The complexity of DCC and the different possible reaction outcomes is clearly shown by the diversity of results we see when targeting organic cage formation, highlighting the requirement for the use of all three experimental characterisation methods within the automated workflow to fully describe the reaction outcome. By taking into account the automated turbidity analysis of the reaction as a 'pass' (no precipitate) or 'fail' (precipitate), the automated 1 H NMR analysis as a 'pass' only if the aldehyde was fully consumed and a species was present in the aromatic/imine region, and the automated HRMS analysis as a 'pass' if a mass ion of at least one targeted cage assembly was detected, it was possible to identify a range of different organic cages. Representative examples of this sequential categorisation for different combinations can be seen in Figure .