diff --git a/Content.Server/Contests/ContestsSystem.cs b/Content.Server/Contests/ContestsSystem.cs
index 114b927cdf..5598716280 100644
--- a/Content.Server/Contests/ContestsSystem.cs
+++ b/Content.Server/Contests/ContestsSystem.cs
@@ -23,7 +23,7 @@ namespace Content.Server.Contests
         /// </summary>
         public float MassContest(EntityUid roller, EntityUid target, PhysicsComponent? rollerPhysics = null, PhysicsComponent? targetPhysics = null)
         {
-            if (!Resolve(roller, ref rollerPhysics) || !Resolve(target, ref targetPhysics))
+            if (!Resolve(roller, ref rollerPhysics, false) || !Resolve(target, ref targetPhysics, false))
                 return 1f;
 
             if (rollerPhysics == null || targetPhysics == null)
@@ -43,7 +43,7 @@ namespace Content.Server.Contests
         /// <summary>
         public float DamageContest(EntityUid roller, EntityUid target, DamageableComponent? rollerDamage = null, DamageableComponent? targetDamage = null)
         {
-            if (!Resolve(roller, ref rollerDamage) || !Resolve(target, ref targetDamage))
+            if (!Resolve(roller, ref rollerDamage, false) || !Resolve(target, ref targetDamage, false))
                 return 1f;
 
             if (rollerDamage == null || targetDamage == null)
diff --git a/Content.Server/Resist/CanEscapeInventoryComponent.cs b/Content.Server/Resist/CanEscapeInventoryComponent.cs
index dd27b159af..6ba05bfec7 100644
--- a/Content.Server/Resist/CanEscapeInventoryComponent.cs
+++ b/Content.Server/Resist/CanEscapeInventoryComponent.cs
@@ -6,17 +6,11 @@ namespace Content.Server.Resist;
 public sealed class CanEscapeInventoryComponent : Component
 {
     /// <summary>
-    /// How long it takes to break out of storage. Default at 5 seconds.
+    /// Base doafter length for uncontested breakouts.
     /// </summary>
     [ViewVariables]
-    [DataField("resistTime")]
-    public float ResistTime = 5f;
-
-    /// <summary>
-    /// For quick exit if the player attempts to move while already resisting
-    /// </summary>
-    [ViewVariables]
-    public bool IsResisting = false;
+    [DataField("baseResistTime")]
+    public float BaseResistTime = 5f;
 
     /// <summary>
     /// Cancellation token used to cancel the DoAfter if the mob is removed before it's complete
diff --git a/Content.Server/Resist/EscapeInventorySystem.cs b/Content.Server/Resist/EscapeInventorySystem.cs
index bbc7ff0513..47991b19c9 100644
--- a/Content.Server/Resist/EscapeInventorySystem.cs
+++ b/Content.Server/Resist/EscapeInventorySystem.cs
@@ -1,13 +1,14 @@
-using Content.Shared.Movement;
 using Content.Server.DoAfter;
+using Content.Server.Contests;
 using Robust.Shared.Containers;
 using Content.Server.Popups;
 using Robust.Shared.Player;
 using Content.Shared.Storage;
 using Content.Shared.Inventory;
-using Content.Shared.Hands.Components;
+using Content.Shared.Hands.EntitySystems;
 using Content.Shared.ActionBlocker;
 using Content.Shared.Movement.Events;
+using Content.Shared.Interaction.Events;
 
 namespace Content.Server.Resist;
 
@@ -17,6 +18,13 @@ public sealed class EscapeInventorySystem : EntitySystem
     [Dependency] private readonly PopupSystem _popupSystem = default!;
     [Dependency] private readonly SharedContainerSystem _containerSystem = default!;
     [Dependency] private readonly ActionBlockerSystem _actionBlockerSystem = default!;
+    [Dependency] private readonly SharedHandsSystem _handsSystem = default!;
+    [Dependency] private readonly ContestsSystem _contests = default!;
+
+    /// <summary>
+    /// You can't escape the hands of an entity this many times more massive than you.
+    /// </summary>
+    public const float MaximumMassDisadvantage = 6f;
 
