diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/config/FreeMarkerConfiguration.java b/packtrain-service/src/main/java/edu/mines/packtrain/config/FreeMarkerConfiguration.java
index 721b88a6..94c2693a 100644
--- a/packtrain-service/src/main/java/edu/mines/packtrain/config/FreeMarkerConfiguration.java
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/config/FreeMarkerConfiguration.java
@@ -17,6 +17,8 @@
 public class FreeMarkerConfiguration {
     private final TemplateLoader templateLoader;
     private final Template extensionCreatedStudentEmailTemplate;
+    private final Template extensionApprovedStudentEmailTemplate;
+    private final Template extensionDeniedStudentEmailTemplate;
     private final Template extensionCreatedInstructorEmailTemplate;
 
     public FreeMarkerConfiguration(
@@ -24,8 +26,13 @@ public FreeMarkerConfiguration(
             String templatePath,
             @Value("${grading-admin.email.templates.extension-created-student}") 
             String extensionCreatedStudentTemplateName,
+            @Value("${grading-admin.email.templates.extension-approved-student}") 
+            String extensionApprovedStudentTemplateName, 
+            @Value("${grading-admin.email.templates.extension-denied-student}") 
+            String extensionDeniedStudentTemplateName, 
             @Value("${grading-admin.email.templates.extension-created-instructor}") 
-            String extensionCreatedInstructorTemplateName) {
+            String extensionCreatedInstructorTemplateName
+            ) {
         templateLoader = new ClassTemplateLoader(this.getClass(), templatePath);
 
         freemarker.template.Configuration configuration = new freemarker.template.Configuration(
@@ -34,6 +41,8 @@ public FreeMarkerConfiguration(
         configuration.setTemplateLoader(templateLoader);
 
         extensionCreatedStudentEmailTemplate = readTemplates(configuration, extensionCreatedStudentTemplateName);
+        extensionApprovedStudentEmailTemplate = readTemplates(configuration, extensionApprovedStudentTemplateName);
+        extensionDeniedStudentEmailTemplate = readTemplates(configuration, extensionDeniedStudentTemplateName);
         extensionCreatedInstructorEmailTemplate = readTemplates(configuration, extensionCreatedInstructorTemplateName);
 
     }
@@ -64,6 +73,16 @@ public Template getExtensionCreatedStudentEmailTemplate() {
         return extensionCreatedStudentEmailTemplate;
     }
 
+    @Bean(name = "extensionApprovedStudentEmailTemplate")
+    public Template getExtensionApprovedStudentEmailTemplate() {
+        return extensionApprovedStudentEmailTemplate;
+    }
+
+    @Bean(name = "extensionDeniedStudentEmailTemplate")
+    public Template extensionDeniedStudentEmailTemplate() {
+        return extensionDeniedStudentEmailTemplate;
+    }
+
     @Bean(name = "extensionCreatedInstructorEmailTemplate")
     public Template getExtensionCreatedInstructorEmailTemplate() {
         return extensionCreatedInstructorEmailTemplate;
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/controllers/InstructorApiImpl.java b/packtrain-service/src/main/java/edu/mines/packtrain/controllers/InstructorApiImpl.java
index 153b74eb..d3088cec 100644
--- a/packtrain-service/src/main/java/edu/mines/packtrain/controllers/InstructorApiImpl.java
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/controllers/InstructorApiImpl.java
@@ -321,12 +321,14 @@ public ResponseEntity<List<CourseMemberDTO>> getInstructorEnrollments(UUID cours
     }
 
     @Override
+    @Transactional
     public ResponseEntity<LateRequestDTO> approveExtension(UUID courseId, UUID extensionId, String reason) {
         LateRequest lateRequest = extensionService.approveExtension(extensionId, reason);
         return ResponseEntity.accepted().body(DTOFactory.toDto(lateRequest));
     }
 
