diff --git a/Content.Shared/Blocking/BlockingSystem.cs b/Content.Shared/Blocking/BlockingSystem.cs
index d70f12430e..0392428c3c 100644
--- a/Content.Shared/Blocking/BlockingSystem.cs
+++ b/Content.Shared/Blocking/BlockingSystem.cs
@@ -1,11 +1,14 @@
 using Content.Shared.Actions;
 using Content.Shared.Actions.ActionTypes;
+using Content.Shared.Buckle.Components;
 using Content.Shared.Hands;
 using Content.Shared.Hands.EntitySystems;
 using Content.Shared.IdentityManagement;
 using Content.Shared.Physics;
 using Content.Shared.Popups;
 using Content.Shared.Toggleable;
+using Robust.Shared.Containers;
+using Robust.Shared.Map;
 using Robust.Shared.Physics;
 using Robust.Shared.Physics.Dynamics;
 using Robust.Shared.Player;
@@ -21,6 +24,8 @@ public sealed class BlockingSystem : EntitySystem
     [Dependency] private readonly FixtureSystem _fixtureSystem = default!;
     [Dependency] private readonly SharedHandsSystem _handsSystem = default!;
     [Dependency] private readonly SharedPopupSystem _popupSystem = default!;
+    [Dependency] private readonly IMapManager _mapManager = default!;
+    [Dependency] private readonly SharedContainerSystem _containerSystem = default!;
 
     public override void Initialize()
     {
@@ -71,6 +76,17 @@ public sealed class BlockingSystem : EntitySystem
         if(args.Handled)
             return;
 
+        foreach (var shield in _handsSystem.EnumerateHeld(args.Performer))
+        {
+            if (shield == uid)
+                continue;
+            if (TryComp<BlockingComponent>(shield, out var otherBlockComp) && otherBlockComp.IsBlocking)
+            {
+                CantBlockError(args.Performer);
+                return;
+            }
+        }
+
         if (component.IsBlocking)
             StopBlocking(uid, component, args.Performer);
         else
@@ -112,11 +128,16 @@ public sealed class BlockingSystem : EntitySystem
 
         if (component.BlockingToggleAction != null)
         {
+            if (_containerSystem.IsEntityInContainer(user) || !_mapManager.TryFindGridAt(xform.MapPosition, out var grid))
+            {
+                CantBlockError(user);
+                return false;
+            }
+
             _transformSystem.AnchorEntity(xform);
             if (!xform.Anchored)
             {
-                var msgError = Loc.GetString("action-popup-blocking-user-cant-block");
-                _popupSystem.PopupEntity(msgError, user, Filter.Entities(user));
+                CantBlockError(user);
                 return false;
             }
             _actionsSystem.SetToggled(component.BlockingToggleAction, true);
@@ -141,6 +162,12 @@ public sealed class BlockingSystem : EntitySystem
         return true;
     }
 
+    private void CantBlockError(EntityUid user)
+    {
+        var msgError = Loc.GetString("action-popup-blocking-user-cant-block");
+        _popupSystem.PopupEntity(msgError, user, Filter.Entities(user));
+    }
+
     /// <summary>
     /// Called where you want the user to stop blocking.
     /// </summary>
@@ -166,7 +193,9 @@ public sealed class BlockingSystem : EntitySystem
         if (component.BlockingToggleAction != null && TryComp<BlockingUserComponent>(user, out var blockingUserComponent)
                                                      && TryComp<PhysicsComponent>(user, out var physicsComponent))
         {
-            _transformSystem.Unanchor(xform);
+            if (xform.Anchored)
+                _transformSystem.Unanchor(xform);
+
             _actionsSystem.SetToggled(component.BlockingToggleAction, false);
             _fixtureSystem.DestroyFixture(physicsComponent, BlockingComponent.BlockFixtureID);
             physicsComponent.BodyType = blockingUserComponent.OriginalBodyType;
@@ -181,6 +210,7 @@ public sealed class BlockingSystem : EntitySystem
 
