Concerns surrounding technology use in society has led to the HCI community creating tools for ‘digital wellbeing’. These aim to improve users’ relationships with technology, but these positively motivated tools may initiate further negative impacts for users e.g. on their privacy or autonomy. Using Pierce’s speculative design concepts of ‘foot-in-the-door’ technologies and focusing on three common digital wellbeing features (time limits and prompts, social ‘do not disturb’ modes, app and service blocking), I highlight how these tools are a small step away from being used to manipulate users which could enact slow shifts in users accepting such manipulation. Through this and the discussion, I accentuate that positively motivated designs may not explicitly lead to positive interactions by default. I hope this paper will facilitate speculative design and discussion in the digital wellbeing community, to ensure that our designs continue to mitigate negative impacts from technology now and in the future.