Update Canvas and Gradescope integrations to handle late due dates for extensions

.env.example

@@ -21,8 +21,8 @@ CANVAS_URL='https://ucberkeleysandbox.instructure.com'
 # We use a single username/password for Gradescope
 # This should be a "service account" that can be used to set course settings
 # This email must be invited to each Gradescope course as a TA or Instructor
-GRADESCOPE_EMAIL='gradescope-bot@berkeley.edu'
-GRADESCOPE_PASSWORD=
+GRADESCOPE_EMAIL='michael@gradescope.com'
+GRADESCOPE_PASSWORD=KoH-z92-oVJ-yqr
 # This is required to be set.
 DEFAULT_FROM_EMAIL='flextensions@berkeley.edu'
 # Generally recommended / best practices

.gitignore

@@ -12,6 +12,8 @@ rerun.txt
 pickle-email-*.html
 # All Heroku dumps.
 *.dump
+# GenAI stuff
+.claude
 
 # Ignore all logfiles and tempfiles.
 /log/*

.rubocop.yml

@@ -95,6 +95,11 @@ RSpec:
 RSpec/ExampleLength:
   Max: 40
 
+# Default 3
+# I'm not sure this is good?
+RSpec/NestedGroups:
+  Max: 5
+
 RSpec/MultipleMemoizedHelpers:
   Max: 20
 

app/controllers/course_settings_controller.rb

@@ -66,6 +66,7 @@ def course_settings_params
       :max_auto_approve,
       :enable_gradescope,
       :gradescope_course_url,
+      :extend_late_due_date,
       :enable_emails,
       :reply_email,
       :email_subject,

app/facades/canvas_facade.rb

@@ -310,10 +310,11 @@ def delete_assignment_override(courseId, assignmentId, overrideId)
   # @param   [Integer] studentId the student to provisoin the extension for.
   # @param   [Integer] assignmentId the assignment the extension should be provisioned for.
   # @param   [String]  newDueDate the date the assignment should be due.
+  # @param   [String]  new_close_date the close date for submissions (optional, nil means no close date set).
   # @return  [Lmss::Canvas::Override] the override that acts as the extension.
   # @raises  [FailedPipelineError] if the creation response body could not be parsed.
   # @raises  [NotFoundError]       if the user has an existing override that cannot be located.
-  def provision_extension(course_id, student_id, assignment_id, new_due_date)
+  def provision_extension(course_id, student_id, assignment_id, new_due_date, new_close_date = nil)
     # get existing_overrides for an assignment
     student_override = get_existing_student_override(course_id, student_id, assignment_id)
     if !student_override.nil?
@@ -323,7 +324,7 @@ def provision_extension(course_id, student_id, assignment_id, new_due_date)
     # create new override
     override_title = "#{student_id} extended to #{new_due_date}"
     create_response = create_assignment_override(
-      course_id, assignment_id, [ student_id ], override_title, new_due_date, get_current_formatted_time, new_due_date
+      course_id, assignment_id, [ student_id ], override_title, new_due_date, get_current_formatted_time, new_close_date
     )
 
     decoded_response = parse_create_response(create_response)
@@ -334,7 +335,7 @@ def provision_extension(course_id, student_id, assignment_id, new_due_date)
     curr_override = fetch_existing_override(course_id, student_id, assignment_id)
     handle_response = handle_override_logic(
       course_id, curr_override, student_id, assignment_id, override_title,
-      new_due_date
+      new_due_date, new_close_date
     )
     Lmss::Canvas::Override.new(parse_create_response(handle_response))
   end
@@ -455,17 +456,18 @@ def fetch_existing_override(courseId, studentId, assignmentId)
   # @param  [Integer] assignmentId the assignmentId to handle the override logic for.
   # @param  [String] overrideTitle the title of the override.
   # @param  [String] newDueDate the new due date for the override.
+  # @param  [String] newCloseDate the close date for the override (maps to lock_at in Canvas API).
   # @return [Faraday::Response] the response from updating or creating the override.
-  def handle_override_logic(courseId, curr_override, studentId, assignmentId, overrideTitle, newDueDate)
+  def handle_override_logic(courseId, curr_override, studentId, assignmentId, overrideTitle, newDueDate, newCloseDate)
     if curr_override.student_ids.length == 1
       update_assignment_override(
         courseId, assignmentId, curr_override.id, curr_override.student_ids, overrideTitle, newDueDate,
-        get_current_formatted_time, newDueDate
+        get_current_formatted_time, newCloseDate
       )
     else
       remove_student_from_override(courseId, curr_override, studentId)
       create_assignment_override(
-        courseId, assignmentId, [ studentId ], overrideTitle, newDueDate, get_current_formatted_time, newDueDate
+        courseId, assignmentId, [ studentId ], overrideTitle, newDueDate, get_current_formatted_time, newCloseDate
       )
     end
   end

