diff --git a/Content.Server/Parkstation/Slippery/DropOnSlipComponent.cs b/Content.Server/Parkstation/Slippery/DropOnSlipComponent.cs
new file mode 100644
index 0000000000..18b9191e0c
--- /dev/null
+++ b/Content.Server/Parkstation/Slippery/DropOnSlipComponent.cs
@@ -0,0 +1,15 @@
+namespace Content.Server.Parkstation.Slippery;
+
+/// <summary>
+///     Marks this item as one that may be dropped when its wearer slips with it equipped.
+/// </summary>
+[RegisterComponent]
+public sealed partial class DropOnSlipComponent : Component
+{
+    /// <summary>
+    ///     Percent chance to drop this item when slipping
+    /// </summary>
+    [DataField("chance")]
+    [ViewVariables(VVAccess.ReadWrite)]
+    public int Chance = 20;
+}
diff --git a/Content.Server/Parkstation/Slippery/DropOnSlipSystem.cs b/Content.Server/Parkstation/Slippery/DropOnSlipSystem.cs
new file mode 100644
index 0000000000..88f77aeb61
--- /dev/null
+++ b/Content.Server/Parkstation/Slippery/DropOnSlipSystem.cs
@@ -0,0 +1,96 @@
+using System.Numerics;
+using Content.Server.Popups;
+using Content.Shared.Administration.Logs;
+using Content.Shared.Database;
+using Content.Shared.Interaction.Components;
+using Content.Shared.Inventory;
+using Content.Shared.Popups;
+using Content.Shared.Slippery;
+using Content.Shared.Throwing;
+using Robust.Shared.Physics.Components;
+using Robust.Shared.Physics.Systems;
+using Robust.Shared.Random;
+
+namespace Content.Server.Parkstation.Slippery;
+
+public sealed class DropOnSlipSystem : EntitySystem
+{
+    [Dependency] private readonly ISharedAdminLogManager _adminLogger = default!;
+    [Dependency] private readonly PopupSystem _popup = default!;
+    [Dependency] private readonly IRobustRandom _random = default!;
+    [Dependency] private readonly InventorySystem _inventory = default!;
+    [Dependency] private readonly SharedPhysicsSystem _physics = default!;
+    [Dependency] private readonly ThrowingSystem _throwing = default!;
+
+    public float PocketDropChance = 10f;
+    public float PocketThrowChance = 5f;
+
+    public float ClumsyDropChance = 5f;
+    public float ClumsyThrowChance = 90f;
+
+
+    public override void Initialize()
+    {
+        base.Initialize();
+
+        SubscribeLocalEvent<InventoryComponent, ParkSlipEvent>(HandleSlip);
+    }
+
+
+    private void HandleSlip(EntityUid entity, InventoryComponent invComp, ParkSlipEvent args)
+    {
+        if (!_inventory.TryGetSlots(entity, out var slotDefinitions))
+            return;
+
+        foreach (var slot in slotDefinitions)
+        {
+            if (!_inventory.TryGetSlotEntity(entity, slot.Name, out var item))
+                continue;
+
+            if (ShouldBeDropped(entity, slot, item))
+            {
+                var popupString = Loc.GetString("system-drop-on-slip-text-component", ("name", entity), ("item", item));
+
+                Drop(entity, item.Value, slot.Name, popupString);
+            }
+        }
+    }
+
+    private bool ShouldBeDropped(EntityUid entity, SlotDefinition slot, EntityUid? item)
+    {
+        // Check for any items in pockets or other criteria
+        if (slot.SlotFlags == SlotFlags.POCKET && _random.NextFloat(0, 100) < PocketDropChance)
+            return true;
+
+        // Check for DropOnSlipComponent
+        if (EntityManager.TryGetComponent<Parkstation.Slippery.DropOnSlipComponent>(item, out var dropComp) && _random.NextFloat(0, 100) < dropComp.Chance)
+            return true;
+
+        // Check for ClumsyComponent
+        if (slot.Name != "jumpsuit" && _random.NextFloat(0, 100) < ClumsyDropChance && HasComp<ClumsyComponent>(entity))
+            return true;
+
+        return false;
+    }
+
+    private void Drop(EntityUid entity, EntityUid item, string slot, string popupString)
+    {
+        if (!_inventory.TryUnequip(entity, slot, false, true))
+            return;
+
+        EntityManager.TryGetComponent<PhysicsComponent>(entity, out var entPhysComp);
+
+        if (entPhysComp != null)
+        {
+            var strength = entPhysComp.LinearVelocity.Length() / 1.5f;
+            Vector2 direction = new Vector2(_random.Next(-8, 8), _random.Next(-8, 8));
+
+            _throwing.TryThrow(item, direction, strength, entity);
+        }
+
+        _popup.PopupEntity(popupString, item, PopupType.MediumCaution);
+
+        var logMessage = Loc.GetString("system-drop-on-slip-log", ("entity", ToPrettyString(entity)), ("item", ToPrettyString(item)));
+        _adminLogger.Add(LogType.Slip, LogImpact.Low, $"{logMessage}");
+    }
+}
diff --git a/Content.Shared/Slippery/SlipperySystem.cs b/Content.Shared/Slippery/SlipperySystem.cs
index d20495cfa6..b97c93c2e3 100644
--- a/Content.Shared/Slippery/SlipperySystem.cs
+++ b/Content.Shared/Slippery/SlipperySystem.cs
@@ -101,6 +101,8 @@ private void TrySlip(EntityUid uid, SlipperyComponent component, EntityUid other
 
