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I don't know if it just me being stupid or what but 1.08 doesn't want to work as a debug eboot. I think I had an issue with 1.07 too but I did not need one then so I didn't care.
The eboots I am building run the game fine but when I connect it pauses like usual but no processes show up in TM so I can not continue the process although I can debug the halted process.
Anyone having better luck than me want to share their secret?