diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 53c0934ae..e5e291169 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -36,9 +36,13 @@ jobs:
 
           - category: macos
             platform: x64
-            instance: macos-13
+            instance: macos-14
 
-        python: ["3.10", "3.11", "3.12", "3.13"]
+          - category: macos
+            platform: arm64
+            instance: macos-14-arm64
+
+        python: ["3.10", "3.11", "3.12", "3.13", "3.14"]
 
     steps:
       - name: Set Environment on macOS
diff --git a/pyproject.toml b/pyproject.toml
index e3fba0dda..664df8b01 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -13,7 +13,7 @@ dependencies = [
     "clr_loader>=0.2.7,<0.3.0"
 ]
 
-requires-python = ">=3.10, <3.14"
+requires-python = ">=3.10, <3.15"
 
 classifiers = [
     "Development Status :: 5 - Production/Stable",
diff --git a/src/runtime/CollectionWrappers/ListWrapper.cs b/src/runtime/CollectionWrappers/ListWrapper.cs
index 41ccb8fae..91c156c32 100644
--- a/src/runtime/CollectionWrappers/ListWrapper.cs
+++ b/src/runtime/CollectionWrappers/ListWrapper.cs
@@ -14,12 +14,14 @@ public T this[int index]
         {
             get
             {
+                using var _ = Py.GIL();
                 var item = Runtime.PyList_GetItem(pyObject, index);
                 var pyItem = new PyObject(item);
                 return pyItem.As<T>()!;
             }
             set
             {
+                using var _ = Py.GIL();
                 var pyItem = value.ToPython();
                 var result = Runtime.PyList_SetItem(pyObject, index, new NewReference(pyItem).Steal());
                 if (result == -1)
@@ -37,6 +39,7 @@ public void Insert(int index, T item)
             if (IsReadOnly)
                 throw new InvalidOperationException("Collection is read-only");
 
+            using var _ = Py.GIL();
             var pyItem = item.ToPython();
 
             int result = Runtime.PyList_Insert(pyObject, index, pyItem);
diff --git a/src/runtime/CollectionWrappers/SequenceWrapper.cs b/src/runtime/CollectionWrappers/SequenceWrapper.cs
index fcc5c23f4..feb0e515d 100644
--- a/src/runtime/CollectionWrappers/SequenceWrapper.cs
+++ b/src/runtime/CollectionWrappers/SequenceWrapper.cs
@@ -14,10 +14,14 @@ public int Count
         {
             get
             {
-                var size = Runtime.PySequence_Size(pyObject.Reference);
-                if (size == -1)
+                nint size = -1;
                 {
-                    Runtime.CheckExceptionOccurred();
+                    using var _ = Py.GIL();
+                    size = Runtime.PySequence_Size(pyObject.Reference);
+                    if (size == -1)
+                    {
+                        Runtime.CheckExceptionOccurred();
+                    }
                 }
 
                 return checked((int)size);
@@ -38,6 +42,7 @@ public void Clear()
         {
             if (IsReadOnly)
                 throw new NotImplementedException();
+            using var _ = Py.GIL();
             int result = Runtime.PySequence_DelSlice(pyObject, 0, Count);
             if (result == -1)
             {
@@ -77,12 +82,16 @@ protected bool removeAt(int index)
             if (index >= Count || index < 0)
                 return false;
 
-            int result = Runtime.PySequence_DelItem(pyObject, index);
 
-            if (result == 0)
-                return true;
+            {
+                using var _ = Py.GIL();
+                int result = Runtime.PySequence_DelItem(pyObject, index);
+
+                if (result == 0)
+                    return true;
 
-            Runtime.CheckExceptionOccurred();
+                Runtime.CheckExceptionOccurred();
+            }
             return false;
         }
 
