diff --git a/app/controllers/requests_controller.rb b/app/controllers/requests_controller.rb
index 1ba636e5..1c4200c5 100644
--- a/app/controllers/requests_controller.rb
+++ b/app/controllers/requests_controller.rb
@@ -136,7 +136,8 @@ def cancel
   def approve
     @assignment = Assignment.find_by(id: @request.assignment_id)
     lms_facade = @assignment.lms_facade
-    if @request.approve(lms_facade.from_user(@user), @user)
+    feedback_message = params[:feedback_message]
+    if @request.approve(lms_facade.from_user(@user), @user, feedback_message: feedback_message)
       redirect_to course_requests_path(@course), notice: 'Request approved and extension created successfully in Canvas.'
     else
       flash[:alert] = "Failed to approve the request. #{@request.errors.full_messages.join(', ')}"
@@ -145,7 +146,8 @@ def approve
   end
 
   def reject
-    if @request.reject(@user)
+    feedback_message = params[:feedback_message]
+    if @request.reject(@user, feedback_message: feedback_message)
       redirect_to course_requests_path(@course), notice: 'Request denied successfully.'
     else
       redirect_to course_requests_path(@course), alert: 'Failed to deny the request.'
diff --git a/app/models/course_settings.rb b/app/models/course_settings.rb
index 4368abc9..330048fb 100644
--- a/app/models/course_settings.rb
+++ b/app/models/course_settings.rb
@@ -48,6 +48,21 @@ class CourseSettings < ApplicationRecord
     {{course_name}} Staff
   LIQUID
 
+  DEFAULT_REJECTION_EMAIL_SUBJECT = 'Extension Request Status: {{status}} - {{course_code}}'
+
+  DEFAULT_REJECTION_EMAIL_TEMPLATE = <<~LIQUID.freeze
+    Hello {{student_name}},
+
+    Your extension request for {{assignment_name}} in {{course_name}} ({{course_code}}) has been {{status}}.
+
+    Reason for rejection: {{feedback_message}}
+
+    If you have any questions, please reach out to your course staff.
+
+    Thank you,
+    {{course_name}} Staff
+  LIQUID
+
   belongs_to :course
 
   before_save :ensure_system_user_for_auto_approval
diff --git a/app/models/request.rb b/app/models/request.rb
index db55e928..fc95c2a4 100644
--- a/app/models/request.rb
+++ b/app/models/request.rb
@@ -34,6 +34,8 @@
 #  fk_rails_...  (user_id => users.id)
 #
 class Request < ApplicationRecord
+  DEFAULT_FEEDBACK_MESSAGE = 'No additional feedback provided.'
+
   belongs_to :course
   belongs_to :assignment
   belongs_to :user
@@ -145,7 +147,7 @@ def auto_approve(lms_facade_from_user)
   end
 
   # TODO: All of these code should really be moved to each LMS' facade class
-  def approve(lms_facade, processed_user_id)
+  def approve(lms_facade, processed_user_id, feedback_message: nil)
     begin
       case lms_facade
       when CanvasFacade
@@ -173,13 +175,14 @@ def approve(lms_facade, processed_user_id)
     update(
       status: 'approved',
       last_processed_by_user_id: processed_user_id.id,
-      external_extension_id: override&.id)
+      external_extension_id: override&.id,
+      feedback_message: feedback_message)
     send_email_response if course.course_settings&.enable_emails
     true
   end
 
-  def reject(processed_user_id)
-    update(status: 'denied', last_processed_by_user_id: processed_user_id.id)
+  def reject(processed_user_id, feedback_message: nil)
+    update(status: 'denied', last_processed_by_user_id: processed_user_id.id, feedback_message: feedback_message)
     # Only send email if the person processing is the same as the request's user
     send_email_response if course.course_settings&.enable_emails && processed_user_id.id != user_id
     true
@@ -204,7 +207,7 @@ def calculate_new_assignment_dates
     }
   end
 
-def send_email_response
+  def send_email_response
     return unless course.course_settings&.enable_emails
 
     cs = course.course_settings
@@ -220,15 +223,25 @@ def send_email_response
       'status' => status.capitalize,
       'original_due_date' => assignment.due_date.strftime('%a, %b %-d, %Y %-I:%M %p'),
       'new_due_date' => requested_due_date.strftime('%a, %b %-d, %Y %-I:%M %p'),
-      'extension_days' => calculate_days_difference.to_s
+      'extension_days' => calculate_days_difference.to_s,
+      'feedback_message' => feedback_message.presence || DEFAULT_FEEDBACK_MESSAGE
     }
 
