This article analyses strategies of material commemoration in contemporary urban spaces. Deploying a philosophical and socialtheoretical interpretation systematised by, in particular, Multimodal Critical Discourse Studies and its analysis of material commemoration, the article compares the semiotics of modes of commemorating through monuments and counter-monuments. As is argued, counter-monumental commemoration aligns much better than the traditionally static and non-dialogic monuments with the ongoing post-modern transformation and fluidity of contemporary urban spaces. By the same token, countermonuments also allow commemoration of complex and difficult past events -such as the Holocaust -that are traditionally surrounded by multiple interpretations and often-conflicting attempts to commemorate them. The analysis at the core of the paper looks in-depth at counter-monumental installations known as Stolpersteine, or Stumbling Blocks, developed since the early 1990s by the German artist Gunter Demnig as a form of commemoration of victims of National Socialism and especially the Holocaust. As is suggested, counter-monuments such as the Stolpersteine carry multiple meanings and have multiple functions which allow for diverse patterns of interaction with past/present. They also allow embedding the dialogue between forms of commemoration (monument/counter-monument) various recipients (locals/tourists, spectators/passers-by) as well as their varied interpretations and expectations of commemoration in the discourse of contemporary urban space.