     public override void Initialize()
     {
@@ -26,20 +34,38 @@ public sealed class EscapeInventorySystem : EntitySystem
         SubscribeLocalEvent<CanEscapeInventoryComponent, UpdateCanMoveEvent>(OnMoveAttempt);
         SubscribeLocalEvent<CanEscapeInventoryComponent, EscapeDoAfterComplete>(OnEscapeComplete);
         SubscribeLocalEvent<CanEscapeInventoryComponent, EscapeDoAfterCancel>(OnEscapeFail);
+        SubscribeLocalEvent<CanEscapeInventoryComponent, DroppedEvent>(OnDropped);
     }
 
     private void OnRelayMovement(EntityUid uid, CanEscapeInventoryComponent component, ref MoveInputEvent args)
     {
-        //Prevents the user from creating multiple DoAfters if they're already resisting.
-        if (component.IsResisting == true)
+        if (component.CancelToken != null)
             return;
 
-        if (_containerSystem.TryGetContainingContainer(uid, out var container)
-            && (HasComp<SharedStorageComponent>(container.Owner) || HasComp<InventoryComponent>(container.Owner) || HasComp<SharedHandsComponent>(container.Owner)))
+        if (!_containerSystem.TryGetContainingContainer(uid, out var container) || !_actionBlockerSystem.CanInteract(uid, container.Owner))
+            return;
+
+        // Contested
+        if (_handsSystem.IsHolding(container.Owner, uid, out var inHand))
         {
-            if (_actionBlockerSystem.CanInteract(uid, container.Owner))
-                AttemptEscape(uid, container.Owner, component);
+            var contestResults = _contests.MassContest(uid, container.Owner);
+
+            // Inverse if we aren't going to divide by 0, otherwise just use a default multiplier of 1.
+            if (contestResults != 0)
+                contestResults = 1 / contestResults;
+            else
+                contestResults = 1;
+
+            if (contestResults >= MaximumMassDisadvantage)
+                return;
+
+            AttemptEscape(uid, container.Owner, component, contestResults);
+            return;
         }
+
+        // Uncontested
+        if (HasComp<SharedStorageComponent>(container.Owner) || HasComp<InventoryComponent>(container.Owner))
+            AttemptEscape(uid, container.Owner, component);
     }
 
     private void OnMoveAttempt(EntityUid uid, CanEscapeInventoryComponent component, UpdateCanMoveEvent args)
@@ -48,10 +74,10 @@ public sealed class EscapeInventorySystem : EntitySystem
             args.Cancel();
     }
 
-    private void AttemptEscape(EntityUid user, EntityUid container, CanEscapeInventoryComponent component)
+    private void AttemptEscape(EntityUid user, EntityUid container, CanEscapeInventoryComponent component, float multiplier = 1f)
     {
         component.CancelToken = new();
-        var doAfterEventArgs = new DoAfterEventArgs(user, component.ResistTime, component.CancelToken.Token, container)
+        var doAfterEventArgs = new DoAfterEventArgs(user, component.BaseResistTime * multiplier, component.CancelToken.Token, container)
         {
             BreakOnTargetMove = false,
             BreakOnUserMove = false,
@@ -62,7 +88,6 @@ public sealed class EscapeInventorySystem : EntitySystem
             UserCancelledEvent = new EscapeDoAfterCancel(),
         };
 
-        component.IsResisting = true;
         _popupSystem.PopupEntity(Loc.GetString("escape-inventory-component-start-resisting"), user, Filter.Entities(user));
         _popupSystem.PopupEntity(Loc.GetString("escape-inventory-component-start-resisting-target"), container, Filter.Entities(container));
         _doAfterSystem.DoAfter(doAfterEventArgs);
@@ -72,12 +97,17 @@ public sealed class EscapeInventorySystem : EntitySystem
     {
         //Drops the mob on the tile below the container
         Transform(uid).AttachParentToContainerOrGrid(EntityManager);
-        component.IsResisting = false;
+        component.CancelToken = null;
     }
 
     private void OnEscapeFail(EntityUid uid, CanEscapeInventoryComponent component, EscapeDoAfterCancel ev)
     {
-        component.IsResisting = false;
+        component.CancelToken = null;
+    }
+
+    private void OnDropped(EntityUid uid, CanEscapeInventoryComponent component, DroppedEvent args)
+    {
+        component.CancelToken?.Cancel();
     }
 
     private sealed class EscapeDoAfterComplete : EntityEventArgs { }