diff --git a/src/registrar/admin.py b/src/registrar/admin.py
index 8ecf36f52..31c75e05e 100644
--- a/src/registrar/admin.py
+++ b/src/registrar/admin.py
@@ -1329,6 +1329,14 @@ class UserPortfolioPermissionAdmin(ListHeaderAdmin):
 
     get_roles.short_description = "Roles"  # type: ignore
 
+    def delete_queryset(self, request, queryset):
+        """We override the delete method in the model.
+        When deleting in DJA, if you select multiple items in a table using checkboxes and apply a delete action
+        the model delete does not get called. This method gets called instead.
+        This override makes sure our code in the model gets executed in these situations."""
+        for obj in queryset:
+            obj.delete()  # Calls the overridden delete method on each instance
+
 
 class UserDomainRoleAdmin(ListHeaderAdmin, ImportExportModelAdmin):
     """Custom user domain role admin class."""
@@ -1407,10 +1415,13 @@ class BaseInvitationAdmin(ListHeaderAdmin):
         Normal flow on successful save_model on add is to redirect to changelist_view.
         If there are errors, flow is modified to instead render change form.
         """
-        # store current messages from request so that they are preserved throughout the method
+        # store current messages from request in storage so that they are preserved throughout the
+        # method, as some flows remove and replace all messages, and so we store here to retrieve
+        # later
         storage = get_messages(request)
-        # Check if there are any error or warning messages in the `messages` framework
-        has_errors = any(message.level_tag in ["error", "warning"] for message in storage)
+        # Check if there are any error messages in the `messages` framework
+        # error messages stop the workflow; other message levels allow flow to continue as normal
+        has_errors = any(message.level_tag in ["error"] for message in storage)
 
         if has_errors:
             # Re-render the change form if there are errors or warnings
@@ -1552,13 +1563,14 @@ class DomainInvitationAdmin(BaseInvitationAdmin):
                         portfolio_invitation.save()
                     messages.success(request, f"{requested_email} has been invited to the organization: {domain_org}")
 
-                send_domain_invitation_email(
+                if not send_domain_invitation_email(
                     email=requested_email,
                     requestor=requestor,
                     domains=domain,
                     is_member_of_different_org=member_of_a_different_org,
                     requested_user=requested_user,
-                )
+                ):
+                    messages.warning(request, "Could not send email confirmation to existing domain managers.")
                 if requested_user is not None:
                     # Domain Invitation creation for an existing User
                     obj.retrieve()
@@ -1657,6 +1669,14 @@ class PortfolioInvitationAdmin(BaseInvitationAdmin):
         # Call the parent save method to save the object
         super().save_model(request, obj, form, change)
 
+    def delete_queryset(self, request, queryset):
+        """We override the delete method in the model.
+        When deleting in DJA, if you select multiple items in a table using checkboxes and apply a delete action,
+        the model delete does not get called. This method gets called instead.
+        This override makes sure our code in the model gets executed in these situations."""
+        for obj in queryset:
+            obj.delete()  # Calls the overridden delete method on each instance
+
 
 class DomainInformationResource(resources.ModelResource):
     """defines how each field in the referenced model should be mapped to the corresponding fields in the
diff --git a/src/registrar/assets/src/sass/_theme/_tooltips.scss b/src/registrar/assets/src/sass/_theme/_tooltips.scss
index 22b5cf534..e1e31cbec 100644
--- a/src/registrar/assets/src/sass/_theme/_tooltips.scss
+++ b/src/registrar/assets/src/sass/_theme/_tooltips.scss
@@ -29,7 +29,7 @@
   font-weight: 400 !important;
 }
 
-.domains__table {
+.domains__table, .usa-table {
   /*
   Trick tooltips in the domains table to do 2 things...
   1 - Shrink itself to a padded viewport window
diff --git a/src/registrar/config/settings.py b/src/registrar/config/settings.py
index a58e3e2f9..58250e85c 100644
--- a/src/registrar/config/settings.py
+++ b/src/registrar/config/settings.py
@@ -25,6 +25,7 @@ from typing import Final
 from botocore.config import Config
 import json
 import logging
+import traceback
 from django.utils.log import ServerFormatter
 
 # # #                          ###
@@ -471,7 +472,11 @@ class JsonFormatter(logging.Formatter):
             "lineno": record.lineno,
             "message": record.getMessage(),
         }
-        return json.dumps(log_record)
+        # Capture exception info if it exists
+        if record.exc_info:
+            log_record["exception"] = "".join(traceback.format_exception(*record.exc_info))
+
+        return json.dumps(log_record, ensure_ascii=False)
 
