Numerous attempts have been made to conceive and implement appropriate information systems to support architectural designers in their creative design thinking processes. These information systems aim at providing support in very diverse ways: enabling designers to make diverse kinds of visual representations of a design, enabling them to make complex calculations and simulations which take into account numerous relevant parameters in the design context, providing them with loads of information and knowledge from all over the world, and so forth. Notwithstanding the continued efforts to develop these information systems, they still fail to provide essential support in the core creative activities of architectural designers. In order to understand why an appropriately effective support from information systems is so hard to realize, we started to look into the nature of design thinking and on how reasoning processes are at play in this design thinking. This investigation suggests that creative designing rests on a cyclic combination of abductive, deductive and inductive reasoning processes. Because traditional information systems typically target only one of these reasoning processes at a time, this could explain the limited applicability and usefulness of these systems. As research in information technology is increasingly targeting the combination of these reasoning modes, improvements may be within reach for design thinking support by information systems.