diff --git a/crates/red_knot_ide/src/db.rs b/crates/red_knot_ide/src/db.rs
index ba49ee864f..9d98db1dcb 100644
--- a/crates/red_knot_ide/src/db.rs
+++ b/crates/red_knot_ide/src/db.rs
@@ -10,7 +10,7 @@ pub(crate) mod tests {
 
     use super::Db;
     use red_knot_python_semantic::lint::{LintRegistry, RuleSelection};
-    use red_knot_python_semantic::{default_lint_registry, Db as SemanticDb};
+    use red_knot_python_semantic::{default_lint_registry, Db as SemanticDb, Program};
     use ruff_db::files::{File, Files};
     use ruff_db::system::{DbWithTestSystem, System, TestSystem};
     use ruff_db::vendored::VendoredFileSystem;
@@ -83,6 +83,10 @@ pub(crate) mod tests {
         fn files(&self) -> &Files {
             &self.files
         }
+
+        fn python_version(&self) -> ruff_python_ast::PythonVersion {
+            Program::get(self).python_version(self)
+        }
     }
 
     impl Upcast<dyn SourceDb> for TestDb {
diff --git a/crates/red_knot_project/src/db.rs b/crates/red_knot_project/src/db.rs
index e1d19983e0..d724ebc3f3 100644
--- a/crates/red_knot_project/src/db.rs
+++ b/crates/red_knot_project/src/db.rs
@@ -149,6 +149,10 @@ impl SourceDb for ProjectDatabase {
     fn files(&self) -> &Files {
         &self.files
     }
+
+    fn python_version(&self) -> ruff_python_ast::PythonVersion {
+        Program::get(self).python_version(self)
+    }
 }
 
 #[salsa::db]
@@ -207,7 +211,7 @@ pub(crate) mod tests {
     use salsa::Event;
 
     use red_knot_python_semantic::lint::{LintRegistry, RuleSelection};
-    use red_knot_python_semantic::Db as SemanticDb;
+    use red_knot_python_semantic::{Db as SemanticDb, Program};
     use ruff_db::files::Files;
     use ruff_db::system::{DbWithTestSystem, System, TestSystem};
     use ruff_db::vendored::VendoredFileSystem;
@@ -281,6 +285,10 @@ pub(crate) mod tests {
         fn files(&self) -> &Files {
             &self.files
         }
+
+        fn python_version(&self) -> ruff_python_ast::PythonVersion {
+            Program::get(self).python_version(self)
+        }
     }
 
     impl Upcast<dyn SemanticDb> for TestDb {
diff --git a/crates/red_knot_project/src/lib.rs b/crates/red_knot_project/src/lib.rs
index a0a7c531d7..fd6545972a 100644
--- a/crates/red_knot_project/src/lib.rs
+++ b/crates/red_knot_project/src/lib.rs
@@ -10,7 +10,8 @@ use red_knot_python_semantic::lint::{LintRegistry, LintRegistryBuilder, RuleSele
 use red_knot_python_semantic::register_lints;
 use red_knot_python_semantic::types::check_types;
 use ruff_db::diagnostic::{
-    create_parse_diagnostic, Annotation, Diagnostic, DiagnosticId, Severity, Span,
+    create_parse_diagnostic, create_unsupported_syntax_diagnostic, Annotation, Diagnostic,
+    DiagnosticId, Severity, Span,
 };
 use ruff_db::files::File;
 use ruff_db::parsed::parsed_module;
@@ -424,6 +425,13 @@ fn check_file_impl(db: &dyn Db, file: File) -> Vec<Diagnostic> {
             .map(|error| create_parse_diagnostic(file, error)),
     );
 
+    diagnostics.extend(
+        parsed
+            .unsupported_syntax_errors()
+            .iter()
+            .map(|error| create_unsupported_syntax_diagnostic(file, error)),
+    );
+
     diagnostics.extend(check_types(db.upcast(), file).into_iter().cloned());
 
     diagnostics.sort_unstable_by_key(|diagnostic| {
@@ -520,11 +528,13 @@ mod tests {
     use crate::db::tests::TestDb;
     use crate::{check_file_impl, ProjectMetadata};
     use red_knot_python_semantic::types::check_types;
+    use red_knot_python_semantic::{Program, ProgramSettings, PythonPlatform, SearchPathSettings};
     use ruff_db::files::system_path_to_file;
     use ruff_db::source::source_text;
     use ruff_db::system::{DbWithTestSystem, DbWithWritableSystem as _, SystemPath, SystemPathBuf};
     use ruff_db::testing::assert_function_query_was_not_run;
     use ruff_python_ast::name::Name;
+    use ruff_python_ast::PythonVersion;
 