     @Override
+    @Transactional
     public ResponseEntity<LateRequestDTO> denyExtension(UUID courseId, UUID extensionId, String reason) {
         LateRequest lateRequest = extensionService.denyExtension(extensionId, reason);
         return ResponseEntity.accepted().body(DTOFactory.toDto(lateRequest));
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionApprovedStudentEmailDTO.java b/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionApprovedStudentEmailDTO.java
new file mode 100644
index 00000000..e0c60467
--- /dev/null
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionApprovedStudentEmailDTO.java
@@ -0,0 +1,13 @@
+package edu.mines.packtrain.data.templates;
+
+import lombok.Data;
+
+@Data
+public class ExtensionApprovedStudentEmailDTO {
+    private String reviewer;
+    private String student;
+    private String assignmentName;
+    private String courseName;
+    private int extensionDays;
+    private String reviewerResponse;
+}
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionDeniedStudentEmailDTO.java b/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionDeniedStudentEmailDTO.java
new file mode 100644
index 00000000..c86daeb9
--- /dev/null
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/data/templates/ExtensionDeniedStudentEmailDTO.java
@@ -0,0 +1,13 @@
+package edu.mines.packtrain.data.templates;
+
+import lombok.Data;
+
+@Data
+public class ExtensionDeniedStudentEmailDTO {
+    private String reviewer;
+    private String student;
+    private String assignmentName;
+    private String courseName;
+    private int extensionDays;
+    private String reviewerResponse;
+}
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/services/EmailService.java b/packtrain-service/src/main/java/edu/mines/packtrain/services/EmailService.java
index f1af87fe..3f617939 100644
--- a/packtrain-service/src/main/java/edu/mines/packtrain/services/EmailService.java
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/services/EmailService.java
@@ -46,14 +46,14 @@ public void sendEmail(String to, List<String> cc, String subject, String html) {
         if (!enabled) {
             return;
         }
-
+        
         EmailPopulatingBuilder builder = EmailBuilder.startingBlank()
                 .from(fromName, fromEmail)
-                .to(overrideTo != null ? overrideTo : to)
+                .to(!overrideTo.isEmpty() ? overrideTo : to)
                 .withSubject(subject)
                 .withHTMLText(html);
 
-        // (overrideCC != null ? List.of(overrideCC) : cc).forEach(s -> builder.cc(s));
+        (!overrideCC.isEmpty() ? List.of(overrideCC) : cc).forEach(s -> builder.cc(s));
 
         log.debug("Sending email '{}' to '{}'", subject, to);
 
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionEmailService.java b/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionEmailService.java
index 9ba902de..5e4c35e2 100644
--- a/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionEmailService.java
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionEmailService.java
@@ -9,14 +9,18 @@
 import org.springframework.stereotype.Service;
 import com.fasterxml.jackson.core.type.TypeReference;
 import com.fasterxml.jackson.databind.ObjectMapper;
+
+import edu.mines.packtrain.data.templates.ExtensionApprovedStudentEmailDTO;
 import edu.mines.packtrain.data.templates.ExtensionCreatedInstructorEmailDTO;
 import edu.mines.packtrain.data.templates.ExtensionCreatedStudentEmailDTO;
+import edu.mines.packtrain.data.templates.ExtensionDeniedStudentEmailDTO;
 import edu.mines.packtrain.models.Course;
 import edu.mines.packtrain.models.LateRequest;
 import edu.mines.packtrain.models.User;
 import edu.mines.packtrain.models.enums.LateRequestType;
 import freemarker.template.Template;
 import freemarker.template.TemplateException;
+import jakarta.transaction.Transactional;
 import lombok.extern.slf4j.Slf4j;
 
 @Service
@@ -24,18 +28,24 @@
 public class ExtensionEmailService {
     private final EmailService emailService;
     private final Template extensionCreatedStudentEmailTemplate;
+    private final Template extensionApprovedStudentEmailTemplate;
+    private final Template extensionDeniedStudentEmailTemplate;
     private final Template extensionCreatedInStructorEmailTemplate;
     private final ObjectMapper mapper;
     private final String frontendUrl;
 
     public ExtensionEmailService(EmailService emailService,
             @Qualifier("extensionCreatedStudentEmailTemplate") Template extensionCreatedStudentEmailTemplate,
+            @Qualifier("extensionApprovedStudentEmailTemplate") Template extensionApprovedStudentEmailTemplate,
+            @Qualifier("extensionDeniedStudentEmailTemplate") Template extensionDeniedStudentEmailTemplate,
             @Qualifier("extensionCreatedInstructorEmailTemplate") Template extensionCreatedInStructorEmailTemplate,
             @Value("${grading-admin.frontend-url}") String frontendUrl,
 
             ObjectMapper mapper) {
         this.emailService = emailService;
         this.extensionCreatedStudentEmailTemplate = extensionCreatedStudentEmailTemplate;
+        this.extensionApprovedStudentEmailTemplate = extensionApprovedStudentEmailTemplate;
+        this.extensionDeniedStudentEmailTemplate = extensionDeniedStudentEmailTemplate;
         this.extensionCreatedInStructorEmailTemplate = extensionCreatedInStructorEmailTemplate;
         this.frontendUrl = frontendUrl;
         this.mapper = mapper;
@@ -58,11 +68,10 @@ public void handleExtensionCreated(LateRequest lateRequest, Course course, User
             return;
         }
 