app/facades/gradescope_facade.rb

@@ -87,8 +87,9 @@ def get_existing_student_override(course_id, assignment_id, student_id)
   # @param   [String] email of student to provision the extension for.
   # @param   [String] assignmentId the assignment the extension should be provisioned for.
   # @param   [String] newDueDate the date the assignment should be due.
+  # @param   [String] newLateDueDate the late due date (optional, nil means no late due date set).
   # @return  [Lmss::Gradescope::BaseExtension] the extension that was provisioned.
-  def provision_extension(course_id, student_email, assignment_id, new_due_date)
+  def provision_extension(course_id, student_email, assignment_id, new_due_date, new_late_due_date = nil)
     ensure_authenticated!
     begin
       # get extension page
@@ -123,10 +124,13 @@ def provision_extension(course_id, student_email, assignment_id, new_due_date)
           'type' => 'absolute',
           'value' => new_due_date
         }
-        request_payload['override']['settings']['hard_due_date'] = {
-          'type' => 'absolute',
-          'value' => new_due_date
-        }
+        # Only set hard_due_date (late due date) if explicitly provided
+        if new_late_due_date
+          request_payload['override']['settings']['hard_due_date'] = {
+            'type' => 'absolute',
+            'value' => new_late_due_date
+          }
+        end
       end
 
       @gradescope_conn.post(

app/models/course_settings.rb

@@ -12,6 +12,7 @@
 #  enable_extensions                  :boolean          default(FALSE)
 #  enable_gradescope                  :boolean          default(FALSE)
 #  enable_slack_webhook_url           :boolean
+#  extend_late_due_date               :boolean          default(TRUE), not null
 #  gradescope_course_url              :string
 #  max_auto_approve                   :integer          default(0)
 #  reply_email                        :string

app/models/request.rb

@@ -157,11 +157,14 @@ def approve(lms_facade, processed_user_id)
       else
         raise "Unsupported LMS Facade: #{lms_facade.class.name}"
       end
+
+      dates = date_calculator.calculate
       override = lms_facade.provision_extension(
         course_id,
         user_id,
         assignment.external_assignment_id,
-        requested_due_date.iso8601
+        dates[:due_date].iso8601,
+        dates[:late_due_date]&.iso8601
       )
     rescue => e
       Rails.logger.error "Error during LMS extension provisioning: #{e.message}"
@@ -178,6 +181,22 @@ def approve(lms_facade, processed_user_id)
     true
   end
 
+  # Returns the AssignmentDateCalculator for this request
+  def date_calculator
+    @date_calculator ||= AssignmentDateCalculator.new(
+      assignment: assignment,
+      request: self,
+      course_settings: course.course_settings
+    )
+  end
+
+  # Calculates the new late due date for an extension based on course settings.
+  # Returns nil if the assignment has no late due date.
+  # Delegates to AssignmentDateCalculator for the actual calculation.
+  def calculate_new_late_due_date
+    date_calculator.late_due_date
+  end
+
   def reject(processed_user_id)
     update(status: 'denied', last_processed_by_user_id: processed_user_id.id)
     # Only send email if the person processing is the same as the request's user

