diff --git a/crates/ty_python_semantic/resources/mdtest/conditional/match.md b/crates/ty_python_semantic/resources/mdtest/conditional/match.md
index 1b92e7e8a7..52513d6698 100644
--- a/crates/ty_python_semantic/resources/mdtest/conditional/match.md
+++ b/crates/ty_python_semantic/resources/mdtest/conditional/match.md
@@ -201,8 +201,7 @@ def _(target: Literal[True, False]):
         case None:
             y = 4
 
-    # TODO: with exhaustiveness checking, this should be Literal[2, 3]
-    reveal_type(y)  # revealed: Literal[1, 2, 3]
+    reveal_type(y)  # revealed: Literal[2, 3]
 
 def _(target: bool):
     y = 1
@@ -215,8 +214,7 @@ def _(target: bool):
         case None:
             y = 4
 
-    # TODO: with exhaustiveness checking, this should be Literal[2, 3]
-    reveal_type(y)  # revealed: Literal[1, 2, 3]
+    reveal_type(y)  # revealed: Literal[2, 3]
 
 def _(target: None):
     y = 1
@@ -242,8 +240,7 @@ def _(target: None | Literal[True]):
         case None:
             y = 4
 
-    # TODO: with exhaustiveness checking, this should be Literal[2, 4]
-    reveal_type(y)  # revealed: Literal[1, 2, 4]
+    reveal_type(y)  # revealed: Literal[2, 4]
 
 # bool is an int subclass
 def _(target: int):
@@ -292,7 +289,7 @@ def _(answer: Answer):
             reveal_type(answer)  # revealed: Literal[Answer.NO]
             y = 2
 