         _stun.TryParalyze(other, TimeSpan.FromSeconds(component.ParalyzeTime), true);
 
+        RaiseLocalEvent(other, new ParkSlipEvent(uid)); // Parkstation-DropOnSlip
+
         // Preventing from playing the slip sound when you are already knocked down.
         if (playSound)
         {
@@ -131,3 +133,10 @@ public record struct SlipCausingAttemptEvent (bool Cancelled);
 /// <param name="Slipped">The entity being slipped</param>
 [ByRefEvent]
 public readonly record struct SlipEvent(EntityUid Slipped);
+
+// Parkstation-DropOnSlip-Start
+/// <summary>
+///     This is an event raised on an entity after they slip. Duh.
+/// </summary>
+public readonly record struct ParkSlipEvent(EntityUid Tripper);
+// Parkstation-DropOnSlip-End
diff --git a/Resources/Locale/en-US/parkstation/Content/Slippery/dropOnSlip.ftl b/Resources/Locale/en-US/parkstation/Content/Slippery/dropOnSlip.ftl
new file mode 100644
index 0000000000..518e2028e6
--- /dev/null
+++ b/Resources/Locale/en-US/parkstation/Content/Slippery/dropOnSlip.ftl
@@ -0,0 +1,5 @@
+system-drop-on-slip-text-component = {$name}'s {$item} slips off!
+system-drop-on-slip-text-pocket = Something falls out of {$name}'s pocket!
+system-drop-on-slip-text-clumsy = The {$item} tumbles off of {$name}!
+
+system-drop-on-slip-log = {$entity} dropped {$item} when slipping.
diff --git a/Resources/Prototypes/Entities/Clothing/Ears/headsets.yml b/Resources/Prototypes/Entities/Clothing/Ears/headsets.yml
index df160f8e5a..04a22a4f7b 100644
--- a/Resources/Prototypes/Entities/Clothing/Ears/headsets.yml
+++ b/Resources/Prototypes/Entities/Clothing/Ears/headsets.yml
@@ -26,6 +26,8 @@
   - type: GuideHelp
     guides:
     - Radio
+  - type: DropOnSlip
+    chance: 5
 
 - type: entity
   parent: ClothingHeadset
diff --git a/Resources/Prototypes/Entities/Clothing/Ears/headsets_alt.yml b/Resources/Prototypes/Entities/Clothing/Ears/headsets_alt.yml
index 5dfa1df150..ca66723b2a 100644
--- a/Resources/Prototypes/Entities/Clothing/Ears/headsets_alt.yml
+++ b/Resources/Prototypes/Entities/Clothing/Ears/headsets_alt.yml
@@ -9,6 +9,8 @@
     state: icon_alt
   - type: Clothing
     equippedPrefix: alt
+  - type: DropOnSlip
+    chance: 0
 
 - type: entity
   parent: ClothingHeadsetAlt
diff --git a/Resources/Prototypes/Entities/Clothing/Eyes/glasses.yml b/Resources/Prototypes/Entities/Clothing/Eyes/glasses.yml
index 9af8edb002..385e87b6a3 100644
--- a/Resources/Prototypes/Entities/Clothing/Eyes/glasses.yml
+++ b/Resources/Prototypes/Entities/Clothing/Eyes/glasses.yml
@@ -66,6 +66,8 @@
   - type: Tag
     tags:
     - SecDogWearable # DeltaV - let Laika wear meson goggles
+  - type: DropOnSlip
+    chance: 30
 
