diff --git a/src/fable-library-py/fable_library/core/option.pyi b/src/fable-library-py/fable_library/core/option.pyi
index b0ec30ff99..ef88a73827 100644
--- a/src/fable-library-py/fable_library/core/option.pyi
+++ b/src/fable-library-py/fable_library/core/option.pyi
@@ -5,7 +5,8 @@ from typing import overload
 from . import Array
 
 class SomeWrapper[T]:
-    value: T
+    @property
+    def value(self) -> T: ...
     def __init__(self, value: T) -> None: ...
     def __repr__(self) -> str: ...
     def __str__(self) -> str: ...
diff --git a/src/fable-library-py/src/options.rs b/src/fable-library-py/src/options.rs
index 9d59505f12..5121e8ce2a 100644
--- a/src/fable-library-py/src/options.rs
+++ b/src/fable-library-py/src/options.rs
@@ -67,9 +67,12 @@ impl SomeWrapper {
         op: CompareOp,
         py: Python<'py>,
     ) -> PyResult<bool> {
+        if other.is_none() {
+            return Ok(matches!(op, CompareOp::Ne | CompareOp::Gt | CompareOp::Ge));
+        }
+
         let other_value = extract_value(py, other)?;
-        let result = self.value.bind(py).rich_compare(other_value, op)?;
-        result.is_truthy()
+        compare_values(self.value.bind(py), other_value.bind(py), op)
     }
 
     pub fn __repr__(&self, py: Python<'_>) -> PyResult<String> {
@@ -167,6 +170,16 @@ impl SomeWrapper {
     }
 }
 
+// A `None` argument here is the inner option's `None` case, not an absent value.
+fn compare_values(a: &Bound<'_, PyAny>, b: &Bound<'_, PyAny>, op: CompareOp) -> PyResult<bool> {
+    match (a.is_none(), b.is_none()) {
+        (true, true) => Ok(matches!(op, CompareOp::Eq | CompareOp::Le | CompareOp::Ge)),
+        (true, false) => Ok(matches!(op, CompareOp::Ne | CompareOp::Lt | CompareOp::Le)),
+        (false, true) => Ok(matches!(op, CompareOp::Ne | CompareOp::Gt | CompareOp::Ge)),
+        (false, false) => a.rich_compare(b, op)?.is_truthy(),
+    }
+}
+
 // Helper function to check if an object is a Some wrapper
 fn is_some_wrapper(py: Python<'_>, obj: &Bound<'_, PyAny>) -> bool {
     obj.is_instance(&py.get_type::<SomeWrapper>())
diff --git a/src/fable-library-py/tests/test_option.py b/src/fable-library-py/tests/test_option.py
new file mode 100644
index 0000000000..fc6323fb98
--- /dev/null
+++ b/src/fable-library-py/tests/test_option.py
@@ -0,0 +1,46 @@
+"""Tests for nested options, represented by `fable_library.core.option.SomeWrapper`.
+
+Only nesting materializes a wrapper: `Some 42` and `Some (Some 42)` are the bare value,
+`Some None` is `SomeWrapper(None)`. Two options of the same F# type can therefore put a
+wrapper next to `None` or next to a bare value.
+"""
+
+from fable_library.option import some
+from fable_library.util import compare, compare_arrays, equal_arrays, equals
+
+
+def test_equality_between_different_nesting_depths() -> None:
+    assert (some(None) == some(some(None))) is False
+    assert (some(some(None)) == some(None)) is False
+    assert (some(None) != some(some(None))) is True
+    assert equals(some(None), some(some(None))) is False
+
+
+def test_equality_between_equal_nesting_depths() -> None:
+    assert (some(None) == some(None)) is True
+    assert (some(some(None)) == some(some(None))) is True
+    assert equals(some(some(None)), some(some(None))) is True
+
+
+def test_equality_against_none_and_bare_values() -> None:
+    assert (some(None) == None) is False  # noqa: E711
+    assert (None == some(None)) is False  # noqa: E711
+    assert (some(None) == 42) is False
+    assert (42 == some(None)) is False
+
+
+def test_equality_is_inherited_by_containers() -> None:
+    assert equal_arrays([some(None)], [some(some(None))]) is False
+    assert equal_arrays([some(None)], [some(None)]) is True
+    assert compare_arrays([some(None)], [some(some(None))]) == -1
+
+
+def test_comparison_orders_none_before_some() -> None:
+    assert compare(some(None), some(some(None))) == -1
+    assert compare(some(some(None)), some(None)) == 1
+    assert compare(some(None), some(None)) == 0
+    assert compare(None, some(None)) == -1
+    assert compare(some(None), None) == 1
+    # `int option option`: `Some None` against `Some (Some 42)`
+    assert compare(some(None), 42) == -1
+    assert compare(42, some(None)) == 1
diff --git a/tests/Python/TestOption.fs b/tests/Python/TestOption.fs
index f776bdb992..f15d8b3745 100644
--- a/tests/Python/TestOption.fs
+++ b/tests/Python/TestOption.fs
@@ -191,6 +191,38 @@ let ``test Option.map/map2/map3/bind/filter with nested options work`` () =
     Some(Some 5) |> Option.bind (fun inner -> Some inner) |> equal (Some(Some 5))
     Some(Some 5) |> Option.filter Option.isSome |> equal (Some(Some 5))
 
+[<Fact>]
+let ``test equality on nested options of different depth works`` () =
+    let a: int option option option = Some None
+    let b: int option option option = Some(Some None)
+    (a = b) |> equal false
+    (b = a) |> equal false
+    (a = a) |> equal true
+    (b = b) |> equal true
+    notEqual a b
+    let ra: Result<int option option option, string> = Ok a
+    let rb: Result<int option option option, string> = Ok b
+    (ra = rb) |> equal false
+    notEqual ra rb
+    let c: int option option = Some None
+    let d: int option option = Some(Some 42)
+    (c = d) |> equal false
+    (d = c) |> equal false
+
+[<Fact>]
+let ``test comparison on nested options of different depth works`` () =
+    let a: int option option option = Some None
+    let b: int option option option = Some(Some None)
+    compare a b |> equal -1
+    compare b a |> equal 1
+    compare a a |> equal 0
+    compare (None: int option option option) a |> equal -1
+    compare a (None: int option option option) |> equal 1
+    let c: int option option = Some None
+    let d: int option option = Some(Some 42)
+    compare c d |> equal -1
+    compare d c |> equal 1
+
 [<Fact>]
 let ``test ValueOption.map/map2/map3/bind/filter/defaultWith/orElseWith work`` () =
     ValueSome 5 |> ValueOption.map (fun x -> x + 1) |> equal (ValueSome 6)