 
 class JsonServerFormatter(ServerFormatter):
diff --git a/src/registrar/models/portfolio_invitation.py b/src/registrar/models/portfolio_invitation.py
index 11c564c36..8feeb0794 100644
--- a/src/registrar/models/portfolio_invitation.py
+++ b/src/registrar/models/portfolio_invitation.py
@@ -8,6 +8,7 @@ from registrar.models import DomainInvitation, UserPortfolioPermission
 from .utility.portfolio_helper import (
     UserPortfolioPermissionChoices,
     UserPortfolioRoleChoices,
+    cleanup_after_portfolio_member_deletion,
     validate_portfolio_invitation,
 )  # type: ignore
 from .utility.time_stamped_model import TimeStampedModel
@@ -115,3 +116,27 @@ class PortfolioInvitation(TimeStampedModel):
         """Extends clean method to perform additional validation, which can raise errors in django admin."""
         super().clean()
         validate_portfolio_invitation(self)
+
+    def delete(self, *args, **kwargs):
+
+        User = get_user_model()
+
+        email = self.email  # Capture the email before the instance is deleted
+        portfolio = self.portfolio  # Capture the portfolio before the instance is deleted
+
+        # Call the superclass delete method to actually delete the instance
+        super().delete(*args, **kwargs)
+
+        if self.status == self.PortfolioInvitationStatus.INVITED:
+
+            # Query the user by email
+            users = User.objects.filter(email=email)
+
+            if users.count() > 1:
+                # This should never happen, log an error if more than one object is returned
+                logger.error(f"Multiple users found with the same email: {email}")
+
+            # Retrieve the first user, or None if no users are found
+            user = users.first()
+
+            cleanup_after_portfolio_member_deletion(portfolio=portfolio, email=email, user=user)
diff --git a/src/registrar/models/user_portfolio_permission.py b/src/registrar/models/user_portfolio_permission.py
index c4be90a9b..11d9c56e3 100644
--- a/src/registrar/models/user_portfolio_permission.py
+++ b/src/registrar/models/user_portfolio_permission.py
@@ -5,6 +5,7 @@ from registrar.models.utility.portfolio_helper import (
     UserPortfolioRoleChoices,
     DomainRequestPermissionDisplay,
     MemberPermissionDisplay,
+    cleanup_after_portfolio_member_deletion,
     validate_user_portfolio_permission,
 )
 from .utility.time_stamped_model import TimeStampedModel
@@ -188,3 +189,13 @@ class UserPortfolioPermission(TimeStampedModel):
         """Extends clean method to perform additional validation, which can raise errors in django admin."""
         super().clean()
         validate_user_portfolio_permission(self)
+
+    def delete(self, *args, **kwargs):
+
+        user = self.user  # Capture the user before the instance is deleted
+        portfolio = self.portfolio  # Capture the portfolio before the instance is deleted
+
+        # Call the superclass delete method to actually delete the instance
+        super().delete(*args, **kwargs)
+
+        cleanup_after_portfolio_member_deletion(portfolio=portfolio, email=user.email, user=user)
diff --git a/src/registrar/models/utility/portfolio_helper.py b/src/registrar/models/utility/portfolio_helper.py
index b3bb07c3d..8c42b80c7 100644
--- a/src/registrar/models/utility/portfolio_helper.py
+++ b/src/registrar/models/utility/portfolio_helper.py
@@ -210,3 +210,32 @@ def validate_portfolio_invitation(portfolio_invitation):
                 "This user is already assigned to a portfolio invitation. "
                 "Based on current waffle flag settings, users cannot be assigned to multiple portfolios."
             )
+
+
+def cleanup_after_portfolio_member_deletion(portfolio, email, user=None):
+    """
+    Cleans up after removing a portfolio member or a portfolio invitation.
+
+    Args:
+    portfolio: portfolio
+    user: passed when removing a portfolio member.
+    email: passed when removing a portfolio invitation, or passed as user.email
+    when removing a portfolio member.
+    """
+
+    DomainInvitation = apps.get_model("registrar.DomainInvitation")
+    UserDomainRole = apps.get_model("registrar.UserDomainRole")
+
+    # Fetch domain invitations matching the criteria
+    invitations = DomainInvitation.objects.filter(
+        email=email, domain__domain_info__portfolio=portfolio, status=DomainInvitation.DomainInvitationStatus.INVITED
+    )
+
+    # Call `cancel_invitation` on each invitation
+    for invitation in invitations:
+        invitation.cancel_invitation()
+        invitation.save()
+
+    if user:
+        # Remove user's domain roles for the current portfolio
+        UserDomainRole.objects.filter(user=user, domain__domain_info__portfolio=portfolio).delete()
diff --git a/src/registrar/templates/includes/header_extended.html b/src/registrar/templates/includes/header_extended.html
index 1e40a508d..83b71c3ab 100644
--- a/src/registrar/templates/includes/header_extended.html
+++ b/src/registrar/templates/includes/header_extended.html
@@ -92,11 +92,13 @@
             {% endif %}
 
             {% if has_organization_members_flag %}
+                {% if has_view_members_portfolio_permission %}
                 <li class="usa-nav__primary-item">
                     <a href="{% url 'members' %}" class="usa-nav-link {% if path|is_members_subpage %} usa-current{% endif %}">
                         Members
                     </a>
                 </li>
+                {% endif %}
             {% endif %}
 
             <li class="usa-nav__primary-item">
diff --git a/src/registrar/tests/test_admin.py b/src/registrar/tests/test_admin.py
index 036e35a50..387319663 100644
--- a/src/registrar/tests/test_admin.py
+++ b/src/registrar/tests/test_admin.py
@@ -1427,7 +1427,7 @@ class TestPortfolioInvitationAdmin(TestCase):
 
     @less_console_noise_decorator
     @patch("registrar.admin.send_portfolio_invitation_email")
-    @patch("django.contrib.messages.warning")  # Mock the `messages.error` call
+    @patch("django.contrib.messages.error")  # Mock the `messages.error` call
     def test_save_exception_generic_error(self, mock_messages_error, mock_send_email):
         """Handle generic exceptions correctly during portfolio invitation."""
         self.client.force_login(self.superuser)
diff --git a/src/registrar/tests/test_email_invitations.py b/src/registrar/tests/test_email_invitations.py
index b9fef1bf8..1377dec42 100644
--- a/src/registrar/tests/test_email_invitations.py
+++ b/src/registrar/tests/test_email_invitations.py
@@ -1,8 +1,11 @@
 import unittest
 from unittest.mock import patch, MagicMock
 from datetime import date
+from registrar.models.domain import Domain
+from registrar.models.user import User
+from registrar.models.user_domain_role import UserDomainRole
 from registrar.utility.email import EmailSendingError
-from registrar.utility.email_invitations import send_domain_invitation_email
+from registrar.utility.email_invitations import send_domain_invitation_email, send_emails_to_domain_managers
 
 from api.tests.common import less_console_noise_decorator
 
@@ -290,16 +293,16 @@ class DomainInvitationEmail(unittest.TestCase):
         email = "invitee@example.com"
         is_member_of_different_org = False
 
-        mock_send_domain_manager_emails.side_effect = EmailSendingError("Error sending email")
+        # Change the return value to False for mock_send_domain_manager_emails
+        mock_send_domain_manager_emails.return_value = False
 
-        # Call and assert exception
-        with self.assertRaises(EmailSendingError) as context:
-            send_domain_invitation_email(
-                email=email,
-                requestor=mock_requestor,
-                domains=mock_domain,
-                is_member_of_different_org=is_member_of_different_org,
-            )
+        # Call and assert that send_domain_invitation_email returns False
+        result = send_domain_invitation_email(
+            email=email,
+            requestor=mock_requestor,
+            domains=mock_domain,
+            is_member_of_different_org=is_member_of_different_org,
+        )
 
