diff --git a/BaseClasses.py b/BaseClasses.py
index dfb7cded..60d18ac6 100644
--- a/BaseClasses.py
+++ b/BaseClasses.py
@@ -5,7 +5,7 @@ from enum import Enum, unique
 import logging
 import json
 from collections import OrderedDict, Counter, deque
-from typing import Union, Optional, List, Set, Dict
+from typing import Union, Optional, List, Set, Dict, NamedTuple
 import secrets
 import random
 
@@ -16,7 +16,7 @@ from Items import item_name_groups
 
 class World(object):
     debug_types = False
-    player_names: list
+    player_names: Dict[int, List[str]]
     _region_cache: dict
     difficulty_requirements: dict
     required_medallions: dict
@@ -135,6 +135,7 @@ class World(object):
             set_player_attr('sprite_pool', [])
             set_player_attr('dark_room_logic', "lamp")
             set_player_attr('restrict_dungeon_item_on_boss', False)
+            set_player_attr('plando_items', [])
 
     def secure(self):
         self.random = secrets.SystemRandom()
@@ -1037,6 +1038,9 @@ class Item(object):
         self.world = None
         self.player = player
 
+    def __eq__(self, other):
+        return self.name == other.name and self.player == other.player
+
     @property
     def crystal(self) -> bool:
         return self.type == 'Crystal'
@@ -1452,3 +1456,10 @@ class Spoiler(object):
                 path_listings.append("{}\n        {}".format(location, "\n   =>   ".join(path_lines)))
 
             outfile.write('\n'.join(path_listings))
+
+
+class PlandoItem(NamedTuple):
+    item: str
+    location: str
+    world: Union[bool, str] = False  # False -> own world, True -> not own world
+    from_pool: bool = True  # if item should be removed from item pool
diff --git a/EntranceRandomizer.py b/EntranceRandomizer.py
index 5c9ab56c..6c94351e 100755
--- a/EntranceRandomizer.py
+++ b/EntranceRandomizer.py
@@ -355,6 +355,10 @@ def parse_arguments(argv, no_defaults=False):
             parser.add_argument(f'--p{player}', default=defval(''), help=argparse.SUPPRESS)
 
     ret = parser.parse_args(argv)
+
+    # cannot be set through CLI currently
+    ret.plando_items = {}
+
     ret.glitch_boots = not ret.disable_glitch_boots
     if ret.timer == "none":
         ret.timer = False
@@ -382,9 +386,10 @@ def parse_arguments(argv, no_defaults=False):
                          'shufflebosses', 'enemy_shuffle', 'enemy_health', 'enemy_damage', 'shufflepots',
                          'ow_palettes', 'uw_palettes', 'sprite', 'disablemusic', 'quickswap', 'fastmenu', 'heartcolor',
                          'heartbeep', "skip_progression_balancing", "triforce_pieces_available",
-                         "triforce_pieces_required", "shop_shuffle",
+                         "triforce_pieces_required", "shop_shuffle", "plando_items",
                          'remote_items', 'progressive', 'dungeon_counters', 'glitch_boots', 'killable_thieves',
-                         'tile_shuffle', 'bush_shuffle', 'shuffle_prizes', 'sprite_pool', 'dark_room_logic', 'restrict_dungeon_item_on_boss',
+                         'tile_shuffle', 'bush_shuffle', 'shuffle_prizes', 'sprite_pool', 'dark_room_logic',
+                         'restrict_dungeon_item_on_boss',
                          'hud_palettes', 'sword_palettes', 'shield_palettes', 'link_palettes']:
                 value = getattr(defaults, name) if getattr(playerargs, name) is None else getattr(playerargs, name)
                 if player == 1:
diff --git a/Fill.py b/Fill.py
index 1212f6e0..a4ef61d9 100644
--- a/Fill.py
+++ b/Fill.py
@@ -54,7 +54,8 @@ def fill_restrictive(world, base_state: CollectionState, locations, itempool, si
                         for location in region.locations:
                             if location.item and not location.event:
                                 placements.append(location)
-
+                    # fill in name of world for item
+                    item_to_place.world = world
                     raise FillError(f'No more spots to place {item_to_place}, locations {locations} are invalid. '
                                     f'Already placed {len(placements)}: {", ".join(str(place) for place in placements)}')
 
