How far back can Trailwise read, and how far back can I reopen a conversation?

Two different fences. Reopening your own conversations: the last 7 days on Trailwise, and everything you have while you subscribe on Trailwise pro. Nothing is ever deleted to enforce that, so if you move up you get the whole transcript back. How far back Trailwise reasons over raw history: 56 days on Trailwise, complete on Trailwise pro. That fence is on what the model reads, not on the maths. The scores keep their own full windows on every plan, so your Load, Engine and Resilience are worked out over the same history whichever plan you are on.