         # Assertions
         mock_normalize_domains.assert_called_once_with(mock_domain)
@@ -308,4 +311,161 @@ class DomainInvitationEmail(unittest.TestCase):
             email, None, [mock_domain], mock_requestor, is_member_of_different_org
         )
         mock_send_invitation_email.assert_called_once_with(email, mock_requestor_email, [mock_domain], None)
-        self.assertEqual(str(context.exception), "Error sending email")
+
+        # Assert that the result is False
+        self.assertFalse(result)
+
+    @less_console_noise_decorator
+    @patch("registrar.utility.email_invitations.send_templated_email")
+    @patch("registrar.models.UserDomainRole.objects.filter")
+    def test_send_emails_to_domain_managers_all_emails_sent_successfully(self, mock_filter, mock_send_templated_email):
+        """Test when all emails are sent successfully."""
+
+        # Setup mocks
+        mock_domain = MagicMock(spec=Domain)
+        mock_requestor_email = "requestor@example.com"
+        mock_email = "invitee@example.com"
+
+        # Create mock user and UserDomainRole
+        mock_user = MagicMock(spec=User)
+        mock_user.email = "manager@example.com"
+        mock_user_domain_role = MagicMock(spec=UserDomainRole, user=mock_user)
+
+        # Mock the filter method to return a list of mock UserDomainRole objects
+        mock_filter.return_value = [mock_user_domain_role]
+
+        # Mock successful email sending
+        mock_send_templated_email.return_value = None  # No exception means success
+
+        # Call function
+        result = send_emails_to_domain_managers(mock_email, mock_requestor_email, mock_domain)
+
+        # Assertions
+        self.assertTrue(result)  # All emails should be successfully sent
+        mock_send_templated_email.assert_called_once_with(
+            "emails/domain_manager_notification.txt",
+            "emails/domain_manager_notification_subject.txt",
+            to_address="manager@example.com",
+            context={
+                "domain": mock_domain,
+                "requestor_email": mock_requestor_email,
+                "invited_email_address": mock_email,
+                "domain_manager": mock_user,
+                "date": date.today(),
+            },
+        )
+
+    @less_console_noise_decorator
+    @patch("registrar.utility.email_invitations.send_templated_email")
+    @patch("registrar.models.UserDomainRole.objects.filter")
+    def test_send_emails_to_domain_managers_email_send_fails(self, mock_filter, mock_send_templated_email):
+        """Test when sending an email fails (raises EmailSendingError)."""
+
+        # Setup mocks
+        mock_domain = MagicMock(spec=Domain)
+        mock_requestor_email = "requestor@example.com"
+        mock_email = "invitee@example.com"
+
+        # Create mock user and UserDomainRole
+        mock_user = MagicMock(spec=User)
+        mock_user.email = "manager@example.com"
+        mock_user_domain_role = MagicMock(spec=UserDomainRole, user=mock_user)
+
+        # Mock the filter method to return a list of mock UserDomainRole objects
+        mock_filter.return_value = [mock_user_domain_role]
+
+        # Mock sending email to raise an EmailSendingError
+        mock_send_templated_email.side_effect = EmailSendingError("Email sending failed")
+
+        # Call function
+        result = send_emails_to_domain_managers(mock_email, mock_requestor_email, mock_domain)
+
+        # Assertions
+        self.assertFalse(result)  # The result should be False as email sending failed
+        mock_send_templated_email.assert_called_once_with(
+            "emails/domain_manager_notification.txt",
+            "emails/domain_manager_notification_subject.txt",
+            to_address="manager@example.com",
+            context={
+                "domain": mock_domain,
+                "requestor_email": mock_requestor_email,
+                "invited_email_address": mock_email,
+                "domain_manager": mock_user,
+                "date": date.today(),
+            },
+        )
+
+    @less_console_noise_decorator
+    @patch("registrar.utility.email_invitations.send_templated_email")
+    @patch("registrar.models.UserDomainRole.objects.filter")
+    def test_send_emails_to_domain_managers_no_domain_managers(self, mock_filter, mock_send_templated_email):
+        """Test when there are no domain managers."""
+
+        # Setup mocks
+        mock_domain = MagicMock(spec=Domain)
+        mock_requestor_email = "requestor@example.com"
+        mock_email = "invitee@example.com"
+
+        # Mock no domain managers (empty UserDomainRole queryset)
+        mock_filter.return_value = []
+
+        # Call function
+        result = send_emails_to_domain_managers(mock_email, mock_requestor_email, mock_domain)
+
+        # Assertions
+        self.assertTrue(result)  # No emails to send, so it should return True
+        mock_send_templated_email.assert_not_called()  # No emails should be sent
+
+    @less_console_noise_decorator
+    @patch("registrar.utility.email_invitations.send_templated_email")
+    @patch("registrar.models.UserDomainRole.objects.filter")
+    def test_send_emails_to_domain_managers_some_emails_fail(self, mock_filter, mock_send_templated_email):
+        """Test when some emails fail to send."""
+
+        # Setup mocks
+        mock_domain = MagicMock(spec=Domain)
+        mock_requestor_email = "requestor@example.com"
+        mock_email = "invitee@example.com"
+
+        # Create mock users and UserDomainRoles
+        mock_user_1 = MagicMock(spec=User)
+        mock_user_1.email = "manager1@example.com"
+        mock_user_2 = MagicMock(spec=User)
+        mock_user_2.email = "manager2@example.com"
+
+        mock_user_domain_role_1 = MagicMock(spec=UserDomainRole, user=mock_user_1)
+        mock_user_domain_role_2 = MagicMock(spec=UserDomainRole, user=mock_user_2)
+        mock_filter.return_value = [mock_user_domain_role_1, mock_user_domain_role_2]
+
+        # Mock first email success and second email failure
+        mock_send_templated_email.side_effect = [None, EmailSendingError("Failed to send email")]
+
+        # Call function
+        result = send_emails_to_domain_managers(mock_email, mock_requestor_email, mock_domain)
+
+        # Assertions
+        self.assertFalse(result)  # One email failed, so result should be False
+        mock_send_templated_email.assert_any_call(
+            "emails/domain_manager_notification.txt",
+            "emails/domain_manager_notification_subject.txt",
+            to_address="manager1@example.com",
+            context={
+                "domain": mock_domain,
+                "requestor_email": mock_requestor_email,
+                "invited_email_address": mock_email,
+                "domain_manager": mock_user_1,
+                "date": date.today(),
+            },
+        )
+        mock_send_templated_email.assert_any_call(
+            "emails/domain_manager_notification.txt",
+            "emails/domain_manager_notification_subject.txt",
+            to_address="manager2@example.com",
+            context={
+                "domain": mock_domain,
+                "requestor_email": mock_requestor_email,
+                "invited_email_address": mock_email,
+                "domain_manager": mock_user_2,
+                "date": date.today(),
+            },
+        )
diff --git a/src/registrar/tests/test_models.py b/src/registrar/tests/test_models.py
index 0f55c8ebe..82fca3fc4 100644
--- a/src/registrar/tests/test_models.py
+++ b/src/registrar/tests/test_models.py
@@ -165,6 +165,7 @@ class TestPortfolioInvitations(TestCase):
         DomainInformation.objects.all().delete()
         Domain.objects.all().delete()
         UserPortfolioPermission.objects.all().delete()
+        UserDomainRole.objects.all().delete()
         Portfolio.objects.all().delete()
         PortfolioInvitation.objects.all().delete()
         User.objects.all().delete()
@@ -443,6 +444,294 @@ class TestPortfolioInvitations(TestCase):
 
