Approaches for managing potentially malicious files using one or more virtual machines. In response to receiving a request to perform an action on a file, a client applies a policy to determine whether the action is deemed trustworthy. The client identifies, without human intervention, a virtual machine, executing or to be executed on the client, in which the action is to be performed based on whether the action is deemed trustworthy. In this way, embodiments allow a user to make use of data deemed untrusted in certain cases without allowing the untrusted data from having unfettered access to the resources of the client. If the requested action is performed in a different virtual machine from which the action was requested, embodiments enable the performance of the action to be performed seamlessly to the user.