diff --git a/mods/randomizer/generator/logic/item_pool.cpp b/mods/randomizer/generator/logic/item_pool.cpp
index 8eb2d31048..30eaa7d82d 100644
--- a/mods/randomizer/generator/logic/item_pool.cpp
+++ b/mods/randomizer/generator/logic/item_pool.cpp
@@ -299,10 +299,10 @@ namespace randomizer::logic::item_pool
             itemPool.erase("Gerudo Desert Bulblin Camp Key");
         }
 
-        // Remove sky book characters if we're starting with the sky canon open
+        // Remove all but 1 sky book characters if we're starting with the sky canon open
         if (world->Setting("City Does Not Require Filled Skybook") == "On")
         {
-            itemPool.erase("Progressive Sky Book");
+            itemPool["Progressive Sky Book"] = 1;
         }
 
         // Remove Small Keys if we're playing without them
diff --git a/mods/randomizer/generator/logic/world.cpp b/mods/randomizer/generator/logic/world.cpp
index 1a7a8bfe24..63c1a0c3ee 100644
--- a/mods/randomizer/generator/logic/world.cpp
+++ b/mods/randomizer/generator/logic/world.cpp
@@ -679,10 +679,6 @@ namespace randomizer::logic::world
                   (this->Setting("Big Keys") == "Keysy" && originalItem->IsBigKey()) ||
                   (this->Setting("Maps and Compasses") == "Start With" &&
                    (originalItem->IsDungeonMap() || originalItem->IsCompass())))) ||
-                // Sky Characters are not randomized, but City in the Sky doesn't require Sky Book Characters (Sky characters
-                // shouldn't exist)
-                (this->Setting("Sky Characters") == "Off" && this->Setting("City Does Not Require Filled Skybook") == "On" &&
-                 location->HasCategories("Sky Character")) ||
                 // We're starting with a shop item, but shop items aren't randomized
                 (this->Setting("Shop Items") == "Off" && location->HasCategories("Shop") &&
                  utility::container::ElementInContainer(this->_startingItemPool, originalItem)))