         pass
 
+    @less_console_noise_decorator
+    def test_delete_portfolio_invitation_deletes_portfolio_domain_invitations(self):
+        """Deleting a portfolio invitation causes domain invitations for the same email on the same
+        portfolio to be canceled."""
+
+        email_with_no_user = "email-with-no-user@email.gov"
+
+        domain_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_1.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_1, portfolio=self.portfolio
+        )
+        invite_1, _ = DomainInvitation.objects.get_or_create(email=email_with_no_user, domain=domain_in_portfolio_1)
+
+        domain_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_2, portfolio=self.portfolio
+        )
+        invite_2, _ = DomainInvitation.objects.get_or_create(email=email_with_no_user, domain=domain_in_portfolio_2)
+
+        domain_not_in_portfolio, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio)
+        invite_3, _ = DomainInvitation.objects.get_or_create(email=email_with_no_user, domain=domain_not_in_portfolio)
+
+        invitation_of_email_with_no_user, _ = PortfolioInvitation.objects.get_or_create(
+            email=email_with_no_user,
+            portfolio=self.portfolio,
+            roles=[self.portfolio_role_base, self.portfolio_role_admin],
+            additional_permissions=[self.portfolio_permission_1, self.portfolio_permission_2],
+        )
+
+        # The domain invitations start off as INVITED
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # Delete member (invite)
+        invitation_of_email_with_no_user.delete()
+
+        # Reload the objects from the database
+        invite_1 = DomainInvitation.objects.get(pk=invite_1.pk)
+        invite_2 = DomainInvitation.objects.get(pk=invite_2.pk)
+        invite_3 = DomainInvitation.objects.get(pk=invite_3.pk)
+
+        # The domain invitations to the portfolio domains have been canceled
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+
+        # Invite 3 is unaffected
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+    @less_console_noise_decorator
+    def test_deleting_a_retrieved_invitation_has_no_side_effects(self):
+        """Deleting a retrieved portfolio invitation causes no side effects."""
+
+        domain_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_1.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_1, portfolio=self.portfolio
+        )
+        invite_1, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_in_portfolio_1)
+
+        domain_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_2, portfolio=self.portfolio
+        )
+        invite_2, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_in_portfolio_2)
+
+        domain_in_portfolio_3, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_3.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_3, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_3, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_in_portfolio_4, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_4.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_4, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_4, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_not_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_1)
+        invite_3, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_not_in_portfolio_1)
+
+        domain_not_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_2)
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_not_in_portfolio_2, role=UserDomainRole.Roles.MANAGER
+        )
+
+        # The domain invitations start off as INVITED
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # The user domain roles exist
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
+        # retrieve the invitation
+        self.invitation.retrieve()
+        self.invitation.save()
+
+        # Delete member (invite)
+        self.invitation.delete()
+
+        # Reload the objects from the database
+        invite_1 = DomainInvitation.objects.get(pk=invite_1.pk)
+        invite_2 = DomainInvitation.objects.get(pk=invite_2.pk)
+        invite_3 = DomainInvitation.objects.get(pk=invite_3.pk)
+
+        # Test that no side effects have been triggered
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
+    @less_console_noise_decorator
+    def test_delete_portfolio_invitation_deletes_user_domain_roles(self):
+        """Deleting a portfolio invitation causes domain invitations for the same email on the same
+        portfolio to be canceled, also deletes any exiting user domain roles on the portfolio for the
+        user if the user exists."""
+
+        domain_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_1.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_1, portfolio=self.portfolio
+        )
+        invite_1, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_in_portfolio_1)
+
+        domain_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_2, portfolio=self.portfolio
+        )
+        invite_2, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_in_portfolio_2)
+
+        domain_in_portfolio_3, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_3.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_3, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_3, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_in_portfolio_4, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_4.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_4, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_4, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_not_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_1)
+        invite_3, _ = DomainInvitation.objects.get_or_create(email=self.email, domain=domain_not_in_portfolio_1)
+
+        domain_not_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_2)
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_not_in_portfolio_2, role=UserDomainRole.Roles.MANAGER
+        )
+
+        # The domain invitations start off as INVITED
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # The user domain roles exist
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
+        # Delete member (invite)
+        self.invitation.delete()
+
+        # Reload the objects from the database
+        invite_1 = DomainInvitation.objects.get(pk=invite_1.pk)
+        invite_2 = DomainInvitation.objects.get(pk=invite_2.pk)
+        invite_3 = DomainInvitation.objects.get(pk=invite_3.pk)
+
+        # The domain invitations to the portfolio domains have been canceled
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+
+        # Invite 3 is unaffected
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # The user domain roles have been deleted for the domains in portfolio
+        self.assertFalse(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertFalse(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+
+        # The user domain role on the domain not in portfolio still exists
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
 
 class TestUserPortfolioPermission(TestCase):
     @less_console_noise_decorator
@@ -458,6 +747,7 @@ class TestUserPortfolioPermission(TestCase):
         Domain.objects.all().delete()
         DomainInformation.objects.all().delete()
         DomainRequest.objects.all().delete()
+        DomainInvitation.objects.all().delete()
         UserPortfolioPermission.objects.all().delete()
         Portfolio.objects.all().delete()
         User.objects.all().delete()
@@ -751,6 +1041,129 @@ class TestUserPortfolioPermission(TestCase):
         # Should return the forbidden permissions for member role
         self.assertEqual(member_only_permissions, set(member_forbidden))
 
