diff --git a/Gemfile.lock b/Gemfile.lock
index f280cf10b..a88961748 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -484,9 +484,10 @@ GEM
       rack (>= 1.1)
       rubocop (>= 1.75.0, < 2.0)
       rubocop-ast (>= 1.44.0, < 2.0)
-    rubocop-rspec (3.9.0)
+    rubocop-rspec (3.10.0)
       lint_roller (~> 1.1)
-      rubocop (~> 1.81)
+      regexp_parser (>= 2.0)
+      rubocop (~> 1.86, >= 1.86.2)
     rubocop-rspec_rails (2.32.0)
       lint_roller (~> 1.1)
       rubocop (~> 1.72, >= 1.72.1)
diff --git a/spec/concepts/class_member/create_spec.rb b/spec/concepts/class_member/create_spec.rb
index a4744dd98..de9081c70 100644
--- a/spec/concepts/class_member/create_spec.rb
+++ b/spec/concepts/class_member/create_spec.rb
@@ -83,7 +83,7 @@
 
       it 'returns the error message in the operation response' do
         response = described_class.call(school_class:, students:, teachers:)
-        expect(response[:error]).to match(/No valid school members provided/)
+        expect(response[:error]).to include('No valid school members provided')
       end
 
       it 'sent the exception to Sentry' do
diff --git a/spec/concepts/class_member/delete_spec.rb b/spec/concepts/class_member/delete_spec.rb
index 3d87ff4fa..974c86eb5 100644
--- a/spec/concepts/class_member/delete_spec.rb
+++ b/spec/concepts/class_member/delete_spec.rb
@@ -33,7 +33,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school_class:, class_member_id:)
-      expect(response[:error]).to match(/does-not-exist/)
+      expect(response[:error]).to include('does-not-exist')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/feedback/create_spec.rb b/spec/concepts/feedback/create_spec.rb
index d70a66d3a..0a1d5a11b 100644
--- a/spec/concepts/feedback/create_spec.rb
+++ b/spec/concepts/feedback/create_spec.rb
@@ -80,12 +80,12 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(feedback_params:)
-      expect(response[:error]).to match(/Error creating feedback/)
+      expect(response[:error]).to include('Error creating feedback')
     end
 
     it 'raises school project not found error when no school project' do
       response = described_class.call(feedback_params:)
-      expect(response[:error]).to match(/School project must exist/)
+      expect(response[:error]).to include('School project must exist')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/feedback/delete_spec.rb b/spec/concepts/feedback/delete_spec.rb
index 4183a6473..72fe75768 100644
--- a/spec/concepts/feedback/delete_spec.rb
+++ b/spec/concepts/feedback/delete_spec.rb
@@ -34,7 +34,7 @@
 
       it 'returns the error message in the operation response' do
         response = described_class.call(feedback_id:)
-        expect(response[:error]).to match(/does-not-exist/)
+        expect(response[:error]).to include('does-not-exist')
       end
 
       it 'sent the exception to Sentry' do
diff --git a/spec/concepts/lesson/create_copy_spec.rb b/spec/concepts/lesson/create_copy_spec.rb
index e0bbaa95c..b4e4a70d0 100644
--- a/spec/concepts/lesson/create_copy_spec.rb
+++ b/spec/concepts/lesson/create_copy_spec.rb
@@ -199,7 +199,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(lesson:, lesson_params:)
-      expect(response[:error]).to match(/Error creating copy of lesson/)
+      expect(response[:error]).to include('Error creating copy of lesson')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/lesson/create_spec.rb b/spec/concepts/lesson/create_spec.rb
index c9d6b073c..253aff556 100644
--- a/spec/concepts/lesson/create_spec.rb
+++ b/spec/concepts/lesson/create_spec.rb
@@ -113,7 +113,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(lesson_params:)
-      expect(response[:error]).to match(/Error creating lesson/)
+      expect(response[:error]).to include('Error creating lesson')
     end
 
     it 'sent the exception to Sentry' do
@@ -151,7 +151,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(lesson_params:)
-      expect(response[:error]).to match(/Error creating lesson/)
+      expect(response[:error]).to include('Error creating lesson')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/lesson/update_spec.rb b/spec/concepts/lesson/update_spec.rb
index fb1d6c5ee..5ba8eb477 100644
--- a/spec/concepts/lesson/update_spec.rb
+++ b/spec/concepts/lesson/update_spec.rb
@@ -57,7 +57,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(lesson:, lesson_params:)
-      expect(response[:error]).to match(/Error updating lesson/)
+      expect(response[:error]).to include('Error updating lesson')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/project/update_spec.rb b/spec/concepts/project/update_spec.rb
index e30d0035e..153b68946 100644
--- a/spec/concepts/project/update_spec.rb
+++ b/spec/concepts/project/update_spec.rb
@@ -93,7 +93,7 @@
       end
 
