diff --git a/portal/portal-service-impl/impl/src/java/org/sakaiproject/portal/service/PortalServiceImpl.java b/portal/portal-service-impl/impl/src/java/org/sakaiproject/portal/service/PortalServiceImpl.java
index 64578bece954..7d74fe2f6644 100644
--- a/portal/portal-service-impl/impl/src/java/org/sakaiproject/portal/service/PortalServiceImpl.java
+++ b/portal/portal-service-impl/impl/src/java/org/sakaiproject/portal/service/PortalServiceImpl.java
@@ -1061,9 +1061,8 @@ public void syncUserSitesWithPortalNav(final String userId) {
 					sitesToPin.remove(id);
 				});
 
-		// remove unpinned and recent sites as they should not be pinned
+		// remove unpinned as they should not be pinned
 		sitesToPin.removeAll(unPinnedSites);
-		sitesToPin.removeAll(recentSites);
 		// any remaining sites should be auto pinned
 		savePinnedSites(userId, new ArrayList<>(sitesToPin));
 
diff --git a/portal/portal-service-impl/impl/src/test/org/sakaiproject/portal/service/PortalServiceTests.java b/portal/portal-service-impl/impl/src/test/org/sakaiproject/portal/service/PortalServiceTests.java
index 943249e6097e..e4b8914598ec 100644
--- a/portal/portal-service-impl/impl/src/test/org/sakaiproject/portal/service/PortalServiceTests.java
+++ b/portal/portal-service-impl/impl/src/test/org/sakaiproject/portal/service/PortalServiceTests.java
@@ -403,10 +403,24 @@ public void testRecentlyUnpinned() {
         // simulate another login
         ((Observer) portalService).update(null, event);
 
-        // should be no change to sites pinned, unpinned, or recent
+        // no change after login, results in 0 pinned, 4 unpinned, 3 recent
         Assert.assertEquals(0, portalService.getPinnedSites(user1).size());
         Assert.assertEquals(4, portalService.getUnpinnedSites(user1).size());
         Assert.assertEquals(3, portalService.getRecentSites(user1).size());
+
+        // re pin site3, results in 1 pinned, 3 unpinned, 3 recent
+        portalService.addPinnedSite(user1, "site3", true);
+        Assert.assertEquals(1, portalService.getPinnedSites(user1).size());
+        Assert.assertEquals(3, portalService.getUnpinnedSites(user1).size());
+        Assert.assertEquals(3, portalService.getRecentSites(user1).size());
+
+        // simulate another login
+        ((Observer) portalService).update(null, event);
+
+        // no change after login, results in 1 pinned, 3 unpinned, 3 recent
+        Assert.assertEquals(1, portalService.getPinnedSites(user1).size());
+        Assert.assertEquals(3, portalService.getUnpinnedSites(user1).size());
+        Assert.assertEquals(3, portalService.getRecentSites(user1).size());
     }
 
     @Test