Is it better to pay an insurance deductible, or get an upgrade?
I think you have a few choices that cannot be described by math alone: Repair current phone:  149 Replace current phone with new model from carrier:  100 + cost of new phone Replace current phone with new model on payment plan from carrier:  100 + cost of new phone + finance charge (could be zero or cleverly hidden). You can also replace the current phone with either a used or new bought from a separate party.  Quite recently I was selling some gently used IPhones 4S for around $140.   So really you have to determine what is most important to you guys.  Is it important to have the newest model phone with laying out the least amount of cash now?  Then by all means go with the payment plan with your current carrier. Is it most important to be financially efficient, while having a good working phone?  Then pay the deductible; or buy something gently used.   In my opinion, having a phone payment is a losing game, akin to buying a new car every three years or so.  You are buying something on time that quickly depreciates and hiding the true cost of the item in "painless" monthly payments.