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No bosses should not always drop their rare item. For one this server isn't like others where they include torva sets, chaotic weapons and the primal items thus making a 100% for a rare drop every kill would kill this servers longevity since only a select few OS items are available.
And I can understand the frustration in not looting a rare item after long hours spent on a dry spell as the only rare drops I have ever gotten were 2 black masks and a godsword shard.
But having 100% chance for drops would kill the server.