-    reveal_type(y)  # revealed: Literal[0, 1, 2]
+    reveal_type(y)  # revealed: Literal[1, 2]
 ```
 
 ## Or match
@@ -311,8 +308,7 @@ def _(target: Literal["foo", "baz"]):
         case "baz":
             y = 3
 
-    # TODO: with exhaustiveness, this should be Literal[2, 3]
-    reveal_type(y)  # revealed: Literal[1, 2, 3]
+    reveal_type(y)  # revealed: Literal[2, 3]
 
 def _(target: None):
     y = 1
diff --git a/crates/ty_python_semantic/resources/mdtest/directives/assert_never.md b/crates/ty_python_semantic/resources/mdtest/directives/assert_never.md
index abb5117564..f9e4ced7d5 100644
--- a/crates/ty_python_semantic/resources/mdtest/directives/assert_never.md
+++ b/crates/ty_python_semantic/resources/mdtest/directives/assert_never.md
@@ -119,8 +119,6 @@ def match_singletons_success(obj: Literal[1, "a"] | None):
         case None:
             pass
         case _ as obj:
-            # TODO: Ideally, we would not emit an error here
-            # error: [type-assertion-failure] "Argument does not have asserted type `Never`"
             assert_never(obj)
 
 def match_singletons_error(obj: Literal[1, "a"] | None):
diff --git a/crates/ty_python_semantic/resources/mdtest/enums.md b/crates/ty_python_semantic/resources/mdtest/enums.md
index 6981f5c06a..d1265225cf 100644
--- a/crates/ty_python_semantic/resources/mdtest/enums.md
+++ b/crates/ty_python_semantic/resources/mdtest/enums.md
@@ -720,8 +720,6 @@ def color_name(color: Color) -> str:
         case _:
             assert_never(color)
 
-# TODO: this should not be an error, see https://github.com/astral-sh/ty/issues/99#issuecomment-2983054488
-# error: [invalid-return-type] "Function can implicitly return `None`, which is not assignable to return type `str`"
 def color_name_without_assertion(color: Color) -> str:
     match color:
         case Color.RED:
diff --git a/crates/ty_python_semantic/resources/mdtest/exhaustiveness_checking.md b/crates/ty_python_semantic/resources/mdtest/exhaustiveness_checking.md
index 9ecc26be0e..713cd05b2d 100644
--- a/crates/ty_python_semantic/resources/mdtest/exhaustiveness_checking.md
+++ b/crates/ty_python_semantic/resources/mdtest/exhaustiveness_checking.md
@@ -50,13 +50,10 @@ def match_exhaustive(x: Literal[0, 1, "a"]):
         case "a":
             pass
         case _:
-            # TODO: this should not be an error
-            no_diagnostic_here  # error: [unresolved-reference]
+            no_diagnostic_here
 
             assert_never(x)
 
-# TODO: there should be no error here
-# error: [invalid-return-type] "Function can implicitly return `None`, which is not assignable to return type `int`"
 def match_exhaustive_no_assertion(x: Literal[0, 1, "a"]) -> int:
     match x:
         case 0:
@@ -130,13 +127,21 @@ def match_exhaustive(x: Color):
         case Color.BLUE:
             pass
         case _:
-            # TODO: this should not be an error
-            no_diagnostic_here  # error: [unresolved-reference]
+            no_diagnostic_here
+
+            assert_never(x)
+
+def match_exhaustive_2(x: Color):
+    match x:
+        case Color.RED:
+            pass
+        case Color.GREEN | Color.BLUE:
+            pass
+        case _:
+            no_diagnostic_here
 
             assert_never(x)
 
-# TODO: there should be no error here
-# error: [invalid-return-type] "Function can implicitly return `None`, which is not assignable to return type `int`"
 def match_exhaustive_no_assertion(x: Color) -> int:
     match x:
         case Color.RED:
@@ -208,13 +213,10 @@ def match_exhaustive(x: A | B | C):
         case C():
             pass
         case _:
-            # TODO: this should not be an error
-            no_diagnostic_here  # error: [unresolved-reference]
+            no_diagnostic_here
 
             assert_never(x)
 
-# TODO: there should be no error here
-# error: [invalid-return-type] "Function can implicitly return `None`, which is not assignable to return type `int`"
 def match_exhaustive_no_assertion(x: A | B | C) -> int:
     match x:
         case A():
diff --git a/crates/ty_python_semantic/src/semantic_index/builder.rs b/crates/ty_python_semantic/src/semantic_index/builder.rs
index cac8287d49..b6079d42ec 100644
--- a/crates/ty_python_semantic/src/semantic_index/builder.rs
+++ b/crates/ty_python_semantic/src/semantic_index/builder.rs
@@ -734,7 +734,8 @@ impl<'db, 'ast> SemanticIndexBuilder<'db, 'ast> {
         subject: Expression<'db>,
         pattern: &ast::Pattern,
         guard: Option<&ast::Expr>,
-    ) -> PredicateOrLiteral<'db> {
+        previous_pattern: Option<PatternPredicate<'db>>,
+    ) -> (PredicateOrLiteral<'db>, PatternPredicate<'db>) {
         // This is called for the top-level pattern of each match arm. We need to create a
         // standalone expression for each arm of a match statement, since they can introduce
         // constraints on the match subject. (Or more accurately, for the match arm's pattern,
@@ -756,13 +757,14 @@ impl<'db, 'ast> SemanticIndexBuilder<'db, 'ast> {
             subject,