       it 'returns an error message' do
-        expect(update[:error]).to match(/Projects with instructions must belong to a school/)
+        expect(update[:error]).to include('Projects with instructions must belong to a school')
       end
     end
 
diff --git a/spec/concepts/school/delete_spec.rb b/spec/concepts/school/delete_spec.rb
index cdc102f85..ca3c67659 100644
--- a/spec/concepts/school/delete_spec.rb
+++ b/spec/concepts/school/delete_spec.rb
@@ -48,7 +48,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school_id:)
-      expect(response[:error]).to match(/does-not-exist/)
+      expect(response[:error]).to include('does-not-exist')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school/update_spec.rb b/spec/concepts/school/update_spec.rb
index 74c77db5e..2a26ce26b 100644
--- a/spec/concepts/school/update_spec.rb
+++ b/spec/concepts/school/update_spec.rb
@@ -40,7 +40,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, school_params:)
-      expect(response[:error]).to match(/Error updating school/)
+      expect(response[:error]).to include('Error updating school')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_class/create_spec.rb b/spec/concepts/school_class/create_spec.rb
index 4a16a84e3..6cafd927c 100644
--- a/spec/concepts/school_class/create_spec.rb
+++ b/spec/concepts/school_class/create_spec.rb
@@ -57,7 +57,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, school_class_params:, current_user: teacher)
-      expect(response[:error]).to match(/Error creating school class/)
+      expect(response[:error]).to include('Error creating school class')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_class/delete_spec.rb b/spec/concepts/school_class/delete_spec.rb
index 347906f92..010e17718 100644
--- a/spec/concepts/school_class/delete_spec.rb
+++ b/spec/concepts/school_class/delete_spec.rb
@@ -44,7 +44,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, school_class_id:)
-      expect(response[:error]).to match(/does-not-exist/)
+      expect(response[:error]).to include('does-not-exist')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_class/update_spec.rb b/spec/concepts/school_class/update_spec.rb
index 5ce9011ab..ecd7d298d 100644
--- a/spec/concepts/school_class/update_spec.rb
+++ b/spec/concepts/school_class/update_spec.rb
@@ -42,7 +42,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school_class:, school_class_params:)
-      expect(response[:error]).to match(/Error updating school/)
+      expect(response[:error]).to include('Error updating school')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_student/create_spec.rb b/spec/concepts/school_student/create_spec.rb
index 202b3815b..8db329ac1 100644
--- a/spec/concepts/school_student/create_spec.rb
+++ b/spec/concepts/school_student/create_spec.rb
@@ -67,7 +67,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, school_student_params:, token:)
-      expect(response[:error]).to match(/username '' is invalid/)
+      expect(response[:error]).to include("username '' is invalid")
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_student/delete_spec.rb b/spec/concepts/school_student/delete_spec.rb
index 32c26daba..a79285982 100644
--- a/spec/concepts/school_student/delete_spec.rb
+++ b/spec/concepts/school_student/delete_spec.rb
@@ -37,7 +37,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, student_id:, token:)
-      expect(response[:error]).to match(/Some API error/)
+      expect(response[:error]).to include('Some API error')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_student/list_spec.rb b/spec/concepts/school_student/list_spec.rb
index 5015cd99e..fa2c3a3c7 100644
--- a/spec/concepts/school_student/list_spec.rb
+++ b/spec/concepts/school_student/list_spec.rb
@@ -107,7 +107,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, token:, student_ids:)
-      expect(response[:error]).to match(/Some API error/)
+      expect(response[:error]).to include('Some API error')
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_student/update_spec.rb b/spec/concepts/school_student/update_spec.rb
index b24d0152c..a87b54bf0 100644
--- a/spec/concepts/school_student/update_spec.rb
+++ b/spec/concepts/school_student/update_spec.rb
@@ -58,7 +58,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, student_id:, school_student_params:, token:)
-      expect(response[:error]).to match(/username ' ' is invalid/)
+      expect(response[:error]).to include("username ' ' is invalid")
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/concepts/school_teacher/invite_spec.rb b/spec/concepts/school_teacher/invite_spec.rb
index 31f851c3f..9fdd1ad58 100644
--- a/spec/concepts/school_teacher/invite_spec.rb
+++ b/spec/concepts/school_teacher/invite_spec.rb
@@ -41,7 +41,7 @@
 
