Disclosure up front: I build Claude Sessions Pro , a paid Mac app that does this. Most of this post is the free way to do it yourself, plus what I learned about why the DIY versions misbehave. The app gets one short section near the end. If you have a company Claude account and a personal one, or one account per client, you've hit this: Claude Desktop is signed in to one account. To check the other one, you sign out, sign in, lose your place, and do it again an hour later. Claude Code ...