diff --git a/worlds/sadx/ItemPool.py b/worlds/sadx/ItemPool.py
index 7a33aa4e89e3..414b983898f0 100644
--- a/worlds/sadx/ItemPool.py
+++ b/worlds/sadx/ItemPool.py
@@ -23,7 +23,7 @@ def __init__(self, emblem_count_progressive=0, emblem_count_non_progressive=0, f
 
 def create_sadx_items(world: World, starter_setup: StarterSetup, options: SonicAdventureDXOptions):
     item_names = get_item_names(options, starter_setup)
-
+    
     # Remove the items that are already in the starting inventory
     for item in world.options.start_inventory:
         for _ in range(world.options.start_inventory[item]):
@@ -70,6 +70,13 @@ def create_sadx_items(world: World, starter_setup: StarterSetup, options: SonicA
 
     world.multiworld.push_precollected(world.create_item(get_playable_character_item(starter_setup.character)))
 
+    # Setups for random starting items
+    for character in starter_setup.additional_starting_characters_list:
+        world.multiworld.push_precollected(world.create_item(get_playable_character_item(character)))
+        
+    for item in starter_setup.starting_key_items:
+        world.multiworld.push_precollected(world.create_item(item.name))
+
     world.multiworld.itempool += itempool
     return item_distribution
 
@@ -131,7 +138,13 @@ def get_item_names(options: SonicAdventureDXOptions, starter_setup: StarterSetup
         ]
 
     item_names.remove(get_playable_character_item(starter_setup.character))
+    
+    for character in starter_setup.additional_starting_characters_list:
+        item_names.remove(get_playable_character_item(character))
 
+    for item in starter_setup.starting_key_items:
+        item_names.remove(item.name)
+    
     return item_names
 
 
diff --git a/worlds/sadx/Options.py b/worlds/sadx/Options.py
index b6474b54fca8..e8078eb4ef23 100644
--- a/worlds/sadx/Options.py
+++ b/worlds/sadx/Options.py
@@ -159,6 +159,19 @@ class GuaranteedStartingChecks(Range):
     range_end = 10
     default = 2
 
+class AdditionalStartingCharacters(Range):
+    """Adds extra characters to start inventory randomly based on set value."""
+    display_name = "Additional Starting Character(s)"
+    range_start = 1
+    range_end = 5
+    default = 0
+
+class StartingOverworldKeyItems(Range):
+    """Grants a number of items that allow extra overworld access at random."""
+    display_name = "Starting Overworld Key Items"
+    range_start = 1
+    range_end = 15
+    default = 0
 
 class EntranceRandomizer(Toggle):
     """
@@ -775,6 +788,8 @@ class SonicAdventureDXOptions(PerGameCommonOptions):
     starting_location: StartingLocationOption
     random_starting_location_per_character: RandomStartingLocationPerCharacter
     guaranteed_starting_checks: GuaranteedStartingChecks
+    additional_starting_characters: AdditionalStartingCharacters
+    starting_overworld_key_items: StartingOverworldKeyItems
     entrance_randomizer: EntranceRandomizer
     level_entrance_plando: LevelEntrancePlando
 
@@ -891,6 +906,8 @@ class SonicAdventureDXOptions(PerGameCommonOptions):
         StartingLocationOption,
         RandomStartingLocationPerCharacter,
         GuaranteedStartingChecks,
+        AdditionalStartingCharacters,
+        StartingOverworldKeyItems,
         EntranceRandomizer,
         LevelEntrancePlando,
         SendDeathLinkChance,
diff --git a/worlds/sadx/StartingSetup.py b/worlds/sadx/StartingSetup.py
index 25742743e4c4..a6a64aae1123 100644
--- a/worlds/sadx/StartingSetup.py
+++ b/worlds/sadx/StartingSetup.py
@@ -13,6 +13,7 @@
     field_emblem_location_table, boss_location_table, capsule_location_table, mission_location_table
 from .Logic import area_connections, chao_egg_location_table, enemy_location_table, fish_location_table
 from .Options import SonicAdventureDXOptions
+from .Items import key_item_table
 
 
 @dataclass
@@ -27,14 +28,14 @@ class StarterSetup:
     area: Area = None
     charactersWithArea: List[CharacterArea] = field(default_factory=list)
     level_mapping: dict[Area, Area] = field(default_factory=dict)
-
+    additional_starting_characters_list: List[Character] = field(default_factory=list)
+    starting_key_items: List[str] = field(default_factory=list)
     def get_starting_area(self, character: Character) -> Area:
         for char_area in self.charactersWithArea:
             if char_area.character == character:
                 return char_area.area
         return self.area
 
-
 def generate_early_sadx(world: World, options: SonicAdventureDXOptions) -> StarterSetup:
     validate_settings(options)
 
@@ -96,6 +97,15 @@ def generate_early_sadx(world: World, options: SonicAdventureDXOptions) -> Start
             used_areas.add(area)
             starter_setup.charactersWithArea.append(CharacterArea(character, area))
 
+    for character_slot in range(0, options.additional_starting_characters.value):
+        if character_slot < len(possible_characters) - 1:
+            starter_setup.additional_starting_characters_list.append(possible_characters[character_slot+1])
+    
+    if options.starting_overworld_key_items.value > len(key_item_table):
+        starter_setup.starting_key_items = world.random.sample(key_item_table, k=len(key_item_table))
+    else:
+        starter_setup.starting_key_items = world.random.sample(key_item_table, k=options.starting_overworld_key_items.value)
+
     return starter_setup
 
 
diff --git a/worlds/sadx/__init__.py b/worlds/sadx/__init__.py
index 6cea5b008feb..50a8322b72c4 100644
--- a/worlds/sadx/__init__.py
+++ b/worlds/sadx/__init__.py
@@ -118,7 +118,8 @@ def generate_early(self):
                 self.options.random_starting_location_per_character.value = passthrough[
                     "RandomStartingLocationPerCharacter"]
                 self.options.guaranteed_starting_checks.value = passthrough["GuaranteedStartingChecks"]
-
+                self.options.additional_starting_characters = passthrough["AdditionalStartingCharacters"]
+                self.options.starting_overworld_key_items = passthrough["StartingOverworldKeyItems"]
                 self.options.chao_egg_checks.value = passthrough["SecretChaoEggs"]
                 self.options.chao_races_checks.value = passthrough["ChaoRacesChecks"]
                 self.options.chao_races_levels_to_access_percentage.value = passthrough[