             kind,
             guard,
+            previous_pattern.map(Box::new),
         );
         let predicate = PredicateOrLiteral::Predicate(Predicate {
             node: PredicateNode::Pattern(pattern_predicate),
             is_positive: true,
         });
         self.record_narrowing_constraint(predicate);
-        predicate
+        (predicate, pattern_predicate)
     }
 
     /// Record an expression that needs to be a Salsa ingredient, because we need to infer its type
@@ -1747,7 +1749,7 @@ impl<'ast> Visitor<'ast> for SemanticIndexBuilder<'_, 'ast> {
                     .is_some_and(|case| case.guard.is_none() && case.pattern.is_wildcard());
 
                 let mut post_case_snapshots = vec![];
-                let mut match_predicate;
+                let mut previous_pattern: Option<PatternPredicate<'_>> = None;
 
                 for (i, case) in cases.iter().enumerate() {
                     self.current_match_case = Some(CurrentMatchCase::new(&case.pattern));
@@ -1757,11 +1759,14 @@ impl<'ast> Visitor<'ast> for SemanticIndexBuilder<'_, 'ast> {
                     // here because the effects of visiting a pattern is binding
                     // symbols, and this doesn't occur unless the pattern
                     // actually matches
-                    match_predicate = self.add_pattern_narrowing_constraint(
-                        subject_expr,
-                        &case.pattern,
-                        case.guard.as_deref(),
-                    );
+                    let (match_predicate, match_pattern_predicate) = self
+                        .add_pattern_narrowing_constraint(
+                            subject_expr,
+                            &case.pattern,
+                            case.guard.as_deref(),
+                            previous_pattern,
+                        );
+                    previous_pattern = Some(match_pattern_predicate);
                     let reachability_constraint =
                         self.record_reachability_constraint(match_predicate);
 
diff --git a/crates/ty_python_semantic/src/semantic_index/predicate.rs b/crates/ty_python_semantic/src/semantic_index/predicate.rs
index acd232ed05..35d738c6c4 100644
--- a/crates/ty_python_semantic/src/semantic_index/predicate.rs
+++ b/crates/ty_python_semantic/src/semantic_index/predicate.rs
@@ -150,6 +150,9 @@ pub(crate) struct PatternPredicate<'db> {
     pub(crate) kind: PatternPredicateKind<'db>,
 
     pub(crate) guard: Option<Expression<'db>>,
+
+    /// A reference to the pattern of the previous match case
+    pub(crate) previous_predicate: Option<Box<PatternPredicate<'db>>>,
 }
 
 // The Salsa heap is tracked separately.
diff --git a/crates/ty_python_semantic/src/semantic_index/reachability_constraints.rs b/crates/ty_python_semantic/src/semantic_index/reachability_constraints.rs
index caa0b7c247..03f8ac0ace 100644
--- a/crates/ty_python_semantic/src/semantic_index/reachability_constraints.rs
+++ b/crates/ty_python_semantic/src/semantic_index/reachability_constraints.rs
@@ -202,13 +202,14 @@ use crate::Db;
 use crate::dunder_all::dunder_all_names;
 use crate::place::{RequiresExplicitReExport, imported_symbol};
 use crate::rank::RankBitBox;
-use crate::semantic_index::expression::Expression;
 use crate::semantic_index::place_table;
 use crate::semantic_index::predicate::{
     CallableAndCallExpr, PatternPredicate, PatternPredicateKind, Predicate, PredicateNode,
     Predicates, ScopedPredicateId,
 };
-use crate::types::{Truthiness, Type, infer_expression_type};
+use crate::types::{
+    IntersectionBuilder, Truthiness, Type, UnionBuilder, UnionType, infer_expression_type,
+};
 
 /// A ternary formula that defines under what conditions a binding is visible. (A ternary formula
 /// is just like a boolean formula, but with `Ambiguous` as a third potential result. See the
@@ -311,6 +312,55 @@ const AMBIGUOUS: ScopedReachabilityConstraintId = ScopedReachabilityConstraintId
 const ALWAYS_FALSE: ScopedReachabilityConstraintId = ScopedReachabilityConstraintId::ALWAYS_FALSE;
 const SMALLEST_TERMINAL: ScopedReachabilityConstraintId = ALWAYS_FALSE;
 
+fn singleton_to_type(db: &dyn Db, singleton: ruff_python_ast::Singleton) -> Type<'_> {
+    let ty = match singleton {
+        ruff_python_ast::Singleton::None => Type::none(db),
+        ruff_python_ast::Singleton::True => Type::BooleanLiteral(true),
+        ruff_python_ast::Singleton::False => Type::BooleanLiteral(false),
+    };
+    debug_assert!(ty.is_singleton(db));
+    ty
+}
+
+/// Turn a `match` pattern kind into a type that represents the set of all values that would definitely
+/// match that pattern.
+fn pattern_kind_to_type<'db>(db: &'db dyn Db, kind: &PatternPredicateKind<'db>) -> Type<'db> {
+    match kind {
+        PatternPredicateKind::Singleton(singleton) => singleton_to_type(db, *singleton),
+        PatternPredicateKind::Value(value) => infer_expression_type(db, *value),
+        PatternPredicateKind::Class(class_expr, kind) => {