diff --git a/src/runtime/Native/PyIdentifier_.cs b/src/runtime/Native/PyIdentifier_.cs
index 1ea2b704c..8d693c09f 100644
--- a/src/runtime/Native/PyIdentifier_.cs
+++ b/src/runtime/Native/PyIdentifier_.cs
@@ -13,8 +13,6 @@ static class PyIdentifier
          public static BorrowedReference __doc__ => new(f__doc__);
          static IntPtr f__class__;
          public static BorrowedReference __class__ => new(f__class__);
-         static IntPtr f__clear_reentry_guard__;
-         public static BorrowedReference __clear_reentry_guard__ => new(f__clear_reentry_guard__);
          static IntPtr f__module__;
          public static BorrowedReference __module__ => new(f__module__);
          static IntPtr f__file__;
@@ -24,6 +22,8 @@ static class PyIdentifier
          static IntPtr f__self__;
          public static BorrowedReference __self__ => new(f__self__);
          static IntPtr f__annotations__;
+         public static BorrowedReference __dictoffset__ => new(f__dictoffset__);
+         static IntPtr f__dictoffset__;
          public static BorrowedReference __annotations__ => new(f__annotations__);
          static IntPtr f__init__;
          public static BorrowedReference __init__ => new(f__init__);
@@ -51,12 +51,12 @@ static partial class InternString
             "__dict__",
             "__doc__",
             "__class__",
-            "__clear_reentry_guard__",
             "__module__",
             "__file__",
             "__slots__",
             "__self__",
             "__annotations__",
+            "__dictoffset__",
             "__init__",
             "__repr__",
             "__import__",
diff --git a/src/runtime/Native/PyIdentifier_.tt b/src/runtime/Native/PyIdentifier_.tt
index 9350cde43..72dc1d70e 100644
--- a/src/runtime/Native/PyIdentifier_.tt
+++ b/src/runtime/Native/PyIdentifier_.tt
@@ -7,12 +7,12 @@
         "__dict__",
         "__doc__",
         "__class__",
-        "__clear_reentry_guard__",
         "__module__",
         "__file__",
         "__slots__",
         "__self__",
         "__annotations__",
+        "__dictoffset__",
 
         "__init__",
         "__repr__",
diff --git a/src/runtime/Native/TypeOffset.cs b/src/runtime/Native/TypeOffset.cs
index 803b86bfa..282107432 100644
--- a/src/runtime/Native/TypeOffset.cs
+++ b/src/runtime/Native/TypeOffset.cs
@@ -77,6 +77,8 @@ static partial class TypeOffset
         internal static int tp_setattro { get; private set; }
         internal static int tp_str { get; private set; }
         internal static int tp_traverse { get; private set; }
+        // Special case: Only available in Python 3.14 onwards, set to -1 by default
+        internal static int ht_token { get; private set; } = -1;
 
         internal static void Use(ITypeOffsets offsets, int extraHeadOffset)
         {
@@ -89,6 +91,19 @@ internal static void Use(ITypeOffsets offsets, int extraHeadOffset)
                 slotNames.Add(offsetProperty.Name);
 
