If a University supplies health Insurance to a student it could be reported in Box 5 of a 1098-T since Health Insurance Premiums are not considered as an education expenses, but I would ask why, rather than posting on the 1098-T (taxable) they don't report it on a W-2 (non-taxable)
If it's reported in box 5 of your 1098-T, it would need to be matched to a Qualifying Education Expense in order to be considered tax-free.
According to the University of Connecticut:
“Since insurance (both medical and dental) is not considered to be a qualified tuition and related expense, this expense it is not reported on your Form 1098-T. However, if the University subsidizes the cost of your insurance then the University subsidy is reported in Box 5 of the Form 1098-T.”
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