Auto-categorize Transactions is a backend setting (in the "Accounting" group of Sprwt's internal configuration screen) — in the current version it is not exposed as a toggle on your own Client Config page, so store admins can't turn it on themselves; it has to be enabled for your account by Sprwt. It is off by default. Once it's on for your account:

1. Every transaction imported the first time you connect a bank account is checked against your rules right away and categorized automatically if one matches; anything with no match stays in Uncategorized Income/Expense.
2. It also reveals the Re-categorize All button on the Transactions page.
3. Transactions picked up later by the scheduled background bank sync are still stored as Uncategorized regardless of this setting — use Re-categorize All to apply your rules to those.

If you'd like automatic categorization turned on for your account, contact Sprwt support.