                 var sourceProperty = typeof(ITypeOffsets).GetProperty(offsetProperty.Name);
+                if (sourceProperty == null)
+                {
+                    if ((int)offsetProperty.GetValue(null) == -1)
+                    {
+                        // Skip, this is an optional offset value
+                        continue;
+                    }
+                    else
+                    {
+                        throw new Exception($"No offset defined for necessary slot {offsetProperty.Name}");
+                    }
+                }
+
                 int value = (int)sourceProperty.GetValue(offsets, null);
                 value += extraHeadOffset;
                 offsetProperty.SetValue(obj: null, value: value, index: null);
diff --git a/src/runtime/Native/TypeOffset314.cs b/src/runtime/Native/TypeOffset314.cs
new file mode 100644
index 000000000..28101ba12
--- /dev/null
+++ b/src/runtime/Native/TypeOffset314.cs
@@ -0,0 +1,153 @@
+
+// Auto-generated by geninterop.py.
+// DO NOT MODIFY BY HAND.
+
+// Python 3.14: ABI flags: ''
+
+// ReSharper disable InconsistentNaming
+// ReSharper disable IdentifierTypo
+
+using System;
+using System.Diagnostics.CodeAnalysis;
+using System.Runtime.InteropServices;
+
+using Python.Runtime.Native;
+
+namespace Python.Runtime
+{
+    [SuppressMessage("Style", "IDE1006:Naming Styles",
+                     Justification = "Following CPython",
+                     Scope = "type")]
+
+    [StructLayout(LayoutKind.Sequential)]
+    internal class TypeOffset314 : GeneratedTypeOffsets, ITypeOffsets
+    {
+        public TypeOffset314() { }
+        // Auto-generated from PyHeapTypeObject in Python.h
+        public int ob_refcnt_full  { get; private set; }
+        public int ob_type  { get; private set; }
+        public int ob_size  { get; private set; }
+        public int tp_name  { get; private set; }
+        public int tp_basicsize  { get; private set; }
+        public int tp_itemsize  { get; private set; }
+        public int tp_dealloc  { get; private set; }
+        public int tp_vectorcall_offset  { get; private set; }
+        public int tp_getattr  { get; private set; }
+        public int tp_setattr  { get; private set; }
+        public int tp_as_async  { get; private set; }
+        public int tp_repr  { get; private set; }
+        public int tp_as_number  { get; private set; }
+        public int tp_as_sequence  { get; private set; }
+        public int tp_as_mapping  { get; private set; }
+        public int tp_hash  { get; private set; }
+        public int tp_call  { get; private set; }
+        public int tp_str  { get; private set; }
+        public int tp_getattro  { get; private set; }
+        public int tp_setattro  { get; private set; }
+        public int tp_as_buffer  { get; private set; }
+        public int tp_flags  { get; private set; }
+        public int tp_doc  { get; private set; }
+        public int tp_traverse  { get; private set; }
+        public int tp_clear  { get; private set; }
+        public int tp_richcompare  { get; private set; }
+        public int tp_weaklistoffset  { get; private set; }
+        public int tp_iter  { get; private set; }
+        public int tp_iternext  { get; private set; }
+        public int tp_methods  { get; private set; }
+        public int tp_members  { get; private set; }
+        public int tp_getset  { get; private set; }
+        public int tp_base  { get; private set; }
+        public int tp_dict  { get; private set; }
+        public int tp_descr_get  { get; private set; }
+        public int tp_descr_set  { get; private set; }
+        public int tp_dictoffset  { get; private set; }
+        public int tp_init  { get; private set; }
+        public int tp_alloc  { get; private set; }
+        public int tp_new  { get; private set; }
+        public int tp_free  { get; private set; }
+        public int tp_is_gc  { get; private set; }
+        public int tp_bases  { get; private set; }
+        public int tp_mro  { get; private set; }
+        public int tp_cache  { get; private set; }
+        public int tp_subclasses  { get; private set; }
+        public int tp_weaklist  { get; private set; }
+        public int tp_del  { get; private set; }
+        public int tp_version_tag  { get; private set; }
+        public int tp_finalize  { get; private set; }
+        public int tp_vectorcall  { get; private set; }
+        // This is an error in our generator:
+        //
+        // The fields below are actually not pointers (like we incorrectly
+        // assume for all other fields) but instead a char (1 byte) and a short
+        // (2 bytes). By dropping one of the fields, we still get the correct
+        // overall size of the struct.
+        public int tp_watched  { get; private set; }
+        // public int tp_versions_used  { get; private set; }
+        public int am_await  { get; private set; }
+        public int am_aiter  { get; private set; }
+        public int am_anext  { get; private set; }
+        public int am_send  { get; private set; }
+        public int nb_add  { get; private set; }
+        public int nb_subtract  { get; private set; }
+        public int nb_multiply  { get; private set; }
+        public int nb_remainder  { get; private set; }
+        public int nb_divmod  { get; private set; }
+        public int nb_power  { get; private set; }
+        public int nb_negative  { get; private set; }
+        public int nb_positive  { get; private set; }
+        public int nb_absolute  { get; private set; }
+        public int nb_bool  { get; private set; }
+        public int nb_invert  { get; private set; }
+        public int nb_lshift  { get; private set; }
+        public int nb_rshift  { get; private set; }
+        public int nb_and  { get; private set; }
+        public int nb_xor  { get; private set; }
+        public int nb_or  { get; private set; }
+        public int nb_int  { get; private set; }
+        public int nb_reserved  { get; private set; }
+        public int nb_float  { get; private set; }
+        public int nb_inplace_add  { get; private set; }
+        public int nb_inplace_subtract  { get; private set; }
+        public int nb_inplace_multiply  { get; private set; }
+        public int nb_inplace_remainder  { get; private set; }
+        public int nb_inplace_power  { get; private set; }
+        public int nb_inplace_lshift  { get; private set; }
+        public int nb_inplace_rshift  { get; private set; }
+        public int nb_inplace_and  { get; private set; }
+        public int nb_inplace_xor  { get; private set; }
+        public int nb_inplace_or  { get; private set; }
+        public int nb_floor_divide  { get; private set; }
+        public int nb_true_divide  { get; private set; }
+        public int nb_inplace_floor_divide  { get; private set; }
+        public int nb_inplace_true_divide  { get; private set; }
+        public int nb_index  { get; private set; }
+        public int nb_matrix_multiply  { get; private set; }
+        public int nb_inplace_matrix_multiply  { get; private set; }
+        public int mp_length  { get; private set; }
+        public int mp_subscript  { get; private set; }
+        public int mp_ass_subscript  { get; private set; }
+        public int sq_length  { get; private set; }
+        public int sq_concat  { get; private set; }
+        public int sq_repeat  { get; private set; }
+        public int sq_item  { get; private set; }
+        public int was_sq_slice  { get; private set; }
+        public int sq_ass_item  { get; private set; }
+        public int was_sq_ass_slice  { get; private set; }
+        public int sq_contains  { get; private set; }
+        public int sq_inplace_concat  { get; private set; }
+        public int sq_inplace_repeat  { get; private set; }
+        public int bf_getbuffer  { get; private set; }
+        public int bf_releasebuffer  { get; private set; }
+        public int name  { get; private set; }
+        public int ht_slots  { get; private set; }
+        public int qualname  { get; private set; }
+        public int ht_cached_keys  { get; private set; }
+        public int ht_module  { get; private set; }
+        public int _ht_tpname  { get; private set; }
+        public int ht_token  { get; private set; }
+        public int spec_cache_getitem  { get; private set; }
+        public int getitem_version  { get; private set; }
+        public int init  { get; private set; }
+    }
+}
+
diff --git a/src/runtime/PythonEngine.cs b/src/runtime/PythonEngine.cs
index 0b28c3a35..13855adef 100644
--- a/src/runtime/PythonEngine.cs
+++ b/src/runtime/PythonEngine.cs
@@ -135,7 +135,7 @@ public static string PythonPath
         }
 
