As digital services increasingly replace traditional analogue systems, ensuring that older adults are not left behind is critical to fostering inclusive access. This study explores how digital educators support older adults in developing essential digital skills, drawing insights from interviews with $34$ educators in Ireland. These educators, both professional and volunteer, offer instruction through a range of formats, including workshops, remote calls, and in-person sessions. Our findings highlight the importance of personalized, step-by-step guidance tailored to older adults' learning needs, as well as fostering confidence through hands-on engagement with technology. Key challenges identified include limited transportation options, poor internet connectivity, outdated devices, and a lack of familial support for learning. To address these barriers, we propose enhanced public funding, expanded access to resources, and sustainable strategies such as providing relevant and practical course materials. Additionally, innovative tools like simulated online platforms for practicing digital transactions can help reduce anxiety and enhance digital literacy among older adults. This study underscores the vital role that digital educators play in bridging the digital divide, creating a more inclusive, human-centered approach to digital learning for older adults.

Subscribing to online services is typically a straightforward process, but cancelling them can be arduous and confusing — causing many to resign and continue paying for services they no longer use. Making the cancellation process intentionally difficult is recognized as a dark pattern called Roach Motel. This paper characterizes the subscription and cancellation flows of popular news websites from four different countries, and discusses them in the context of recent regulatory changes. We study the design features that make it difficult to cancel a subscription and find several cancellation flows that feature intentional barriers, such as forcing users to call a representative or type in a phrase. Further, we find many subscription flows that do not adequately inform users about recurring charges. Our results point to a growing need for effective regulation of designs that trick, coerce, or manipulate users into paying for subscriptions they do not want.