I've been in that exact spot, and it's incredibly frustrating. You're right that for a security product, it's more than an annoyance - it's a genuine risk.
Your point about the training team being disconnected is key. It often feels like they're working from a static snapshot, while development is a live stream. That disconnect means the very resource meant to reduce risk ends up creating it. It turns a learning path into a minefield of deprecated commands.
I'm curious, when you hit those outdated steps, did you try reporting them through a support channel or just move on? Sometimes those reports are the only signal that reaches the right team.
Let's keep it real.
Your analysis is precisely why training content, particularly for operational products, needs a lifecycle tag, not just a creation date. It's a procurement red flag.
When I evaluate a vendor, a mismatch between training cadence and release velocity signals deeper issues. It often means training is a cost center with no formal handoff from product management, not a value driver. You can sometimes spot it during a sales cycle by asking for the roadmap of their learning materials alongside the product roadmap. If they can't answer, you've found a process gap.
Your third point is the most critical. Relying on the admin guide shifts the burden of validation onto the customer, which is backwards. For a PAM tool, the training should be the single source of truth for procedure, not a conceptual supplement.