     /// <summary>
     /// Called where you want someone to stop blocking and to remove the <see cref="BlockingUserComponent"/> from them
+    /// Won't remove the <see cref="BlockingUserComponent"/> if they're holding another blocking item
     /// </summary>
     /// <param name="uid"> The item the component is attached to</param>
     /// <param name="component"> The <see cref="BlockingComponent"/> </param>
@@ -190,6 +220,15 @@ public sealed class BlockingSystem : EntitySystem
         if (component.IsBlocking)
             StopBlocking(uid, component, user);
 
+        foreach (var shield in _handsSystem.EnumerateHeld(user))
+        {
+            if (HasComp<BlockingComponent>(shield) && TryComp<BlockingUserComponent>(user, out var blockingUserComponent))
+            {
+                blockingUserComponent.BlockingItem = shield;
+                return;
+            }
+        }
+
         RemComp<BlockingUserComponent>(user);
         component.User = null;
     }
diff --git a/Content.Shared/Blocking/BlockingUserSystem.cs b/Content.Shared/Blocking/BlockingUserSystem.cs
index a14d42c293..7cc6ad7025 100644
--- a/Content.Shared/Blocking/BlockingUserSystem.cs
+++ b/Content.Shared/Blocking/BlockingUserSystem.cs
@@ -1,8 +1,10 @@
 using Content.Shared.Audio;
+using Content.Shared.Buckle.Components;
 using Content.Shared.Damage;
 using Content.Shared.Damage.Prototypes;
 using Content.Shared.Hands.EntitySystems;
 using Robust.Shared.Audio;
+using Robust.Shared.Containers;
 using Robust.Shared.Player;
 using Robust.Shared.Prototypes;
 
@@ -21,12 +23,30 @@ public sealed class BlockingUserSystem : EntitySystem
         SubscribeLocalEvent<BlockingUserComponent, DamageChangedEvent>(OnDamageChanged);
         SubscribeLocalEvent<BlockingUserComponent, DamageModifyEvent>(OnUserDamageModified);
 
+        SubscribeLocalEvent<BlockingUserComponent, EntParentChangedMessage>(OnParentChanged);
+        SubscribeLocalEvent<BlockingUserComponent, ContainerGettingInsertedAttemptEvent>(OnInsertAttempt);
         SubscribeLocalEvent<BlockingUserComponent, AnchorStateChangedEvent>(OnAnchorChanged);
     }
 
+    private void OnParentChanged(EntityUid uid, BlockingUserComponent component, ref EntParentChangedMessage args)
+    {
+        if (TryComp<BlockingComponent>(component.BlockingItem, out var blockComp) && blockComp.IsBlocking)
+        {
+            _blockingSystem.StopBlocking(component.BlockingItem.Value, blockComp, uid);
+        }
+    }
+
+    private void OnInsertAttempt(EntityUid uid, BlockingUserComponent component, ContainerGettingInsertedAttemptEvent args)
+    {
+        if (TryComp<BlockingComponent>(component.BlockingItem, out var blockComp) && blockComp.IsBlocking)
+        {
+            _blockingSystem.StopBlocking(component.BlockingItem.Value, blockComp, uid);
+        }
+    }
+
     private void OnAnchorChanged(EntityUid uid, BlockingUserComponent component, ref AnchorStateChangedEvent args)
     {
-        if (!args.Anchored)
+        if (args.Anchored)
             return;
 
         if (TryComp<BlockingComponent>(component.BlockingItem, out var blockComp) && blockComp.IsBlocking)
diff --git a/Resources/Locale/en-US/actions/actions/blocking.ftl b/Resources/Locale/en-US/actions/actions/blocking.ftl
index 6cfe9314a9..cc58e59610 100644
--- a/Resources/Locale/en-US/actions/actions/blocking.ftl
+++ b/Resources/Locale/en-US/actions/actions/blocking.ftl
@@ -7,4 +7,4 @@ action-popup-blocking-disabling-user = You lower your {$shield}!
 action-popup-blocking-other = {CAPITALIZE(THE($blockerName))} raises {POSS-ADJ($blockerName)} {$shield}!
 action-popup-blocking-disabling-other = {CAPITALIZE(THE($blockerName))} lowers {POSS-ADJ($blockerName)} {$shield}!
 
-action-popup-blocking-user-cant-block = The gravity here prevents you from blocking.
+action-popup-blocking-user-cant-block = You tried to raise your shield, but it was no use.