     #[test]
     fn check_file_skips_type_checking_when_file_cant_be_read() -> ruff_db::system::Result<()> {
@@ -532,6 +542,16 @@ mod tests {
         let mut db = TestDb::new(project);
         let path = SystemPath::new("test.py");
 
+        Program::from_settings(
+            &db,
+            ProgramSettings {
+                python_version: PythonVersion::default(),
+                python_platform: PythonPlatform::default(),
+                search_paths: SearchPathSettings::new(vec![SystemPathBuf::from(".")]),
+            },
+        )
+        .expect("Failed to configure program settings");
+
         db.write_file(path, "x = 10")?;
         let file = system_path_to_file(&db, path).unwrap();
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/annotations/callable.md b/crates/red_knot_python_semantic/resources/mdtest/annotations/callable.md
index 06388bb72f..e906b5de39 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/annotations/callable.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/annotations/callable.md
@@ -237,6 +237,11 @@ def _(c: Callable[[Concatenate[int, str, ...], int], int]):
 
 ## Using `typing.ParamSpec`
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 Using a `ParamSpec` in a `Callable` annotation:
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/annotations/deferred.md b/crates/red_knot_python_semantic/resources/mdtest/annotations/deferred.md
index 7f44fd7f76..7ee6e84060 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/annotations/deferred.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/annotations/deferred.md
@@ -48,6 +48,11 @@ reveal_type(get_foo())  # revealed: Foo
 
 ## Deferred self-reference annotations in a class definition
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from __future__ import annotations
 
@@ -94,6 +99,11 @@ class Foo:
 
 ## Non-deferred self-reference annotations in a class definition
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 class Foo:
     # error: [unresolved-reference]
diff --git a/crates/red_knot_python_semantic/resources/mdtest/annotations/starred.md b/crates/red_knot_python_semantic/resources/mdtest/annotations/starred.md
index a71a89bcc1..61887e7f29 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/annotations/starred.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/annotations/starred.md
@@ -1,5 +1,10 @@
 # Starred expression annotations
 
+```toml
+[environment]
+python-version = "3.11"
+```
+
 Type annotations for `*args` can be starred expressions themselves:
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/annotations/unsupported_special_forms.md b/crates/red_knot_python_semantic/resources/mdtest/annotations/unsupported_special_forms.md
index 175ada1236..80161644ab 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/annotations/unsupported_special_forms.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/annotations/unsupported_special_forms.md
@@ -79,6 +79,11 @@ reveal_type(F.__mro__)  # revealed: tuple[Literal[F], @Todo(Support for Callable
 
 ## Subscriptability
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 Some of these are not subscriptable:
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/assignment/annotations.md b/crates/red_knot_python_semantic/resources/mdtest/assignment/annotations.md
index 42a70bf04d..171ade213e 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/assignment/annotations.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/assignment/annotations.md
@@ -25,6 +25,11 @@ x = "foo"  # error: [invalid-assignment] "Object of type `Literal["foo"]` is not
 
 ## Tuple annotations are understood
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 `module.py`:
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/call/function.md b/crates/red_knot_python_semantic/resources/mdtest/call/function.md
index 10db8aaa80..54c35384c8 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/call/function.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/call/function.md
@@ -21,6 +21,11 @@ reveal_type(get_int_async())  # revealed: @Todo(generic types.CoroutineType)
 
 ## Generic
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 def get_int[T]() -> int:
     return 42
diff --git a/crates/red_knot_python_semantic/resources/mdtest/call/methods.md b/crates/red_knot_python_semantic/resources/mdtest/call/methods.md
index 0d3e94cd92..c7a63beff2 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/call/methods.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/call/methods.md
@@ -399,6 +399,11 @@ reveal_type(getattr_static(C, "f").__get__("dummy", C))  # revealed: bound metho
 