@@ -128,9 +129,12 @@ def distribute_items_restrictive(world, gftower_trash=False, fill_locations=None
     world.random.shuffle(fill_locations)
 
     # Make sure the escape small key is placed first in standard with key shuffle to prevent running out of spots
-    progitempool.sort(
-        key=lambda item: 1 if item.name == 'Small Key (Hyrule Castle)' and world.mode[item.player] == 'standard' and
-                              world.keyshuffle[item.player] else 0)
+    standard_keyshuffle_players = {player for player, mode in world.mode.items() if mode == 'standard' and
+                                   world.keyshuffle[player] is True}
+    if standard_keyshuffle_players:
+        progitempool.sort(
+            key=lambda item: 1 if item.name == 'Small Key (Hyrule Castle)' and
+                                  item.player in standard_keyshuffle_players else 0)
 
     fill_restrictive(world, world.state, fill_locations, progitempool)
 
diff --git a/Main.py b/Main.py
index 39efede3..28218982 100644
--- a/Main.py
+++ b/Main.py
@@ -9,7 +9,7 @@ import time
 import zlib
 import concurrent.futures
 
-from BaseClasses import World, CollectionState, Item, Region, Location, Shop
+from BaseClasses import World, CollectionState, Item, Region, Location, PlandoItem
 from Items import ItemFactory, item_table, item_name_groups
 from Regions import create_regions, create_shops, mark_light_world_regions, lookup_vanilla_location_to_entrance
 from InvertedRegions import create_inverted_regions, mark_dark_world_regions
@@ -87,6 +87,7 @@ def main(args, seed=None):
     world.shuffle_prizes = args.shuffle_prizes.copy()
     world.sprite_pool = args.sprite_pool.copy()
     world.dark_room_logic = args.dark_room_logic.copy()
+    world.plando_items = args.plando_items.copy()
     world.restrict_dungeon_item_on_boss = args.restrict_dungeon_item_on_boss.copy()
 
     world.rom_seeds = {player: random.Random(world.random.randint(0, 999999999)) for player in range(1, world.players + 1)}
@@ -172,11 +173,50 @@ def main(args, seed=None):
 
     fill_prizes(world)
 
+    logger.info("Running Item Plando")
+
+    world_name_lookup = {world.player_names[player_id][0]: player_id for player_id in world.player_ids}
+
+    for player in world.player_ids:
+        placement: PlandoItem
+        for placement in world.plando_items[player]:
+            target_world: int = placement.world
+            if target_world is False or world.players == 1:
+                target_world = player  # in own world
+            elif target_world is True:  # in any other world
+                target_world = player
+                while target_world == player:
+                    target_world = world.random.randint(1, world.players + 1)
+            elif target_world is None:  # any random world
+                target_world = world.random.randint(1, world.players + 1)
+            elif type(target_world) == int:  # target world by player id
+                pass
+            else:  # find world by name
+                target_world = world_name_lookup[target_world]
+
+            location = world.get_location(placement.location, target_world)
+            if location.item:
+                raise Exception(f"Cannot place item into already filled location {location}.")
+            item = ItemFactory(placement.item, player)
+            if placement.from_pool:
+                try:
+                    world.itempool.remove(item)
+                except ValueError:
+                    logger.warning(f"Could not remove {item} from pool as it's already missing from it.")
+
+            if location.can_fill(world.state, item, False):
+                world.push_item(location, item, collect=False)
+                location.event = True  # flag location to be checked during fill
+                location.locked = True
+                logger.debug(f"Plando placed {item} at {location}")
+            else:
+                raise Exception(f"Can't place {item} at {location} due to fill condition not met.")
+
     logger.info('Placing Dungeon Items.')
 
