The internet offers tremendous access to services, social connections, and needed products. However, to those without sufficient experience, engaging with businesses and friends across the internet can be daunting due to the ever present danger of scammers and thieves, to say nothing of the myriad of potential computer viruses. Like a forest rich with both edible and poisonous plants, those familiar with the norms inhabit it safely with ease while newcomers need a guide. However, reliance on a human digital guide can be taxing and often impractical. We propose and pilot a simple but unexplored idea: could an LLM provide the necessary support to help the elderly who are separated by the digital divide safely achieve digital autonomy?