diff --git a/ccflow/_flow_model_binding.py b/ccflow/_flow_model_binding.py
index 78373e0..5057ba3 100644
--- a/ccflow/_flow_model_binding.py
+++ b/ccflow/_flow_model_binding.py
@@ -75,6 +75,7 @@ class _ParsedAnnotation:
     base: Any
     is_lazy: bool
     is_from_context: bool
+    optional_context: bool = False
 
 
 @dataclass(frozen=True)
@@ -390,6 +391,7 @@ def _resolved_flow_signature(
 def _parse_annotation(annotation: Any) -> _ParsedAnnotation:
     is_lazy = False
     is_from_context = False
+    optional_context = False
 
     while get_origin(annotation) is Annotated:
         args = get_args(annotation)
@@ -400,12 +402,38 @@ def _parse_annotation(annotation: Any) -> _ParsedAnnotation:
             elif isinstance(metadata, _FromContextMarker):
                 is_from_context = True
 
+    # Detect markers nested inside a top-level Optional/Union, e.g.
+    # ``Optional[FromContext[int]]`` == ``Union[Annotated[int, FromContext], None]``.
+    # Such a parameter is contextual but not required: when absent from the runtime
+    # context it is bound to ``None`` (an implicit default synthesized in
+    # ``_analyze_flow_function``). This is distinct from ``FromContext[Optional[int]]``,
+    # which is required-in-context but may carry a ``None`` value.
+    if not is_from_context and not is_lazy and get_origin(annotation) in _UNION_ORIGINS:
+        members = get_args(annotation)
+        non_none = [member for member in members if member is not type(None)]
+        has_none = len(non_none) != len(members)
+        marked = [(member, _parse_annotation(member)) for member in non_none]
+        marker_members = [(member, parsed) for member, parsed in marked if parsed.is_from_context or parsed.is_lazy]
+        if marker_members:
+            if any(parsed.is_lazy for _, parsed in marker_members):
+                raise TypeError("Lazy[...] cannot be nested inside Optional/Union; mark the whole parameter as Lazy[T].")
+            if len(marker_members) != 1 or not has_none or len(non_none) != 1:
+                raise TypeError(
+                    "FromContext[...] inside a Union is only supported as Optional[FromContext[T]] "
+                    "(exactly one contextual member plus None). Use FromContext[Optional[T]] for a "
+                    "required-but-nullable contextual input."
+                )
+            inner = marker_members[0][1].base
+            annotation = Optional[inner]
+            is_from_context = True
+            optional_context = True
+
     if annotation is FromContext:
         raise TypeError("FromContext is an annotation marker; use FromContext[T] in @Flow.model signatures.")
     if annotation is Lazy:
         raise TypeError("Lazy is an annotation marker; use Lazy[T] in @Flow.model signatures.")
 
-    return _ParsedAnnotation(base=annotation, is_lazy=is_lazy, is_from_context=is_from_context)
+    return _ParsedAnnotation(base=annotation, is_lazy=is_lazy, is_from_context=is_from_context, optional_context=optional_context)
 
 
 def _strip_annotated(annotation: Any) -> Any:
@@ -520,14 +548,26 @@ def _analyze_flow_function(
         if parsed.is_from_context and has_default and is_model_dependency(param.default):
             raise TypeError(f"Parameter '{param.name}' is marked FromContext[...] and cannot default to a CallableModel.")
 
+        # ``Optional[FromContext[T]]`` is contextual with an implicit ``None`` default unless
+        # the signature already provides one. An explicit default always wins.
+        if has_default:
+            stored_has_default = True
+            stored_default = param.default
+        elif parsed.optional_context:
+            stored_has_default = True
+            stored_default = None
+        else:
+            stored_has_default = False
+            stored_default = _UNSET
+
         analyzed_params.append(
             _FlowModelParam(
                 name=param.name,
                 annotation=parsed.base,
                 is_contextual=parsed.is_from_context,
                 is_lazy=parsed.is_lazy,
-                has_function_default=has_default,
-                function_default=param.default if has_default else _UNSET,
+                has_function_default=stored_has_default,
+                function_default=stored_default,
             )
         )
 