+    # Use rejection templates for denied status
+    if status == 'denied'
+      subject_template = cs.rejection_email_subject.presence || CourseSettings::DEFAULT_REJECTION_EMAIL_SUBJECT
+      body_template = cs.rejection_email_template.presence || CourseSettings::DEFAULT_REJECTION_EMAIL_TEMPLATE
+    else
+      subject_template = cs.email_subject
+      body_template = cs.email_template
+    end
+
     EmailService.send_email(
       to: to,
       from: ENV.fetch('DEFAULT_FROM_EMAIL'),
       reply_to: reply_to,
-      subject_template: cs.email_subject,
-      body_template: cs.email_template,
+      subject_template: subject_template,
+      body_template: body_template,
       mapping: mapping,
       deliver_later: false # or true if you prefer .deliver_later
     )
diff --git a/app/views/requests/instructor_show.html.erb b/app/views/requests/instructor_show.html.erb
index 16141ade..5ded1c10 100644
--- a/app/views/requests/instructor_show.html.erb
+++ b/app/views/requests/instructor_show.html.erb
@@ -120,8 +120,12 @@
 			<!-- Display Buttons -->
 			<div class="d-flex justify-content-center mt-4">
 			  <% if @request.status == 'pending' %>
-			    <%= button_to 'Approve', approve_course_request_path(@course, @request), method: :post, class: 'btn btn-success me-3' %>
-			    <%= button_to 'Reject', reject_course_request_path(@course, @request), method: :post, class: 'btn btn-danger me-3' %>
+			    <button type="button" class="btn btn-success me-3" data-bs-toggle="modal" data-bs-target="#approveModal">
+			      Approve
+			    </button>
+			    <button type="button" class="btn btn-danger me-3" data-bs-toggle="modal" data-bs-target="#rejectModal">
+			      Reject
+			    </button>
 				<%= link_to 'Edit Request', edit_course_request_path(@course, @request), class: "btn btn-secondary me-3" %>
 				<%= link_to 'Back', course_requests_path(@course), class: "btn btn-dark" %>
 			  <% else %>
@@ -130,4 +134,64 @@
 			</div>
 		</div>
 	</div>
+
+	<!-- Approve Modal -->
+	<div class="modal fade" id="approveModal" tabindex="-1" aria-labelledby="approveModalLabel" aria-hidden="true">
+	  <div class="modal-dialog">
+	    <div class="modal-content">
+	      <%= form_with url: approve_course_request_path(@course, @request), method: :post, local: true do |form| %>
+	        <div class="modal-header">
+	          <h5 class="modal-title" id="approveModalLabel">Approve Extension Request</h5>
+	          <button type="button" class="btn-close" data-bs-dismiss="modal" aria-label="Close"></button>
+	        </div>
+	        <div class="modal-body">
+	          <p>Are you sure you want to approve this extension request?</p>
+	          <div class="mb-3">
+	            <%= form.label :feedback_message, "Optional feedback message:", class: "form-label" %>
+	            <%= form.text_area :feedback_message, class: "form-control", rows: 3, 
+	                placeholder: "Optionally provide additional feedback for the student...",
+	                aria_describedby: "approveFeedbackHelpText" %>
+	            <div id="approveFeedbackHelpText" class="form-text">
+	              This message will be included in the approval email if provided.
+	            </div>
+	          </div>
+	        </div>
+	        <div class="modal-footer">
+	          <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+	          <%= form.submit "Approve Request", class: "btn btn-success" %>
+	        </div>
+	      <% end %>
+	    </div>
+	  </div>
+	</div>
+
+	<!-- Reject Modal -->
+	<div class="modal fade" id="rejectModal" tabindex="-1" aria-labelledby="rejectModalLabel" aria-hidden="true">
+	  <div class="modal-dialog">
+	    <div class="modal-content">
+	      <%= form_with url: reject_course_request_path(@course, @request), method: :post, local: true do |form| %>
+	        <div class="modal-header">
+	          <h5 class="modal-title" id="rejectModalLabel">Reject Extension Request</h5>
+	          <button type="button" class="btn-close" data-bs-dismiss="modal" aria-label="Close"></button>
+	        </div>
+	        <div class="modal-body">
+	          <div class="mb-3">
+	            <%= form.label :feedback_message, "Reason for rejection:", class: "form-label" %>
+	            <%= form.text_area :feedback_message, class: "form-control", rows: 4, 
+	                placeholder: "Please provide a reason for rejecting this extension request...",
+	                aria_describedby: "rejectFeedbackHelpText",
+	                required: true %>
+	            <div id="rejectFeedbackHelpText" class="form-text">
+	              This message will be sent to the student via email.
+	            </div>
+	          </div>
+	        </div>
+	        <div class="modal-footer">
+	          <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Cancel</button>
+	          <%= form.submit "Reject Request", class: "btn btn-danger" %>
+	        </div>
+	      <% end %>
+	    </div>
+	  </div>
+	</div>
 </div>
\ No newline at end of file
diff --git a/db/migrate/20260123233143_add_feedback_message_to_requests.rb b/db/migrate/20260123233143_add_feedback_message_to_requests.rb
new file mode 100644
index 00000000..ed7783ae
--- /dev/null
+++ b/db/migrate/20260123233143_add_feedback_message_to_requests.rb
@@ -0,0 +1,5 @@
+class AddFeedbackMessageToRequests < ActiveRecord::Migration[7.2]
+  def change
+    add_column :requests, :feedback_message, :text
+  end
+end
diff --git a/db/migrate/20260123233144_add_rejection_email_template_to_course_settings.rb b/db/migrate/20260123233144_add_rejection_email_template_to_course_settings.rb
new file mode 100644
index 00000000..9b6d13cd
--- /dev/null
+++ b/db/migrate/20260123233144_add_rejection_email_template_to_course_settings.rb
@@ -0,0 +1,6 @@
+class AddRejectionEmailTemplateToCourseSettings < ActiveRecord::Migration[7.2]
+  def change
+    add_column :course_settings, :rejection_email_subject, :string
+    add_column :course_settings, :rejection_email_template, :text
+  end
+end
diff --git a/docs/instructors.md b/docs/instructors.md
index 7e120468..31355f41 100644
--- a/docs/instructors.md
+++ b/docs/instructors.md
@@ -68,6 +68,21 @@ You can respond to requests in two ways:
 3. Click **Approve** or **Reject** at the bottom.
 4. The request status will update in real time.
 