+    @less_console_noise_decorator
+    def test_delete_portfolio_permission_deletes_user_domain_roles(self):
+        """Deleting a user portfolio permission causes domain invitations for the same email on the same
+        portfolio to be canceled, also deletes any exiting user domain roles on the portfolio for the
+        user if the user exists."""
+
+        domain_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_1.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_1, portfolio=self.portfolio
+        )
+        invite_1, _ = DomainInvitation.objects.get_or_create(email=self.user.email, domain=domain_in_portfolio_1)
+
+        domain_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_2, portfolio=self.portfolio
+        )
+        invite_2, _ = DomainInvitation.objects.get_or_create(email=self.user.email, domain=domain_in_portfolio_2)
+
+        domain_in_portfolio_3, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_3.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_3, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_3, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_in_portfolio_4, _ = Domain.objects.get_or_create(
+            name="domain_in_portfolio_and_invited_4.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(
+            creator=self.user, domain=domain_in_portfolio_4, portfolio=self.portfolio
+        )
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_in_portfolio_4, role=UserDomainRole.Roles.MANAGER
+        )
+
+        domain_not_in_portfolio_1, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_1)
+        invite_3, _ = DomainInvitation.objects.get_or_create(email=self.user.email, domain=domain_not_in_portfolio_1)
+
+        domain_not_in_portfolio_2, _ = Domain.objects.get_or_create(
+            name="domain_not_in_portfolio_2.gov", state=Domain.State.READY
+        )
+        DomainInformation.objects.get_or_create(creator=self.user, domain=domain_not_in_portfolio_2)
+        UserDomainRole.objects.get_or_create(
+            user=self.user, domain=domain_not_in_portfolio_2, role=UserDomainRole.Roles.MANAGER
+        )
+
+        # Create portfolio permission
+        portfolio_permission, _ = UserPortfolioPermission.objects.get_or_create(
+            portfolio=self.portfolio, user=self.user, roles=[UserPortfolioRoleChoices.ORGANIZATION_ADMIN]
+        )
+
+        # The domain invitations start off as INVITED
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.INVITED)
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # The user domain roles exist
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
+        # Delete member (user portfolio permission)
+        portfolio_permission.delete()
+
+        # Reload the objects from the database
+        invite_1 = DomainInvitation.objects.get(pk=invite_1.pk)
+        invite_2 = DomainInvitation.objects.get(pk=invite_2.pk)
+        invite_3 = DomainInvitation.objects.get(pk=invite_3.pk)
+
+        # The domain invitations to the portfolio domains have been canceled
+        self.assertEqual(invite_1.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+        self.assertEqual(invite_2.status, DomainInvitation.DomainInvitationStatus.CANCELED)
+
+        # Invite 3 is unaffected
+        self.assertEqual(invite_3.status, DomainInvitation.DomainInvitationStatus.INVITED)
+
+        # The user domain roles have been deleted for the domains in portfolio
+        self.assertFalse(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_3,
+            ).exists()
+        )
+        self.assertFalse(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_in_portfolio_4,
+            ).exists()
+        )
+
+        # The user domain role on the domain not in portfolio still exists
+        self.assertTrue(
+            UserDomainRole.objects.filter(
+                user=self.user,
+                domain=domain_not_in_portfolio_2,
+            ).exists()
+        )
+
 
 class TestUser(TestCase):
     """Test actions that occur on user login,
diff --git a/src/registrar/tests/test_views_domain.py b/src/registrar/tests/test_views_domain.py
index 7d1e69783..02b61fda9 100644
--- a/src/registrar/tests/test_views_domain.py
+++ b/src/registrar/tests/test_views_domain.py
@@ -925,6 +925,40 @@ class TestDomainManagers(TestDomainOverview):
         success_page = success_result.follow()
         self.assertContains(success_page, "notauser@igorville.gov")
 
+    @override_flag("organization_feature", active=True)
+    @less_console_noise_decorator
+    @patch("registrar.views.domain.send_portfolio_invitation_email")
+    @patch("registrar.views.domain.send_domain_invitation_email")
+    def test_domain_user_add_form_fails_to_send_to_some_managers(
+        self, mock_send_domain_email, mock_send_portfolio_email
+    ):
+        """Adding an email not associated with a user works and sends portfolio invitation,
+        and when domain managers email(s) fail to send, assert proper warning displayed."""
+        add_page = self.app.get(reverse("domain-users-add", kwargs={"pk": self.domain.id}))
+        session_id = self.app.cookies[settings.SESSION_COOKIE_NAME]
+
+        add_page.form["email"] = "notauser@igorville.gov"
+
+        self.app.set_cookie(settings.SESSION_COOKIE_NAME, session_id)
+
+        mock_send_domain_email.return_value = False
+
+        success_result = add_page.form.submit()
+
+        self.assertEqual(success_result.status_code, 302)
+        self.assertEqual(
+            success_result["Location"],
+            reverse("domain-users", kwargs={"pk": self.domain.id}),
+        )
+
+        # Verify that the invitation emails were sent
+        mock_send_portfolio_email.assert_called_once()
+        mock_send_domain_email.assert_called_once()
+
+        self.app.set_cookie(settings.SESSION_COOKIE_NAME, session_id)
+        success_page = success_result.follow()
+        self.assertContains(success_page, "Could not send email confirmation to existing domain managers.")
+
     @boto3_mocking.patching
     @override_flag("organization_feature", active=True)
     @less_console_noise_decorator
diff --git a/src/registrar/tests/test_views_portfolio.py b/src/registrar/tests/test_views_portfolio.py
index 3afbb2a7b..b50c9a36f 100644
--- a/src/registrar/tests/test_views_portfolio.py
+++ b/src/registrar/tests/test_views_portfolio.py
@@ -1097,8 +1097,10 @@ class TestPortfolio(WebTest):
     @less_console_noise_decorator
     @override_flag("organization_feature", active=True)
     @override_flag("organization_requests", active=True)
+    @override_flag("organization_members", active=True)
     def test_main_nav_when_user_has_no_permissions(self):
-        """Test the nav contains a link to the no requests page"""
+        """Test the nav contains a link to the no requests page
+        Also test that members link not present"""
         UserPortfolioPermission.objects.get_or_create(
             user=self.user, portfolio=self.portfolio, roles=[UserPortfolioRoleChoices.ORGANIZATION_MEMBER]
         )
@@ -1118,20 +1120,23 @@ class TestPortfolio(WebTest):
         self.assertNotContains(portfolio_landing_page, "basic-nav-section-two")
         # link to requests
         self.assertNotContains(portfolio_landing_page, 'href="/requests/')
-        # link to create
+        # link to create request
         self.assertNotContains(portfolio_landing_page, 'href="/request/')
+        # link to members
+        self.assertNotContains(portfolio_landing_page, 'href="/members/')
 
