diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_api.md b/crates/red_knot_python_semantic/resources/mdtest/type_api.md
index c4e7aa1a16..715ceef584 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_api.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_api.md
@@ -94,6 +94,36 @@ reveal_type(C.__mro__)
 u: Unknown[str]
 ```
 
+### `AlwaysTruthy` and `AlwaysFalsy`
+
+`AlwaysTruthy` and `AlwaysFalsy` represent the sets of all possible objects whose truthiness is
+always truthy or falsy, respectively.
+
+They do not accept any type arguments.
+
+```py
+from typing_extensions import Literal
+
+from knot_extensions import AlwaysFalsy, AlwaysTruthy, is_subtype_of, static_assert
+
+static_assert(is_subtype_of(Literal[True], AlwaysTruthy))
+static_assert(is_subtype_of(Literal[False], AlwaysFalsy))
+
+static_assert(not is_subtype_of(int, AlwaysFalsy))
+static_assert(not is_subtype_of(str, AlwaysFalsy))
+
+def _(t: AlwaysTruthy, f: AlwaysFalsy):
+    reveal_type(t)  # revealed: AlwaysTruthy
+    reveal_type(f)  # revealed: AlwaysFalsy
+
+def f(
+    a: AlwaysTruthy[int],  # error: [invalid-type-form]
+    b: AlwaysFalsy[str],  # error: [invalid-type-form]
+):
+    reveal_type(a)  # revealed: Unknown
+    reveal_type(b)  # revealed: Unknown
+```
+
 ## Static assertions
 
 ### Basics
diff --git a/crates/red_knot_python_semantic/src/types.rs b/crates/red_knot_python_semantic/src/types.rs
index 9c22c45ae3..3bec7b5e46 100644
--- a/crates/red_knot_python_semantic/src/types.rs
+++ b/crates/red_knot_python_semantic/src/types.rs
@@ -2292,6 +2292,8 @@ impl<'db> Type<'db> {
                 fallback_type: Type::unknown(),
             }),
             Type::KnownInstance(KnownInstanceType::Unknown) => Ok(Type::unknown()),
+            Type::KnownInstance(KnownInstanceType::AlwaysTruthy) => Ok(Type::AlwaysTruthy),
+            Type::KnownInstance(KnownInstanceType::AlwaysFalsy) => Ok(Type::AlwaysFalsy),
             _ => Ok(todo_type!(
                 "Unsupported or invalid type in a type expression"
             )),
@@ -2827,6 +2829,10 @@ pub enum KnownInstanceType<'db> {
     TypeAliasType(TypeAliasType<'db>),
     /// The symbol `knot_extensions.Unknown`
     Unknown,
+    /// The symbol `knot_extensions.AlwaysTruthy`
+    AlwaysTruthy,
+    /// The symbol `knot_extensions.AlwaysFalsy`
+    AlwaysFalsy,
     /// The symbol `knot_extensions.Not`
     Not,
     /// The symbol `knot_extensions.Intersection`
@@ -2888,6 +2894,8 @@ impl<'db> KnownInstanceType<'db> {
             Self::OrderedDict => "OrderedDict",
             Self::ReadOnly => "ReadOnly",
             Self::Unknown => "Unknown",
+            Self::AlwaysTruthy => "AlwaysTruthy",
+            Self::AlwaysFalsy => "AlwaysFalsy",
             Self::Not => "Not",
             Self::Intersection => "Intersection",
             Self::TypeOf => "TypeOf",
@@ -2931,6 +2939,8 @@ impl<'db> KnownInstanceType<'db> {
             | Self::ReadOnly
             | Self::TypeAliasType(_)
             | Self::Unknown
+            | Self::AlwaysTruthy
+            | Self::AlwaysFalsy
             | Self::Not
             | Self::Intersection
             | Self::TypeOf => Truthiness::AlwaysTrue,
@@ -2974,6 +2984,8 @@ impl<'db> KnownInstanceType<'db> {
             Self::TypeVar(typevar) => typevar.name(db),
             Self::TypeAliasType(_) => "typing.TypeAliasType",
             Self::Unknown => "knot_extensions.Unknown",
+            Self::AlwaysTruthy => "knot_extensions.AlwaysTruthy",
+            Self::AlwaysFalsy => "knot_extensions.AlwaysFalsy",
             Self::Not => "knot_extensions.Not",
             Self::Intersection => "knot_extensions.Intersection",
             Self::TypeOf => "knot_extensions.TypeOf",
@@ -3020,6 +3032,8 @@ impl<'db> KnownInstanceType<'db> {
             Self::Not => KnownClass::SpecialForm,
             Self::Intersection => KnownClass::SpecialForm,
             Self::Unknown => KnownClass::Object,
+            Self::AlwaysTruthy => KnownClass::Object,
