cowork-session-sync v1.0.0 provides session continuity for Claude Cowork

cowork-session-sync v1.0.0 is a stable release of a tool that provides session continuity for Claude Cowork, addressing the problem of losing context between sessions and the associated cost of re-establishing that context.

Key features from v1.0.0

• Readable session titles: Instead of Cowork's random codenames like 'stoic-serene-gauss', the tool synthesizes human-readable titles from the first user message (e.g., 'LXC backup with Wake-on-LAN').
• Archive filtering: Since Claude Desktop's archive action is server-side, the tool manages its own archive list. After catching up on a session, it offers to mark it as archived, preventing archived sessions from cluttering the list on subsequent runs.
• One-phrase bootstrap: Type 'catchup-bunny' in a fresh Cowork chat to get a numbered list of active sessions. Pick one to restore full context without bootstrap failures or re-explaining infrastructure.

Technical implementation

The pipeline consists of:

• Sync-CoworkSessions.ps1 runs every 5 minutes as a Windows Scheduled Task
• Reads %APPDATA%\Claude\local-agent-mode-sessions
• Archives raw transcripts and distills them to Markdown (~5% of original size)
• Generates SESSION-INDEX.md with project tags, turn counts, and cost tracking
• Python version (cowork_sync.py) available for macOS/Linux

Cost context

The developer reports sessions average $10–25 each (using Opus 4.6). Without catchup, they were burning $5–10 per session just re-establishing context. The distilled files are 1–5 KB, resulting in near-zero token cost to restore context.

This type of tool is useful for developers who use Claude Cowork for extended technical conversations where maintaining context across sessions is critical to productivity.