     @less_console_noise_decorator
     @override_flag("organization_feature", active=True)
     @override_flag("organization_requests", active=True)
+    @override_flag("organization_members", active=True)
     def test_main_nav_when_user_has_all_permissions(self):
         """Test the nav contains a dropdown with a link to create and another link to view requests
-        Also test for the existence of the Create a new request btn on the requests page"""
+        Also test for the existence of the Create a new request btn on the requests page
+        Also test for the existence of the members link"""
         UserPortfolioPermission.objects.get_or_create(
             user=self.user,
             portfolio=self.portfolio,
             roles=[UserPortfolioRoleChoices.ORGANIZATION_ADMIN],
-            additional_permissions=[UserPortfolioPermissionChoices.EDIT_REQUESTS],
         )
         self.client.force_login(self.user)
         # create and submit a domain request
@@ -1151,6 +1156,8 @@ class TestPortfolio(WebTest):
         self.assertContains(portfolio_landing_page, 'href="/requests/')
         # link to create
         self.assertContains(portfolio_landing_page, 'href="/request/')
+        # link to members
+        self.assertContains(portfolio_landing_page, 'href="/members/')
 
         requests_page = self.client.get(reverse("domain-requests"))
 
@@ -1160,15 +1167,18 @@ class TestPortfolio(WebTest):
     @less_console_noise_decorator
     @override_flag("organization_feature", active=True)
     @override_flag("organization_requests", active=True)
+    @override_flag("organization_members", active=True)
     def test_main_nav_when_user_has_view_but_not_edit_permissions(self):
         """Test the nav contains a simple link to view requests
-        Also test for the existence of the Create a new request btn on the requests page"""
+        Also test for the existence of the Create a new request btn on the requests page
+        Also test for the existence of members link"""
         UserPortfolioPermission.objects.get_or_create(
             user=self.user,
             portfolio=self.portfolio,
             additional_permissions=[
                 UserPortfolioPermissionChoices.VIEW_PORTFOLIO,
                 UserPortfolioPermissionChoices.VIEW_ALL_REQUESTS,
+                UserPortfolioPermissionChoices.VIEW_MEMBERS,
             ],
         )
         self.client.force_login(self.user)
@@ -1189,6 +1199,8 @@ class TestPortfolio(WebTest):
         self.assertContains(portfolio_landing_page, 'href="/requests/')
         # link to create
         self.assertNotContains(portfolio_landing_page, 'href="/request/')
+        # link to members
+        self.assertContains(portfolio_landing_page, 'href="/members/')
 
         requests_page = self.client.get(reverse("domain-requests"))
 
@@ -3254,7 +3266,7 @@ class TestPortfolioInviteNewMemberView(TestWithUser, WebTest):
             # assert that response is a redirect to reverse("members")
             self.assertRedirects(response, reverse("members"))
             # assert that messages contains message, "Could not send email invitation"
-            mock_warning.assert_called_once_with(response.wsgi_request, "Could not send email invitation.")
+            mock_warning.assert_called_once_with(response.wsgi_request, "Could not send portfolio email invitation.")
             # assert that portfolio invitation is not created
             self.assertFalse(
                 PortfolioInvitation.objects.filter(email=self.new_member_email, portfolio=self.portfolio).exists(),
@@ -3339,7 +3351,7 @@ class TestPortfolioInviteNewMemberView(TestWithUser, WebTest):
             # assert that response is a redirect to reverse("members")
             self.assertRedirects(response, reverse("members"))
             # assert that messages contains message, "Could not send email invitation"
-            mock_warning.assert_called_once_with(response.wsgi_request, "Could not send email invitation.")
+            mock_warning.assert_called_once_with(response.wsgi_request, "Could not send portfolio email invitation.")
             # assert that portfolio invitation is not created
             self.assertFalse(
                 PortfolioInvitation.objects.filter(email=self.new_member_email, portfolio=self.portfolio).exists(),
diff --git a/src/registrar/utility/email_invitations.py b/src/registrar/utility/email_invitations.py
index d589f814f..f9c3b89b2 100644
--- a/src/registrar/utility/email_invitations.py
+++ b/src/registrar/utility/email_invitations.py
@@ -27,6 +27,9 @@ def send_domain_invitation_email(
         is_member_of_different_org (bool): if an email belongs to a different org
         requested_user (User | None): The recipient if the email belongs to a user in the registrar
 
+    Returns:
+        Boolean indicating if all messages were sent successfully.
+
     Raises:
         MissingEmailError: If the requestor has no email associated with their account.
         AlreadyDomainManagerError: If the email corresponds to an existing domain manager.
@@ -41,22 +44,28 @@ def send_domain_invitation_email(
 
     send_invitation_email(email, requestor_email, domains, requested_user)
 