+            Self::AlwaysFalsy => KnownClass::Object,
         }
     }
 
@@ -3071,6 +3085,8 @@ impl<'db> KnownInstanceType<'db> {
             "NotRequired" => Self::NotRequired,
             "LiteralString" => Self::LiteralString,
             "Unknown" => Self::Unknown,
+            "AlwaysTruthy" => Self::AlwaysTruthy,
+            "AlwaysFalsy" => Self::AlwaysFalsy,
             "Not" => Self::Not,
             "Intersection" => Self::Intersection,
             "TypeOf" => Self::TypeOf,
@@ -3123,9 +3139,12 @@ impl<'db> KnownInstanceType<'db> {
             | Self::TypeVar(_) => {
                 matches!(module, KnownModule::Typing | KnownModule::TypingExtensions)
             }
-            Self::Unknown | Self::Not | Self::Intersection | Self::TypeOf => {
-                module.is_knot_extensions()
-            }
+            Self::Unknown
+            | Self::AlwaysTruthy
+            | Self::AlwaysFalsy
+            | Self::Not
+            | Self::Intersection
+            | Self::TypeOf => module.is_knot_extensions(),
         }
     }
 
diff --git a/crates/red_knot_python_semantic/src/types/class_base.rs b/crates/red_knot_python_semantic/src/types/class_base.rs
index 1b4a357914..18f0605b0d 100644
--- a/crates/red_knot_python_semantic/src/types/class_base.rs
+++ b/crates/red_knot_python_semantic/src/types/class_base.rs
@@ -105,7 +105,9 @@ impl<'db> ClassBase<'db> {
                 | KnownInstanceType::Optional
                 | KnownInstanceType::Not
                 | KnownInstanceType::Intersection
-                | KnownInstanceType::TypeOf => None,
+                | KnownInstanceType::TypeOf
+                | KnownInstanceType::AlwaysTruthy
+                | KnownInstanceType::AlwaysFalsy => None,
                 KnownInstanceType::Unknown => Some(Self::unknown()),
                 KnownInstanceType::Any => Some(Self::any()),
                 // TODO: Classes inheriting from `typing.Type` et al. also have `Generic` in their MRO
diff --git a/crates/red_knot_python_semantic/src/types/infer.rs b/crates/red_knot_python_semantic/src/types/infer.rs
index 4923285adb..194ce6c634 100644
--- a/crates/red_knot_python_semantic/src/types/infer.rs
+++ b/crates/red_knot_python_semantic/src/types/infer.rs
@@ -4539,7 +4539,7 @@ impl<'db> TypeInferenceBuilder<'db> {
 
                         return dunder_getitem_method
                             .call(self.db(), &CallArguments::positional([value_ty, slice_ty]))
-                            .return_ty_result( &self.context, value_node.into())
+                            .return_ty_result(&self.context, value_node.into())
                             .unwrap_or_else(|err| {
                                 self.context.report_lint(
                                     &CALL_NON_CALLABLE,
@@ -5373,7 +5373,11 @@ impl<'db> TypeInferenceBuilder<'db> {
                 self.infer_type_expression(arguments_slice);
                 todo_type!("`Unpack[]` special form")
             }
-            KnownInstanceType::NoReturn | KnownInstanceType::Never | KnownInstanceType::Any => {
+            KnownInstanceType::NoReturn
+            | KnownInstanceType::Never
+            | KnownInstanceType::Any
+            | KnownInstanceType::AlwaysTruthy
+            | KnownInstanceType::AlwaysFalsy => {
                 self.context.report_lint(
                     &INVALID_TYPE_FORM,
                     subscript.into(),
diff --git a/crates/red_knot_vendored/knot_extensions/knot_extensions.pyi b/crates/red_knot_vendored/knot_extensions/knot_extensions.pyi
index 581b2a3d29..e2695caa97 100644
--- a/crates/red_knot_vendored/knot_extensions/knot_extensions.pyi
+++ b/crates/red_knot_vendored/knot_extensions/knot_extensions.pyi
@@ -5,6 +5,8 @@ def static_assert(condition: object, msg: LiteralString | None = None) -> None:
 
 # Types
 Unknown = object()
+AlwaysTruthy = object()
+AlwaysFalsy = object()
 
 # Special forms
 Not: _SpecialForm