 ### Classmethods mixed with other decorators
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 When a `@classmethod` is additionally decorated with another decorator, it is still treated as a
 class method:
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/class/super.md b/crates/red_knot_python_semantic/resources/mdtest/class/super.md
index 2fa7d0d767..5c5ca3a063 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/class/super.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/class/super.md
@@ -265,6 +265,11 @@ def f(flag: bool):
 
 ## Supers with Generic Classes
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from knot_extensions import TypeOf, static_assert, is_subtype_of
 
@@ -316,6 +321,11 @@ class A:
 
 ### Failing Condition Checks
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 `super()` requires its first argument to be a valid class, and its second argument to be either an
 instance or a subclass of the first. If either condition is violated, a `TypeError` is raised at
 runtime.
diff --git a/crates/red_knot_python_semantic/resources/mdtest/conditional/match.md b/crates/red_knot_python_semantic/resources/mdtest/conditional/match.md
index 5037484212..8b8a3dca34 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/conditional/match.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/conditional/match.md
@@ -1,5 +1,10 @@
 # Pattern matching
 
+```toml
+[environment]
+python-version = "3.10"
+```
+
 ## With wildcard
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/dataclasses.md b/crates/red_knot_python_semantic/resources/mdtest/dataclasses.md
index 000c600317..28baa67ba4 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/dataclasses.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/dataclasses.md
@@ -297,6 +297,11 @@ reveal_type(WithoutEq(1) == WithoutEq(2))  # revealed: bool
 
 ### `order`
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 `order` is set to `False` by default. If `order=True`, `__lt__`, `__le__`, `__gt__`, and `__ge__`
 methods will be generated:
 
@@ -471,6 +476,11 @@ reveal_type(C.__init__)  # revealed: (x: int = Literal[15], y: int = Literal[0],
 
 ## Generic dataclasses
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from dataclasses import dataclass
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/diagnostics/version_related_syntax_errors.md b/crates/red_knot_python_semantic/resources/mdtest/diagnostics/version_related_syntax_errors.md
new file mode 100644
index 0000000000..0a35fe4153
--- /dev/null
+++ b/crates/red_knot_python_semantic/resources/mdtest/diagnostics/version_related_syntax_errors.md
@@ -0,0 +1,37 @@
+# Version-related syntax error diagnostics
+
+## `match` statement
+
+The `match` statement was introduced in Python 3.10.
+
+### Before 3.10
+
+<!-- snapshot-diagnostics -->
+
+We should emit a syntax error before 3.10.
+
+```toml
+[environment]
+python-version = "3.9"
+```
+
+```py
+match 2:  # error: 1 [invalid-syntax] "Cannot use `match` statement on Python 3.9 (syntax was added in Python 3.10)"
+    case 1:
+        print("it's one")
+```
+
+### After 3.10
+
+On or after 3.10, no error should be reported.
+
+```toml
+[environment]
+python-version = "3.10"
+```
+
+```py
+match 2:
+    case 1:
+        print("it's one")
+```
diff --git a/crates/red_knot_python_semantic/resources/mdtest/directives/assert_never.md b/crates/red_knot_python_semantic/resources/mdtest/directives/assert_never.md
index b4d51b3927..712fbad35c 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/directives/assert_never.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/directives/assert_never.md
@@ -26,6 +26,11 @@ def _(never: Never, any_: Any, unknown: Unknown, flag: bool):
 
 ## Use case: Type narrowing and exhaustiveness checking
 
+```toml
+[environment]
+python-version = "3.10"
+```
+
 `assert_never` can be used in combination with type narrowing as a way to make sure that all cases
 are handled in a series of `isinstance` checks or other narrowing patterns that are supported.
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/function/parameters.md b/crates/red_knot_python_semantic/resources/mdtest/function/parameters.md
index 8c7cdfd42c..a4efccbd3a 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/function/parameters.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/function/parameters.md
@@ -76,6 +76,11 @@ def g(x: Any = "foo"):
 
 ## Stub functions
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ### In Protocol
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/function/return_type.md b/crates/red_knot_python_semantic/resources/mdtest/function/return_type.md
index 9afeda9f75..f3ce3f4b20 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/function/return_type.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/function/return_type.md
@@ -56,6 +56,11 @@ def f() -> int:
 
 ### In Protocol
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from typing import Protocol, TypeVar
 
@@ -85,6 +90,11 @@ class Lorem(t[0]):
 
