diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 5e1933e185f9d..259714fe6f705 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -7899,6 +7899,7 @@ namespace ts {
             }
             else if (flags & TypeFlags.Any) {
                 includes |= TypeIncludes.Any;
+                if (type === wildcardType) includes |= TypeIncludes.Wildcard;
             }
             else if (flags & TypeFlags.Never) {
                 includes |= TypeIncludes.Never;
@@ -7950,7 +7951,7 @@ namespace ts {
                 return neverType;
             }
             if (includes & TypeIncludes.Any) {
-                return anyType;
+                return includes & TypeIncludes.Wildcard ? wildcardType : anyType;
             }
             if (includes & TypeIncludes.EmptyObject && !(includes & TypeIncludes.ObjectType)) {
                 typeSet.push(emptyObjectType);
@@ -8188,6 +8189,9 @@ namespace ts {
         }
 
         function getIndexedAccessType(objectType: Type, indexType: Type, accessNode?: ElementAccessExpression | IndexedAccessTypeNode): Type {
+            if (objectType === wildcardType || indexType === wildcardType) {
+                return wildcardType;
+            }
             // If the index type is generic, or if the object type is generic and doesn't originate in an expression,
             // we are performing a higher-order index access where we cannot meaningfully access the properties of the
             // object type. Note that for a generic T and a non-generic K, we eagerly resolve T[K] if it originates in
@@ -8253,37 +8257,45 @@ namespace ts {
         function getConditionalType(root: ConditionalRoot, mapper: TypeMapper): Type {
             const checkType = instantiateType(root.checkType, mapper);
             const extendsType = instantiateType(root.extendsType, mapper);
-            // Return falseType for a definitely false extends check. We check an instantations of the two
-            // types with type parameters mapped to the wildcard type, the most permissive instantiations
-            // possible (the wildcard type is assignable to and from all types). If those are not related,
-            // then no instatiations will be and we can just return the false branch type.
-            if (!typeMaybeAssignableTo(getWildcardInstantiation(checkType), getWildcardInstantiation(extendsType))) {
-                return instantiateType(root.falseType, mapper);
-            }
-            // The check could be true for some instantiation
-            let combinedMapper: TypeMapper;
-            if (root.inferTypeParameters) {
-                const inferences = map(root.inferTypeParameters, createInferenceInfo);
-                // We don't want inferences from constraints as they may cause us to eagerly resolve the
-                // conditional type instead of deferring resolution. Also, we always want strict function
-                // types rules (i.e. proper contravariance) for inferences.
-                inferTypes(inferences, checkType, extendsType, InferencePriority.NoConstraints | InferencePriority.AlwaysStrict);
-                // We infer {} when there are no candidates for a type parameter
-                const inferredTypes = map(inferences, inference => getTypeFromInference(inference) || emptyObjectType);
-                combinedMapper = combineTypeMappers(mapper, createTypeMapper(root.inferTypeParameters, inferredTypes));
-            }
-            // Return union of trueType and falseType for 'any' since it matches anything
-            if (checkType.flags & TypeFlags.Any) {
-                return getUnionType([instantiateType(root.trueType, combinedMapper || mapper), instantiateType(root.falseType, mapper)]);
-            }
-            // Instantiate the extends type including inferences for 'infer T' type parameters
-            const inferredExtendsType = combinedMapper ? instantiateType(root.extendsType, combinedMapper) : extendsType;
-            // Return trueType for a definitely true extends check. The definitely assignable relation excludes
-            // type variable constraints from consideration. Without the definitely assignable relation, the type
-            //   type Foo<T extends { x: any }> = T extends { x: string } ? string : number
-            // would immediately resolve to 'string' instead of being deferred.
-            if (checkTypeRelatedTo(checkType, inferredExtendsType, definitelyAssignableRelation, /*errorNode*/ undefined)) {
-                return instantiateType(root.trueType, combinedMapper || mapper);
+            if (checkType === wildcardType || extendsType === wildcardType) {
+                return wildcardType;
+            }
+            // If this is a distributive conditional type and the check type is generic, we need to defer
+            // resolution of the conditional type such that a later instantiation will properly distribute
+            // over union types.
+            if (!root.isDistributive || !maybeTypeOfKind(checkType, TypeFlags.Instantiable)) {
+                // Return falseType for a definitely false extends check. We check an instantations of the two
+                // types with type parameters mapped to the wildcard type, the most permissive instantiations
+                // possible (the wildcard type is assignable to and from all types). If those are not related,
+                // then no instatiations will be and we can just return the false branch type.
+                if (!isTypeAssignableTo(getWildcardInstantiation(checkType), getWildcardInstantiation(extendsType))) {
+                    return instantiateType(root.falseType, mapper);
+                }
+                // The check could be true for some instantiation
+                let combinedMapper: TypeMapper;
+                if (root.inferTypeParameters) {
+                    const inferences = map(root.inferTypeParameters, createInferenceInfo);
+                    // We don't want inferences from constraints as they may cause us to eagerly resolve the
+                    // conditional type instead of deferring resolution. Also, we always want strict function
+                    // types rules (i.e. proper contravariance) for inferences.
+                    inferTypes(inferences, checkType, extendsType, InferencePriority.NoConstraints | InferencePriority.AlwaysStrict);
+                    // We infer {} when there are no candidates for a type parameter
+                    const inferredTypes = map(inferences, inference => getTypeFromInference(inference) || emptyObjectType);
+                    combinedMapper = combineTypeMappers(mapper, createTypeMapper(root.inferTypeParameters, inferredTypes));
+                }
+                // Return union of trueType and falseType for 'any' since it matches anything
+                if (checkType.flags & TypeFlags.Any) {
+                    return getUnionType([instantiateType(root.trueType, combinedMapper || mapper), instantiateType(root.falseType, mapper)]);
+                }
+                // Instantiate the extends type including inferences for 'infer T' type parameters
+                const inferredExtendsType = combinedMapper ? instantiateType(root.extendsType, combinedMapper) : extendsType;
+                // Return trueType for a definitely true extends check. The definitely assignable relation excludes
+                // type variable constraints from consideration. Without the definitely assignable relation, the type
+                //   type Foo<T extends { x: any }> = T extends { x: string } ? string : number
+                // would immediately resolve to 'string' instead of being deferred.
+                if (checkTypeRelatedTo(checkType, inferredExtendsType, definitelyAssignableRelation, /*errorNode*/ undefined)) {
+                    return instantiateType(root.trueType, combinedMapper || mapper);
+                }
             }
             // Return a deferred type for a check that is neither definitely true nor definitely false
             const erasedCheckType = getActualTypeParameter(checkType);
diff --git a/tests/baselines/reference/inferTypes1.errors.txt b/tests/baselines/reference/inferTypes1.errors.txt
index b36528f721d9e..5531ec08c7f39 100644
--- a/tests/baselines/reference/inferTypes1.errors.txt
+++ b/tests/baselines/reference/inferTypes1.errors.txt
@@ -191,4 +191,19 @@ tests/cases/conformance/types/conditional/inferTypes1.ts(134,40): error TS2322:
     type B<T> = string extends T ? { [P in T]: void; } : T;  // Error
                                            ~
 !!! error TS2322: Type 'T' is not assignable to type 'string'.
+    
+    // Repro from #22302
+    
+    type MatchingKeys<T, U, K extends keyof T = keyof T> =
+        K extends keyof T ? T[K] extends U ? K : never : never;
+    
+    type VoidKeys<T> = MatchingKeys<T, void>;
+    
+    interface test {
+        a: 1,
+        b: void
+    }
+    
+    type T80 = MatchingKeys<test, void>;
+    type T81 = VoidKeys<test>;
     
