~> 3.5)
-  shoulda-matchers (~> 2.0)
+  shoulda (~> 4.0.0)
+  shoulda-matchers (~> 4.4.0)
   sidekiq (< 7)
   sidekiq-cron (~> 1.1)
   simple_form
diff --git a/test/models/questionnaire_test.rb b/test/models/questionnaire_test.rb
index 7cf590185..4fa2d3863 100644
--- a/test/models/questionnaire_test.rb
+++ b/test/models/questionnaire_test.rb
@@ -5,7 +5,7 @@ class QuestionnaireTest < ActiveSupport::TestCase
 
   should belong_to :user
   should belong_to :school
-  should belong_to :bus_list
+  should belong_to(:bus_list).optional
   should have_and_belong_to_many :agreements
 
   should validate_uniqueness_of :user_id
diff --git a/test/models/user_test.rb b/test/models/user_test.rb
index 1b288f72f..a5956b0a0 100644
--- a/test/models/user_test.rb
+++ b/test/models/user_test.rb
@@ -7,7 +7,7 @@ class UserTest < ActiveSupport::TestCase
   should strip_attribute :last_name
   should strip_attribute :email
 
-  should validate_uniqueness_of :email
+  should validate_uniqueness_of(:email).ignoring_case_sensitivity
 
   should validate_presence_of :first_name
   should validate_presence_of :last_name
diff --git a/test/test_helper.rb b/test/test_helper.rb
index 2d3f333a8..4208de352 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -51,3 +51,10 @@ class ActiveSupport::TestCase
 class ActionController::TestCase
   include Devise::Test::ControllerHelpers
 end
+
+Shoulda::Matchers.configure do |config|
+  config.integrate do |with|
+    with.test_framework :minitest
+    with.library :rails
+  end
+end
diff --git a/vendor/cache/shoulda-3.5.0.gem b/vendor/cache/shoulda-3.5.0.gem
deleted file mode 100644
index a79d90d9d..000000000
Binary files a/vendor/cache/shoulda-3.5.0.gem and /dev/null differ
diff --git a/vendor/cache/shoulda-4.0.0.gem b/vendor/cache/shoulda-4.0.0.gem
new file mode 100644
index 000000000..3f271dc15
Binary files /dev/null and b/vendor/cache/shoulda-4.0.0.gem differ
diff --git a/vendor/cache/shoulda-context-1.2.2.gem b/vendor/cache/shoulda-context-1.2.2.gem
deleted file mode 100644
index 9f93a904e..000000000
Binary files a/vendor/cache/shoulda-context-1.2.2.gem and /dev/null differ
diff --git a/vendor/cache/shoulda-context-2.0.0.gem b/vendor/cache/shoulda-context-2.0.0.gem
new file mode 100644
index 000000000..ced302fb3
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diff --git a/vendor/cache/shoulda-matchers-2.8.0.gem b/vendor/cache/shoulda-matchers-2.8.0.gem
deleted file mode 100644
index 950440762..000000000
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diff --git a/vendor/cache/shoulda-matchers-4.4.1.gem b/vendor/cache/shoulda-matchers-4.4.1.gem
new file mode 100644
index 000000000..6695d1a87
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diff --git a/vendor/cache/tzinfo-1.2.9.gem b/vendor/cache/tzinfo-1.2.9.gem
new file mode 100644
index 000000000..9f596f54b
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