For them, moving between the classroom, the playing field and the online space feels entirely seamless. For us as adults, it can sometimes feel rather less so. Yet if we are to guide them wisely, we must be willing to step into that world with interest, confidence and care.

This week we marked Safer Internet Day 2026, whose theme focused on making smart choices in an age increasingly shaped by artificial intelligence. It is a timely reminder that technology is not standing still. The platforms our children use - and the systems that shape what they see - are becoming ever more sophisticated. Algorithms recommend videos; games incorporate live chat; search results are increasingly generated by AI. For a prep-school child, these systems can feel authoritative and trustworthy, even when they are not.

At Pilgrims’, we speak often about character: about discernment, kindness, courage and responsibility. These virtues are just as necessary online as they are in the playground. However, we must remember that boys under eleven are still developing the judgement and emotional maturity needed to navigate complex digital spaces independently. Supervision, therefore, is not a lack of trust; it is an expression of good parenting.

Many of the platforms children discuss  (YouTube, TikTok, Instagram and popular gaming environments such as Roblox) are not designed primarily with younger users in mind. While they may contain perfectly appropriate and even enriching material, they also rely on automated recommendation systems that can quickly lead children towards content that is confusing, unsuitable or simply overwhelming. Messaging apps such as WhatsApp and Discord, similarly, are built for older audiences and can expose younger users to unmoderated conversations if accessed without oversight.

The presence of artificial intelligence adds another layer of complexity. Children may interact with chatbots or view AI-generated content without realising that it has not been created by a human being. They may assume that a confident answer must be a correct one. One of the most valuable habits we can cultivate in our children is the willingness to pause and ask, “Is this reliable? Who made this? Does this make sense?”

Practical measures remain essential. Parental controls, supervised accounts and sensible screen-time boundaries are not optional extras; they are foundational safeguards. Devices kept in shared family spaces, clear expectations about which apps are permitted, and technology-free time before bed all contribute to healthier habits. Just as importantly, regular and relaxed conversation about what your child is seeing and doing online will build trust. A simple, open-ended question at the supper table (“What did you watch today?”) can reveal far more than a formal interrogation.

We must also resist the temptation to view technology purely as a threat. Used wisely, it offers creativity, learning and connection. Our aim is not to remove the digital world from our children’s lives, but to ensure that they inhabit it with good sense and strong values. The habits formed now - curiosity, caution, courtesy - will serve them well in senior school and beyond.

Thank you for the care and thought you give to this area of parenting. As ever, the partnership between home and school is crucial. If you would value guidance or conversation about online safety, please do not hesitate to be in touch. Together, we can help our boys grow not only in knowledge, but in wisdom - online as well as offline.

Craig Cuyler
Designated Safeguarding Lead/Director of Wellbeing/
Head of PSHEe/Assistant Housemaster (Main School)