\ No newline at end of file
diff --git a/tests/baselines/reference/inferTypes1.js b/tests/baselines/reference/inferTypes1.js
index bc53f23899701..6e41cfe199844 100644
--- a/tests/baselines/reference/inferTypes1.js
+++ b/tests/baselines/reference/inferTypes1.js
@@ -133,6 +133,21 @@ type C2<S, U extends void> = S extends A2<infer T, U> ? [T, U] : never;
 
 type A<T> = T extends string ? { [P in T]: void; } : T;
 type B<T> = string extends T ? { [P in T]: void; } : T;  // Error
+
+// Repro from #22302
+
+type MatchingKeys<T, U, K extends keyof T = keyof T> =
+    K extends keyof T ? T[K] extends U ? K : never : never;
+
+type VoidKeys<T> = MatchingKeys<T, void>;
+
+interface test {
+    a: 1,
+    b: void
+}
+
+type T80 = MatchingKeys<test, void>;
+type T81 = VoidKeys<test>;
 
 
 //// [inferTypes1.js]
diff --git a/tests/baselines/reference/inferTypes1.symbols b/tests/baselines/reference/inferTypes1.symbols
index 784482e72c9e7..9e09eaea21d51 100644
--- a/tests/baselines/reference/inferTypes1.symbols
+++ b/tests/baselines/reference/inferTypes1.symbols
@@ -575,3 +575,47 @@ type B<T> = string extends T ? { [P in T]: void; } : T;  // Error
 >T : Symbol(T, Decl(inferTypes1.ts, 133, 7))
 >T : Symbol(T, Decl(inferTypes1.ts, 133, 7))
 