-    shuffled_locations = None
-    if args.algorithm in ['balanced', 'vt26'] or any(list(args.mapshuffle.values()) + list(args.compassshuffle.values()) +
-                                                     list(args.keyshuffle.values()) + list(args.bigkeyshuffle.values())):
+    if args.algorithm in ['balanced', 'vt26'] or any(
+            list(args.mapshuffle.values()) + list(args.compassshuffle.values()) +
+            list(args.keyshuffle.values()) + list(args.bigkeyshuffle.values())):
         fill_dungeons_restrictive(world)
     else:
         fill_dungeons(world)
@@ -188,7 +228,7 @@ def main(args, seed=None):
     elif args.algorithm == 'vt25':
         distribute_items_restrictive(world, False)
     elif args.algorithm == 'vt26':
-        distribute_items_restrictive(world, True, shuffled_locations)
+        distribute_items_restrictive(world, True)
     elif args.algorithm == 'balanced':
         distribute_items_restrictive(world, True)
 
diff --git a/MultiMystery.py b/MultiMystery.py
index bc84dd57..237e432b 100644
--- a/MultiMystery.py
+++ b/MultiMystery.py
@@ -50,6 +50,7 @@ if __name__ == "__main__":
         player_files_path = multi_mystery_options["player_files_path"]
         target_player_count = multi_mystery_options["players"]
         race = multi_mystery_options["race"]
+        plando_options = multi_mystery_options["plando_options"]
         create_spoiler = multi_mystery_options["create_spoiler"]
         zip_roms = multi_mystery_options["zip_roms"]
         zip_diffs = multi_mystery_options["zip_diffs"]
@@ -104,7 +105,7 @@ if __name__ == "__main__":
 
         command = f"{basemysterycommand} --multi {target_player_count} {player_string} " \
                   f"--rom \"{rom_file}\" --enemizercli \"{enemizer_path}\" " \
-                  f"--outputpath \"{output_path}\" --teams {teams}"
+                  f"--outputpath \"{output_path}\" --teams {teams} --plando \"{plando_options}\""
 
         if create_spoiler:
             command += " --create_spoiler"
diff --git a/Mystery.py b/Mystery.py
index e44a3e48..3e7ab91c 100644
--- a/Mystery.py
+++ b/Mystery.py
@@ -7,6 +7,7 @@ import typing
 import os
 
 import ModuleUpdate
+from BaseClasses import PlandoItem
 
 ModuleUpdate.update()
 
@@ -44,10 +45,13 @@ def mystery_argparse():
     parser.add_argument('--create_diff', action="store_true")
     parser.add_argument('--yaml_output', default=0, type=lambda value: min(max(int(value), 0), 255),
                         help='Output rolled mystery results to yaml up to specified number (made for async multiworld)')
+    parser.add_argument('--plando', default="bosses",
+                        help='List of options that can be set manually. Can be combined, for example "bosses, items"')
 
     for player in range(1, multiargs.multi + 1):
         parser.add_argument(f'--p{player}', help=argparse.SUPPRESS)
     args = parser.parse_args()
+    args.plando: typing.Set[str] = {arg.strip().lower() for arg in args.plando.split(",")}
     return args
 
 
@@ -144,7 +148,8 @@ def main(args=None, callback=ERmain):
     if args.enemizercli:
         erargs.enemizercli = args.enemizercli
 
-    settings_cache = {k: (roll_settings(v) if args.samesettings else None) for k, v in weights_cache.items()}
+    settings_cache = {k: (roll_settings(v, args.plando) if args.samesettings else None)
+                      for k, v in weights_cache.items()}
     player_path_cache = {}
     for player in range(1, args.multi + 1):
         player_path_cache[player] = getattr(args, f'p{player}') if getattr(args, f'p{player}') else args.weights
@@ -167,7 +172,8 @@ def main(args=None, callback=ERmain):
         path = player_path_cache[player]
         if path:
             try:
-                settings = settings_cache[path] if settings_cache[path] else roll_settings(weights_cache[path])
+                settings = settings_cache[path] if settings_cache[path] else \
+                    roll_settings(weights_cache[path], args.plando)
                 if settings.sprite and not os.path.isfile(settings.sprite) and not Sprite.get_sprite_from_name(
                         settings.sprite):
                     logging.warning(
@@ -275,7 +281,13 @@ boss_shuffle_options = {None: 'none',
                         }
 