 ### In abstract method
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from abc import ABC, abstractmethod
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/generics/classes.md b/crates/red_knot_python_semantic/resources/mdtest/generics/classes.md
index 85574c615c..9421d16c36 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/generics/classes.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/generics/classes.md
@@ -1,5 +1,10 @@
 # Generic classes
 
+```toml
+[environment]
+python-version = "3.13"
+```
+
 ## PEP 695 syntax
 
 TODO: Add a `red_knot_extension` function that asserts whether a function or class is generic.
diff --git a/crates/red_knot_python_semantic/resources/mdtest/generics/functions.md b/crates/red_knot_python_semantic/resources/mdtest/generics/functions.md
index 7fe3cf9ef0..10732bf3a2 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/generics/functions.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/generics/functions.md
@@ -1,5 +1,10 @@
 # Generic functions
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ## Typevar must be used at least twice
 
 If you're only using a typevar for a single parameter, you don't need the typevar — just use
diff --git a/crates/red_knot_python_semantic/resources/mdtest/generics/pep695.md b/crates/red_knot_python_semantic/resources/mdtest/generics/pep695.md
index 907e18c307..7870e8b62f 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/generics/pep695.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/generics/pep695.md
@@ -1,5 +1,10 @@
 # PEP 695 Generics
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 [PEP 695] and Python 3.12 introduced new, more ergonomic syntax for type variables.
 
 ## Type variables
diff --git a/crates/red_knot_python_semantic/resources/mdtest/generics/scoping.md b/crates/red_knot_python_semantic/resources/mdtest/generics/scoping.md
index b4f9992a9a..da09b7c7bc 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/generics/scoping.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/generics/scoping.md
@@ -1,5 +1,10 @@
 # Scoping rules for type variables
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 Most of these tests come from the [Scoping rules for type variables][scoping] section of the typing
 spec.
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/import/star.md b/crates/red_knot_python_semantic/resources/mdtest/import/star.md
index 023d46ab10..5cad39a51e 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/import/star.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/import/star.md
@@ -122,6 +122,11 @@ from c import Y  # error: [unresolved-import]
 
 ## Esoteric definitions and redefinintions
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 We understand all public symbols defined in an external module as being imported by a `*` import,
 not just those that are defined in `StmtAssign` nodes and `StmtAnnAssign` nodes. This section
 provides tests for definitions, and redefinitions, that use more esoteric AST nodes.
diff --git a/crates/red_knot_python_semantic/resources/mdtest/metaclass.md b/crates/red_knot_python_semantic/resources/mdtest/metaclass.md
index 33cd463848..fc66cc1220 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/metaclass.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/metaclass.md
@@ -216,6 +216,11 @@ reveal_type(A.__class__)  # revealed: type[Unknown]
 
 ## PEP 695 generic
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 class M(type): ...
 class A[T: str](metaclass=M): ...
diff --git a/crates/red_knot_python_semantic/resources/mdtest/narrow/match.md b/crates/red_knot_python_semantic/resources/mdtest/narrow/match.md
index d6f0246f29..27b01efe7b 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/narrow/match.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/narrow/match.md
@@ -1,5 +1,10 @@
 # Narrowing for `match` statements
 
+```toml
+[environment]
+python-version = "3.10"
+```
+
 ## Single `match` pattern
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/narrow/type.md b/crates/red_knot_python_semantic/resources/mdtest/narrow/type.md
index e77a6152e7..927670b508 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/narrow/type.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/narrow/type.md
@@ -111,6 +111,11 @@ def _(x: A | B):
 
 ## Narrowing for generic classes
 
+```toml
+[environment]
+python-version = "3.13"
+```
+
 Note that `type` returns the runtime class of an object, which does _not_ include specializations in
 the case of a generic class. (The typevars are erased.) That means we cannot narrow the type to the
 specialization that we compare with; we must narrow to an unknown specialization of the generic
diff --git a/crates/red_knot_python_semantic/resources/mdtest/protocols.md b/crates/red_knot_python_semantic/resources/mdtest/protocols.md
index 0b2c0eacc3..cf7f49ac5e 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/protocols.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/protocols.md
@@ -15,6 +15,11 @@ types, on the other hand: a type which is defined by its properties and behaviou
 
 ## Defining a protocol
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 A protocol is defined by inheriting from the `Protocol` class, which is annotated as an instance of
 `_SpecialForm` in typeshed's stubs.
 
