diff --git a/Gemfile b/Gemfile
index 484c1ef11..7ae844852 100644
--- a/Gemfile
+++ b/Gemfile
@@ -132,7 +132,7 @@ gem 'oj_mimic_json'
 # Admin toggles
 gem 'rails-settings-ui'
 gem 'rails-settings-cached', '0.7.2'
-gem 'dry-validation', '0.12.0'
+gem 'dry-validation', '0.12.3'
 
 gem 'scout_apm', '~> 3.0.x'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index 4978d50a6..28a3ea627 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -80,7 +80,7 @@ GEM
     ast (2.4.0)
     autoprefixer-rails (9.6.0)
       execjs
-    awesome_print (1.7.0)
+    awesome_print (1.8.0)
     aws-ses (0.6.0)
       builder
       mail (> 2.2.5)
@@ -179,12 +179,12 @@ GEM
     dry-container (0.7.2)
       concurrent-ruby (~> 1.0)
       dry-configurable (~> 0.1, >= 0.1.3)
-    dry-core (0.4.8)
+    dry-core (0.4.9)
       concurrent-ruby (~> 1.0)
     dry-equalizer (0.2.2)
     dry-inflector (0.1.2)
-    dry-logic (0.6.1)
-      concurrent-ruby (~> 1.0)
+    dry-logic (0.4.2)
+      dry-container (~> 0.2, >= 0.2.6)
       dry-core (~> 0.2)
       dry-equalizer (~> 0.2)
     dry-types (0.13.4)
@@ -194,12 +194,12 @@ GEM
       dry-equalizer (~> 0.2)
       dry-inflector (~> 0.1, >= 0.1.2)
       dry-logic (~> 0.4, >= 0.4.2)
-    dry-validation (0.12.0)
+    dry-validation (0.12.3)
       concurrent-ruby (~> 1.0)
       dry-configurable (~> 0.1, >= 0.1.3)
       dry-core (~> 0.2, >= 0.2.1)
       dry-equalizer (~> 0.2)
-      dry-logic (~> 0.4, >= 0.4.0)
+      dry-logic (~> 0.4.2)
       dry-types (~> 0.13.1)
     em-websocket (0.5.1)
       eventmachine (>= 0.12.9)
@@ -656,7 +656,7 @@ DEPENDENCIES
   delayed_job_active_record (~> 4.1.3)
   doorkeeper
   dotenv-rails (= 2.7.2)
-  dry-validation (= 0.12.0)
+  dry-validation (= 0.12.3)
   factory_bot_rails
   faker
   fakeredis
diff --git a/app/models/user.rb b/app/models/user.rb
index ec1d4565c..22ba51be9 100644
--- a/app/models/user.rb
+++ b/app/models/user.rb
@@ -238,12 +238,12 @@ def guessed_preferred_confirmed_email
       manual_emails = verified_emails.reject { |email| email.confirmation_sent_at.nil? }
       manual_emails.any? ? manual_emails.max_by(&:created_at) : verified_emails.min_by(&:created_at)
     else
-      email_addresses.verified.order(
+      email_addresses.verified.order(Arel.sql(
         <<-SQL.strip_heredoc
           CASE WHEN "confirmation_sent_at" IS NULL THEN '-infinity' ELSE "created_at" END DESC,
           "created_at" ASC
         SQL
-      ).first
+      )).first
     end.try!(:value)
   end
 
diff --git a/spec/controllers/contact_infos_controller_spec.rb b/spec/controllers/contact_infos_controller_spec.rb
index ee6f05298..3e5ce9e88 100644
--- a/spec/controllers/contact_infos_controller_spec.rb
+++ b/spec/controllers/contact_infos_controller_spec.rb
@@ -76,7 +76,7 @@
 
     it "returns success if code matches" do
       get(:confirm, params: { code: @email.confirmation_code })
-      expect(response).to be_success
+      expect(response).to be_successful
       expect(response.body).to have_no_missing_translations
       expect(response.body).to have_content(t :"contact_infos.confirm.page_heading.success")
       expect(response.body).to(
@@ -103,7 +103,7 @@
 
     it "returns success if code matches" do
       get(:confirm_unclaimed, params: { code: email.confirmation_code })
-      expect(response).to be_success
+      expect(response).to be_successful
       expect(response.body).to have_no_missing_translations
       expect(response.body).to(
         have_content(t :"contact_infos.confirm_unclaimed.thanks_for_validating")
diff --git a/spec/mailers/dev_mailer_spec.rb b/spec/mailers/dev_mailer_spec.rb
index f240bbfcb..d3e4571cd 100644
--- a/spec/mailers/dev_mailer_spec.rb
+++ b/spec/mailers/dev_mailer_spec.rb
@@ -12,7 +12,7 @@
       expect(mail.from).to eq(['sender@localhost'])
       expect(mail.subject).to eq "[OpenStax] [Accounts] (test) Howdy"
       expect(mail.body.encoded).to eq(
-        "[\r\n  [0] {\r\n    :a => 2\r\n  },\r\n  [1] {\r\n    :b => \"yo yo yo\"\r\n  }\r\n]\r\n"
+        "[\r\n  [0] {\r\n    a: 2\r\n  },\r\n  [1] {\r\n    b: \"yo yo yo\"\r\n  }\r\n]\r\n"
       )
     end
 
diff --git a/spec/rails_helper.rb b/spec/rails_helper.rb
index 0115569d1..11b0c7638 100644
--- a/spec/rails_helper.rb
+++ b/spec/rails_helper.rb
@@ -52,6 +52,8 @@
 
 Capybara.asset_host = 'http://localhost:2999'
 
+Capybara.server = :puma, { Silent: true } # To clean up your test output
+
 # Normalize whitespaces
 Capybara.default_normalize_ws = true