     it 'returns the error message in the operation response' do
       response = described_class.call(school:, school_teacher_params:, token:)
-      expect(response[:error]).to match(/Email address 'invalid' is invalid/)
+      expect(response[:error]).to include("Email address 'invalid' is invalid")
     end
 
     it 'sent the exception to Sentry' do
diff --git a/spec/features/class_member/creating_a_batch_of_class_members_spec.rb b/spec/features/class_member/creating_a_batch_of_class_members_spec.rb
index f5ad035ba..819d62120 100644
--- a/spec/features/class_member/creating_a_batch_of_class_members_spec.rb
+++ b/spec/features/class_member/creating_a_batch_of_class_members_spec.rb
@@ -137,7 +137,7 @@
       post("/api/schools/#{school.id}/classes/#{school_class.id}/members/batch", headers:, params:)
       data = JSON.parse(response.body, symbolize_names: true)
       member_not_added = data.find { |result| result[:user_id] == existing_class_member_id && result[:success] == false }
-      expect(member_not_added[:error]).to match(/Student has already been taken/)
+      expect(member_not_added[:error]).to include('Student has already been taken')
     end
 
     it 'returns success result for members that could be added' do
@@ -187,7 +187,7 @@
     it 'returns the error message in the operation response' do
       post("/api/schools/#{school.id}/classes/#{school_class.id}/members/batch", headers:, params: invalid_params)
       data = JSON.parse(response.body, symbolize_names: true)
-      expect(data[:error]).to match(/No valid school members provided/)
+      expect(data[:error]).to include('No valid school members provided')
     end
   end
 
diff --git a/spec/features/class_member/creating_a_class_member_spec.rb b/spec/features/class_member/creating_a_class_member_spec.rb
index 52e672d88..04230818e 100644
--- a/spec/features/class_member/creating_a_class_member_spec.rb
+++ b/spec/features/class_member/creating_a_class_member_spec.rb
@@ -216,7 +216,7 @@
       post("/api/schools/#{school.id}/classes/#{school_class.id}/members", headers:, params: invalid_params)
       data = JSON.parse(response.body, symbolize_names: true)
 
-      expect(data[:error]).to match(/No valid school members provided/)
+      expect(data[:error]).to include('No valid school members provided')
     end
   end
 
diff --git a/spec/features/feedback/deleting_feedback_spec.rb b/spec/features/feedback/deleting_feedback_spec.rb
index c442be724..00101c6da 100644
--- a/spec/features/feedback/deleting_feedback_spec.rb
+++ b/spec/features/feedback/deleting_feedback_spec.rb
@@ -45,7 +45,7 @@
 
       it 'returns an error message' do
         data = JSON.parse(response.body, symbolize_names: true)
-        expect(data[:error]).to match(/Couldn't find Feedback with 'id'="invalid-id"/)
+        expect(data[:error]).to include("Couldn't find Feedback with 'id'=\"invalid-id\"")
       end
     end
   end
diff --git a/spec/features/school_student/batch_deleting_school_students_spec.rb b/spec/features/school_student/batch_deleting_school_students_spec.rb
index c8a6e42f9..76d2543d5 100644
--- a/spec/features/school_student/batch_deleting_school_students_spec.rb
+++ b/spec/features/school_student/batch_deleting_school_students_spec.rb
@@ -208,7 +208,7 @@
 
         # First student should have error
         failed_result = json['results'].find { |r| r['user_id'] == student_1.id }
-        expect(failed_result['error']).to match(/StandardError: Profile API error/)
+        expect(failed_result['error']).to include('StandardError: Profile API error')
 
         # Second student should succeed
         success_result = json['results'].find { |r| r['user_id'] == student_2.id }
diff --git a/spec/graphql/mutations/delete_project_mutation_spec.rb b/spec/graphql/mutations/delete_project_mutation_spec.rb
index f48c95256..5611cc60d 100644
--- a/spec/graphql/mutations/delete_project_mutation_spec.rb
+++ b/spec/graphql/mutations/delete_project_mutation_spec.rb
@@ -56,7 +56,7 @@
         let(:project_id) { 'dummy' }
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not found/)
+          expect(result.dig('errors', 0, 'message')).to include('not found')
         end
       end
 
@@ -67,7 +67,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not permitted/)
+          expect(result.dig('errors', 0, 'message')).to include('not permitted')
         end
       end
 
