Upon start up occassionaly, when exhaust brake is used on steep grades, and recently on heavy rains, the drive belt squeals loudly for some time. Only 35000 miles, no power loss and I don't have any fluid losses. Should I attempt fan belt dressing, does Cummins cover belt changes and/or is this a dramatic service related item I should be concerned with soon?
What engine? No such thing as ISD as far as I know.
Cummins does make an ISB, ISC, and ISL. Suspect it is an ISB 340 HP.
And if inspection of the belt shows it to be OK AND properly installed on each pulley, you have either an issue with the automatic belt tensioner or with a bearing in one of the accessories or tensioner. Cummins should help with this.
Here is a good, short video by Gates Corp on belt tensioners:
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