+    all_manager_emails_sent = True
     # send emails to domain managers
     for domain in domains:
-        send_emails_to_domain_managers(
+        if not send_emails_to_domain_managers(
             email=email,
             requestor_email=requestor_email,
             domain=domain,
             requested_user=requested_user,
-        )
+        ):
+            all_manager_emails_sent = False
+
+    return all_manager_emails_sent
 
 
 def send_emails_to_domain_managers(email: str, requestor_email, domain: Domain, requested_user=None):
     """
     Notifies all domain managers of the provided domain of a change
-    Raises:
-        EmailSendingError
+
+    Returns:
+        Boolean indicating if all messages were sent successfully.
     """
+    all_emails_sent = True
     # Get each domain manager from list
     user_domain_roles = UserDomainRole.objects.filter(domain=domain)
     for user_domain_role in user_domain_roles:
@@ -75,10 +84,12 @@ def send_emails_to_domain_managers(email: str, requestor_email, domain: Domain,
                     "date": date.today(),
                 },
             )
-        except EmailSendingError as err:
-            raise EmailSendingError(
-                f"Could not send email manager notification to {user.email} for domain: {domain.name}"
-            ) from err
+        except EmailSendingError:
+            logger.warning(
+                f"Could not send email manager notification to {user.email} for domain: {domain.name}", exc_info=True
+            )
+            all_emails_sent = False
+    return all_emails_sent
 
 
 def normalize_domains(domains: Domain | list[Domain]) -> list[Domain]:
diff --git a/src/registrar/views/domain.py b/src/registrar/views/domain.py
index 72e0e4b35..297cb689a 100644
--- a/src/registrar/views/domain.py
+++ b/src/registrar/views/domain.py
@@ -1255,24 +1255,26 @@ class DomainAddUserView(DomainFormBaseView):
 
     def _handle_new_user_invitation(self, email, requestor, member_of_different_org):
         """Handle invitation for a new user who does not exist in the system."""
-        send_domain_invitation_email(
+        if not send_domain_invitation_email(
             email=email,
             requestor=requestor,
             domains=self.object,
             is_member_of_different_org=member_of_different_org,
-        )
+        ):
+            messages.warning(self.request, "Could not send email confirmation to existing domain managers.")
         DomainInvitation.objects.get_or_create(email=email, domain=self.object)
         messages.success(self.request, f"{email} has been invited to the domain: {self.object}")
 
     def _handle_existing_user(self, email, requestor, requested_user, member_of_different_org):
         """Handle adding an existing user to the domain."""
-        send_domain_invitation_email(
+        if not send_domain_invitation_email(
             email=email,
             requestor=requestor,
             domains=self.object,
             is_member_of_different_org=member_of_different_org,
             requested_user=requested_user,
-        )
+        ):
+            messages.warning(self.request, "Could not send email confirmation to existing domain managers.")
         UserDomainRole.objects.create(
             user=requested_user,
             domain=self.object,
diff --git a/src/registrar/views/portfolios.py b/src/registrar/views/portfolios.py
index f5db165d1..212ce089d 100644
--- a/src/registrar/views/portfolios.py
+++ b/src/registrar/views/portfolios.py
@@ -303,13 +303,14 @@ class PortfolioMemberDomainsEditView(PortfolioMemberDomainsEditPermissionView, V
             # get added_domains from ids to pass to send email method and bulk create
             added_domains = Domain.objects.filter(id__in=added_domain_ids)
             member_of_a_different_org, _ = get_org_membership(portfolio, member.email, member)
-            send_domain_invitation_email(
+            if not send_domain_invitation_email(
                 email=member.email,
                 requestor=requestor,
                 domains=added_domains,
                 is_member_of_different_org=member_of_a_different_org,
                 requested_user=member,
-            )
+            ):
+                messages.warning(self.request, "Could not send email confirmation to existing domain managers.")
             # Bulk create UserDomainRole instances for added domains
             UserDomainRole.objects.bulk_create(
                 [
@@ -525,12 +526,13 @@ class PortfolioInvitedMemberDomainsEditView(PortfolioMemberDomainsEditPermission
             # get added_domains from ids to pass to send email method and bulk create
             added_domains = Domain.objects.filter(id__in=added_domain_ids)
             member_of_a_different_org, _ = get_org_membership(portfolio, email, None)
-            send_domain_invitation_email(
+            if not send_domain_invitation_email(
                 email=email,
                 requestor=requestor,
                 domains=added_domains,
                 is_member_of_different_org=member_of_a_different_org,
-            )
+            ):
+                messages.warning(self.request, "Could not send email confirmation to existing domain managers.")
 
             # Update existing invitations from CANCELED to INVITED
             existing_invitations = DomainInvitation.objects.filter(domain__in=added_domains, email=email)
@@ -807,7 +809,7 @@ class PortfolioAddMemberView(PortfolioMembersPermissionView, FormMixin):
                 portfolio,
                 exc_info=True,
             )
-            messages.warning(self.request, "Could not send email invitation.")
+            messages.warning(self.request, "Could not send portfolio email invitation.")
         elif isinstance(exception, MissingEmailError):
             messages.error(self.request, str(exception))
             logger.error(
@@ -816,4 +818,4 @@ class PortfolioAddMemberView(PortfolioMembersPermissionView, FormMixin):
             )
         else:
             logger.warning("Could not send email invitation (Other Exception)", exc_info=True)
-            messages.warning(self.request, "Could not send email invitation.")
+            messages.warning(self.request, "Could not send portfolio email invitation.")
diff --git a/src/registrar/views/report_views.py b/src/registrar/views/report_views.py
index 694d1e205..ee2c079f3 100644
--- a/src/registrar/views/report_views.py
+++ b/src/registrar/views/report_views.py
@@ -5,17 +5,20 @@ from django.views import View
 from django.shortcuts import render
 from django.contrib import admin
 from django.db.models import Avg, F
+
+from registrar.views.utility.mixins import DomainAndRequestsReportsPermission, PortfolioReportsPermission
 from .. import models
 import datetime
 from django.utils import timezone
-
+from django.contrib.admin.views.decorators import staff_member_required
+from django.utils.decorators import method_decorator
 from registrar.utility import csv_export
-
 import logging
 
 logger = logging.getLogger(__name__)
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class AnalyticsView(View):
     def get(self, request):
         thirty_days_ago = datetime.datetime.today() - datetime.timedelta(days=30)
@@ -149,6 +152,7 @@ class AnalyticsView(View):
         return render(request, "admin/analytics.html", context)
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataType(View):
     def get(self, request, *args, **kwargs):
         # match the CSV example with all the fields
@@ -158,7 +162,7 @@ class ExportDataType(View):
         return response
 