+### Providing Feedback to Students
+
+When approving or rejecting requests, you can provide feedback that will be included in the email notification sent to the student:
+
+**Approving Requests:**
+- An optional feedback field allows you to provide additional context or instructions
+- Example: "Approved. Please ensure you submit by the extended deadline."
+- If no feedback is provided, a standard approval email will be sent
+
+**Rejecting Requests:**
+- A feedback field is **required** when rejecting a request
+- Provide a clear reason for the rejection to help students understand the decision
+- Example: "The requested due date is past the final exam. Please contact me during office hours to discuss alternatives."
+- This feedback will be included in the rejection email sent to the student
+
 ## Viewing Request History
 To view all requests made in the course, click the **View all Requests** button at the top left.
 
@@ -139,7 +154,29 @@ Use provided dynamic variables to personalize each email.
   `{{course_name}}, {{course_code}}, {{assignment_name}}`
 
 - **Extension Information**
-  `{{original_due_date}}, {{new_due_date}}, {{extension_days}}, {{status}}`
+  `{{original_due_date}}, {{new_due_date}}, {{extension_days}}, {{status}}, {{feedback_message}}`
+
+#### Rejection Email Template
+
+You can create a separate email template specifically for rejected requests. This allows you to customize the messaging when denying extension requests.
+
+To set up a custom rejection template:
+1. In the **Email Settings** section, configure the rejection email subject and body
+2. Include the `{{feedback_message}}` variable to insert the rejection reason you provided
+
+**Example Rejection Template:**
+```
+Hello {{student_name}},
+
+Your extension request for {{assignment_name}} in {{course_name}} ({{course_code}}) has been denied.
+
+Reason for rejection: {{feedback_message}}
+
+If you have any questions or would like to discuss this decision, please reach out to your course staff.
+
+Thank you,
+{{course_name}} Staff
+```
 
 Click **Reset to Default** to restore the system default template.
 
