Local CLI sessions and Cloud/App sessions don't share history — feels like losing work

What happened

I was working on a project with Claude Code from the local terminal (a long session, hours of conversation, accumulated context and decisions). At some point the app closed unexpectedly. When I reopened it and used the "work on this project remotely" option, it created a brand new, completely empty cloud session — with no indication that a local session with my full history still existed.

I only found out my previous conversation was still intact because I asked Claude directly, and it explained that local CLI sessions (~/.claude/projects/...) and cloud sessions are separate stores that never sync. I had to go back to a raw terminal and run claude --resume to recover it.

Why this is a problem

Most users are not developers who understand session storage internals. Many people "vibe-code" through the GUI without ever touching a terminal. If their app closes and they're offered "continue in the cloud," they will reasonably assume that continues their work — not realize it silently starts from zero. This reads as data loss even when it technically isn't, and it's very frustrating to face what looks like an empty project.

Related prior reports

• Related: #56038 (requesting sync across CLI, Desktop, and web). This issue specifically focuses on the unexpected crash / "continue in the cloud" flow that leads to perceived data loss for non-technical users.

Suggestions

• When offering to open a cloud/remote session for a project that already has local session history, the app should detect that and either offer to resume/import that local session, or at minimum warn clearly: "This starts a new, separate session. Your local session '<name>' will not be included."
• Longer term, consider letting local CLI sessions be resumable from within the desktop/web app UI directly (not just via terminal --resume), so users aren't forced back to the command line to avoid losing context.