 
-def roll_settings(weights):
+def roll_percentage(percentage: typing.Union[int, float]) -> bool:
+    """Roll a percentage chance.
+    percentage is expected to be in range [0, 100]"""
+    return random.random() < (float(percentage) / 100)
+
+
+def roll_settings(weights, plando_options: typing.Set[str] = frozenset(("bosses"))):
     ret = argparse.Namespace()
     if "linked_options" in weights:
         weights = weights.copy()  # make sure we don't write back to other weights sets in same_settings
@@ -283,7 +295,7 @@ def roll_settings(weights):
             if "name" not in option_set:
                 raise ValueError("One of your linked options does not have a name.")
             try:
-                if random.random() < (float(option_set["percentage"]) / 100):
+                if roll_percentage(option_set["percentage"]):
                     logging.debug(f"Linked option {option_set['name']} triggered.")
                     logging.debug(f'Applying {option_set["options"]}')
                     new_options = set(option_set["options"]) - set(weights)
@@ -415,7 +427,7 @@ def roll_settings(weights):
 
     if boss_shuffle in boss_shuffle_options:
         ret.shufflebosses = boss_shuffle_options[boss_shuffle]
-    else:
+    elif "bosses" in plando_options:
         options = boss_shuffle.lower().split(";")
         remainder_shuffle = "none"  # vanilla
         bosses = []
@@ -427,6 +439,8 @@ def roll_settings(weights):
             else:
                 bosses.append(boss)
         ret.shufflebosses = ";".join(bosses + [remainder_shuffle])
+    else:
+        raise Exception(f"Boss Shuffle {boss_shuffle} is unknown and boss plando is turned off.")
 
     ret.enemy_shuffle = {'none': False,
                          'shuffled': 'shuffled',
@@ -534,6 +548,17 @@ def roll_settings(weights):
 
     ret.non_local_items = ",".join(ret.non_local_items)
 
+    ret.plando_items = []
+    if "items" in plando_options:
+        options = weights.get("plando_items", [])
+        for placement in options:
+            if roll_percentage(get_choice("percentage", placement, 100)):
+                item = get_choice("item", placement)
+                location = get_choice("location", placement)
+                from_pool = get_choice("from_pool", placement, True)
+                location_world = get_choice("world", placement, False)
+                ret.plando_items.append(PlandoItem(item, location, location_world, from_pool))
+
     if 'rom' in weights:
         romweights = weights['rom']
 
@@ -571,7 +596,7 @@ def roll_settings(weights):
         ret.sword_palettes = get_choice('sword_palettes', romweights, "default")
         ret.shield_palettes = get_choice('shield_palettes', romweights, "default")
         ret.link_palettes = get_choice('link_palettes', romweights, "default")
-        
+
     else:
         ret.quickswap = True
         ret.sprite = "Link"
diff --git a/Utils.py b/Utils.py
index 7d17da6f..1967b9d7 100644
--- a/Utils.py
+++ b/Utils.py
@@ -1,10 +1,12 @@
 from __future__ import annotations
+
 import typing
 
 
 def tuplize_version(version: str) -> typing.Tuple[int, ...]:
     return Version(*(int(piece, 10) for piece in version.split(".")))
 
