XSS is a security vulnerability that permits injecting malicious code into the client side of a web application. In the simplest situations, XSS vulnerabilities arise when a web application includes the user input in the web output without due sanitization. Such simple XSS vulnerabilities can be detected fairly reliably with blackbox scanners, which inject malicious payload into sensitive parts of HTTP requests and look for the reflected values in the web output. Contemporary blackbox scanners are not effective against stored XSS vulnerabilities, where the malicious payload in an HTTP response originates from the database storage of the web application, rather than from the associated HTTP request. Similarly, many blackbox scanners do not systematically handle context-sensitive XSS vulnerabilities, where the user input is included in the web output after a transformation that prevents the scanner from recognizing the original value, but does not sanitize the value sufficiently. Among the combination of two basic data sources (stored vs reflected) and two basic vulnerability patterns (context sensitive vs not so), only one is therefore tested systematically by state-of-the-art blackbox scanners. Our work focuses on systematic coverage of the three remaining combinations. We present a graybox mechanism that extends a general purpose database to cooperate with our XSS scanner, reporting and injecting the test inputs at the boundary between the database and the web application. Furthermore, we design a mechanism for identifying the injected inputs in the web output even after encoding by the web application, and check whether the encoding sanitizes the injected inputs correctly in the respective browser context. We evaluate our approach on eight mature and technologically diverse web applications, discovering previously unknown and exploitable XSS flaws in each of those applications.