Do-It-Yourself (DIY) home improvement projects require a combination of specific knowledge and practical abilities. Novice users often lack both and thus tend to fail or be frightful of performing DIY projects – even though they would like to. By providing suitable and individualised assistance in the form of step-by-step instructions, the assistant Robert allows even novice users to successfully complete their DIY projects. Simultaneously, Robert allows its users to learn how to perform these steps themselves and thus enables them to become more independent in the future. In this paper, we report on the latest progress with Robert. Compared to earlier versions, Robert is now able to adaptively change its instructions based on the wishes and preferences of the user. Further, Robert is now able to use connected tools – i.e. tools that are able to sense and communicate their status – to check whether the user is performing the project's steps correctly and to provide further assistance in the case of failure. Lastly, we present the results of an empirical study conducted to show Robert's effectiveness.