A method of transferring a virtual machine between a virtualized computing system and a cloud computing system includes determining that a virtual machine is to be transferred from a virtualized computing system to a cloud computing system and determining a connection between a first resource in the virtualized computing system and a second resource in the cloud computing system. Files that enable implementation of the virtual machine at the virtualized computing system and identified, as are file portions of the files for transfer from the virtualized computing system to the cloud computing system. At least one compliance check is executed on each of the file portions using at least one compliance checker. Each of the file portions that fails a compliance check is blocked from being maintained in the cloud computing system.