1. A computing system for detecting file upload vulnerabilities in web applications comprising: at least one processor; at least one memory architecture coupled with the at least one processor, the at least one processor configured for: automatically uploading, via a file upload interface exposed by a web application, a file together with a signature associated with the file, wherein a black box tester automatically examines the web application during execution of the web application to identify the file upload interface exposed by the web application and automatically uploads the file via the file upload interface; receiving, via an execution monitor, information provided by instrumentation instructions within the web application during the execution of the web application; wherein the execution monitor recognizes the signature of the uploaded file as identifying the black-box tester as the origin of the uploaded the file, wherein the signature includes a name of the uploaded file; wherein the execution monitor uses any of the information, including the signature, to make at least one predefined determination assessing the vulnerability of the web application to a file upload exploit; and wherein the at least one predefined determination includes using a static analysis to determine if the uploaded file includes one or more predefined control characters associated with vulnerabilities.