I have been monitoring the ambient temps over the last year with the starting issue, 109*-45* starts the same for all intent and purpose.

I have a Walbro in-tank pump with ~30K on it.

 

Yes i do, the superchips programmer that came with the kit is what was used for the programming! For the first two months the supercharger was installed on the truck i never had a slightest bit of problem at all and then it seemed that one day it started do this problem back in august!

 

By 'tuning software', I meant HPT or EFI Live. Your programmer doesn't have any scanning/recording ability, and is very limited on what you can adjust. If you were to get one of the above programs, you could record the event, and try to troubleshoot the problem. You may have a sensor malfunctioning, or may need some slight tuning adjustments. You can even post up or e-mail the recording, and others can try to help. I wish there was more that I could offer as help, but it sounds like some real troubleshooting/diagnosis needs to be done here. Good luck to you, I hope you solve your issue.