-
         {
             ExtensionCreatedInstructorEmailDTO model = new ExtensionCreatedInstructorEmailDTO();
-            model.setCourseName(lateRequest.getAssignment().getName());
-            model.setAssignmentName(course.getName());
+            model.setCourseName(course.getName());
+            model.setAssignmentName(lateRequest.getAssignment().getName());
             model.setStudent(requester.getName());
             model.setInstructor(instructor.getName());
             model.setExtensionDays(lateRequest.getDaysRequested());
@@ -73,6 +82,32 @@ public void handleExtensionCreated(LateRequest lateRequest, Course course, User
         }
     }
 
+    @Transactional
+    public void handleExtensionApproved(LateRequest lateRequest, Course course, User student, User approver) {
+        ExtensionApprovedStudentEmailDTO model = new ExtensionApprovedStudentEmailDTO();
+
+        model.setAssignmentName(lateRequest.getAssignment().getName());
+        model.setStudent(student.getName());
+        model.setReviewer(approver.getName());
+        model.setReviewerResponse(lateRequest.getExtension().getReviewerResponse());
+        model.setExtensionDays(lateRequest.getDaysRequested());
+
+        createExtensionApprovedStudentEmail(student.getEmail(), approver.getEmail(), model);
+    }
+
+    @Transactional
+    public void handleExtensionDenied(LateRequest lateRequest, Course course, User student, User approver) {
+        ExtensionDeniedStudentEmailDTO model = new ExtensionDeniedStudentEmailDTO();
+
+        model.setAssignmentName(lateRequest.getAssignment().getName());
+        model.setStudent(student.getName());
+        model.setReviewer(approver.getName());
+        model.setReviewerResponse(lateRequest.getExtension().getReviewerResponse());
+        model.setExtensionDays(lateRequest.getDaysRequested());
+
+        createExtensionDeniedStudentEmail(student.getEmail(), approver.getEmail(), model);
+    }
+
     private void createExtensionCreatedStudentEmail(String emailAddress, ExtensionCreatedStudentEmailDTO model) {
 
         StringWriter writer = new StringWriter();
@@ -124,4 +159,56 @@ private void createExtensionCreatedInstructorEmail(String emailAddress, Extensio
                 renderedTemplate);
     }
 
+    private void createExtensionApprovedStudentEmail(String studentEmail, String instructorEmail,
+            ExtensionApprovedStudentEmailDTO model) {
+        StringWriter writer = new StringWriter();
+
+        try {
+            extensionApprovedStudentEmailTemplate
+                    .process(mapper.convertValue(model, new TypeReference<Map<String, Object>>() {
+                    }), writer);
+        } catch (TemplateException | IOException e) {
+            log.error("Failed to render email template!", e);
+            return;
+        }
+
+        String renderedTemplate = writer.toString();
+
+        if (renderedTemplate.isEmpty()) {
+            log.error("Failed to render email template! Template is empty!");
+            return;
+        }
+
+        emailService.sendEmail(studentEmail, List.of(instructorEmail),
+                String.format("[Packtrain] [%s] [%s] Extension Request Approved", model.getCourseName(),
+                        model.getAssignmentName()),
+                renderedTemplate);
+    }
+
+    private void createExtensionDeniedStudentEmail(String studentEmail, String instructorEmail,
+            ExtensionDeniedStudentEmailDTO model) {
+        StringWriter writer = new StringWriter();
+
+        try {
+           extensionDeniedStudentEmailTemplate 
+                    .process(mapper.convertValue(model, new TypeReference<Map<String, Object>>() {
+                    }), writer);
+        } catch (TemplateException | IOException e) {
+            log.error("Failed to render email template!", e);
+            return;
+        }
+
+        String renderedTemplate = writer.toString();
+
+        if (renderedTemplate.isEmpty()) {
+            log.error("Failed to render email template! Template is empty!");
+            return;
+        }
+
+        emailService.sendEmail(studentEmail, List.of(instructorEmail),
+                String.format("[Packtrain] [%s] [%s] Extension Request Denied", model.getCourseName(),
+                        model.getAssignmentName()),
+                renderedTemplate);
+    }
+
 }
diff --git a/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionService.java b/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionService.java
index d3f1aecf..d5929fe4 100644
--- a/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionService.java
+++ b/packtrain-service/src/main/java/edu/mines/packtrain/services/ExtensionService.java
@@ -24,6 +24,7 @@
 import edu.mines.packtrain.models.enums.LateRequestType;
 import edu.mines.packtrain.repositories.ExtensionRepo;
 import edu.mines.packtrain.repositories.LateRequestRepo;
+import jakarta.transaction.Transactional;
 import lombok.RequiredArgsConstructor;
 import lombok.extern.slf4j.Slf4j;
 
