I’ve enjoyed my stay in the guilds I’ve been in, but the Mok’lohn Command was the best out of them all. My first major guild. I am glad to see it making a comeback too!
The Sunwarders will always have a special place in my memories of AD. It was my first serious foray into guild RP and one that I still recall with fondness.
Runner-up is a bit of a cheat, seeing as I wasn’t in it myself, but interacted with them often enough that their roster influenced my time IC quite a bit. The “FFS Stormdogs” Stormguard.
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It has to be the Lost Soul when it was still alive. It’s GM sadly does not play anymore but we became really good friends, and when events were still held, it was honestly one of the best times I’ve had. Now the guild is sadly dead and I’m just running around in it still because I am honestly rather hesitant about joining other guilds ( the one time I did finally join another one, the Sons of Thaurissan, it sadly died).
Sadly, it is a relic now the name I hold but, ‘The Light Watch’, also known as ‘The Light Watch Order’.
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There’s a few that stick out in my mind, and several that I didn’t appreciate as much as I should have at the time, but here’s the biggest two for me:
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Lionheart
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The Sanguine Eye
Honourable mentions to the Silver Company and the Ashen Company.
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How could it not be? Over the past 10 months, I’ve had so much fun and been so inspired to RP every single day.
And to think it might not have happened if I hadn’t thought ‘Maybe I’ll play that one alt I haven’t touched in years…’
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I’d go for a close one between (early) Bladecrest Sentinels, Sixty Thieves & Myrmidon
Silver Archaeology Company, hands down. I was only in it for about a month before they went on hiatus, but it was the best I’ve tried before or since.
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The Steel Gauntlet in 2016. Encountered some of the best roleplayers there.
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Wardens of Azeroth.
Colton’s Red Company.
And The Stormguard, of course.
I was in the guild at the same time. I don’t recognize your name though!
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Eventide Initiative. However sadly the guild fall to pieces and as in my cases before drama time happened. While it lasted however, and lasted for strong year and a half or so for me, it was the best RP guild I ever had. The most complex and intriguing stories and campaigns I was part of took place there. The storytelling was so incredible I still can’t get over it. Each action taken on events had impact and mattered in addition to sick combat system and small - tight knit group it felt like being part of D&D sessions.
I loved how close to WoW story they sticked, we went all the way to Argus and back with epic victories and dreadfull fails.
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I was Jeyssa, not sure how memorable I were 
Either Hand of Conquest or the Order of Oronaar.
NEXT.
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I think I may have been in the Steel Gauntlet back in 2016 too, albeit only briefly.
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Ellesencia. 
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Its moreso the core group of friends I made but definately the Arcane Circle.
I had a very good time in Tilted Coin when it was going good.
The Office of Allegiance and Elluinae on Horde circa Cata/MoP and Onyx Vanguard on Alliance (not to be confused with the later created Tesco-variant the Onyxguard) were good times.
Ignoring the guilds I personally led, it’d be the Stormwind Irregulars when it was led by the late Demlock Cratus. It was my first real role-playing guild, especially a military one and it was just a great introduction to this side of the world and especially fun with the concept of being a penal military unit, adding that extra element of uncertainty working alongside ‘former’ cutthroats and villains.
The Red Company was fantastic for individual character interactions, though wasn’t without faults. In terms of raw investment of time, that was where I found some of my best moments in RP.
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