diff --git a/Lib/test/test_isinstance.py b/Lib/test/test_isinstance.py
index 5834e0884..a2e95793c 100644
--- a/Lib/test/test_isinstance.py
+++ b/Lib/test/test_isinstance.py
@@ -224,8 +224,6 @@ class TestIsInstanceIsSubclass(unittest.TestCase):
         self.assertEqual(False, isinstance(AbstractChild(), Super))
         self.assertEqual(False, isinstance(AbstractChild(), Child))
 
-    # TODO: RUSTPYTHON
-    @unittest.expectedFailure
     def test_subclass_normal(self):
         # normal classes
         self.assertEqual(True, issubclass(Super, Super))
@@ -299,6 +297,7 @@ class TestIsInstanceIsSubclass(unittest.TestCase):
 
     # TODO: RUSTPYTHON
     @unittest.expectedFailure
+    @unittest.skipIf(sys.platform == "win32", "thread 'main' has overflowed its stack")
     def test_infinite_recursion_in_bases(self):
         class X:
             @property
diff --git a/extra_tests/snippets/issubclass.py b/extra_tests/snippets/issubclass.py
index 62577f213..7f1d87abb 100644
--- a/extra_tests/snippets/issubclass.py
+++ b/extra_tests/snippets/issubclass.py
@@ -49,6 +49,13 @@ assert issubclass(AlwaysSubClass, AlwaysSubClass)
 assert issubclass(InheritedAlwaysSubClass, AlwaysSubClass)
 assert issubclass(AlwaysSubClass, InheritedAlwaysSubClass)
 
+class GenericInstance:
+    def __subclasscheck__(self, _):
+        return True
+
+assert issubclass(A, GenericInstance())
+assert issubclass(list, GenericInstance())
+assert issubclass([], GenericInstance())
 
 class MCAVirtualSubClass(type):
     def __subclasscheck__(self, subclass):
diff --git a/vm/src/builtins/make_module.rs b/vm/src/builtins/make_module.rs
index 5bb858b05..73c87bf69 100644
--- a/vm/src/builtins/make_module.rs
+++ b/vm/src/builtins/make_module.rs
@@ -25,9 +25,7 @@ mod decl {
     use crate::common::{hash::PyHash, str::to_ascii};
     #[cfg(feature = "rustpython-compiler")]
     use crate::compile;
-    use crate::function::{
-        single_or_tuple_any, Args, FuncArgs, KwArgs, OptionalArg, OptionalOption,
-    };
+    use crate::function::{Args, FuncArgs, KwArgs, OptionalArg, OptionalOption};
     use crate::iterator;
     use crate::readline::{Readline, ReadlineResult};
     use crate::scope::Scope;
@@ -412,18 +410,8 @@ mod decl {
     }
 
     #[pyfunction]
-    fn issubclass(subclass: PyTypeRef, typ: PyObjectRef, vm: &VirtualMachine) -> PyResult<bool> {
-        single_or_tuple_any(
-            typ,
-            &|cls: &PyTypeRef| vm.issubclass(&subclass, cls),
-            &|o| {
-                format!(
-                    "issubclass() arg 2 must be a class or tuple of classes, not {}",
-                    o.class()
-                )
-            },
-            vm,
-        )
+    fn issubclass(subclass: PyObjectRef, typ: PyObjectRef, vm: &VirtualMachine) -> PyResult<bool> {
+        vm.issubclass(&subclass, &typ)
     }
 
     #[pyfunction]
diff --git a/vm/src/vm.rs b/vm/src/vm.rs
index d8067d24f..78d1192ef 100644
--- a/vm/src/vm.rs
+++ b/vm/src/vm.rs
@@ -985,15 +985,86 @@ impl VirtualMachine {
         self._isinstance(obj, cls)
     }
 
+    fn abstract_issubclass(&self, subclass: PyObjectRef, cls: &PyObjectRef) -> PyResult<bool> {
+        let mut derived = subclass;
+        loop {
+            if derived.class().is(cls) {
+                return Ok(true);
+            }
+
+            let bases = self.get_attribute(derived, "__bases__")?;
+            let tuple = PyTupleRef::try_from_object(self, bases)?;
+
+            let n = tuple.len();
+            match n {
+                0 => {
+                    return Ok(false);
+                }
+                1 => {
+                    derived = tuple.fast_getitem(0);
+                    continue;
+                }
+                _ => {
+                    for i in 0..n {
+                        if let Ok(true) = self.abstract_issubclass(tuple.fast_getitem(i), cls) {
+                            return Ok(true);
+                        }
+                    }
+                }
+            }
+
+            return Ok(false);
+        }
+    }
+
+    fn recursive_issubclass(&self, subclass: &PyObjectRef, cls: &PyObjectRef) -> PyResult<bool> {
+        if let (Ok(subclass), Ok(cls)) = (
+            PyTypeRef::try_from_object(self, subclass.clone()),
+            PyTypeRef::try_from_object(self, cls.clone()),
+        ) {
+            Ok(subclass.issubclass(cls))
+        } else {
+            if self.get_attribute(subclass.clone(), "__bases__").is_err() {
+                return Err(self.new_type_error(format!(
+                    "issubclass() arg 1 must be a class, not {}",
+                    subclass.class()
+                )));
+            }
+            if self.get_attribute(cls.clone(), "__bases__").is_err() {
+                return Err(self.new_type_error(format!(
+                    "issubclass() arg 2 must be a class or tuple of classes, not {}",
+                    cls.class()
+                )));
+            }
+            self.abstract_issubclass(subclass.clone(), cls)
+        }
+    }
+
     /// Determines if `subclass` is a subclass of `cls`, either directly, indirectly or virtually
     /// via the __subclasscheck__ magic method.
-    pub fn issubclass(&self, subclass: &PyTypeRef, cls: &PyTypeRef) -> PyResult<bool> {
-        let ret = self.call_special_method(
-            cls.as_object().clone(),
-            "__subclasscheck__",
-            (subclass.clone(),),
-        )?;
-        pybool::boolval(self, ret)
+    pub fn issubclass(&self, subclass: &PyObjectRef, cls: &PyObjectRef) -> PyResult<bool> {
+        if cls.class().is(&self.ctx.types.type_type) {
+            if subclass.is(cls) {
+                return Ok(true);
+            }
+            return self.recursive_issubclass(subclass, cls);
+        }
+
+        if let Ok(tuple) = PyTupleRef::try_from_object(self, cls.clone()) {
+            for typ in tuple.as_slice().iter() {
+                if self.issubclass(subclass, typ)? {
+                    return Ok(true);
+                }
+            }
+            return Ok(false);
+        }
+
+        if let Ok(meth) = self.get_special_method(cls.clone(), "__subclasscheck__")? {
+            let ret = meth.invoke((subclass.clone(),), self)?;
+            return pybool::boolval(self, ret);
+        }
+
+        self.recursive_issubclass(subclass, cls)
     }
 
     pub fn call_get_descriptor_specific(