In Dante’s Inferno, do the sins of the dammed fit the punishment that they experience?

In Dante's Inferno, one of the few rules operating in Hell is contrapasso. Briefly, this states that for every sinner's crime, there must be an appropriate, fitting punishment. However, as we descend further and further into Hell with Dante and Virgil, we become acutely aware that this principle does not seem to be applied in a consistent manner. For instance, in the sixth circle, we find Pope Anastasius II set on fire and entombed for committing the sin of heresy. Even allowing for the huge cultural and religious differences between Dante's day and ours, the fate of Anastasius's soul does seem a trifle harsh.
However, Dante is much too good of a writer to make a simple connection between sin and punishment. The correspondence between the two is metaphorical, rather than literal. That being the case, we are in a better position to understand the rather puzzling discrepancies between sin and punishment that Dante often presents.
Contrary to popular belief, Dante does not subscribe to "an eye for an eye." In that regard, he departs from the traditional biblical notion of punishment as relating to its harmful effects upon the wider community of believers. Instead, Dante emphasizes that punishment arises out of the sin itself, rather than its specific consequences. What matters more than anything else is the degree of offense that each sin represents to God. In that sense, Dante does not abandon the biblical tradition of punishment, he expands on it, adding his own unique interpretation to create a series of unforgettable scenes in his most important work.