diff --git a/crates/red_knot_python_semantic/resources/mdtest/snapshots/version_related_syntax_errors.md_-_Version-related_syntax_error_diagnostics_-_`match`_statement_-_Before_3.10.snap b/crates/red_knot_python_semantic/resources/mdtest/snapshots/version_related_syntax_errors.md_-_Version-related_syntax_error_diagnostics_-_`match`_statement_-_Before_3.10.snap
new file mode 100644
index 0000000000..5cdf0e8838
--- /dev/null
+++ b/crates/red_knot_python_semantic/resources/mdtest/snapshots/version_related_syntax_errors.md_-_Version-related_syntax_error_diagnostics_-_`match`_statement_-_Before_3.10.snap
@@ -0,0 +1,32 @@
+---
+source: crates/red_knot_test/src/lib.rs
+expression: snapshot
+---
+---
+mdtest name: version_related_syntax_errors.md - Version-related syntax error diagnostics - `match` statement - Before 3.10
+mdtest path: crates/red_knot_python_semantic/resources/mdtest/diagnostics/version_related_syntax_errors.md
+---
+
+# Python source files
+
+## mdtest_snippet.py
+
+```
+1 | match 2:  # error: 1 [invalid-syntax] "Cannot use `match` statement on Python 3.9 (syntax was added in Python 3.10)"
+2 |     case 1:
+3 |         print("it's one")
+```
+
+# Diagnostics
+
+```
+error: invalid-syntax
+ --> /src/mdtest_snippet.py:1:1
+  |
+1 | match 2:  # error: 1 [invalid-syntax] "Cannot use `match` statement on Python 3.9 (syntax was added in Python 3.10)"
+  | ^^^^^ Cannot use `match` statement on Python 3.9 (syntax was added in Python 3.10)
+2 |     case 1:
+3 |         print("it's one")
+  |
+
+```
diff --git a/crates/red_knot_python_semantic/resources/mdtest/statically_known_branches.md b/crates/red_knot_python_semantic/resources/mdtest/statically_known_branches.md
index 20f8efe7bb..c1d979d955 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/statically_known_branches.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/statically_known_branches.md
@@ -996,6 +996,11 @@ reveal_type(x)  # revealed: Literal[1]
 
 ## `match` statements
 
+```toml
+[environment]
+python-version = "3.10"
+```
+
 ### Single-valued types, always true
 
 ```py
@@ -1118,6 +1123,7 @@ def _(s: str):
 ```toml
 [environment]
 python-platform = "darwin"
+python-version = "3.10"
 ```
 
 ```py
diff --git a/crates/red_knot_python_semantic/resources/mdtest/stubs/class.md b/crates/red_knot_python_semantic/resources/mdtest/stubs/class.md
index 233fa3f6f2..715571e021 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/stubs/class.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/stubs/class.md
@@ -2,6 +2,11 @@
 
 ## Cyclical class definition
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 In type stubs, classes can reference themselves in their base class definitions. For example, in
 `typeshed`, we have `class str(Sequence[str]): ...`.
 
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 d68656d725..c76f0f1374 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_api.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_api.md
@@ -42,6 +42,11 @@ def static_truthiness(not_one: Not[Literal[1]]) -> None:
 
 ### Intersection
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from knot_extensions import Intersection, Not, is_subtype_of, static_assert
 from typing_extensions import Literal, Never
diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_disjoint_from.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_disjoint_from.md
index fb5fe478cf..173e643f3a 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_disjoint_from.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_disjoint_from.md
@@ -246,6 +246,11 @@ static_assert(is_disjoint_from(Intersection[LiteralString, Not[AlwaysFalsy]], No
 
 ### Class, module and function literals
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 ```py
 from types import ModuleType, FunctionType
 from knot_extensions import TypeOf, is_disjoint_from, static_assert
diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
index 7763b3b1a6..aa5f025e13 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
@@ -1,5 +1,10 @@
 # Subtype relation
 
+```toml
+[environment]
+python-version = "3.12"
+```
+
 The `is_subtype_of(S, T)` relation below checks if type `S` is a subtype of type `T`.
 
