However, those updates can even end up causing several issues on the system and hinder smooth operation. They also expect to improve the performance of the system and assure the overall security. In general, Windows offer timely updates on their operating systems to offer better user-experience. In fact, it can happen either due to the settings of Outlook or recent Windows updates. Some individuals say that their ‘ Outlook keeps asking for password‘ even if you have entered it several times. Have you come across a similar situation? Tried various tricks but had no luck so far? If that’s the case, continue reading and find out how to fix it. As we have noticed, several other users had a similar type of issue, and they were looking for some help. The above lines were extracted from one of our help forums. Does anyone know the reason & how to get rid of this error? Thanks a bunch!” “ Outlook keeps asking for password even after logging in successfully.