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Upright Citizens
Recruit three extra citizens during the Assault quest "Not Too Sober Citizens Brigade".
Upright Citizens requires you to recruit three extra citizens during the Assault quest 'Not Too Sober Citizens Brigade' in Tiragarde Sound, rewarding the 
Citizens Brigade Whistle toy upon completion.
Wait for Tiragarde Assault
This achievement is only obtainable while the quest 'Not Too Sober Citizens Brigade' is active during a Horde Assault on Tiragarde Sound. The quest is not guaranteed to appear during every Assault — which quests are active is random, so check for it each time an Assault is up.
Locate the Spawned NPC
Only one of three named NPCs spawns per Assault event. Use the macro '/tar Russel the Bard /tar Flynn Fairwind /tar Leeroy Jenkins /script SetRaidTarget("target",8)' to quickly identify which one is present. Flynn Fairwind can be found at 72.24, 61.68 in Boralus, Leeroy Jenkins at 66.8, 64.1 in Boralus (Mariners Row), and Russel the Bard at 72.7, 69.2 in Boralus.
Repeat Across Multiple Assaults
Since only one of the three NPCs — Flynn Fairwind, Leeroy Jenkins, or Russel the Bard — appears per Assault, and the quest itself is not always selected, completing this achievement requires a minimum of three separate Tiragarde Sound Assault events where the quest is active and a different NPC spawns each time. Track upcoming Tiragarde Sound Assault schedules using an external timer site to avoid missing events at inconvenient times.
Tips
The three NPCs rotate across separate Assault events rather than all appearing in one — you need each of the three at least once, requiring at least three qualifying Assault events to complete the achievement.
Use the targeting macro in Step 2 immediately upon the Assault starting to confirm which NPC is present before investing time in the event.