+
 class Version(typing.NamedTuple):
     major: int
     minor: int
@@ -42,11 +44,11 @@ def int32_as_bytes(value):
 
 
 def pc_to_snes(value):
-    return ((value<<1) & 0x7F0000)|(value & 0x7FFF)|0x8000
+    return ((value << 1) & 0x7F0000) | (value & 0x7FFF) | 0x8000
 
 
 def snes_to_pc(value):
-    return ((value & 0x7F0000)>>1)|(value & 0x7FFF)
+    return ((value & 0x7F0000) >> 1) | (value & 0x7FFF)
 
 
 def parse_player_names(names, players, teams):
@@ -87,6 +89,7 @@ def local_path(*path):
 
     return os.path.join(local_path.cached_path, *path)
 
+
 local_path.cached_path = None
 
 
@@ -98,8 +101,10 @@ def output_path(*path):
     os.makedirs(os.path.dirname(path), exist_ok=True)
     return path
 
+
 output_path.cached_path = None
 
+
 def open_file(filename):
     if sys.platform == 'win32':
         os.startfile(filename)
@@ -107,9 +112,10 @@ def open_file(filename):
         open_command = 'open' if sys.platform == 'darwin' else 'xdg-open'
         subprocess.call([open_command, filename])
 
+
 def close_console():
     if sys.platform == 'win32':
-        #windows
+        # windows
         import ctypes.wintypes
         try:
             ctypes.windll.kernel32.FreeConsole()
@@ -143,6 +149,7 @@ class Hint(typing.NamedTuple):
     def __hash__(self):
         return hash((self.receiving_player, self.finding_player, self.location, self.item, self.entrance))
 
+
 def get_public_ipv4() -> str:
     import socket
     import urllib.request
@@ -158,6 +165,7 @@ def get_public_ipv4() -> str:
             pass  # we could be offline, in a local game, so no point in erroring out
     return ip
 
+
 def get_public_ipv6() -> str:
     import socket
     import urllib.request
@@ -173,56 +181,56 @@ def get_public_ipv6() -> str:
 
 def get_default_options() -> dict:
     if not hasattr(get_default_options, "options"):
-        options = dict()
-
         # Refer to host.yaml for comments as to what all these options mean.
-        generaloptions = dict()
-        generaloptions["rom_file"] = "Zelda no Densetsu - Kamigami no Triforce (Japan).sfc"
-        generaloptions["qusb2snes"] = "QUsb2Snes\\QUsb2Snes.exe"
-        generaloptions["rom_start"] = True
-        generaloptions["output_path"] = "output"
-        options["general_options"] = generaloptions
+        options = {
+            "general_options": {
+                "rom_file": "Zelda no Densetsu - Kamigami no Triforce (Japan).sfc",
+                "qusb2snes": "QUsb2Snes\\QUsb2Snes.exe",
+                "rom_start": True,
+                "output_path": "output",
+            },
+            "server_options": {
+                "host": None,
+                "port": 38281,
+                "password": None,
+                "multidata": None,
+                "savefile": None,
+                "disable_save": False,
+                "loglevel": "info",
+                "server_password": None,
+                "disable_item_cheat": False,
+                "location_check_points": 1,
+                "hint_cost": 1000,
+                "forfeit_mode": "goal",
+                "remaining_mode": "goal",
+                "auto_shutdown": 0,
+                "compatibility": 2,
+            },
+            "multi_mystery_options": {
+                "teams": 1,
+                "enemizer_path": "EnemizerCLI/EnemizerCLI.Core.exe",
+                "player_files_path": "Players",
+                "players": 0,
+                "weights_file_path": "weights.yaml",
+                "meta_file_path": "meta.yaml",
+                "player_name": "",
+                "create_spoiler": 1,
+                "zip_roms": 0,
+                "zip_diffs": 2,
+                "zip_spoiler": 0,
+                "zip_multidata": 1,
+                "zip_format": 1,
+                "race": 0,
+                "cpu_threads": 0,
+                "max_attempts": 0,
+                "take_first_working": False,
+                "keep_all_seeds": False,
+                "log_output_path": "Output Logs",
+                "log_level": None,
+                "plando_options": "bosses",
+            }
+        }
 
