Joseph Garcia
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Since there is a relatively small amount of data being transferred, and since transmission speed is not an issue in this application, the 100' USB cable extension is not an issue.100' is awful long for a USB cable but if it works, it works. I think that the flat cable that comes with the Tech 2 and has RJ45 ends is wired the same as a standard ethernet cable, so you may be able to use a long one of those for 1) the computer connection to the router - if your wifi doesn't reach - or 2) the cable between the laptop and the Tech 2.
Yes, the ribbon cable that comes with the Tech 2 is an equivalent of a CAT3 Ethernet cable. For a long run, you could replace it with a CAT5 or CAT6 cable. Of course, your Tech 2 would be at your computer, rather than at your truck during the programming process, but that does not really matter, as you don't need to be doing anything specific with the Tech 2 during the pass-thru programming process.