diff --git a/src/registrar/models/utility/portfolio_helper.py b/src/registrar/models/utility/portfolio_helper.py
index 8c42b80c7..7c82413ae 100644
--- a/src/registrar/models/utility/portfolio_helper.py
+++ b/src/registrar/models/utility/portfolio_helper.py
@@ -1,5 +1,6 @@
 from registrar.utility import StrEnum
 from django.db import models
+from django.db.models import Q
 from django.apps import apps
 from django.forms import ValidationError
 from registrar.utility.waffle import flag_is_active_for_user
@@ -136,9 +137,10 @@ def validate_user_portfolio_permission(user_portfolio_permission):
                 "Based on current waffle flag settings, users cannot be assigned to multiple portfolios."
             )
 
-        existing_invitations = PortfolioInvitation.objects.exclude(
-            portfolio=user_portfolio_permission.portfolio
-        ).filter(email=user_portfolio_permission.user.email)
+        existing_invitations = PortfolioInvitation.objects.filter(email=user_portfolio_permission.user.email).exclude(
+            Q(portfolio=user_portfolio_permission.portfolio)
+            | Q(status=PortfolioInvitation.PortfolioInvitationStatus.RETRIEVED)
+        )
         if existing_invitations.exists():
             raise ValidationError(
                 "This user is already assigned to a portfolio invitation. "