 A fully static type `S` is a subtype of another fully static type `T` iff the set of values
diff --git a/crates/red_knot_python_semantic/src/db.rs b/crates/red_knot_python_semantic/src/db.rs
index 976235f926..00956ccf07 100644
--- a/crates/red_knot_python_semantic/src/db.rs
+++ b/crates/red_knot_python_semantic/src/db.rs
@@ -98,6 +98,10 @@ pub(crate) mod tests {
         fn files(&self) -> &Files {
             &self.files
         }
+
+        fn python_version(&self) -> PythonVersion {
+            Program::get(self).python_version(self)
+        }
     }
 
     impl Upcast<dyn SourceDb> for TestDb {
diff --git a/crates/red_knot_python_semantic/src/semantic_index.rs b/crates/red_knot_python_semantic/src/semantic_index.rs
index 5771220788..7bcfa969fc 100644
--- a/crates/red_knot_python_semantic/src/semantic_index.rs
+++ b/crates/red_knot_python_semantic/src/semantic_index.rs
@@ -497,11 +497,10 @@ impl FusedIterator for ChildrenIter<'_> {}
 mod tests {
     use ruff_db::files::{system_path_to_file, File};
     use ruff_db::parsed::parsed_module;
-    use ruff_db::system::DbWithWritableSystem as _;
-    use ruff_python_ast as ast;
+    use ruff_python_ast::{self as ast};
     use ruff_text_size::{Ranged, TextRange};
 
-    use crate::db::tests::TestDb;
+    use crate::db::tests::{TestDb, TestDbBuilder};
     use crate::semantic_index::ast_ids::{HasScopedUseId, ScopedUseId};
     use crate::semantic_index::definition::{Definition, DefinitionKind};
     use crate::semantic_index::symbol::{
@@ -528,11 +527,15 @@ mod tests {
         file: File,
     }
 
-    fn test_case(content: impl AsRef<str>) -> TestCase {
-        let mut db = TestDb::new();
-        db.write_file("test.py", content).unwrap();
+    fn test_case(content: &str) -> TestCase {
+        const FILENAME: &str = "test.py";
 
-        let file = system_path_to_file(&db, "test.py").unwrap();
+        let db = TestDbBuilder::new()
+            .with_file(FILENAME, content)
+            .build()
+            .unwrap();
+
+        let file = system_path_to_file(&db, FILENAME).unwrap();
 
         TestCase { db, file }
     }
diff --git a/crates/red_knot_test/src/assertion.rs b/crates/red_knot_test/src/assertion.rs
index d88c7d2b27..8f31b5de66 100644
--- a/crates/red_knot_test/src/assertion.rs
+++ b/crates/red_knot_test/src/assertion.rs
@@ -489,13 +489,27 @@ pub(crate) enum ErrorAssertionParseError<'a> {
 #[cfg(test)]
 mod tests {
     use super::*;
+    use red_knot_python_semantic::{Program, ProgramSettings, PythonPlatform, SearchPathSettings};
     use ruff_db::files::system_path_to_file;
     use ruff_db::system::DbWithWritableSystem as _;
+    use ruff_python_ast::PythonVersion;
     use ruff_python_trivia::textwrap::dedent;
     use ruff_source_file::OneIndexed;
 
     fn get_assertions(source: &str) -> InlineFileAssertions {
         let mut db = Db::setup();
+
+        let settings = ProgramSettings {
+            python_version: PythonVersion::default(),
+            python_platform: PythonPlatform::default(),
+            search_paths: SearchPathSettings::new(Vec::new()),
+        };
+        match Program::try_get(&db) {
+            Some(program) => program.update_from_settings(&mut db, settings),
+            None => Program::from_settings(&db, settings).map(|_| ()),
+        }
+        .expect("Failed to update Program settings in TestDb");
+
         db.write_file("/src/test.py", source).unwrap();
         let file = system_path_to_file(&db, "/src/test.py").unwrap();
         InlineFileAssertions::from_file(&db, file)
diff --git a/crates/red_knot_test/src/db.rs b/crates/red_knot_test/src/db.rs
index 770be68128..b4fcccb927 100644
--- a/crates/red_knot_test/src/db.rs
+++ b/crates/red_knot_test/src/db.rs
@@ -1,6 +1,6 @@
 use camino::{Utf8Component, Utf8PathBuf};
 use red_knot_python_semantic::lint::{LintRegistry, RuleSelection};
-use red_knot_python_semantic::{default_lint_registry, Db as SemanticDb};
+use red_knot_python_semantic::{default_lint_registry, Db as SemanticDb, Program};
 use ruff_db::files::{File, Files};
 use ruff_db::system::{
     CaseSensitivity, DbWithWritableSystem, InMemorySystem, OsSystem, System, SystemPath,
@@ -64,6 +64,10 @@ impl SourceDb for Db {
     fn files(&self) -> &Files {
         &self.files
     }
+
+    fn python_version(&self) -> ruff_python_ast::PythonVersion {
+        Program::get(self).python_version(self)
+    }
 }
 
