An installer running on a computing device automates crash recovery of attended operating system installations. The installer initializes a provisioning event of an application on a computing device, presents an application configuration option for the application, receives a decision corresponding to the application configuration option, provisions the application based upon the decision, and updates an answer file with the decision. The installer also, in response to a detected provisioning event failure, generates a custom answer file, initializes a new provisioning event of the application on the computing device, detects the custom answer file, and provisions the application according to the custom answer file.