The penal system in Skyrim is nearly uniform across the game world's nine Holds, where shockingly short sentence lengths indicate there may be a systemic issue with the province's prison population. Even the most heinous crimes committed by the player only land them in one of the region's small prisons for only a week. Avoiding sentencing of any kind by paying a fine regardless of crime committed is a questionable legal policy, but it may actually be an unfortunate result of a prison system constantly flooded with inmates.
Although it was likely designed so that it didn't inhibit gameplay, Skyrim's prison system doesn't make any sense in the ways criminals are punished. Being able to exonerate oneself by paying a fine to the first guard to arrive on the scene essentially makes any crime legal for the upper class, given they are willing to literally pay the price. Beyond that, it is impossible for the player to be given a sentence that exceeds seven days. The Dragonborn going on a killing spree and nearly wiping out an entire city only gets them locked up for a week at most.
One of the few plausible explanations for such a confounding penal system is that the province of Skyrim is so littered with crime that prison populations are exceedingly high, so the prisons themselves have effectively been operating on revolving door policies. The prominence of the Thieves Guild in Skyrim is good evidence for how little control the government has over its rampant crime issue. So many prisoners must be coming into the system that the guards have no choice but to cap sentences at seven days, lest the prisons become overcrowded.
Skyrim's Prison System May Be Suffering From Tax Theft
Prisoners are an expensive burden on the state; each one must be housed, clothed, and fed while generating little to no value for the local economy. Money to run the prisons likely comes from taxation, but the ones in Skyrim are mostly small and managed by few guards. With crime seemingly a widespread issue, it's almost like the prisons are purposefully made inadequate. Instead of the state performing its due diligence in holding criminal offenders, it seems to be doing the bare minimum. Skyrim lets players be the bad guy to a point, but never severely punishes them for it - so where has all the tax money gone?
Somewhere along the chain of command, the funding to properly deal with the province's crime has apparently dwindled. The Jarls occupy lavish homes, and every city has an extensive security force filled with well-equipped guards ready to cut down criminals rather than rehabilitate them. Fines seem as though they'd be a popular alternative to jail time, yet none of the incarceration facilities seem to benefit from that extra cashflow either. Open warfare has likely exacerbated social issues in the province, but criminal activity in Skyrim receives only the bare minimum attention from the state.