 - type: entity
   parent: ClothingEyesBase
@@ -83,6 +85,8 @@
     - HamsterWearable
     - WhitelistChameleon
     - GlassesNearsight # SimpleStation14 NearsightedTrait
+  - type: DropOnSlip
+    chance: 30
 
 - type: entity
   parent: ClothingEyesBase
@@ -144,6 +148,8 @@
     - SecDogWearable # DeltaV - let Laika wear sunglasses
   - type: IdentityBlocker
     coverage: EYES
+  - type: DropOnSlip
+    chance: 30
 
 - type: entity
   parent: ClothingEyesGlassesCheapSunglasses
@@ -210,6 +216,8 @@
       coefficients:
         Heat: 0.95
   - type: GroupExamine
+  - type: DropOnSlip
+    chance: 30
 
 - type: entity
   parent: ClothingEyesBase
diff --git a/Resources/Prototypes/Entities/Clothing/Eyes/hud.yml b/Resources/Prototypes/Entities/Clothing/Eyes/hud.yml
index fabb7bc642..15b85b67d8 100644
--- a/Resources/Prototypes/Entities/Clothing/Eyes/hud.yml
+++ b/Resources/Prototypes/Entities/Clothing/Eyes/hud.yml
@@ -12,6 +12,8 @@
     damageContainers:
     - Inorganic
     - Silicon
+  - type: DropOnSlip
+    chance: 25
 
 - type: entity
   parent: ClothingEyesBase
@@ -32,6 +34,8 @@
   - type: Tag
     tags:
     - HudMedical
+  - type: DropOnSlip
+    chance: 25
 
 - type: entity
   parent: ClothingEyesBase
@@ -47,6 +51,8 @@
   - type: Tag
     tags:
     - HudSecurity
+  - type: DropOnSlip
+    chance: 25
 
 - type: entity
   parent: ClothingEyesBase
diff --git a/Resources/Prototypes/Entities/Clothing/Head/hardhats.yml b/Resources/Prototypes/Entities/Clothing/Head/hardhats.yml
index 15cda5a69f..c333e79f9c 100644
--- a/Resources/Prototypes/Entities/Clothing/Head/hardhats.yml
+++ b/Resources/Prototypes/Entities/Clothing/Head/hardhats.yml
@@ -65,6 +65,8 @@
   - type: Tag
     tags:
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 15
 