@@ -62,6 +63,7 @@ public List<LateRequest> getAllLateRequests(UUID courseId, String lateRequestSta
         return List.of();
     }
 
+    @Transactional
     public LateRequest approveExtension(UUID extensionId, String reason) {
         Optional<LateRequest> lateRequest = getLateRequest(extensionId);
         String userId = securityManager.getUser().getCwid();
@@ -78,9 +80,12 @@ public LateRequest approveExtension(UUID extensionId, String reason) {
 
         extensionRepo.save(lateRequest.get().getExtension());
 
+        extensionEmailService.handleExtensionApproved(lateRequest.get(), lateRequest.get().getAssignment().getCourse(), lateRequest.get().getRequestingUser(), securityManager.getUser());
+
         return lateRequestRepo.save(lateRequest.get());
     }
 
+    @Transactional
     public LateRequest denyExtension(UUID extensionId, String reason) {
         Optional<LateRequest> lateRequest = getLateRequest(extensionId);
         String userId = securityManager.getUser().getCwid();
@@ -96,6 +101,9 @@ public LateRequest denyExtension(UUID extensionId, String reason) {
         lateRequest.get().setStatus(LateRequestStatus.REJECTED);
 
         extensionRepo.save(lateRequest.get().getExtension());
+
+        extensionEmailService.handleExtensionDenied(lateRequest.get(), lateRequest.get().getAssignment().getCourse(), lateRequest.get().getRequestingUser(), securityManager.getUser());
+
         return lateRequestRepo.save(lateRequest.get());
     }
 
diff --git a/packtrain-service/src/main/resources/application.yaml b/packtrain-service/src/main/resources/application.yaml
index 80d43b08..be954437 100644
--- a/packtrain-service/src/main/resources/application.yaml
+++ b/packtrain-service/src/main/resources/application.yaml
@@ -38,6 +38,8 @@ grading-admin:
     templates:
       template-directory: /templates/emails
       extension-created-student: extension-created-student.ftl
+      extension-approved-student: extension-approved-student.ftl
+      extension-denied-student: extension-denied-student.ftl
       extension-created-instructor: extension-created-instructor.ftl
     enabled: true
     smtp-server: ${SMTP_SERVER:localhost.dev}
diff --git a/packtrain-service/src/main/resources/templates/emails/extension-approved-student.ftl b/packtrain-service/src/main/resources/templates/emails/extension-approved-student.ftl
new file mode 100644
index 00000000..0cd7bdfd
--- /dev/null
+++ b/packtrain-service/src/main/resources/templates/emails/extension-approved-student.ftl
@@ -0,0 +1,17 @@
+<!DOCTYPE html>
+<html>
+    <head>
+      <meta http-equiv="Content-Type" content="text/html; charset=UTF-8" />
+    </head>
+    <body>
+      <p>Hi ${student},</p>
+      <p></p>
+
+      <p>Your extension request for <strong>${assignmentName}</strong> for ${extensionDays} days has been approved!</p>
+
+      <p>Your request was reviewed by Professor ${reviewer}. Below is their response:</p>
+
+      <p style="padding-left: 1em; border-left: 2px solid #c7c7c75e;">${reviewerResponse}</p>
+      <p></p>
+    </body>
+</html>
diff --git a/packtrain-service/src/main/resources/templates/emails/extension-denied-student.ftl b/packtrain-service/src/main/resources/templates/emails/extension-denied-student.ftl
new file mode 100644
index 00000000..6e2ed543
--- /dev/null
+++ b/packtrain-service/src/main/resources/templates/emails/extension-denied-student.ftl
@@ -0,0 +1,19 @@
+<!DOCTYPE html>
+<html>
+    <head>
+      <meta http-equiv="Content-Type" content="text/html; charset=UTF-8" />
+    </head>
+    <body>
+      <p>Hi ${student},</p>
+      <p></p>
+
+      <p>Your extension request for <strong>${assignmentName}</strong> for ${extensionDays} days has been denied.</p>
+
+      <p>Your request was reviewed by Professor ${reviewer}. Below is their response:</p>
+
+      <p style="padding-left: 1em; border-left: 2px solid #c7c7c75e;">${reviewerResponse}</p>
+      <p></p>
+
+      <p>Please contact your instructor directly with any questions or concerns.</p>
+    </body>
+</html>