How can traditional literary scholars be introduced to digital methods? And how can the development of annotation tools be specifically oriented to theories and methods of Literary Studies like hermeneutics or scalable reading? Manual annotation is the easiest way to get started: adding comments, markings, underlining and links in the course of close reading may have a counterpart in the digital environment that comes with a number of advantages, such as collaborative work or the sustainability of annotation. The article introduces the manifold annotation modes of the web-based tool CATMA (Computer Assisted Text Markup and Analysis), which has been developed in Hamburg since 2008 against the background of hermeneutic-circular methods of text research and the method of scalable reading. With its ‘undogmatic’, stand-off-markup-based approach, CATMA offers all the freedom of traditional manual-analogue annotation and allows for multiple, overlapping and even taxonomically contradictory annotations by one or more users. CATMA’s markup taxonomies (tagsets) are not limited to binary yes/no, right/wrong oppositions, but can also support the operationalization of semantically challenging literary concepts. In developing a tool for digital text research such as annotation, goals should include providing for an easy, low-threshold introduction to the method, supporting the unstructured and exploratory bottom-up approach characteristic of first-time text encounters and motivating users to apply functions unique to the digital environment. The users should be guided through a continuum of methods in digital text research which range from computer-supported, interactive-manual and ‘close’ to algorithm-based ‘distant’ reading.