`PossibleZeroQ` will numerically check for zero if standard transformations do not work. It, being numerical, is not foolproof, and so it is not a complete rigorous method. For that reason, @Artes' method is superior in this case. Simplify[ 1/12 (\[Pi]^2 + 3 ArcCosh[7/2] ArcCsch[2] - 12 ArcTanh[1/Sqrt[5]]^2), TransformationFunctions -> {Automatic, # /. _?PossibleZeroQ :> 0 &}] > `Simplify::ztest1`: Unable to decide whether numeric quantity `-3 (-Log[1+Times[<<2>>]]+Log[1+1/Sqrt[5]])^2+3 Log[1/2+Sqrt[5]/2] Log[7/2+(3 Sqrt[5])/2]` is equal to zero. Assuming it is. (* \[Pi]^2/12 *) `Simplify` caches results, so the message only appears on first execution.