app/services/assignment_date_calculator.rb

@@ -0,0 +1,75 @@
+# Calculates the dates to be set on an external LMS when provisioning an extension.
+#
+# This service encapsulates the logic for determining:
+# - release_date: When the assignment becomes available (currently always nil)
+# - due_date: The new due date from the approved extension request
+# - late_due_date: The deadline for late submissions, calculated based on course settings
+#
+# The late_due_date logic:
+# - If the assignment has no late_due_date, returns nil (no late due date should be set)
+# - If extend_late_due_date setting is true (default), shifts the late due date by the same
+#   delta as the extension (preserving the gap between due date and late due date)
+# - If extend_late_due_date setting is false, returns the later of the original late due date
+#   and the new extended due date
+class AssignmentDateCalculator
+  attr_reader :assignment, :request, :course_settings
+
+  # @param assignment [Assignment] The assignment being extended
+  # @param request [Request] The extension request with the new requested_due_date
+  # @param course_settings [CourseSettings, nil] The course settings (may be nil)
+  def initialize(assignment:, request:, course_settings:)
+    @assignment = assignment
+    @request = request
+    @course_settings = course_settings
+  end
+
+  # Returns the calculated dates for the extension
+  # @return [Hash] with keys :release_date, :due_date, :late_due_date
+  def calculate
+    {
+      release_date: release_date,
+      due_date: due_date,
+      late_due_date: late_due_date
+    }
+  end
+
+  # The release date for the assignment (currently always nil)
+  # @return [nil]
+  def release_date
+    nil
+  end
+
+  # The new due date from the extension request
+  # @return [DateTime]
+  def due_date
+    request.requested_due_date
+  end
+
+  # Calculates the new late due date for an extension based on course settings.
+  # Returns nil if the assignment has no late due date.
+  # @return [DateTime, nil]
+  def late_due_date
+    original_late_due_date = assignment.late_due_date
+    return nil if original_late_due_date.blank?
+
+    if extend_late_due_date?
+      # Shift the late due date by the same delta as the extension
+      extension_delta = request.requested_due_date - assignment.due_date
+      original_late_due_date + extension_delta
+    else
+      # Return the later of the original late due date and the new extended due date
+      [ original_late_due_date, request.requested_due_date ].max
+    end
+  end
+
+  private
+
+  # Determines whether to extend the late due date by the same delta as the extension.
+  # Defaults to true if the setting is nil (for backwards compatibility).
+  # @return [Boolean]
+  def extend_late_due_date?
+    setting = course_settings&.extend_late_due_date
+    # Default to true if setting is nil (for backwards compatibility)
+    setting.nil? ? true : setting
+  end
+end

app/views/courses/edit.html.erb

@@ -36,7 +36,6 @@
                 <%= hidden_field_tag :course_id, @course.id %>
                 <%= hidden_field_tag :tab, params[:tab] || 'general' %>
                 <div class="tab-content" id="courses-tabContent">
-                    <!-- General Settings Card -->
                     <div class="tab-pane fade <%= params[:tab] == 'email' ? '' : 'show active' %>" id="course-default" role="tabpanel" aria-labelledby="course-default-tab" tabindex="0">
                         <div class="card rounded-0 mb-4">
                             <div class="card-header bg-light">
@@ -89,7 +88,7 @@
                                     </div>
                                 </div>
 
-                                <div class="mb-3 row border-bottom pb-3">
+                                <div class="mb-3 row pb-3">
                                     <label for="max-auto-approve" class="col-sm-4 col-form-label">Maximum requests to auto approve</label>
                                     <div class="col-sm-8">
                                         <%= number_field_tag 'course_settings[max_auto_approve]',
@@ -103,6 +102,23 @@
                                     </div>
                                 </div>
 
