diff --git a/crates/ty_python_semantic/resources/mdtest/scopes/moduletype_attrs.md b/crates/ty_python_semantic/resources/mdtest/scopes/moduletype_attrs.md
index 71c298b8d9b25..09fdefa94278e 100644
--- a/crates/ty_python_semantic/resources/mdtest/scopes/moduletype_attrs.md
+++ b/crates/ty_python_semantic/resources/mdtest/scopes/moduletype_attrs.md
@@ -8,7 +8,8 @@ is unbound.
 
 ```py
 reveal_type(__name__)  # revealed: str
-reveal_type(__file__)  # revealed: str | None
+# Typeshed says this is str | None, but for a pure-Python on-disk module its always str
+reveal_type(__file__)  # revealed: str
 reveal_type(__loader__)  # revealed: LoaderProtocol | None
 reveal_type(__package__)  # revealed: str | None
 reveal_type(__doc__)  # revealed: str | None
@@ -52,6 +53,10 @@ import typing
 reveal_type(typing.__name__)  # revealed: str
 reveal_type(typing.__init__)  # revealed: bound method ModuleType.__init__(name: str, doc: str | None = ellipsis) -> None
 
+# For a stub module, we don't know that `__file__` is a string (at runtime it may be entirely
+# unset, but we follow typeshed here):
+reveal_type(typing.__file__)  # revealed: str | None
+
 # These come from `builtins.object`, not `types.ModuleType`:
 reveal_type(typing.__eq__)  # revealed: bound method ModuleType.__eq__(value: object, /) -> bool
 
diff --git a/crates/ty_python_semantic/src/symbol.rs b/crates/ty_python_semantic/src/symbol.rs
index 920c7ff9e65fa..b18dba7733228 100644
--- a/crates/ty_python_semantic/src/symbol.rs
+++ b/crates/ty_python_semantic/src/symbol.rs
@@ -982,12 +982,18 @@ mod implicit_globals {
         db: &'db dyn Db,
         name: &str,
     ) -> SymbolAndQualifiers<'db> {
+        // We special-case `__file__` here because we know that for an internal implicit global
+        // lookup in a Python module, it is always a string, even though typeshed says `str |
+        // None`.
+        if name == "__file__" {
+            Symbol::bound(KnownClass::Str.to_instance(db)).into()
+        }
         // In general we wouldn't check to see whether a symbol exists on a class before doing the
         // `.member()` call on the instance type -- we'd just do the `.member`() call on the instance
         // type, since it has the same end result. The reason to only call `.member()` on `ModuleType`
         // when absolutely necessary is that this function is used in a very hot path (name resolution
         // in `infer.rs`). We use less idiomatic (and much more verbose) code here as a micro-optimisation.
-        if module_type_symbols(db)
+        else if module_type_symbols(db)
             .iter()
             .any(|module_type_member| &**module_type_member == name)
         {