The purpose of this paper is to explore the problem of inaccuracy in reading that often emerges from Internet text environments and to describe an aspect of critical reading required in such digital literacy contexts. We view inaccuracy as a situated concept which should be defined within a complex coordination of the factors related to reader, text, writer, message, and context of reading. We provide the scenarios of the reading situations in which a reader is forced to cope with and respond to the problem of inaccuracy in Internet settings, using the cooperative principle. We review relevant theories of reading comprehension, from the perspective of inaccuracy, including discourse processing, multiple-documents comprehension, and constructively responsive reading. This presentation closes by interpreting the verbal report data produced by highly-skilled adolescent readers as they attempted to strategically read on the Internet, which provide a clue to understanding and describing the nature of critical reading strategies required for Internet reading.