+
+                                <div class="mb-3 border-bottom pb-3">
+                                    <div class="form-check form-switch">
+                                        <%= hidden_field_tag 'course_settings[extend_late_due_date]', false %>
+                                        <%= check_box_tag 'course_settings[extend_late_due_date]',
+                                                         true,
+                                                         @course.course_settings&.extend_late_due_date.nil? ? true : @course.course_settings&.extend_late_due_date,
+                                                         class: 'form-check-input',
+                                                         id: 'extend-late-due-date' %>
+                                        <label class="form-check-label" for="extend-late-due-date">Extend Late Due Date Automatically</label>
+                                    </div>
+                                    <small class="text-muted">
+                                        When enabled, the late due date (if present) will be shifted by the same amount as the extension.
+                                        When disabled, the new late due date will be set to the later of the original late due date and the extended due date.
+                                    </small>
+                                </div>
+
                                 <div class="mb-3">
                                     <div class="form-check form-switch">
                                         <%= hidden_field_tag 'course_settings[enable_gradescope]', false %>
@@ -128,7 +144,7 @@
                                                           pattern: 'https://(www\.)?gradescope\.com/courses/\d+/?',
                                                           title: 'Must be a valid Gradescope course URL (e.g. https://www.gradescope.com/courses/123456)' %>
                                             <small class="text-muted">
-                                                Please invite the user <code class="js-copytext">gradescope-bot@berkeley.edu</code>
+                                                Please invite the user <code class="js-copytext"><%= ENV.fetch('GRADESCOPE_EMAIL') { 'gradescope-bot@berkeley.edu' } %></code>
                                                 <button class="btn btn-sm btn-link p-0 ms-2" data-action="click->course-settings#copyToClipboard"title="Copy to clipboard"><i class="fas fa-clipboard"></i></button> as a TA to your Gradescope course for integration to work.
                                             </small>
                                             <script>

db/migrate/20260202000001_add_extend_late_due_date_to_course_settings.rb

@@ -0,0 +1,5 @@
+class AddExtendLateDueDateToCourseSettings < ActiveRecord::Migration[7.2]
+  def change
+    add_column :course_settings, :extend_late_due_date, :boolean, default: true, null: false
+  end
+end

db/schema.rb

@@ -10,7 +10,9 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.2].define(version: 2025_10_01_192900) do
+ActiveRecord::Schema[7.2].define(version: 2026_02_02_000001) do
+  create_schema "hypershield"
+
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
 
@@ -102,6 +104,7 @@
     t.boolean "enable_slack_webhook_url"
     t.boolean "enable_gradescope", default: false
     t.string "gradescope_course_url"
+    t.boolean "extend_late_due_date", default: true, null: false
     t.index ["course_id"], name: "index_course_settings_on_course_id"
   end
 

lib/tasks/backfill_extend_late_due_date.rake

@@ -0,0 +1,35 @@
+# frozen_string_literal: true
+
+namespace :course_settings do
+  desc 'Backfill extend_late_due_date setting for all existing courses (sets to true for all courses)'
+  task backfill_extend_late_due_date: :environment do
+    puts 'Starting backfill of extend_late_due_date setting for all courses...'
+
+    total_courses = Course.count
+    updated_count = 0
+    skipped_count = 0
+    created_count = 0
+
+    Course.find_each do |course|
+      if course.course_settings.nil?
+        # Create course settings if they don't exist
+        CourseSettings.create!(course: course, extend_late_due_date: true)
+        created_count += 1
+        puts "Created course settings for course #{course.id} (#{course.course_name})"
+      elsif course.course_settings.extend_late_due_date.nil?
+        # Update existing course settings if extend_late_due_date is nil
+        course.course_settings.update!(extend_late_due_date: true)
+        updated_count += 1
+        puts "Updated course #{course.id} (#{course.course_name})"
+      else
+        skipped_count += 1
+      end
+    end
+
+    puts "\nBackfill complete!"
+    puts "Total courses: #{total_courses}"
+    puts "Settings created: #{created_count}"
+    puts "Settings updated: #{updated_count}"
+    puts "Skipped (already set): #{skipped_count}"
+  end
+end