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I'm Playing All Sides
Ensure that you always come out on top by turning in Obsidian Keys to each of these individuals at the Obsidian Citadel.
I'm Playing All Sides requires you to turn in Restored Obsidian Keys to four specific NPCs at the Obsidian Citadel in Waking Shores: Sabellian, Igys, Wrathion, and Bazentus.
Craft Restored Obsidian Keys
Kill mobs in the Obsidian Citadel area to collect 
Key Fragments and 
Key Framing, then combine 30 Key Fragments and 3 Key Framing fragments to create one 
Restored Obsidian Key. You will need at least 4 keys total for this achievement.
Pledge and Turn In to First Dragon
Choose either Sabellian or Wrathion by pledging allegiance via the Allegiance to One weekly quest, then turn in a Restored Obsidian Key to your chosen dragon. You must complete this step before the second NPC in each pair becomes interactable.
Turn In to Second NPC in Pair
If you started with Sabellian, turn in a key to Igys next. If you started with Wrathion, turn in a key to Bazentus next. You cannot interact with Igys until you have first turned in to Sabellian, and the same order applies for Wrathion and Bazentus.
Complete the Other Pair
Turn in a key to the remaining dragon (Wrathion or Sabellian) and then immediately turn in a key to their corresponding second NPC (Bazentus or Igys) without logging out, completing the sequence Sabellian > Igys > Wrathion > Bazentus or Wrathion > Bazentus > Sabellian > Igys to trigger the achievement.
Tips
Do not log out between key turn-ins, as progress for Igys and Forgemaster resets on relog and you must complete all four turn-ins in a single session.