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I'm running pharo 5 (seaside) in headless mode, with RFB:
./pharo -vm-display-null -vm-sound-null /app/pharo5/Pharo5.0.image --no-quit
Locally works well (Ubuntu 14 with XFCE).
In DigitalOcean (Ubuntu 14 without GUI) it works until the debugger is activated: then it closes. I can connect via VNC with no problem, but when I execute a Halt or an error it triggers the debugger, it leaves ... some clue of the problem?
This sounds like a case where remote debugging might be a reasonable approach. This project, PharmIDE, (previously name, "Remote Debugging", currently named "TelePharo") purports to provide debugging of remote images. There is a repository for it on Github under the current name.
*[Disclaimer, I have not used it.]