A final case study was then attempted using this workflow, which is the same oxindoleforming C-H activation reaction conducted in every other reaction, but this time featured an electronrich aromatic ring rather than an electron-deficient ring. The substrate of interest, N-methyl-2methylchloroacetanilide, also had one ortho position blocked for cyclisation. This study was conducted to further test the limits and the adaptability of the MTBO algorithm, but even with the most forcing conditions possible using our workflow we could only achieve a 29 % product yield. This was also true when using the reported categorical conditions for this substrate in the initial publication -however, the heterogeneity of the reactor systems may have negatively affected the yield outcome, i.e. 6 hour reaction times cannot be achieved easily in flow. Given these observations, we concluded that the reactivity of this species is sufficiently different to previous case studies and therefore cannot be considered as a similar task to the other optimization campaigns. Therefore, for the optimization of these substrates (or any substrates sufficiently different to the tasks of interest) further MTBO campaigns must be conducted for the models to encapsulate these differences to efficiently optimize any case study of interest. With the addition of DFT and reaction similarity scoring, all substrates of interest can be categorized a priori into their respective task bins, avoiding the necessity for additional experimentation. It may also be appropriate in such cases that promising upper bounds leading to full conversion of starting materials are identified, potentially avoiding wasteful experiments in inaccurately defined parameter spaces. Further experimental information on this case study can be found in the ESI.