handling of failed email sends to domain managers

src/registrar/admin.py

@@ -1410,7 +1410,7 @@ class BaseInvitationAdmin(ListHeaderAdmin):
         # store current messages from request so that they are preserved throughout the method
         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)
+        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 +1552,14 @@ 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()

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:
@@ -76,9 +85,9 @@ def send_emails_to_domain_managers(email: str, requestor_email, domain: Domain,
                 },
             )
         except EmailSendingError as err:
-            raise EmailSendingError(
+            logger.warning(f"Could not send email manager notification to {user.email} for domain: {domain.name}")
-                f"Could not send email manager notification to {user.email} for domain: {domain.name}"
+            all_emails_sent = False
-            ) from err
+    return all_emails_sent
 
 
 def normalize_domains(domains: Domain | list[Domain]) -> list[Domain]:

src/registrar/views/domain.py

@@ -1244,24 +1244,26 @@ 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,

src/registrar/views/portfolios.py

@@ -299,13 +299,14 @@ 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(
                 [
@@ -517,12 +518,13 @@ 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)

src/registrar/views/utility/invitation_helper.py

@@ -70,11 +70,11 @@ def handle_invitation_exceptions(request, exception, email):
         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.")