         public static Version MinSupportedVersion => new(3, 7);
-        public static Version MaxSupportedVersion => new(3, 13, int.MaxValue, int.MaxValue);
+        public static Version MaxSupportedVersion => new(3, 14, int.MaxValue, int.MaxValue);
         public static bool IsSupportedVersion(Version version) => version >= MinSupportedVersion && version <= MaxSupportedVersion;
 
         public static string Version
diff --git a/src/runtime/TypeManager.cs b/src/runtime/TypeManager.cs
index 559d5148e..dbff1fbd4 100644
--- a/src/runtime/TypeManager.cs
+++ b/src/runtime/TypeManager.cs
@@ -618,6 +618,11 @@ internal static PyType AllocateTypeObject(string name, PyType metatype)
             Util.WriteIntPtr(type, TypeOffset.tp_traverse, subtype_traverse);
             Util.WriteIntPtr(type, TypeOffset.tp_clear, subtype_clear);
 
+            // This is a new mechanism in Python 3.14. We should eventually use it to implement
+            // a nicer type check, but for now we just need to ensure that it is set to NULL.
+            if (TypeOffset.ht_token != -1)
+                Util.WriteIntPtr(type, TypeOffset.ht_token, IntPtr.Zero);
+
             InheritSubstructs(type.Reference.DangerousGetAddress());
 
             return type;
diff --git a/src/runtime/Types/ClassBase.cs b/src/runtime/Types/ClassBase.cs
index 2d6ce8a47..3fcb7ca4f 100644
--- a/src/runtime/Types/ClassBase.cs
+++ b/src/runtime/Types/ClassBase.cs
@@ -374,6 +374,8 @@ public static int tp_clear(BorrowedReference ob)
             return 0;
         }
 
+        static readonly HashSet<IntPtr> ClearVisited = new();
+
         internal static unsafe int BaseUnmanagedClear(BorrowedReference ob)
         {
             var type = Runtime.PyObject_TYPE(ob);
@@ -385,21 +387,20 @@ internal static unsafe int BaseUnmanagedClear(BorrowedReference ob)
             }
             var clear = (delegate* unmanaged[Cdecl]<BorrowedReference, int>)clearPtr;
 
-            bool usesSubtypeClear = clearPtr == TypeManager.subtype_clear;
-            if (usesSubtypeClear)
+            if (clearPtr == TypeManager.subtype_clear)
             {
-                // workaround for https://bugs.python.org/issue45266 (subtype_clear)
-                using var dict = Runtime.PyObject_GenericGetDict(ob);
-                if (Runtime.PyMapping_HasKey(dict.Borrow(), PyIdentifier.__clear_reentry_guard__) != 0)
+                var addr = ob.DangerousGetAddress();
+                if (!ClearVisited.Add(addr))
                     return 0;
-                int res = Runtime.PyDict_SetItem(dict.Borrow(), PyIdentifier.__clear_reentry_guard__, Runtime.None);
-                if (res != 0) return res;
 
