In my work we might look at implementing pragmatic lessons on the web in two ways: 1) the technical solution seeks to represent the data ‘pragmatically’ somehow; 2) the user solution seeks to scaffold the user to understand the pragmatic context of the data (but doesn’t try to ‘build in’ those into the system).
The two are probably not mutually exclusive – in fact, it would probably be inappropriate to be entirely one or other. On the technical side, the tendency to CONTEXTUALISE ALL OF THE THINGS has issues because: 1) personalisation to users/contexts can mask other facets of information; 2) pragmatic elements of information are often dynamic and discursive – it isn’t just that systems may not represent those properties, it’s that in seeking to do so they become a part of the discursive environment; 3) systems don’t define use (although, they may be a part of the context of use, as in ‘2’). On the latter, the point is to assist users in (and perhaps be involved in) the appropriate giving and asking of reasons for the given context of use, it is about good sensemaking, and facilitating understanding through the ways we represent data, provide “perspectives” and embed data use in high quality discourse.
Contextualising all of the things will not – in the philosophical sense – give us the pragmatic web. It will give us semantics+ (it might give us the linguistic sense of pragmatics, although even here I’m not sure). Philosophically pragmatic approaches emphasise context, but they also respect testimony, understanding the normative properties of warrants, and highlight that use – and understanding the querying of entitlements and commitments – is important. This isn’t possible in any current search engine. Context of use (or, ‘environment’) isn’t everything, although use as context might build in more of those important aspects (but I’m not sure this is how it’s being used). I’ve been reading a bit around the pragmatic web recently, and the below is a sort of “narrative through quotation” on that which reflects the elements of the literature I’m most interested in/most support/I think best reflect philosophical elements of pragmatic theory.
“the Semantic Web is a necessary step from the syntax (HTML) level to the semantics (meaning) level. However, still one crucial level is lacking: that of pragmatics: what is the purpose of the information? How do we use it?” p.3
Moor, Aldo de. “Patterns for the Pragmatic Web.” In Conceptual Structures: Common Semantics for Sharing Knowledge, edited by Frithjof Dau, Marie-Laure Mugnier, and Gerd Stumme, 1–18. Lecture Notes in Computer Science 3596. Springer Berlin Heidelberg, 2005. http://link.springer.com/chapter/10.1007/11524564_1.
“In our vision of the Pragmatic Web, interaction is based on the intentions of people which are materialized by actions (we do not yet want to enter the discussion whether to call the concept action, activity, act, etc.), i.e. interaction abstracts from a service provider who enables the actual action and gives people the control on how the results of their actions are presented and with whom and under which conditions they are shared. ” p.79
“HCI research has acknowledged a long time ago that humans are not simply components of a system that can be studied in isolation in a laboratory environment . This has led to what some researchers call “post-cognitivist theories”, theories that go beyond the study of cognitive abilities, and that have a substantial amount of quantitative and significantly less qualitative elements than more traditional HCI theories rooted in cognitive psychology, human factors or ergonomics. Post-cognitive theories and models often start from the notion of language and the notion of action as a form of language use. Examples are activity theory, distributed cognition, actor-network theory, phenomenology (see  for a comparison of the four theories from the point of view of activity theory), or the language/action perspective . Some of these theories are also employed in the field of information systems research .” p.75
Hornung, Heiko, and M. Cecília C. Baranauskas. “Towards a Conceptual Framework for Interaction Design for the Pragmatic Web.” In Human-Computer Interaction. Design and Development Approaches, edited by Julie A. Jacko, 72–81. Lecture Notes in Computer Science 6761. Springer Berlin Heidelberg, 2011. http://link.springer.com/chapter/10.1007/978-3-642-21602-2_8.
“The central quest in accomplishing automatised question answering in information discovery is to find out logical relations between questions and answers. This, in turn, hinges on the theories of presuppositions. (The task is also related to the extensions of Peirce’s theory of abduction.) This is because requests for information can be viewed as epistemic statements. The query “Bring it about so that S” (S is any proposition of one’s preferred modelling language) has a meaning in non-imperative epistemic sentence “I know that S”. As to the second item, the web nodes are to be viewed as knowledge providers, and via that emerging structure the epistemic statements can be translated to mean that “the user knows S in the information state w if and only if S holds in all the web nodes accessible from w”.” p983
Pietarinen, A. V. “The Semantic+ Pragmatic Web= the Semiotic Web.” In Proceedings of the International IADIS/WWW Conference, 981–984, 2003. http://www.iadis.net/dl/final_uploads/200302C149.pdf.
“In a pragmatic web, the web services need to be able to facilitate communication and negotiate between service consumers and service providers. The multi-agents in the pragmatic web will aid in such processes by catching user’s requests and providing support in each decision point in the business process.” p4
“The concept of the pragmatic web is first proposed by Singh  as a preliminary thought which introduced the three principles of the pragmatic web: user before provider, process before data, and interaction before presentation. ” p5
Liu, Kecheng. “Pragmatic Computing – A Semiotic Perspective to Web Services.” In E-business and Telecommunications, edited by Joaquim Filipe and Mohammad S. Obaidat, 3–15. Communications in Computer and Information Science 23. Springer Berlin Heidelberg, 2009. http://link.springer.com/chapter/10.1007/978-3-540-88653-2_1.
“In order to provide the collective intelligence with meaningful content, it should be embedded in the context of social practices around shared objects and processes of technology use rather than assumed to represent transcendental bodies of thought and ethereal interactions. From syntax (logical forms and symbolic structures) and semantics (meaning of symbols), the idea of the pragmatic web is to move toward pragmatics through addressing the contexts and practices of creating, using, and developing epistemic artifacts [de Moor, 02; Singh, 02]. This implies that users, their communities and network, as well as their evolving epistemic practices become essential in creating, interpreting, sharing, applying, and extending knowledge.” p.686
“While the semantic web has been preoccupied with standardization of knowledge and systems of knowledge based on ontologies determined mainly by experts beforehand, the envisioned pragmatic web is oriented toward adapting to the special needs of customers and user communities. Rather than simply assimilating to already existing knowledge ontologies, the vision is to engage user communities in active negotiation and interpretation of meaning and to the development of knowledge structures grounded on their evolving practices and epistemic pursuits [de Moor, 02].” p.687
“The pragmatic web may elicit knowledge creation by 1) providing a technological infrastructure for augmenting the functioning of more or less distributed epistemic communities, 2) facilitating automated analysis and interpretation of large bodies of data generated by the users, and 3) adapting to and coevolving with human knowledge practices.” p688
“When users participate in defining and generating concepts, they can create user-centered and contextually sensitive semantics in epistemic technologies they use” p.690
“The advancement of pragmatic web for CSCL should offer not only means for negotiating of meaning, but a way to facilitate sustained collaborative efforts to advance shared artefacts and elicit other social practices relevant for creating and advancing knowledge. “p.691
Hakkarainen, K., R. Engeström, S. Paavola, P. Pohjola, and T. Honkela. “Knowledge Practices, Epistemic Technologies, and Pragmatic Web.” In Proceedings of I-KNOW, 9:683–694, 2009. http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.157.91&rep=rep1&type=pdf.
Schoop, M., Moor, A., & Dietz, J. (2006). The pragmatic web: a manifesto Communications of the ACM, 49 (5) DOI: 10.1145/1125944.1125979