Fundamental research that investigates how educators might learn with digital technologies is scarce. There seems to be a pervasive assumption that they will learn with digital technologies. (Fisher et al., 2006). Taking on e-learning can challenge teachers conceptions of themselves as competent, skilled professionals and can lead to potentially unsettling and destabilising experiences that cause them to reject e-learning. (C.Daly et al.,2007)  Guided by three broad questions regarding how educators learn, teach and experience assessment in online learning environments, a series of online modules were investigated using phenomenographic methods. The modules were created in either the WebCT or Blackboard learning management systems and concerned the professional development of HE practitioners in learning how to teach online using a blend of face to face and virtual deliveries. The modules were designed to provide multiple representations of reality, to represent the complexity of the real world ,and to focus on knowledge construction, rather than knowledge reproduction. (Jonassen, 1994) The participants were presented with authentic tasks which required them to apply what they had learned within the context of their own practice and then to report back on what worked for them, what did not, and what they would do better next time.  Three methods of data collection were used - Likert-type evaluation of the online artefacts, reflective blogs developed by the participants and iterative videotaped phenomenographic interviews with some of the participants. Results seem to indicate that the absence of "affinity"  - the so-called "seductive learning spaces" described by Guglielmi & Johannesen(2005) - appears to compromise the learning of these participants in online learning environments . The absence of human affinity generally felt by the participants, largely implicit and generally taken for granted in face to face learning and teaching, suggests, by extrapolation, the need for suitable navigational aids - meta-navigational "explicadors" - in online learning spaces. An online explicador is seen as an interactive meta-map of a virtual learning domain that affords the "affinity architecture" provided by a human teacher in face-to-face learning environments. There appears, in addition, to be evidence that the lack of such affinity in learning designs may be exacerbated by content which favours repackaged procedural knowledge into a medium that requires, perforce, declarative and procedural knowledge awareness. The terms "affinity" and "explicador" are explained in relation to the declarative nature of Web-based learning and teaching and possible solutions to the problem are demonstrated.