A: Hi Brad, great questions.

1. Auto-categorization is automatic, no manual work required. The Smart Tags feature scans each conversation's title and content and automatically assigns tags across five built-in categories: Coding, Writing, Research, Math and Science, and Business. You can also add your own custom rules (your own tag name, keywords, and color) and the engine applies those automatically too. On top of that, manual tagging exists if you want hand-picked labels on specific chats, but it is optional, not required.

One super important detail: the categorization does not send your conversations to an AI model. It runs a keyword and pattern scoring engine locally in your browser, against the conversation cache already stored on your device. That is a deliberate design choice with three benefits: your chat content never leaves your browser for tagging, results are instant, and there are no AI processing costs or quotas attached to it.

2. Yes, it works retroactively. The engine runs across your existing conversation history, not just new chats. On the free plan it tags your 50 most recent conversations; on paid plans it tags your entire history, however far back it goes. Tags also recompute automatically as new conversations sync, so the categorization stays current without you touching anything.

This works on all three modules (ChatGPT, Claude, and Gemini), all covered by the AppSumo All Access license.