+// Repro from #22302
+
+type MatchingKeys<T, U, K extends keyof T = keyof T> =
+>MatchingKeys : Symbol(MatchingKeys, Decl(inferTypes1.ts, 133, 55))
+>T : Symbol(T, Decl(inferTypes1.ts, 137, 18))
+>U : Symbol(U, Decl(inferTypes1.ts, 137, 20))
+>K : Symbol(K, Decl(inferTypes1.ts, 137, 23))
+>T : Symbol(T, Decl(inferTypes1.ts, 137, 18))
+>T : Symbol(T, Decl(inferTypes1.ts, 137, 18))
+
+    K extends keyof T ? T[K] extends U ? K : never : never;
+>K : Symbol(K, Decl(inferTypes1.ts, 137, 23))
+>T : Symbol(T, Decl(inferTypes1.ts, 137, 18))
+>T : Symbol(T, Decl(inferTypes1.ts, 137, 18))
+>K : Symbol(K, Decl(inferTypes1.ts, 137, 23))
+>U : Symbol(U, Decl(inferTypes1.ts, 137, 20))
+>K : Symbol(K, Decl(inferTypes1.ts, 137, 23))
+
+type VoidKeys<T> = MatchingKeys<T, void>;
+>VoidKeys : Symbol(VoidKeys, Decl(inferTypes1.ts, 138, 59))
+>T : Symbol(T, Decl(inferTypes1.ts, 140, 14))
+>MatchingKeys : Symbol(MatchingKeys, Decl(inferTypes1.ts, 133, 55))
+>T : Symbol(T, Decl(inferTypes1.ts, 140, 14))
+
+interface test {
+>test : Symbol(test, Decl(inferTypes1.ts, 140, 41))
+
+    a: 1,
+>a : Symbol(test.a, Decl(inferTypes1.ts, 142, 16))
+
+    b: void
+>b : Symbol(test.b, Decl(inferTypes1.ts, 143, 9))
+}
+
+type T80 = MatchingKeys<test, void>;
+>T80 : Symbol(T80, Decl(inferTypes1.ts, 145, 1))
+>MatchingKeys : Symbol(MatchingKeys, Decl(inferTypes1.ts, 133, 55))
+>test : Symbol(test, Decl(inferTypes1.ts, 140, 41))
+
+type T81 = VoidKeys<test>;
+>T81 : Symbol(T81, Decl(inferTypes1.ts, 147, 36))
+>VoidKeys : Symbol(VoidKeys, Decl(inferTypes1.ts, 138, 59))
+>test : Symbol(test, Decl(inferTypes1.ts, 140, 41))
+
diff --git a/tests/baselines/reference/inferTypes1.types b/tests/baselines/reference/inferTypes1.types
index 4ca78f650815e..523dd669e4cc1 100644
--- a/tests/baselines/reference/inferTypes1.types
+++ b/tests/baselines/reference/inferTypes1.types
@@ -312,7 +312,7 @@ type T60 = infer U;  // Error
 >U : U
 
 type T61<T> = infer A extends infer B ? infer C : infer D;  // Error
->T61 : {}
+>T61 : T61<T>
 >T : T
 >A : A
 >B : B
@@ -582,3 +582,47 @@ type B<T> = string extends T ? { [P in T]: void; } : T;  // Error
 >T : T
 >T : T
 
+// Repro from #22302
+
+type MatchingKeys<T, U, K extends keyof T = keyof T> =
+>MatchingKeys : MatchingKeys<T, U, K>
+>T : T
+>U : U
+>K : K
+>T : T
+>T : T
+
+    K extends keyof T ? T[K] extends U ? K : never : never;
+>K : K
+>T : T
+>T : T
+>K : K
+>U : U
+>K : K
+
+type VoidKeys<T> = MatchingKeys<T, void>;
+>VoidKeys : MatchingKeys<T, void, keyof T>
+>T : T
+>MatchingKeys : MatchingKeys<T, U, K>
+>T : T
+
+interface test {
+>test : test
+
+    a: 1,
+>a : 1
+
+    b: void
+>b : void
+}
+
+type T80 = MatchingKeys<test, void>;
+>T80 : "b"
+>MatchingKeys : MatchingKeys<T, U, K>
+>test : test
+
+type T81 = VoidKeys<test>;
+>T81 : "b"
+>VoidKeys : MatchingKeys<T, void, keyof T>
+>test : test
+
diff --git a/tests/cases/conformance/types/conditional/inferTypes1.ts b/tests/cases/conformance/types/conditional/inferTypes1.ts
index 671d68c324745..1defacc08cc5b 100644
--- a/tests/cases/conformance/types/conditional/inferTypes1.ts
+++ b/tests/cases/conformance/types/conditional/inferTypes1.ts
@@ -135,3 +135,18 @@ type C2<S, U extends void> = S extends A2<infer T, U> ? [T, U] : never;
 
 type A<T> = T extends string ? { [P in T]: void; } : T;
 type B<T> = string extends T ? { [P in T]: void; } : T;  // Error
+
+// Repro from #22302
+
+type MatchingKeys<T, U, K extends keyof T = keyof T> =
+    K extends keyof T ? T[K] extends U ? K : never : never;
+
+type VoidKeys<T> = MatchingKeys<T, void>;
+
+interface test {
+    a: 1,
+    b: void
+}
+
+type T80 = MatchingKeys<test, void>;
+type T81 = VoidKeys<test>;