-                res = clear(ob);
-                Runtime.PyDict_DelItem(dict.Borrow(), PyIdentifier.__clear_reentry_guard__);
+                int res = clear(ob);
+                ClearVisited.Remove(addr);
                 return res;
             }
-            return clear(ob);
+            else
+            {
+                return clear(ob);
+            }
         }
 
         protected override Dictionary<string, object?> OnSave(BorrowedReference ob)
diff --git a/src/runtime/Types/MetaType.cs b/src/runtime/Types/MetaType.cs
index 57fcaa232..ecbc9cac5 100644
--- a/src/runtime/Types/MetaType.cs
+++ b/src/runtime/Types/MetaType.cs
@@ -21,6 +21,7 @@ internal sealed class MetaType : ManagedType
         // set in Initialize
         private static PyType PyCLRMetaType;
         private static SlotsHolder _metaSlotsHodler;
+        private static int TypeDictOffset = -1;
 #pragma warning restore CS8618 // Non-nullable field must contain a non-null value when exiting constructor. Consider declaring as nullable.
 
         internal static readonly string[] CustomMethods = new string[]
@@ -35,6 +36,25 @@ internal sealed class MetaType : ManagedType
         public static PyType Initialize()
         {
             PyCLRMetaType = TypeManager.CreateMetaType(typeof(MetaType), out _metaSlotsHodler);
+
+            // Retrieve the offset of the type's dictionary from PyType_Type for
+            // use in the tp_setattro implementation.
+            using (NewReference dictOffset = Runtime.PyObject_GetAttr(Runtime.PyTypeType, PyIdentifier.__dictoffset__))
+            {
+                if (dictOffset.IsNull())
+                {
+                    throw new InvalidOperationException("Could not get __dictoffset__ from PyType_Type");
+                }
+
+                nint dictOffsetVal = Runtime.PyLong_AsSignedSize_t(dictOffset.Borrow());
+                if (dictOffsetVal <= 0)
+                {
+                    throw new InvalidOperationException("Could not get __dictoffset__ from PyType_Type");
+                }
+
+                TypeDictOffset = checked((int)dictOffsetVal);
+            }
+
             return PyCLRMetaType;
         }
 
@@ -44,6 +64,7 @@ public static void Release()
             {
                 _metaSlotsHodler.ResetSlots();
             }
+            TypeDictOffset = -1;
             PyCLRMetaType.Dispose();
         }
 
@@ -287,7 +308,28 @@ public static int tp_setattro(BorrowedReference tp, BorrowedReference name, Borr
                 }
             }
 
-            int res = Runtime.PyObject_GenericSetAttr(tp, name, value);
+            // Access the type's dictionary directly
+            //
+            // We can not use the PyObject_GenericSetAttr because since Python
+            // 3.14 as https://github.com/python/cpython/pull/118454 intrdoduced
+            // an assertion to prevent it from being called from metatypes.
+            //
+            // The direct dictionary access is equivalent to what Cython does
+            // to work around the same issue: https://github.com/cython/cython/pull/6325
+            BorrowedReference typeDict = new(Util.ReadIntPtr(tp, TypeDictOffset));
+            int res;
+            if (value.IsNull)
+            {
+                res = Runtime.PyDict_DelItem(typeDict, name);
+                if (res != 0)
+                {
+                    Exceptions.SetError(Exceptions.AttributeError, "attribute not found");
+                }
+            }
+            else
+            {
+                res = Runtime.PyDict_SetItem(typeDict, name, value);
+            }
             Runtime.PyType_Modified(tp);
 
             return res;
diff --git a/uv.lock b/uv.lock
index 9f73eb110..25a53fd51 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1,74 +1,103 @@
 version = 1
 revision = 3
-requires-python = ">=3.10, <3.14"
+requires-python = ">=3.10, <3.15"
+resolution-markers = [
+    "python_full_version >= '3.11'",
+    "python_full_version < '3.11'",
+]
 
 [[package]]
 name = "cffi"
-version = "1.17.1"
+version = "2.0.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "pycparser" },
+    { name = "pycparser", marker = "implementation_name != 'PyPy'" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/fc/97/c783634659c2920c3fc70419e3af40972dbaf758daa229a7d6ea6135c90d/cffi-1.17.1.tar.gz", hash = "sha256:1c39c6016c32bc48dd54561950ebd6836e1670f2ae46128f67cf49e789c52824", size = 516621, upload-time = "2024-09-04T20:45:21.852Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/eb/56/b1ba7935a17738ae8453301356628e8147c79dbb825bcbc73dc7401f9846/cffi-2.0.0.tar.gz", hash = "sha256:44d1b5909021139fe36001ae048dbdde8214afa20200eda0f64c068cac5d5529", size = 523588, upload-time = "2025-09-08T23:24:04.541Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/90/07/f44ca684db4e4f08a3fdc6eeb9a0d15dc6883efc7b8c90357fdbf74e186c/cffi-1.17.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14", size = 182191, upload-time = "2024-09-04T20:43:30.027Z" },
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