The first question is: which side of the belt faces in or out? The shiny side or the rougher side? My intuition tells me the not so shiny side since it presumably has more grip and the fan labeling is on the shiny side which would most like wear out and make it unreadable if an old one had to be replaced. Also, on a car's v-belt the ridges face inwards obviously to match the ridges on the pulley and I don't remember reading any fan labeling printed on those ridges. Was that a long-winded enough introduction?
Second, did I need to purchase part number 233804-43 TENSION SCALE (BELT TENSION TESTER). I stumbled upon this part/accessory(?) on the Dewalt Service Net site (DeWALT ServiceNET - Official Online Store for DeWALT, Porter Cable, Delta, and Black and Decker Parts).
Third, I haven't had this compressor for more than a year, is the belt breaking in half a common occurrence? When it broke, I was shutting it on and off manually because I was using HVLP paint sprayer and I didn't have another pressure regulator installed. Could this have been the reason? I admit it was a pretty numbnut-amateur thing to do...the kind of thing your dad would yell at you for when you were a kid.
Thank you in advance for any help.


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Belts break for all kinds of reasons. Over time, of course, any belt will break but I don't suspect your manual operation of the compressor made any difference.