Train Now uses your progression levels to recommend something that’s either achievable or productive. Achievable = less than or close to your current PL, Productive = slightly above your current PL.
The problem is, if you’ve just started or haven’t done any TR workouts at all recently, it doesn’t really know your true level and your PLs will be artificially low. I’d recommend, a) ensure you’re picking one that it lists as ‘productive’ over ‘achievable’ as this will slowly start to boost the level that TR sees you at, and/or b) take the recommended workout, then look it up on the site and look at its alternates - pick one that you think is at a better level for you.