+            if kind.is_irrefutable() {
+                infer_expression_type(db, *class_expr)
+                    .to_instance(db)
+                    .unwrap_or(Type::Never)
+            } else {
+                Type::Never
+            }
+        }
+        PatternPredicateKind::Or(predicates) => {
+            UnionType::from_elements(db, predicates.iter().map(|p| pattern_kind_to_type(db, p)))
+        }
+        PatternPredicateKind::Unsupported => Type::Never,
+    }
+}
+
+/// Go through the list of previous match cases, and accumulate a union of all types that were already
+/// matched by these patterns.
+fn type_excluded_by_previous_patterns<'db>(
+    db: &'db dyn Db,
+    mut predicate: PatternPredicate<'db>,
+) -> Type<'db> {
+    let mut builder = UnionBuilder::new(db);
+    while let Some(previous) = predicate.previous_predicate(db) {
+        predicate = *previous;
+
+        if predicate.guard(db).is_none() {
+            builder = builder.add(pattern_kind_to_type(db, predicate.kind(db)));
+        }
+    }
+    builder.build()
+}
+
 /// A collection of reachability constraints for a given scope.
 #[derive(Debug, PartialEq, Eq, salsa::Update, get_size2::GetSize)]
 pub(crate) struct ReachabilityConstraints {
@@ -637,11 +687,10 @@ impl ReachabilityConstraints {
     fn analyze_single_pattern_predicate_kind<'db>(
         db: &'db dyn Db,
         predicate_kind: &PatternPredicateKind<'db>,
-        subject: Expression<'db>,
+        subject_ty: Type<'db>,
     ) -> Truthiness {
         match predicate_kind {
             PatternPredicateKind::Value(value) => {
-                let subject_ty = infer_expression_type(db, subject);
                 let value_ty = infer_expression_type(db, *value);
 
                 if subject_ty.is_single_valued(db) {
@@ -651,15 +700,7 @@ impl ReachabilityConstraints {
                 }
             }
             PatternPredicateKind::Singleton(singleton) => {
-                let subject_ty = infer_expression_type(db, subject);
-
-                let singleton_ty = match singleton {
-                    ruff_python_ast::Singleton::None => Type::none(db),
-                    ruff_python_ast::Singleton::True => Type::BooleanLiteral(true),
-                    ruff_python_ast::Singleton::False => Type::BooleanLiteral(false),
-                };
-
-                debug_assert!(singleton_ty.is_singleton(db));
+                let singleton_ty = singleton_to_type(db, *singleton);
 
                 if subject_ty.is_equivalent_to(db, singleton_ty) {
                     Truthiness::AlwaysTrue
@@ -671,10 +712,21 @@ impl ReachabilityConstraints {
             }
             PatternPredicateKind::Or(predicates) => {
                 use std::ops::ControlFlow;
+
+                let mut excluded_types = vec![];
                 let (ControlFlow::Break(truthiness) | ControlFlow::Continue(truthiness)) =
                     predicates
                         .iter()
-                        .map(|p| Self::analyze_single_pattern_predicate_kind(db, p, subject))
+                        .map(|p| {
+                            let narrowed_subject_ty = IntersectionBuilder::new(db)
+                                .add_positive(subject_ty)
+                                .add_negative(UnionType::from_elements(db, excluded_types.iter()))
+                                .build();
+
+                            excluded_types.push(pattern_kind_to_type(db, p));
+
+                            Self::analyze_single_pattern_predicate_kind(db, p, narrowed_subject_ty)
+                        })
                         // this is just a "max", but with a slight optimization: `AlwaysTrue` is the "greatest" possible element, so we short-circuit if we get there
                         .try_fold(Truthiness::AlwaysFalse, |acc, next| match (acc, next) {
                             (Truthiness::AlwaysTrue, _) | (_, Truthiness::AlwaysTrue) => {
@@ -690,7 +742,6 @@ impl ReachabilityConstraints {
                 truthiness
             }
             PatternPredicateKind::Class(class_expr, kind) => {
-                let subject_ty = infer_expression_type(db, subject);
                 let class_ty = infer_expression_type(db, *class_expr).to_instance(db);
 
                 class_ty.map_or(Truthiness::Ambiguous, |class_ty| {
@@ -715,10 +766,17 @@ impl ReachabilityConstraints {
     }
 
     fn analyze_single_pattern_predicate(db: &dyn Db, predicate: PatternPredicate) -> Truthiness {
+        let subject_ty = infer_expression_type(db, predicate.subject(db));
+
+        let narrowed_subject_ty = IntersectionBuilder::new(db)
+            .add_positive(subject_ty)
+            .add_negative(type_excluded_by_previous_patterns(db, predicate))
+            .build();
+
         let truthiness = Self::analyze_single_pattern_predicate_kind(
             db,
             predicate.kind(db),
-            predicate.subject(db),
+            narrowed_subject_ty,
         );
 
         if truthiness == Truthiness::AlwaysTrue && predicate.guard(db).is_some() {