File resources that are most likely to be used on a target computer are proactively cached, so that the resources are available before they are needed. This greatly reduces or eliminates associated user wait times. It is determined which file resources are most likely to be used, the cost of transmitting them to the cache, the cost of storing them in the cache and the amount of cache space available. Based on a weighted balancing analysis of factors such as these, specific file resources are proactively streamed for use on the target computer. The determination as to which resources are most likely to be used can be based on a variety of factors, such as usage patterns, schedule based information, user and group based information, target computer and network information, etc.