@@ -79,7 +79,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/Deletion failed/)
+          expect(result.dig('errors', 0, 'message')).to include('Deletion failed')
         end
       end
     end
diff --git a/spec/graphql/mutations/remix_project_mutation_spec.rb b/spec/graphql/mutations/remix_project_mutation_spec.rb
index 3116cd9a4..af0fa170b 100644
--- a/spec/graphql/mutations/remix_project_mutation_spec.rb
+++ b/spec/graphql/mutations/remix_project_mutation_spec.rb
@@ -37,7 +37,7 @@
     end
 
     it 'returns "not permitted to create" error' do
-      expect(result.dig('errors', 0, 'message')).to match(/not permitted to create/)
+      expect(result.dig('errors', 0, 'message')).to include('not permitted to create')
     end
   end
 
@@ -45,7 +45,7 @@
     let(:project_id) { SecureRandom.uuid }
 
     it 'returns "not found" error' do
-      expect(result.dig('errors', 0, 'message')).to match(/not found/)
+      expect(result.dig('errors', 0, 'message')).to include('not found')
     end
 
     it 'does not create a project' do
@@ -60,7 +60,7 @@
     end
 
     it 'returns "not permitted to read" error' do
-      expect(result.dig('errors', 0, 'message')).to match(/not permitted to read/)
+      expect(result.dig('errors', 0, 'message')).to include('not permitted to read')
     end
 
     it 'does not create a project' do
diff --git a/spec/graphql/mutations/update_component_mutation_spec.rb b/spec/graphql/mutations/update_component_mutation_spec.rb
index 79e4b2c87..b3ed06764 100644
--- a/spec/graphql/mutations/update_component_mutation_spec.rb
+++ b/spec/graphql/mutations/update_component_mutation_spec.rb
@@ -73,7 +73,7 @@
         let(:component_id) { 'dummy' }
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not found/)
+          expect(result.dig('errors', 0, 'message')).to include('not found')
         end
       end
 
@@ -84,7 +84,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not permitted/)
+          expect(result.dig('errors', 0, 'message')).to include('not permitted')
         end
       end
 
@@ -96,7 +96,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/An error message/)
+          expect(result.dig('errors', 0, 'message')).to include('An error message')
         end
       end
     end
diff --git a/spec/graphql/mutations/update_project_mutation_spec.rb b/spec/graphql/mutations/update_project_mutation_spec.rb
index f1baacc77..4acb18e1a 100644
--- a/spec/graphql/mutations/update_project_mutation_spec.rb
+++ b/spec/graphql/mutations/update_project_mutation_spec.rb
@@ -69,7 +69,7 @@
         let(:project_id) { 'dummy' }
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not found/)
+          expect(result.dig('errors', 0, 'message')).to include('not found')
         end
       end
 
@@ -80,7 +80,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/not permitted/)
+          expect(result.dig('errors', 0, 'message')).to include('not permitted')
         end
       end
 
@@ -92,7 +92,7 @@
         end
 
         it 'returns an error' do
-          expect(result.dig('errors', 0, 'message')).to match(/An error message/)
+          expect(result.dig('errors', 0, 'message')).to include('An error message')
         end
       end
     end
diff --git a/spec/services/student_removal_service_spec.rb b/spec/services/student_removal_service_spec.rb
index ec493d5c9..d649cbbf9 100644
--- a/spec/services/student_removal_service_spec.rb
+++ b/spec/services/student_removal_service_spec.rb
@@ -168,7 +168,7 @@
         results = service.remove_students
 
         # Should have error in result
-        expect(results.first[:error]).to match(/Profile API failure/)
+        expect(results.first[:error]).to include('Profile API failure')
 
         # Database changes should have been rolled back
         expect(Project.exists?(project.id)).to be true
@@ -181,7 +181,7 @@
       it 'handles errors gracefully' do
         allow(ClassStudent).to receive(:joins).and_raise(StandardError, 'fail')
         results = service.remove_students
-        expect(results.first[:error]).to match(/StandardError: fail/)
+        expect(results.first[:error]).to include('StandardError: fail')
       end
 
       it 'continues processing other students after an error' do
@@ -197,7 +197,7 @@
         results = service.remove_students
 
         expect(results.length).to eq(2)
-        expect(results.first[:error]).to match(/StandardError/)
+        expect(results.first[:error]).to include('StandardError')
         # Second student should succeed
         expect(Role.where(user_id: second_student.id, school: school, role: :student)).not_to exist
       end