TehranAvenue.com was an important online cultural mouthpiece between 2000 and 2010. Though now closed, TA still has a presence in the form of an archive. And though it did not have the same kind of traffic enjoyed by mainstream religious, entertainment, and sports websites in Iran in the 2000s, it served as an important organ for intellectual discussions of music, art, urban life, and open-source software. According to its creators, the web magazine created a community of writers (and, pointedly, not bloggers) and readers around Tehran’s cultural life. At the same time, like much of Iran’s literary history, the content of the website suggested that it’s focus on aesthetics and culture was also an engagement with questions of politics and justice. However, while politics has tended to be coded allegorically in twentieth-century Iranian literature, politics and art are often contiguous in Iran’s blogosphere. In this presentation, I will provide a history of TA based on interviews with the site’s creators. Secondly, by triangulating digital, urban, and transnational theories, I argue that TA created a transnational urban-digital public sphere. After establishing the context of this cyber-urban transnational space, I will offer close readings of specific articles published on TA. The creators and writers of TA very intentionally wrote against the notion of the blog. The blogification of digital space, for TA’s community, amounted to digital navel gazing. By contrast, an article that had passed through an editorial process and addressed a readership functioned as a form of “address” (in Michael Warner’s terms)—of locating the speaker and addressing a public. Given the locatedness of this particular public, the content of these articles take on pointed political urgency. By reading a number of cultural commentaries (particularly art reviews) I argue that TA developed a community of organic intellectuals. As such, their comments on art, on music, and even on open-source software were tantamount to an engagement with political questions of freedom and justice. Cultural commentary functioned not only to challenge the Islamic Republic’s limits on individual self-expression, it also functioned to challenge late capitalist assumptions about Iranian culture in relation to the supposed freedoms of North America or Western Europe. In this sense, TA developed a cyber-urban sensibility (with loyalties to digitally distributed urban publics rather than national or religious formations) that deployed cultural commentary as a kind of political activism.