Session discovery, categorization, and AI summaries (peek, tag, summarize, projects)

[djdarcy]

Session discovery, categorization, and AI summaries

Problem

Users often don't know which session corresponds to which project. Sessions start in one folder but migrate to another. Auto-generated names are unhelpful. With 100+ sessions, finding "the one where I fixed the auth bug" requires opening each one.

csb list and csb scan solve the discovery problem at the folder level -- you can see which folders a session touched. But there's no way to understand what the session was about without opening the full transcript.

Proposed features

Session preview (csb peek <id>)

Show the first user message + last user message from the JSONL. Gives a quick sense of the session's arc without reading the whole thing.

$ csb peek 916441e6
Session: EXT-TOOL__CLAUDE-VAULT
First message (2026-03-23 18:14):
  "Hey Claude I just git cloned claude-vault..."
Last message (2026-03-25 02:28):
  "Let's do a /fullpostmortem and then commit..."

AI-generated summaries (csb summarize <id>)

Parse the first N and last N messages, send to an LLM, get a 1-2 sentence summary. Store in the index for future csb list display.

$ csb summarize 916441e6
Summary: Built Claude-Session-Backup (csb) tool from scratch.
  Evaluated claude-vault, history-viewer, session-logger.
  Implemented git-backed backup with timeline, folder analysis, purge countdown.

Could also batch-summarize: csb summarize --all --unsummarized

Session tagging (csb tag <id> <label>)

User-defined labels for sessions. Stored in the SQLite index. Searchable via csb list.

$ csb tag 916441e6 "csb-development"
$ csb list csb-development

Session grouping by project

Automatically group sessions by their primary working directory. All sessions where aichatnav was the top folder get grouped together.

$ csb projects
  C:\code\chrome-extension\aichatnav\local  (3 sessions, 9500 messages)
  C:\code\ComfyUI_experiment                (5 sessions, 12000 messages)
  C:\code\github-traffic-tracker\local      (2 sessions, 2300 messages)

Project association

Link sessions to GitHub repos based on folder paths. Detect .git/config remote URLs in working directories.

Priority

• peek -- quick win, high value, no external dependencies
• tag -- simple metadata addition
• projects grouping -- derivable from existing folder analysis data
• summarize -- requires LLM access, expensive, but most valuable

Related

• csb list [filter] already provides keyword-based discovery
• csb scan [path] provides directory-scoped discovery
• /renameAI in claude-session-logger does AI naming for active sessions
• Claude Code History Viewer handles full conversation browsing (not our job)

Analysis

See notes/ideas/2026-04-02__19-41-58__both_plugin-architecture-and-session-discovery-vision.md

[djdarcy]

Connection to FTS5 and the session lifecycle

Session discovery/categorization is tightly connected to Issue #3 (FTS5 Content Search). The user articulated a lifecycle model:

• Claude Code's deletion is a feature (declutters active view), not just a threat
• csb's job is to make the archive searchable and recoverable
• Without content search, archived sessions are only findable by name/folder -- not sufficient

This means csb peek and csb summarize (from this issue) complement FTS5 (Issue #3):

• FTS5: "find the session where we discussed auth middleware" (full-text match)
• peek: "show me the first and last message of this session" (quick context)
• summarize: "what was this session about?" (AI-generated, stored in index)

All three serve the rediscovery step of the lifecycle.

See 2026-04-02__19-41-58__both_plugin-architecture-and-session-discovery-vision.md for the full analysis.

Related: Issue #3 (FTS5, re-prioritized as essential), Issue #7 (plugin delivery)