actually it works, you just need to add some waiting in between updating dates

src/test/java/se/su/dsv/scipro/springdata/TestChecklist.java

@@ -123,30 +123,6 @@ public class TestChecklist {
         );
     }
 
-    /**
-     * If we run method, the date should get updated.
-     */
-    @Test
-    @Transactional
-    @Rollback
-    public void testupdateUserLastOpenDate() {
-        /**
-         * Since the date is null ATM, we need to put a new date and save the checklist.
-         */
-        Date oldDate = new Date();
-        checkList.getUserLastOpenDate().put(employee1, oldDate);
-        checkList = checklistService.save(checkList);
-        /**
-         * Then we run the method, which should update the date to a newer date.
-         */
-        checkList = checklistService.updateUserLastOpenDate(checkList, employee1);
-        Date newDate = checkList.getUserLastOpenDate().get(employee1);
-        /**
-         * The old date should now be before the new date.
-         */
-        Assert.assertTrue(oldDate.before(newDate));
-    }
-
     /**
      * If we run method with user, getUserLastOpenUpdate for user should no longer be null.
      */
@@ -158,6 +134,29 @@ public class TestChecklist {
         Assert.assertNotSame(null, checkList.getUserLastOpenDate().get(employee1));
     }
 
+    /**
+     * If we run method, the date should get updated.
+     */
+    @Test
+    @Transactional
+    @Rollback
+    public void testupdateUserLastOpenDate2() {
+
+        checkList = checklistService.updateUserLastOpenDate(checkList, employee1);
+        Date oldDate = checkList.getUserLastOpenDate().get(employee1);
+
+        try {
+            Thread.sleep(10);
+        } catch (InterruptedException e) {
+            e.printStackTrace();  //To change body of catch statement use File | Settings | File Templates.
+        }
+
+        checkList = checklistService.updateUserLastOpenDate(checkList, employee1);
+        Date newDate = checkList.getUserLastOpenDate().get(employee1);
+
+        Assert.assertTrue(oldDate.before(newDate));
+    }
+    
     /**
      * User has not yet opened the checklist with the new functionality. We have no way of knowing
      * when the user last opened the checklist, so method should return false.
@@ -181,25 +180,28 @@ public class TestChecklist {
         Assert.assertFalse(checklistService.hasChangedSinceUserLastOpenDate(checkList, employee1));
     }
 
+    /**
+     * We run the update method to get a date. Then we set an answers lastModified to a later date.
+     * The method should return true, since this would mean changes have been made after the user
+     * last opened the checklist.
+     */
     @Test
     @Transactional
     @Rollback
     public void testhasChangedSinceUserLastOpenDate4() {
-//        Assert.assertTrue(checkList.getUserLastOpenDate().get(employee1)==null); true
-
-//        Date lastModified = checkListAnswer.getLastModified();
-//        Assert.assertTrue(lastModified!=null); true
-
-//        checkList = checklistService.updateUserLastOpenDate(checkList, employee1);
-//        Assert.assertTrue(checkList.getUserLastOpenDate().get(employee1)!=null); true
 
         checkList = checklistService.updateUserLastOpenDate(checkList, employee1);
-        Date newDate = new Date();
-        checkListAnswer.setLastModified(newDate);
 
-//        Assert.assertTrue(checkList.getUserLastOpenDate().get(employee1).before(newDate)); true
+        try {
+            Thread.sleep(10);
+        } catch (InterruptedException e) {
+            e.printStackTrace();  //To change body of catch statement use File | Settings | File Templates.
+        }
         
-        Assert.assertFalse(checklistService.hasChangedSinceUserLastOpenDate(checkList, employee1));
+        checkListAnswer.setLastModified(new Date());
+        checkListAnswerDao.save(checkListAnswer);
+        
+        Assert.assertTrue(checklistService.hasChangedSinceUserLastOpenDate(checkList, employee1));
 
     }