Advising on computer software upgrade decisions for enterprise software by analyzing respective vendor information correlated to influences from user data including periodically checking for vendor software updates for selected software programs. A plurality of factors are assessed for software update risks, and the factors include dimensions of importance of each of the factors. Opinion and comments from users on public websites are collected regarding the software and the software updates. Each of the dimensions for each of one or more factors for a selected software program are weighted. The weighting is based on an importance for each of the dimensions for a respective user. A risk score is calculated based on the assessed software update risk for each dimension which includes the weighting of each of the dimensions, and a notification is sent to a user recommending the software upgrade or not based on the risk score.