diff --git a/crates/red_knot_python_semantic/resources/mdtest/expression/len.md b/crates/red_knot_python_semantic/resources/mdtest/expression/len.md
new file mode 100644
index 0000000000..04f6efff5f
--- /dev/null
+++ b/crates/red_knot_python_semantic/resources/mdtest/expression/len.md
@@ -0,0 +1,219 @@
+# Length (`len()`)
+
+## Literal and constructed iterables
+
+### Strings and bytes literals
+
+```py
+reveal_type(len("no\rmal"))  # revealed: Literal[6]
+reveal_type(len(r"aw stri\ng"))  # revealed: Literal[10]
+reveal_type(len(r"conca\t" "ena\tion"))  # revealed: Literal[14]
+reveal_type(len(b"ytes lite" rb"al"))  # revealed: Literal[11]
+reveal_type(len("𝒰𝕹🄸©🕲𝕕ℇ"))  # revealed: Literal[7]
+
+reveal_type(  # revealed: Literal[7]
+    len(
+        """foo
+bar"""
+    )
+)
+reveal_type(  # revealed: Literal[9]
+    len(
+        r"""foo\r
+bar"""
+    )
+)
+reveal_type(  # revealed: Literal[7]
+    len(
+        b"""foo
+bar"""
+    )
+)
+reveal_type(  # revealed: Literal[9]
+    len(
+        rb"""foo\r
+bar"""
+    )
+)
+```
+
+### Tuples
+
+```py
+reveal_type(len(()))  # revealed: Literal[0]
+reveal_type(len((1,)))  # revealed: Literal[1]
+reveal_type(len((1, 2)))  # revealed: Literal[2]
+
+# TODO: Handle constructor calls
+reveal_type(len(tuple()))  # revealed: int
+
+# TODO: Handle star unpacks; Should be: Literal[0]
+reveal_type(len((*[],)))  # revealed: Literal[1]
+
+# TODO: Handle star unpacks; Should be: Literal[1]
+reveal_type(  # revealed: Literal[2]
+    len(
+        (
+            *[],
+            1,
+        )
+    )
+)
+
+# TODO: Handle star unpacks; Should be: Literal[2]
+reveal_type(len((*[], 1, 2)))  # revealed: Literal[3]
+
+# TODO: Handle star unpacks; Should be: Literal[0]
+reveal_type(len((*[], *{})))  # revealed: Literal[2]
+```
+
+### Lists, sets and dictionaries
+
+```py
+reveal_type(len([]))  # revealed: int
+reveal_type(len([1]))  # revealed: int
+reveal_type(len([1, 2]))  # revealed: int
+reveal_type(len([*{}, *dict()]))  # revealed: int
+
+reveal_type(len({}))  # revealed: int
+reveal_type(len({**{}}))  # revealed: int
+reveal_type(len({**{}, **{}}))  # revealed: int
+
+reveal_type(len({1}))  # revealed: int
+reveal_type(len({1, 2}))  # revealed: int
+reveal_type(len({*[], 2}))  # revealed: int
+
+reveal_type(len(list()))  # revealed: int
+reveal_type(len(set()))  # revealed: int
+reveal_type(len(dict()))  # revealed: int
+reveal_type(len(frozenset()))  # revealed: int
+```
+
+## `__len__`
+
+The returned value of `__len__` is implicitly and recursively converted to `int`.
+
+### Literal integers
+
+```py
+from typing import Literal
+
+class Zero:
+    def __len__(self) -> Literal[0]: ...
+
+class ZeroOrOne:
+    def __len__(self) -> Literal[0, 1]: ...
+
+class ZeroOrTrue:
+    def __len__(self) -> Literal[0, True]: ...
+
+class OneOrFalse:
+    def __len__(self) -> Literal[1] | Literal[False]: ...
+
+class OneOrFoo:
+    def __len__(self) -> Literal[1, "foo"]: ...
+
+class ZeroOrStr:
+    def __len__(self) -> Literal[0] | str: ...
+
+reveal_type(len(Zero()))  # revealed: Literal[0]
+reveal_type(len(ZeroOrOne()))  # revealed: Literal[0, 1]
+reveal_type(len(ZeroOrTrue()))  # revealed: Literal[0, 1]
+reveal_type(len(OneOrFalse()))  # revealed: Literal[0, 1]
+
+# TODO: Emit a diagnostic
+reveal_type(len(OneOrFoo()))  # revealed: int
+
+# TODO: Emit a diagnostic
+reveal_type(len(ZeroOrStr()))  # revealed: int
+```
+
+### Literal booleans
+
+```py
+from typing import Literal
+
+class LiteralTrue:
+    def __len__(self) -> Literal[True]: ...
+
+class LiteralFalse:
+    def __len__(self) -> Literal[False]: ...