 impl Upcast<dyn SourceDb> for Db {
diff --git a/crates/red_knot_test/src/lib.rs b/crates/red_knot_test/src/lib.rs
index c31a68040a..0efa683f2e 100644
--- a/crates/red_knot_test/src/lib.rs
+++ b/crates/red_knot_test/src/lib.rs
@@ -8,7 +8,10 @@ use red_knot_python_semantic::types::check_types;
 use red_knot_python_semantic::{
     Program, ProgramSettings, PythonPath, PythonPlatform, SearchPathSettings, SysPrefixPathOrigin,
 };
-use ruff_db::diagnostic::{create_parse_diagnostic, Diagnostic, DisplayDiagnosticConfig};
+use ruff_db::diagnostic::{
+    create_parse_diagnostic, create_unsupported_syntax_diagnostic, Diagnostic,
+    DisplayDiagnosticConfig,
+};
 use ruff_db::files::{system_path_to_file, File};
 use ruff_db::panic::catch_unwind;
 use ruff_db::parsed::parsed_module;
@@ -305,6 +308,13 @@ fn run_test(
                 .map(|error| create_parse_diagnostic(test_file.file, error))
                 .collect();
 
+            diagnostics.extend(
+                parsed
+                    .unsupported_syntax_errors()
+                    .iter()
+                    .map(|error| create_unsupported_syntax_diagnostic(test_file.file, error)),
+            );
+
             let type_diagnostics = match catch_unwind(|| check_types(db, test_file.file)) {
                 Ok(type_diagnostics) => type_diagnostics,
                 Err(info) => {
diff --git a/crates/red_knot_test/src/matcher.rs b/crates/red_knot_test/src/matcher.rs
index 8a68b5483a..63ae8c44af 100644
--- a/crates/red_knot_test/src/matcher.rs
+++ b/crates/red_knot_test/src/matcher.rs
@@ -343,9 +343,11 @@ impl Matcher {
 #[cfg(test)]
 mod tests {
     use super::FailuresByLine;
+    use red_knot_python_semantic::{Program, ProgramSettings, PythonPlatform, SearchPathSettings};
     use ruff_db::diagnostic::{Annotation, Diagnostic, DiagnosticId, Severity, Span};
     use ruff_db::files::{system_path_to_file, File};
     use ruff_db::system::DbWithWritableSystem as _;
+    use ruff_python_ast::PythonVersion;
     use ruff_python_trivia::textwrap::dedent;
     use ruff_source_file::OneIndexed;
     use ruff_text_size::TextRange;
@@ -385,6 +387,18 @@ mod tests {
         colored::control::set_override(false);
 
         let mut db = crate::db::Db::setup();
+
+        let settings = ProgramSettings {
+            python_version: PythonVersion::default(),
+            python_platform: PythonPlatform::default(),
+            search_paths: SearchPathSettings::new(Vec::new()),
+        };
+        match Program::try_get(&db) {
+            Some(program) => program.update_from_settings(&mut db, settings),
+            None => Program::from_settings(&db, settings).map(|_| ()),
+        }
+        .expect("Failed to update Program settings in TestDb");
+
         db.write_file("/src/test.py", source).unwrap();
         let file = system_path_to_file(&db, "/src/test.py").unwrap();
 