 - type: entity
   parent: ClothingHeadHatHardhatBase
diff --git a/Resources/Prototypes/Entities/Clothing/Head/hats.yml b/Resources/Prototypes/Entities/Clothing/Head/hats.yml
index c845d7cc4a..42ded67423 100644
--- a/Resources/Prototypes/Entities/Clothing/Head/hats.yml
+++ b/Resources/Prototypes/Entities/Clothing/Head/hats.yml
@@ -8,6 +8,8 @@
     sprite: Clothing/Head/Hats/beaver_hat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/beaver_hat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -24,6 +26,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -57,6 +61,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -64,10 +70,12 @@
   name: casa
   description: Cone-shaped hat
   components:
-    - type: Sprite
-      sprite: Clothing/Head/Hats/casa.rsi
-    - type: Clothing
-      sprite: Clothing/Head/Hats/casa.rsi
+  - type: Sprite
+    sprite: Clothing/Head/Hats/casa.rsi
+  - type: Clothing
+    sprite: Clothing/Head/Hats/casa.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -100,6 +108,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -134,6 +144,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -145,6 +157,8 @@
     sprite: DeltaV/Clothing/Head/Hats/beret_warden.rsi # DeltaV - resprite
   - type: Clothing
     sprite: DeltaV/Clothing/Head/Hats/beret_warden.rsi # DeltaV - resprite
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -156,6 +170,8 @@
     sprite: Clothing/Head/Hats/beret_physician.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/beret_physician.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -167,6 +183,8 @@
     sprite: Clothing/Head/Hats/beret_brigmedic.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/beret_brigmedic.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -189,6 +207,8 @@
     sprite: Clothing/Head/Hats/bowler_hat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/bowler_hat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -205,6 +225,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -220,6 +242,8 @@
     proto: robot
   - type: IdentityBlocker
   - type: IngestionBlocker
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -231,6 +255,8 @@
     sprite: Clothing/Head/Hats/centcom.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/centcom.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -257,6 +283,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -273,6 +301,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -284,6 +314,8 @@
     sprite: Clothing/Head/Hats/greyfedora.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/greyfedora.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -295,6 +327,8 @@
     sprite: Clothing/Head/Hats/fez.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/fez.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -311,6 +345,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -327,6 +363,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -338,6 +376,8 @@
     sprite: Clothing/Head/Hats/outlawhat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/outlawhat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -349,6 +389,8 @@
     sprite: Clothing/Head/Hats/witchhat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/witchhat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -360,6 +402,8 @@
     sprite: Clothing/Head/Hats/paper.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/paper.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -371,6 +415,8 @@
     sprite: Clothing/Head/Hats/pirate.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/pirate.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -387,6 +433,8 @@
     - HidesHair
     - WhitelistChameleon
     - ClothMade
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -414,6 +462,8 @@
     sprite: Clothing/Head/Hats/santahat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/santahat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -427,6 +477,8 @@
     sprite: Clothing/Head/Hats/sombrero.rsi
   - type: AddAccentClothing
     accent: SpanishAccent
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -443,6 +495,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -454,6 +508,8 @@
     sprite: Clothing/Head/Hats/surgcap_green.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/surgcap_green.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -465,6 +521,8 @@
     sprite: Clothing/Head/Hats/surgcap_purple.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/surgcap_purple.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -481,6 +539,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -494,6 +554,8 @@
     sprite: Clothing/Head/Hats/ushanka.rsi
   - type: AddAccentClothing
     accent: RussianAccent
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -523,6 +585,8 @@
     sprite: DeltaV/Clothing/Head/Hats/warden.rsi # DeltaV - resprite
   - type: StealTarget
     stealGroup: ClothingHeadHatWarden
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -539,6 +603,8 @@
     - HidesHair
     - WhitelistChameleon
     - ClothMade
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -582,6 +648,8 @@
     sprite: Clothing/Head/Hats/xmascrown.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/xmascrown.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -593,6 +661,8 @@
     sprite: Clothing/Head/Hats/truckershat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/truckershat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -604,6 +674,8 @@
     sprite: Clothing/Head/Hats/pyjamasyndicateblack.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/pyjamasyndicateblack.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -615,6 +687,8 @@
     sprite: Clothing/Head/Hats/pyjamasyndicatepink.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/pyjamasyndicatepink.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -626,6 +700,8 @@
     sprite: Clothing/Head/Hats/pyjamasyndicatered.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/pyjamasyndicatered.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -638,6 +714,8 @@
   - type: Clothing
     sprite: Clothing/Head/Hats/papersack.rsi
   - type: IdentityBlocker
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -650,6 +728,8 @@
   - type: Clothing
     sprite: Clothing/Head/Hats/papersacksmile.rsi
   - type: IdentityBlocker
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -661,6 +741,8 @@
     sprite: Clothing/Head/Hats/fishcap.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/fishcap.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -677,6 +759,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -688,6 +772,8 @@
     sprite: Clothing/Head/Hats/rasta.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/rasta.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -699,6 +785,8 @@
     sprite: Clothing/Head/Hats/safarihat.rsi
   - type: Clothing
     sprite: Clothing/Head/Hats/safarihat.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -710,6 +798,8 @@
       sprite: Clothing/Head/Hats/jester.rsi
     - type: Clothing
       sprite: Clothing/Head/Hats/jester.rsi
+    - type: DropOnSlip
+      chance: 90
 
 - type: entity
   parent: ClothingHeadHatJester
@@ -719,6 +809,8 @@
       sprite: Clothing/Head/Hats/jester2.rsi
     - type: Clothing
       sprite: Clothing/Head/Hats/jester2.rsi
+    - type: DropOnSlip
+      chance: 90
 
 - type: entity
   parent: ClothingHeadBase
@@ -735,6 +827,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadBase
@@ -761,6 +855,8 @@
     modifiers:
       coefficients:
         Blunt: 0.95
+  - type: DropOnSlip
+    chance: 35
 
 - type: entity
   parent: ClothingHeadBase
diff --git a/Resources/Prototypes/Entities/Clothing/Head/misc.yml b/Resources/Prototypes/Entities/Clothing/Head/misc.yml
index 3fd55faf26..1c615acca1 100644
--- a/Resources/Prototypes/Entities/Clothing/Head/misc.yml
+++ b/Resources/Prototypes/Entities/Clothing/Head/misc.yml
@@ -46,6 +46,8 @@
   - type: Construction
     graph: flowercrown
     node: flowercrown
+  - type: DropOnSlip
+    chance: 50
 
 - type: entity
   parent: ClothingHeadBase
@@ -60,6 +62,8 @@
   - type: Construction
     graph: hairflower
     node: hairflower
+  - type: DropOnSlip
+    chance: 60
 
 - type: entity
   parent: ClothingHeadLightBase
@@ -96,6 +100,8 @@
     sprite: Clothing/Head/Misc/pwig.rsi
   - type: Clothing
     sprite: Clothing/Head/Misc/pwig.rsi
+  - type: DropOnSlip
+    chance: 60
 