diff --git a/spec/controllers/requests_controller_spec.rb b/spec/controllers/requests_controller_spec.rb
index 810033d2..9c5ba05b 100644
--- a/spec/controllers/requests_controller_spec.rb
+++ b/spec/controllers/requests_controller_spec.rb
@@ -329,6 +329,16 @@
       expect(flash[:notice]).to match(/approved/i)
     end
 
+    it 'passes feedback_message to approve method when provided' do
+      expect_any_instance_of(Request).to receive(:approve).with(
+        anything, anything, hash_including(feedback_message: 'Great work!')
+      ).and_return(true)
+
+      post :approve, params: { course_id: course.id, id: request.id, feedback_message: 'Great work!' }
+
+      expect(response).to redirect_to(course_requests_path(course))
+    end
+
     # it 'shows error if approval fails' do
     #   # stub the *same* request to return false here
     #   allow(request).to receive(:approve).and_return(false)
@@ -353,6 +363,16 @@
       expect(flash[:notice]).to match(/denied/i)
     end
 
+    it 'passes feedback_message to reject method when provided' do
+      expect_any_instance_of(Request).to receive(:reject).with(
+        anything, hash_including(feedback_message: 'Cannot grant extension.')
+      ).and_return(true)
+
+      post :reject, params: { course_id: course.id, id: request.id, feedback_message: 'Cannot grant extension.' }
+
+      expect(response).to redirect_to(course_requests_path(course))
+    end
+
     it 'shows error if rejection fails' do
       allow_any_instance_of(Request).to receive(:reject).and_return(false)
       post :reject, params: { course_id: course.id, id: request.id }
diff --git a/spec/models/request_spec.rb b/spec/models/request_spec.rb
index 9e4156f3..7cef47ea 100644
--- a/spec/models/request_spec.rb
+++ b/spec/models/request_spec.rb
@@ -512,6 +512,17 @@
         expect(request.status).to eq('approved')
       end
     end
+
+    it 'saves feedback_message when provided' do
+      feedback = 'Approved with a note to complete on time next time.'
+      request.approve(lms_facade, instructor, feedback_message: feedback)
+      expect(request.reload.feedback_message).to eq(feedback)
+    end
+
+    it 'allows nil feedback_message' do
+      request.approve(lms_facade, instructor, feedback_message: nil)
+      expect(request.reload.feedback_message).to be_nil
+    end
   end
 
   describe '#reject' do
@@ -524,6 +535,17 @@
       request.reject(instructor)
       expect(request.last_processed_by_user_id).to eq(instructor.id)
     end
+
+    it 'saves feedback_message when provided' do
+      feedback = 'We cannot approve this request because the deadline is too close.'
+      request.reject(instructor, feedback_message: feedback)
+      expect(request.reload.feedback_message).to eq(feedback)
+    end
+
+    it 'allows nil feedback_message' do
+      request.reject(instructor, feedback_message: nil)
+      expect(request.reload.feedback_message).to be_nil
+    end
   end
 
   describe '#send_email_response' do
@@ -581,5 +603,48 @@
       expect(EmailService).not_to receive(:send_email)
       request.send_email_response
     end
+
+    context 'when request is denied' do
+      let(:rejection_template) do
+        <<~TEMPLATE
+          Dear {{student_name}},
+          Your extension request has been {{status}}.
+          Reason: {{feedback_message}}
+        TEMPLATE
+      end
+
+      before do
+        course_settings.update(
+          rejection_email_subject: 'Rejection: {{course_code}}',
+          rejection_email_template: rejection_template
+        )
+        request.update(status: 'denied', feedback_message: 'Unable to grant extension at this time.')
+      end
+
+      it 'uses rejection email template for denied requests' do
+        expect(EmailService).to receive(:send_email).with(
+          hash_including(
+            subject_template: 'Rejection: {{course_code}}',
+            body_template: rejection_template,
+            mapping: hash_including(
+              'feedback_message' => 'Unable to grant extension at this time.'
+            )
+          )
+        )
+        request.send_email_response
+      end
+    end
+
+    it 'includes feedback_message in mapping with default message when nil' do
+      request.update(feedback_message: nil)
+      expect(EmailService).to receive(:send_email).with(
+        hash_including(
+          mapping: hash_including(
+            'feedback_message' => 'No additional feedback provided.'
+          )
+        )
+      )
+      request.send_email_response
+    end
   end
 end