 
-class ExportDataTypeUser(View):
+class ExportDataTypeUser(DomainAndRequestsReportsPermission, View):
     """Returns a domain report for a given user on the request"""
 
     def get(self, request, *args, **kwargs):
@@ -169,7 +173,7 @@ class ExportDataTypeUser(View):
         return response
 
 
-class ExportMembersPortfolio(View):
+class ExportMembersPortfolio(PortfolioReportsPermission, View):
     """Returns a members report for a given portfolio"""
 
     def get(self, request, *args, **kwargs):
@@ -197,7 +201,7 @@ class ExportMembersPortfolio(View):
         return response
 
 
-class ExportDataTypeRequests(View):
+class ExportDataTypeRequests(DomainAndRequestsReportsPermission, View):
     """Returns a domain requests report for a given user on the request"""
 
     def get(self, request, *args, **kwargs):
@@ -208,6 +212,7 @@ class ExportDataTypeRequests(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataFull(View):
     def get(self, request, *args, **kwargs):
         # Smaller export based on 1
@@ -217,6 +222,7 @@ class ExportDataFull(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataFederal(View):
     def get(self, request, *args, **kwargs):
         # Federal only
@@ -226,6 +232,7 @@ class ExportDataFederal(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDomainRequestDataFull(View):
     """Generates a downloaded report containing all Domain Requests (except started)"""
 
@@ -237,6 +244,7 @@ class ExportDomainRequestDataFull(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataDomainsGrowth(View):
     def get(self, request, *args, **kwargs):
         start_date = request.GET.get("start_date", "")
@@ -249,6 +257,7 @@ class ExportDataDomainsGrowth(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataRequestsGrowth(View):
     def get(self, request, *args, **kwargs):
         start_date = request.GET.get("start_date", "")
@@ -261,6 +270,7 @@ class ExportDataRequestsGrowth(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataManagedDomains(View):
     def get(self, request, *args, **kwargs):
         start_date = request.GET.get("start_date", "")
@@ -272,6 +282,7 @@ class ExportDataManagedDomains(View):
         return response
 
 
+@method_decorator(staff_member_required, name="dispatch")
 class ExportDataUnmanagedDomains(View):
     def get(self, request, *args, **kwargs):
         start_date = request.GET.get("start_date", "")
diff --git a/src/registrar/views/utility/invitation_helper.py b/src/registrar/views/utility/invitation_helper.py
index 98c36b308..18c427940 100644
--- a/src/registrar/views/utility/invitation_helper.py
+++ b/src/registrar/views/utility/invitation_helper.py
@@ -3,7 +3,6 @@ from django.db import IntegrityError
 from registrar.models import PortfolioInvitation, User, UserPortfolioPermission
 from registrar.utility.email import EmailSendingError
 import logging
-
 from registrar.utility.errors import (
     AlreadyDomainInvitedError,
     AlreadyDomainManagerError,
@@ -61,20 +60,19 @@ def get_requested_user(email):
 def handle_invitation_exceptions(request, exception, email):
     """Handle exceptions raised during the process."""
     if isinstance(exception, EmailSendingError):
-        logger.warning(str(exception), exc_info=True)
+        logger.warning(exception, exc_info=True)
         messages.error(request, str(exception))
     elif isinstance(exception, MissingEmailError):
         messages.error(request, str(exception))
-        logger.error(str(exception), exc_info=True)
+        logger.error(exception, exc_info=True)
     elif isinstance(exception, OutsideOrgMemberError):
         messages.error(request, str(exception))
-        logger.warning(str(exception), exc_info=True)
     elif isinstance(exception, AlreadyDomainManagerError):
-        messages.warning(request, str(exception))
+        messages.error(request, str(exception))
     elif isinstance(exception, AlreadyDomainInvitedError):
-        messages.warning(request, str(exception))
+        messages.error(request, str(exception))
     elif isinstance(exception, IntegrityError):
-        messages.warning(request, f"{email} is already a manager for this domain")
+        messages.error(request, f"{email} is already a manager for this domain")
     else:
         logger.warning("Could not send email invitation (Other Exception)", exc_info=True)
-        messages.warning(request, "Could not send email invitation.")
+        messages.error(request, "Could not send email invitation.")
diff --git a/src/registrar/views/utility/mixins.py b/src/registrar/views/utility/mixins.py
index 08212088b..8a4666372 100644
--- a/src/registrar/views/utility/mixins.py
+++ b/src/registrar/views/utility/mixins.py
@@ -153,6 +153,48 @@ class PermissionsLoginMixin(PermissionRequiredMixin):
         return super().handle_no_permission()
 
 
+class DomainAndRequestsReportsPermission(PermissionsLoginMixin):
+    """Permission mixin for domain and requests csv downloads"""
+
+    def has_permission(self):
+        """Check if this user has access to this domain.
+
+        The user is in self.request.user and the domain needs to be looked
+        up from the domain's primary key in self.kwargs["pk"]
+        """
+
+        if not self.request.user.is_authenticated:
+            return False
+
+        if self.request.user.is_restricted():
+            return False
+
+        return True
+
+
+class PortfolioReportsPermission(PermissionsLoginMixin):
+    """Permission mixin for portfolio csv downloads"""
+
+    def has_permission(self):
+        """Check if this user has access to this domain.
+
+        The user is in self.request.user and the domain needs to be looked
+        up from the domain's primary key in self.kwargs["pk"]
+        """
+
+        if not self.request.user.is_authenticated:
+            return False
+
+        if self.request.user.is_restricted():
+            return False
+
+        portfolio = self.request.session.get("portfolio")
+        if not self.request.user.has_view_members_portfolio_permission(portfolio):
+            return False
+
+        return self.request.user.is_org_user(self.request)
+
+
 class DomainPermission(PermissionsLoginMixin):
     """Permission mixin that redirects to domain if user has access,
     otherwise 403"""