diff --git a/ccflow/tests/test_flow_model_optional_context.py b/ccflow/tests/test_flow_model_optional_context.py
new file mode 100644
index 0000000..3f067e4
--- /dev/null
+++ b/ccflow/tests/test_flow_model_optional_context.py
@@ -0,0 +1,100 @@
+"""Tests for ``Optional[FromContext[T]]`` vs ``FromContext[Optional[T]]`` semantics.
+
+Two spellings are both contextual and share the same validation base (``Optional[T]``);
+they differ only in required-ness:
+
+- ``FromContext[Optional[int]]`` is required-in-context but its value may be ``None``.
+- ``Optional[FromContext[int]]`` is optional: when absent from context it is bound to ``None``.
+"""
+
+from typing import Optional, Union
+
+import pytest
+
+from ccflow import Flow, FlowContext, FromContext, Lazy, ModelEvaluationContext
+from ccflow.evaluators.common import cache_key
+
+
+@Flow.model
+def required_ctx(a: FromContext[Optional[int]]) -> int:
+    return -1 if a is None else a
+
+
+@Flow.model
+def optional_ctx(a: Optional[FromContext[int]]) -> int:
+    return -1 if a is None else a
+
+
+@Flow.model
+def explicit_none_default(a: FromContext[Optional[int]] = None) -> int:
+    return -1 if a is None else a
+
+
+@Flow.model
+def optional_with_default(a: Optional[FromContext[int]] = 3) -> int:
+    return -1 if a is None else a
+
+
+class TestRequiredNullableContext:
+    def test_missing_raises(self):
+        with pytest.raises(TypeError, match="Missing contextual input"):
+            required_ctx().flow.compute()
+
+    def test_none_is_valid(self):
+        assert required_ctx().flow.compute(a=None).value == -1
+
+    def test_value(self):
+        assert required_ctx().flow.compute(a=5).value == 5
+
+    def test_inspect_required(self):
+        insp = required_ctx().flow.inspect()
+        assert "a" in insp.required_inputs
+
+
+class TestOptionalContext:
+    def test_missing_binds_none(self):
+        assert optional_ctx().flow.compute().value == -1
+
+    def test_none_explicit(self):
+        assert optional_ctx().flow.compute(a=None).value == -1
+
+    def test_value(self):
+        assert optional_ctx().flow.compute(a=5).value == 5
+
+    def test_inspect_not_required(self):
+        insp = optional_ctx().flow.inspect()
+        assert "a" not in insp.required_inputs
+        assert "a" in insp.context_inputs
+
+
+class TestConsistency:
+    def test_explicit_none_default_equiv_optional(self):
+        # FromContext[Optional[int]] = None is equivalent to Optional[FromContext[int]].
+        assert explicit_none_default().flow.compute().value == -1
+        assert optional_ctx().flow.compute().value == -1
+
+    def test_optional_with_explicit_default_wins(self):
+        # An explicit default overrides the implicit None of Optional[FromContext[int]].
+        assert optional_with_default().flow.compute().value == 3
+
+    def test_node_keys_distinguish_required_vs_optional(self):
+        req_key = cache_key(ModelEvaluationContext(model=required_ctx(), context=FlowContext(a=5)))
+        opt_key = cache_key(ModelEvaluationContext(model=optional_ctx(), context=FlowContext(a=5)))
+        # Different required-ness must give distinct logical identities.
+        assert req_key != opt_key
+
+
+class TestRejections:
+    def test_nested_lazy_rejected(self):
+        with pytest.raises(TypeError, match="Lazy"):
+
+            @Flow.model
+            def bad(a: Optional[Lazy[int]]) -> int:
+                return 0
+
+    def test_non_optional_union_with_fromcontext_rejected(self):
+        with pytest.raises(TypeError, match="only supported as Optional"):
+
+            @Flow.model
+            def bad(a: Union[FromContext[int], str]) -> int:
+                return 0