You shouldn't ever have to. During the winter you might get into that predicament if the battery tender isn't working properly but as long as the batteries are good and the charging system is in proper operating order, these trucks have lots of power.
A JumpStart, whether it's a Ford or a Freightliner, represents a system failure. So actually, jump starting should be rare. Yes, there's battery connection pegs, but that just makes life easier when someone needs a jump.
Two of my four batteries froze in Vermont last February. But that was because they were old. I got all four replaced. (a company truck so it wasn't my $700!)
You're lucky to get 5 years out of most (automotive) batteries. The lead plates break down,over time, and flakes drop to bottom of the case, piling up over time. Once the pile of flake reaches the plate, it shorts that cell(s)...
Here in the Arizona, Mohave desert, 3 years is a good life, 5 is a bonus lol....Cheaper ain't always better when buying a new battery. Pairs or mulitples, usually best to replace all a same time. Taller battery cases sometimes last longer, since there is more distance, from the bottom to the lead plates, meaning longer time span 'til those flakes make contact & short out the affected cell's....
I never believed in block heaters, since I never lived in super cold or snow states. Until I worked for Nissan Forklifts, my service van was an E-350 7.3 diesel. And I lived in the high desert of Calif @ about 4400 foot level.....After a couple cold winter mornings, of hard / no start or having to jump my van to get to work, I started using that dang block heater! Big difference, key in starts right up and off we go.
I've only had to once. I usually am using cables to jump a dead or frozen reefer battery
A refrigerated trailer.
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Just curious... how often to you find yourself having to jump start a month?