1. List the libraries that your application uses. For each one, try to (a) figure out what service it provides to the application and when the application loads the library for use, and (b) selectively deny the application access to these libraries and watch for failures.
2. Find out which registry values your application reads and writes. The best way to isolate interesting registry key is to watch the application during installation and start up under Holodeck. After you have identified the keys, look for sensitive information stored in the registry and tamper with keys that may be read at start up to try to get the program to expose data or functionality.
3. Watch your application run under Holodeck and look at documentation to uncover the files and file types your application reads. Next, start corrupting these files with long strings, escape characters, and commands and observe how the application responds. The potential pay-off is a “safe” file (like a music file) that a user downloads and trust that can exploit a vulnerability in the application to execute commands (through script, buffer overflows, etc).
4. Using the file and libraries you identified in the previous attacks, try to alter then in such a way as to make the application behave insecurely. Good targets are files use to storage configuration information or application data (such as cookies).
Launch your application under Holodeck and observe whether your software can securely handle disk, memory and network errors. The application may crash or hang, but watch for subtle symptoms of security breaches, such as sensitive data being written to the hand drive or dumped to the screen or a file.
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