Elden Ring Nightreign‘s procedurally generated Expeditions offer players plenty of ways to strengthen their chosen character and acquire new equipment and power. These include Forts filled with soldiers, forts manned by deadly golem archers, and broken chapels inhabited by misbegotten, flame monks, or envoys.
Something you’ll see on every map is the plain grey circles that indicate the locations of Elden Ring Nightreign‘s Evergaols. These prisons for deadly foes must be opened using Stonesword Keys, releasing a boss that offers a powerful boon when defeated. Certain Evergaols contain much stronger foes than usual, and proportionally better rewards, and it is these you’ll need to track down to earn the Old Gaol achievement.

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Which Evergaol Bosses Count for the Oldest Gaol Achievement in Elden Ring Nightreign
Only the toughest of the Evergaol Bosses count toward the Oldest Gaol Achievement, and these are the same bosses that grant 30k Runes from their “Rune of the Strong” reward option. Only three Evergaol Bosses seem to count as “Oldest Gaol” bosses, those being the Godskin Duo, the Ancient Dragon, and the Deathrite Bird. Naturally, all three of these bosses have a lot of health and can be incredibly tough to take on, especially if you’re playing solo, so you should prepare before opening the Evergaols on the map by leveling up and acquiring strong weapons from other locations on the map.
How to Find the Oldest Gaol in Elden Ring Nightreign
For the best chances of success, it’s probably worth opening multiple Evergaols on Night 2, ideally after hitting level 10. Check where the Evergaols on the map are, and only open them on night 1 if you’re confident in the strength of yourself and your team so you won’t waste keys only to end up running from the boss inside. Spend Night 1 gathering resources (especially Stonesword Keys), and try to get a +2 weapon and a couple of Flask charges before facing the Night 1 boss. Once the Night 1 boss is down, head for the Evergaols on the outskirts of the map first and work your way inward after clearing them out.
With a bit of luck, you’ll track down one of the Oldest Gaol Bosses pretty quickly, as long as you’re fast at clearing out the Evergaols. However, if you still need to gather resources to help against the Nightlord, you should probably prioritise that first, especially if you’re playing online via matchmaking. Once you find the Oldest Gaol, clear out the boss inside to get the achievement and some hard-earned runes.
The easiest of the three potential Oldest Evergaol Bosses is the Deathrite Bird, especially if you’ve picked up a Holy Weapon since they can shred through its health bar. The Ancient Dragon is particularly vulnerable to big AOE attacks that hit multiple times and can stagger it (Flame of Frenzy, Rock Sling, Ancient Dragon Lightning Strike, and Burn, O Flame! are great for this.) The Godskin Duo is a huge pain, but you can shred them quickly if you have access to status effects like bleed and frostbite to chunk their health bars.