 - type: entity
   parent: ClothingHeadBase
@@ -137,6 +143,8 @@
     tags:
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 60
 
 - type: entity
   parent: ClothingHeadBase
@@ -151,6 +159,8 @@
   - type: PhysicalComposition #you can't just pass up some free plastic!
     materialComposition:
       Plastic: 100
+  - type: DropOnSlip
+    chance: 70
 
 - type: entity
   parent: ClothingHeadBase
diff --git a/Resources/Prototypes/Entities/Clothing/Head/soft.yml b/Resources/Prototypes/Entities/Clothing/Head/soft.yml
index 163d9937f2..22c9c622ea 100644
--- a/Resources/Prototypes/Entities/Clothing/Head/soft.yml
+++ b/Resources/Prototypes/Entities/Clothing/Head/soft.yml
@@ -50,11 +50,16 @@
     sprite: Clothing/Head/Soft/bluesoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/bluesoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatBluesoft]
   id: ClothingHeadHatBluesoftFlipped
   name: blue cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -71,6 +76,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatCargosoft]
@@ -83,6 +90,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -94,11 +103,16 @@
     sprite: Clothing/Head/Soft/qmsoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/qmsoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatQMsoft]
   id: ClothingHeadHatQMsoftFlipped
   name: logistics officer's cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -110,11 +124,16 @@
     sprite: Clothing/Head/Soft/corpsoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/corpsoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatCorpsoft]
   id: ClothingHeadHatCorpsoftFlipped
   name: corporate cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -126,11 +145,16 @@
     sprite: Clothing/Head/Soft/greensoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/greensoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatGreensoft]
   id: ClothingHeadHatGreensoftFlipped
   name: green cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -142,11 +166,16 @@
     sprite: Clothing/Head/Soft/blacksoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/blacksoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatBlacksoft]
   id: ClothingHeadHatBlacksoftFlipped
   name: black cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -158,11 +187,16 @@
     sprite: Clothing/Head/Soft/greysoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/greysoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatGreysoft]
   id: ClothingHeadHatGreysoftFlipped
   name: grey cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -174,11 +208,16 @@
     sprite: Clothing/Head/Soft/mimesoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/mimesoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatMimesoft]
   id: ClothingHeadHatMimesoftFlipped
   name: mime cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -190,11 +229,16 @@
     sprite: Clothing/Head/Soft/orangesoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/orangesoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatOrangesoft]
   id: ClothingHeadHatOrangesoftFlipped
   name: orange cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -211,6 +255,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatPurplesoft]
@@ -222,6 +268,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -233,11 +281,16 @@
     sprite: Clothing/Head/Soft/redsoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/redsoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatRedsoft]
   id: ClothingHeadHatRedsoftFlipped
   name: red cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -249,11 +302,16 @@
     sprite: Clothing/Head/Soft/secsoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/secsoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatSecsoft]
   id: ClothingHeadHatSecsoftFlipped
   name: security cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -265,11 +323,16 @@
     sprite: Clothing/Head/Soft/yellowsoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/yellowsoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatYellowsoft]
   id: ClothingHeadHatYellowsoftFlipped
   name: yellow cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -281,11 +344,16 @@
     sprite: Clothing/Head/Soft/bizarresoft.rsi
   - type: Clothing
     sprite: Clothing/Head/Soft/bizarresoft.rsi
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatBizarreSoft]
   id: ClothingHeadHatBizarreSoftFlipped
   name: troublemaker's cap
+  components:
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: ClothingHeadHeadHatBaseFlippable
@@ -302,6 +370,8 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
 
 - type: entity
   parent: [ClothingHeadHeadHatBaseFlipped, ClothingHeadHatParamedicsoft]
@@ -313,3 +383,5 @@
     - ClothMade
     - HamsterWearable
     - WhitelistChameleon
+  - type: DropOnSlip
+    chance: 20
diff --git a/Resources/Prototypes/Entities/Clothing/Masks/masks.yml b/Resources/Prototypes/Entities/Clothing/Masks/masks.yml
index ad738792a7..cf7d1f8513 100644
--- a/Resources/Prototypes/Entities/Clothing/Masks/masks.yml
+++ b/Resources/Prototypes/Entities/Clothing/Masks/masks.yml
@@ -196,6 +196,8 @@
     - ClownMask
     - WhitelistChameleon
     - HidesNose
+  - type: DropOnSlip
+    chance: 5
 
 - type: entity
   parent: ClothingMaskClownBase