+
+reveal_type(len(LiteralTrue()))  # revealed: Literal[1]
+reveal_type(len(LiteralFalse()))  # revealed: Literal[0]
+```
+
+### Enums
+
+```py
+from enum import Enum, auto
+from typing import Literal
+
+class SomeEnum(Enum):
+    AUTO = auto()
+    INT = 2
+    STR = "4"
+    TUPLE = (8, "16")
+    INT_2 = 3_2
+
+class Auto:
+    def __len__(self) -> Literal[SomeEnum.AUTO]: ...
+
+class Int:
+    def __len__(self) -> Literal[SomeEnum.INT]: ...
+
+class Str:
+    def __len__(self) -> Literal[SomeEnum.STR]: ...
+
+class Tuple:
+    def __len__(self) -> Literal[SomeEnum.TUPLE]: ...
+
+class IntUnion:
+    def __len__(self) -> Literal[SomeEnum.INT, SomeEnum.INT_2]: ...
+
+reveal_type(len(Auto()))  # revealed: int
+reveal_type(len(Int()))  # revealed: Literal[2]
+reveal_type(len(Str()))  # revealed: int
+reveal_type(len(Tuple()))  # revealed: int
+reveal_type(len(IntUnion()))  # revealed: Literal[2, 32]
+```
+
+### Negative integers
+
+```py
+from typing import Literal
+
+class Negative:
+    def __len__(self) -> Literal[-1]: ...
+
+# TODO: Emit a diagnostic
+reveal_type(len(Negative()))  # revealed: int
+```
+
+### Wrong signature
+
+```py
+from typing import Literal
+
+class SecondOptionalArgument:
+    def __len__(self, v: int = 0) -> Literal[0]: ...
+
+class SecondRequiredArgument:
+    def __len__(self, v: int) -> Literal[1]: ...
+
+# TODO: Emit a diagnostic
+reveal_type(len(SecondOptionalArgument()))  # revealed: Literal[0]
+
+# TODO: Emit a diagnostic
+reveal_type(len(SecondRequiredArgument()))  # revealed: Literal[1]
+```
+
+### No `__len__`
+
+```py
+class NoDunderLen:
+    pass
+
+# TODO: Emit a diagnostic
+reveal_type(len(NoDunderLen()))  # revealed: int
+```
diff --git a/crates/red_knot_python_semantic/resources/mdtest/unpacking.md b/crates/red_knot_python_semantic/resources/mdtest/unpacking.md
index 0e9c3943a9..1da17a4f27 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/unpacking.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/unpacking.md
@@ -267,3 +267,42 @@ reveal_type(b)  # revealed: LiteralString
 # TODO: Should be list[int] once support for assigning to starred expression is added
 reveal_type(c)  # revealed: @Todo(starred unpacking)
 ```
+
+### Unicode
+
+```py
+# TODO: Add diagnostic (need more values to unpack)
+(a, b) = "é"
+
+reveal_type(a)  # revealed: LiteralString
+reveal_type(b)  # revealed: Unknown
+```
+
+### Unicode escape (1)
+
+```py
+# TODO: Add diagnostic (need more values to unpack)
+(a, b) = "\u9E6C"
+
+reveal_type(a)  # revealed: LiteralString
+reveal_type(b)  # revealed: Unknown
+```
+
+### Unicode escape (2)
+
+```py
+# TODO: Add diagnostic (need more values to unpack)
+(a, b) = "\U0010FFFF"
+
+reveal_type(a)  # revealed: LiteralString
+reveal_type(b)  # revealed: Unknown
+```
+
+### Surrogates
+
+```py
+(a, b) = "\uD800\uDFFF"
+
+reveal_type(a)  # revealed: LiteralString
+reveal_type(b)  # revealed: LiteralString
+```
diff --git a/crates/red_knot_python_semantic/src/types.rs b/crates/red_knot_python_semantic/src/types.rs
index 97a79434fc..e1e047db03 100644
--- a/crates/red_knot_python_semantic/src/types.rs
+++ b/crates/red_knot_python_semantic/src/types.rs
@@ -1417,21 +1417,76 @@ impl<'db> Type<'db> {
         }
     }
 
+    /// Return the type of `len()` on a type if it is known more precisely than `int`,
+    /// or `None` otherwise.
+    ///
+    /// In the second case, the return type of `len()` in `typeshed` (`int`)
+    /// is used as a fallback.
+    fn len(&self, db: &'db dyn Db) -> Option<Type<'db>> {
+        fn non_negative_int_literal<'db>(db: &'db dyn Db, ty: Type<'db>) -> Option<Type<'db>> {
+            match ty {
+                // TODO: Emit diagnostic for non-integers and negative integers
+                Type::IntLiteral(value) => (value >= 0).then_some(ty),
+                Type::BooleanLiteral(value) => Some(Type::IntLiteral(value.into())),
+                Type::Union(union) => {
+                    let mut builder = UnionBuilder::new(db);
+                    for element in union.elements(db) {
+                        builder = builder.add(non_negative_int_literal(db, *element)?);
+                    }
+                    Some(builder.build())
+                }
+                _ => None,
+            }
+        }
+
+        let usize_len = match self {
+            Type::BytesLiteral(bytes) => Some(bytes.python_len(db)),
+            Type::StringLiteral(string) => Some(string.python_len(db)),
+            Type::Tuple(tuple) => Some(tuple.len(db)),
+            _ => None,
+        };
+
+        if let Some(usize_len) = usize_len {
+            return usize_len.try_into().ok().map(Type::IntLiteral);
+        }
+
+        let return_ty = match self.call_dunder(db, "__len__", &[*self]) {
+            // TODO: emit a diagnostic
+            CallDunderResult::MethodNotAvailable => return None,
+
+            CallDunderResult::CallOutcome(outcome) | CallDunderResult::PossiblyUnbound(outcome) => {
+                outcome.return_ty(db)?
