diff --git a/src/registrar/tests/test_views_portfolio.py b/src/registrar/tests/test_views_portfolio.py
index 10c8724f5..8eec5e9c8 100644
--- a/src/registrar/tests/test_views_portfolio.py
+++ b/src/registrar/tests/test_views_portfolio.py
@@ -17,7 +17,7 @@ from .common import MockSESClient, completed_domain_request, create_test_user
 from waffle.testutils import override_flag
 from django.contrib.sessions.middleware import SessionMiddleware
 import boto3_mocking  # type: ignore
-
+from django.test import Client
 import logging
 
 logger = logging.getLogger(__name__)
@@ -26,6 +26,7 @@ logger = logging.getLogger(__name__)
 class TestPortfolio(WebTest):
     def setUp(self):
         super().setUp()
+        self.client = Client()
         self.user = create_test_user()
         self.domain, _ = Domain.objects.get_or_create(name="igorville.gov")
         self.portfolio, _ = Portfolio.objects.get_or_create(creator=self.user, organization_name="Hotel California")
@@ -644,6 +645,52 @@ class TestPortfolio(WebTest):
         # create new request btn
         self.assertNotContains(requests_page, 'Start a new domain request')
 
-    @skip("TODO")
+    @less_console_noise_decorator
     def test_portfolio_cache_updates_when_modified(self):
-        pass
+        """Test that the portfolio in session updates when the portfolio is modified"""
+        self.client.force_login(self.user)
+        portfolio_roles = [UserPortfolioRoleChoices.ORGANIZATION_ADMIN]
+        UserPortfolioPermission.objects.get_or_create(user=self.user, portfolio=self.portfolio, roles=portfolio_roles)
+        
+        with override_flag("organization_feature", active=True):
+            # Initial request to set the portfolio in session
+            response = self.client.get(reverse("home"), follow=True)
+
+            portfolio = self.client.session.get("portfolio")
+            self.assertEqual(portfolio.organization_name, "Hotel California")
+            self.assertContains(response, "Hotel California")
+            
+            # Modify the portfolio
+            self.portfolio.organization_name = "Updated Hotel California"
+            self.portfolio.save()
+            
+            # Make another request
+            response = self.client.get(reverse("home"), follow=True)
+            
+            # Check if the updated portfolio name is in the response
+            self.assertContains(response, "Updated Hotel California")
+
+            # Verify that the session contains the updated portfolio
+            portfolio = self.client.session.get("portfolio")
+            self.assertEqual(portfolio.organization_name, "Updated Hotel California")
+
+    @less_console_noise_decorator
+    def test_portfolio_cache_updates_when_flag_disabled_while_logged_in(self):
+        """Test that the portfolio in session is set to None when the organization_feature flag is disabled"""
+        self.client.force_login(self.user)
+        portfolio_roles = [UserPortfolioRoleChoices.ORGANIZATION_ADMIN]
+        UserPortfolioPermission.objects.get_or_create(user=self.user, portfolio=self.portfolio, roles=portfolio_roles)
+        
+        with override_flag("organization_feature", active=True):
+            # Initial request to set the portfolio in session
+            response = self.client.get(reverse("home"), follow=True)
+            portfolio = self.client.session.get("portfolio")
+            self.assertEqual(portfolio.organization_name, "Hotel California")
+            self.assertContains(response, "Hotel California")
+        
+        # Disable the organization_feature flag
+        with override_flag("organization_feature", active=False):
+            # Make another request
+            response = self.client.get(reverse("home"))
+            self.assertIsNone(self.client.session.get("portfolio"))
+            self.assertNotContains(response, "Hotel California")
diff --git a/src/registrar/tests/test_views_request.py b/src/registrar/tests/test_views_request.py
index 6642b6471..73f79fe68 100644
--- a/src/registrar/tests/test_views_request.py
+++ b/src/registrar/tests/test_views_request.py
@@ -7,7 +7,7 @@ from api.tests.common import less_console_noise_decorator
 from .common import MockSESClient, completed_domain_request  # type: ignore
 from django_webtest import WebTest  # type: ignore
 import boto3_mocking  # type: ignore
-
+from waffle.testutils import override_flag
 from registrar.models import (
     DomainRequest,
     DraftDomain,
@@ -17,12 +17,14 @@ from registrar.models import (
     User,
     Website,
     FederalAgency,
+    Portfolio,
+    UserPortfolioPermission
 )
 from registrar.views.domain_request import DomainRequestWizard, Step
 
 from .common import less_console_noise
 from .test_views import TestWithUser
-
+from registrar.models.utility.portfolio_helper import UserPortfolioRoleChoices
 import logging
 
 logger = logging.getLogger(__name__)
@@ -2925,6 +2927,41 @@ class DomainRequestTestDifferentStatuses(TestWithUser, WebTest):
         response = self.client.get("/get-domain-requests-json/")
         self.assertContains(response, "Withdrawn")
 
+    @less_console_noise_decorator
+    @override_flag("organization_feature", active=True)
+    def test_domain_request_withdraw_portfolio_redirects_correctly(self):
+        """Tests that the withdraw button on portfolio redirects to the portfolio domain requests page"""
+        portfolio, _ = Portfolio.objects.get_or_create(creator=self.user, organization_name="Test Portfolio")
+        UserPortfolioPermission.objects.get_or_create(
+            user=self.user,
+            portfolio=portfolio,
+            roles=[UserPortfolioRoleChoices.ORGANIZATION_ADMIN]
+        )
+        domain_request = completed_domain_request(status=DomainRequest.DomainRequestStatus.SUBMITTED, user=self.user)
+        domain_request.save()
+
+        detail_page = self.app.get(f"/domain-request/{domain_request.id}")
+        self.assertContains(detail_page, "city.gov")
+        self.assertContains(detail_page, "city1.gov")
+        self.assertContains(detail_page, "Chief Tester")
+        self.assertContains(detail_page, "testy@town.com")
+        self.assertContains(detail_page, "Admin Tester")
+        self.assertContains(detail_page, "Status:")
+        # click the "Withdraw request" button
+        mock_client = MockSESClient()
+        with boto3_mocking.clients.handler_for("sesv2", mock_client):
+            with less_console_noise():
+                withdraw_page = detail_page.click("Withdraw request")
+                self.assertContains(withdraw_page, "Withdraw request for")
+                home_page = withdraw_page.click("Withdraw request")
+
+        # Assert that it redirects to the portfolio requests page and the status has been updated to withdrawn
+        self.assertEqual(home_page.status_code, 302)
+        self.assertEqual(home_page.location, reverse("domain-requests"))
+
+        response = self.client.get("/get-domain-requests-json/")
+        self.assertContains(response, "Withdrawn")
+
     @less_console_noise_decorator
     def test_domain_request_withdraw_no_permissions(self):
         """Can't withdraw domain requests as a restricted user."""