diff --git a/crates/ruff_db/src/diagnostic/mod.rs b/crates/ruff_db/src/diagnostic/mod.rs
index 3bb2b24070..61a3ca6805 100644
--- a/crates/ruff_db/src/diagnostic/mod.rs
+++ b/crates/ruff_db/src/diagnostic/mod.rs
@@ -832,3 +832,16 @@ pub fn create_parse_diagnostic(file: File, err: &ruff_python_parser::ParseError)
     diag.annotate(Annotation::primary(span).message(&err.error));
     diag
 }
+
+/// Creates a `Diagnostic` from an unsupported syntax error.
+///
+/// See [`create_parse_diagnostic`] for more details.
+pub fn create_unsupported_syntax_diagnostic(
+    file: File,
+    err: &ruff_python_parser::UnsupportedSyntaxError,
+) -> Diagnostic {
+    let mut diag = Diagnostic::new(DiagnosticId::InvalidSyntax, Severity::Error, "");
+    let span = Span::from(file).with_range(err.range);
+    diag.annotate(Annotation::primary(span).message(err.to_string()));
+    diag
+}
diff --git a/crates/ruff_db/src/lib.rs b/crates/ruff_db/src/lib.rs
index 55a47d96d1..85beefc1d8 100644
--- a/crates/ruff_db/src/lib.rs
+++ b/crates/ruff_db/src/lib.rs
@@ -1,5 +1,6 @@
 use std::hash::BuildHasherDefault;
 
+use ruff_python_ast::PythonVersion;
 use rustc_hash::FxHasher;
 
 use crate::files::Files;
@@ -27,6 +28,7 @@ pub trait Db: salsa::Database {
     fn vendored(&self) -> &VendoredFileSystem;
     fn system(&self) -> &dyn System;
     fn files(&self) -> &Files;
+    fn python_version(&self) -> PythonVersion;
 }
 
 /// Trait for upcasting a reference to a base trait object.
@@ -107,6 +109,10 @@ mod tests {
         fn files(&self) -> &Files {
             &self.files
         }
+
+        fn python_version(&self) -> ruff_python_ast::PythonVersion {
+            ruff_python_ast::PythonVersion::latest()
+        }
     }
 
     impl DbWithTestSystem for TestDb {
diff --git a/crates/ruff_db/src/parsed.rs b/crates/ruff_db/src/parsed.rs
index a72ef55f71..3d9988cffd 100644
--- a/crates/ruff_db/src/parsed.rs
+++ b/crates/ruff_db/src/parsed.rs
@@ -3,7 +3,7 @@ use std::ops::Deref;
 use std::sync::Arc;
 
 use ruff_python_ast::ModModule;
-use ruff_python_parser::{parse_unchecked_source, Parsed};
+use ruff_python_parser::{parse_unchecked, ParseOptions, Parsed};
 
 use crate::files::File;
 use crate::source::source_text;
@@ -27,7 +27,13 @@ pub fn parsed_module(db: &dyn Db, file: File) -> ParsedModule {
     let source = source_text(db, file);
     let ty = file.source_type(db);
 
-    ParsedModule::new(parse_unchecked_source(&source, ty))
+    let target_version = db.python_version();
+    let options = ParseOptions::from(ty).with_target_version(target_version);
+    let parsed = parse_unchecked(&source, options)
+        .try_into_module()
+        .expect("PySourceType always parses into a module");
+
+    ParsedModule::new(parsed)
 }
 
 /// Cheap cloneable wrapper around the parsed module.
diff --git a/crates/ruff_graph/src/db.rs b/crates/ruff_graph/src/db.rs
index e768c6282a..368d571505 100644
--- a/crates/ruff_graph/src/db.rs
+++ b/crates/ruff_graph/src/db.rs
@@ -71,6 +71,10 @@ impl SourceDb for ModuleDb {
     fn files(&self) -> &Files {
         &self.files
     }
+
+    fn python_version(&self) -> PythonVersion {
+        Program::get(self).python_version(self)
+    }
 }
 
 #[salsa::db]
diff --git a/fuzz/fuzz_targets/red_knot_check_invalid_syntax.rs b/fuzz/fuzz_targets/red_knot_check_invalid_syntax.rs
index 1da7da48dd..225bd10089 100644
--- a/fuzz/fuzz_targets/red_knot_check_invalid_syntax.rs
+++ b/fuzz/fuzz_targets/red_knot_check_invalid_syntax.rs
@@ -62,6 +62,10 @@ impl SourceDb for TestDb {
     fn files(&self) -> &Files {
         &self.files
     }
+
+    fn python_version(&self) -> PythonVersion {
+        Program::get(self).python_version(self)
+    }
 }
 
 impl DbWithTestSystem for TestDb {