Over the last seven years a multidisciplinary research team of the University of São Paulo (USP) with the support of São Paulo Research Foundation - FAPESP (2012/24409-2) has been dedicated to designing a collaborative environment of architectural images on the Web. This collaborative environment denominated ARQUIGRAFIA allows institutional users – such as GLAMs (Galleries, Libraries, Archives and Museums), NGOs, Universities and Research Centers – to collaborate with private users – such as students, teachers, photographers and amateurs – in order to build an open, public and free web digital iconographic collaborative environment on Brazilian architectures and urban spaces. The ARQUIGRAFIA research team has been analyzing the digital repository and the website databases; undertaking analytical-critical studies of the indexing languages for Brazilian architecture images as well as of the tags proposed by the users; raising problems for the metadata accordance between systems; as well as consolidating standards which respond both to international interoperability requirements and to local needs for organization and information access. On the website or on the Android App, users can create an account and share their visual collections (photographs, drawings and videos) by uploading files, as well as indexing, geo referencing and licensing images (Creative Commons). Meanwhile, all users can organize albums, post comments and download high-resolution images with metadata. Institutional users can also ask for an institutional login that allows them to have a collective identity online with a particular name and avatar. Those users can choose, whenever they log in, if they will log as a private user or part of an institutional team. Nowadays, the main images of ARQUIGRAFIA come from the collection of the library of School of Architecture and Urbanism of the University of Sao Paulo (FAUUSP). On a technological perspective, ARQUIGRAFIA plays the role of a pilot program for a template called +GRAFIA that can offer free help for other areas of knowledge to build their own visual collaborative environments, such as a BOTANYGRAFIA dedicated to the flora, or an ARTGRAFIA, dedicated to visual arts. Conceptual and technological challenges concerning the design and the operation of ARQUIGRAFIA allows us to characterize it as an online experimental laboratory and a case study on the opportunities and the risks of digital projects on humanities based on images constellations.