+            }
+        };
+
+        non_negative_int_literal(db, return_ty)
+    }
+
     /// Return the outcome of calling an object of this type.
     #[must_use]
     fn call(self, db: &'db dyn Db, arg_types: &[Type<'db>]) -> CallOutcome<'db> {
         match self {
             // TODO validate typed call arguments vs callable signature
-            Type::FunctionLiteral(function_type) => {
-                if function_type.is_known(db, KnownFunction::RevealType) {
-                    CallOutcome::revealed(
-                        function_type.signature(db).return_ty,
-                        *arg_types.first().unwrap_or(&Type::Unknown),
-                    )
-                } else {
-                    CallOutcome::callable(function_type.signature(db).return_ty)
+            Type::FunctionLiteral(function_type) => match function_type.known(db) {
+                Some(KnownFunction::RevealType) => CallOutcome::revealed(
+                    function_type.signature(db).return_ty,
+                    *arg_types.first().unwrap_or(&Type::Unknown),
+                ),
+
+                Some(KnownFunction::Len) => {
+                    let normal_return_ty = function_type.signature(db).return_ty;
+
+                    let [only_arg] = arg_types else {
+                        // TODO: Emit a diagnostic
+                        return CallOutcome::callable(normal_return_ty);
+                    };
+                    let len_ty = only_arg.len(db);
+
+                    CallOutcome::callable(len_ty.unwrap_or(normal_return_ty))
                 }
-            }
+
+                _ => CallOutcome::callable(function_type.signature(db).return_ty),
+            },
 
             // TODO annotated return type on `__new__` or metaclass `__call__`
             Type::ClassLiteral(ClassLiteralType { class }) => {
@@ -2597,13 +2652,15 @@ pub enum KnownFunction {
     ConstraintFunction(KnownConstraintFunction),
     /// `builtins.reveal_type`, `typing.reveal_type` or `typing_extensions.reveal_type`
     RevealType,
+    /// `builtins.len`
+    Len,
 }
 
 impl KnownFunction {
     pub fn constraint_function(self) -> Option<KnownConstraintFunction> {
         match self {
             Self::ConstraintFunction(f) => Some(f),
-            Self::RevealType => None,
+            Self::RevealType | Self::Len => None,
         }
     }
 
@@ -2620,6 +2677,7 @@ impl KnownFunction {
             "issubclass" if definition.is_builtin_definition(db) => Some(
                 KnownFunction::ConstraintFunction(KnownConstraintFunction::IsSubclass),
             ),
+            "len" if definition.is_builtin_definition(db) => Some(KnownFunction::Len),
             _ => None,
         }
     }
@@ -3074,8 +3132,9 @@ pub struct StringLiteralType<'db> {
 }
 
 impl<'db> StringLiteralType<'db> {
-    pub fn len(&self, db: &'db dyn Db) -> usize {
-        self.value(db).len()
+    /// The length of the string, as would be returned by Python's `len()`.
+    pub fn python_len(&self, db: &'db dyn Db) -> usize {
+        self.value(db).chars().count()
     }
 }
 
@@ -3085,6 +3144,12 @@ pub struct BytesLiteralType<'db> {
     value: Box<[u8]>,
 }
 
+impl<'db> BytesLiteralType<'db> {
+    pub fn python_len(&self, db: &'db dyn Db) -> usize {
+        self.value(db).len()
+    }
+}
+
 #[salsa::interned]
 pub struct SliceLiteralType<'db> {
     start: Option<i32>,
diff --git a/crates/red_knot_python_semantic/src/types/unpacker.rs b/crates/red_knot_python_semantic/src/types/unpacker.rs
index dc96fac252..99d45ecd3e 100644
--- a/crates/red_knot_python_semantic/src/types/unpacker.rs
+++ b/crates/red_knot_python_semantic/src/types/unpacker.rs
@@ -95,7 +95,8 @@ impl<'db> Unpacker<'db> {
                     // there would be a cost and it's not clear that it's worth it.
                     let value_ty = Type::tuple(
                         self.db,
-                        std::iter::repeat(Type::LiteralString).take(string_literal_ty.len(self.db)),
+                        std::iter::repeat(Type::LiteralString)
+                            .take(string_literal_ty.python_len(self.db)),
                     );
                     self.unpack(target, value_ty, scope);
                 }