-        serveroptions = dict()
-        serveroptions["host"] = None
-        serveroptions["port"] = 38281
-        serveroptions["password"] = None
-        serveroptions["multidata"] = None
-        serveroptions["savefile"] = None
-        serveroptions["disable_save"] = False
-        serveroptions["loglevel"] = "info"
-        serveroptions["server_password"] = None
-        serveroptions["disable_item_cheat"] = False
-        serveroptions["location_check_points"] = 1
-        serveroptions["hint_cost"] = 1000
-        serveroptions["forfeit_mode"] = "goal"
-        serveroptions["remaining_mode"] = "goal"
-        serveroptions["auto_shutdown"] = 0
-        serveroptions["compatibility"] = 2
-        options["server_options"] = serveroptions
-
-        multimysteryoptions = dict()
-        multimysteryoptions["teams"] = 1
-        multimysteryoptions["enemizer_path"] = "EnemizerCLI/EnemizerCLI.Core.exe"
-        multimysteryoptions["player_files_path"] = "Players"
-        multimysteryoptions["players"] = 0
-        multimysteryoptions["weights_file_path"] = "weights.yaml"
-        multimysteryoptions["meta_file_path"] = "meta.yaml"
-        multimysteryoptions["player_name"] = ""
-        multimysteryoptions["create_spoiler"] = 1
-        multimysteryoptions["zip_roms"] = 0
-        multimysteryoptions["zip_diffs"] = 2
-        multimysteryoptions["zip_spoiler"] = 0
-        multimysteryoptions["zip_multidata"] = 1
-        multimysteryoptions["zip_format"] = 1
-        multimysteryoptions["race"] = 0
-        multimysteryoptions["cpu_threads"] = 0
-        multimysteryoptions["max_attempts"] = 0
-        multimysteryoptions["take_first_working"] = False
-        multimysteryoptions["keep_all_seeds"] = False
-        multimysteryoptions["log_output_path"] = "Output Logs"
-        multimysteryoptions["log_level"] = None
-        options["multi_mystery_options"] = multimysteryoptions
         get_default_options.options = options
     return get_default_options.options
 
@@ -254,6 +262,7 @@ def update_options(src: dict, dest: dict, filename: str, keys: list) -> dict:
                 dest[key] = update_options(value, dest[key], filename, new_keys)
     return dest
 
+
 def get_options() -> dict:
     if not hasattr(get_options, "options"):
         locations = ("options.yaml", "host.yaml",
@@ -326,7 +335,7 @@ def get_adjuster_settings(romfile: str) -> typing.Tuple[str, bool]:
 
         if hasattr(get_adjuster_settings, "adjust_wanted"):
             adjust_wanted = getattr(get_adjuster_settings, "adjust_wanted")
-        elif persistent_load().get("adjuster", {}).get("never_adjust", False): # never adjust, per user request
+        elif persistent_load().get("adjuster", {}).get("never_adjust", False):  # never adjust, per user request
             return romfile, False
         else:
             adjust_wanted = input(f"Last used adjuster settings were found. Would you like to apply these? \n"
@@ -350,7 +359,6 @@ def get_adjuster_settings(romfile: str) -> typing.Tuple[str, bool]:
     return romfile, False
 
 
-
 class ReceivedItem(typing.NamedTuple):
     item: int
     location: int
diff --git a/WebHostLib/check.py b/WebHostLib/check.py
index a6aaa85c..86d79b02 100644
--- a/WebHostLib/check.py
+++ b/WebHostLib/check.py
@@ -73,7 +73,7 @@ def roll_options(options: Dict[str, Union[dict, str]]) -> Tuple[Dict[str, Union[
             results[filename] = f"Failed to parse YAML data in {filename}: {e}"
         else:
             try:
-                rolled_results[filename] = roll_settings(yaml_data)
+                rolled_results[filename] = roll_settings(yaml_data, plando_options={"bosses"})
             except Exception as e:
                 results[filename] = f"Failed to generate mystery in {filename}: {e}"
             else:
diff --git a/host.yaml b/host.yaml
index 13550f14..dc59c4ef 100644
--- a/host.yaml
+++ b/host.yaml
@@ -99,3 +99,6 @@ multi_mystery_options:
   zip_format: 1
   # Create encrypted race roms
   race: 0
+  # List of options that can be plando'd. Can be combined, for example "bosses, items"
+  # Available options: bosses
+  plando_options: "bosses"