diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 8e4b9e48a28..3d709be779f 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14613,7 +14613,7 @@ namespace ts {
                     combinedMapper = mergeTypeMappers(mapper, context.mapper);
                 }
                 // Instantiate the extends type including inferences for 'infer T' type parameters
-                const inferredExtendsType = combinedMapper ? instantiateType(root.extendsType, combinedMapper) : extendsType;
+                const inferredExtendsType = combinedMapper ? instantiateType(unwrapNondistributiveConditionalTuple(root, root.extendsType), combinedMapper) : extendsType;
                 // We attempt to resolve the conditional type only when the check and extends types are non-generic
                 if (!checkTypeInstantiable && !isGenericObjectType(inferredExtendsType) && !isGenericIndexType(inferredExtendsType)) {
                     // Return falseType for a definitely false extends check. We check an instantiations of the two
diff --git a/tests/baselines/reference/nondistributiveConditionalTypeInfer.js b/tests/baselines/reference/nondistributiveConditionalTypeInfer.js
new file mode 100644
index 00000000000..968f3c1a4d7
--- /dev/null
+++ b/tests/baselines/reference/nondistributiveConditionalTypeInfer.js
@@ -0,0 +1,16 @@
+//// [nondistributiveConditionalTypeInfer.ts]
+type _R<T> = [T] extends [{ _R: (_: infer R) => void }] ? R : never;
+type _E<T> = [T] extends [{ _E: () => infer E }] ? E : never;
+type _A<T> = [T] extends [{ _A: () => infer A }] ? A : never;
+
+interface Sync<R, E, A> {
+  _R: (_: R) => void;
+  _E: () => E;
+  _A: () => A;
+}
+
+type R = _R<Sync<number, string, void>>;
+type E = _E<Sync<number, string, void>>;
+type A = _A<Sync<number, string, void>>;
+
+//// [nondistributiveConditionalTypeInfer.js]
diff --git a/tests/baselines/reference/nondistributiveConditionalTypeInfer.symbols b/tests/baselines/reference/nondistributiveConditionalTypeInfer.symbols
new file mode 100644
index 00000000000..133abc6c6a4
--- /dev/null
+++ b/tests/baselines/reference/nondistributiveConditionalTypeInfer.symbols
@@ -0,0 +1,61 @@
+=== tests/cases/compiler/nondistributiveConditionalTypeInfer.ts ===
+type _R<T> = [T] extends [{ _R: (_: infer R) => void }] ? R : never;
+>_R : Symbol(_R, Decl(nondistributiveConditionalTypeInfer.ts, 0, 0))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 0, 8))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 0, 8))
+>_R : Symbol(_R, Decl(nondistributiveConditionalTypeInfer.ts, 0, 27))
+>_ : Symbol(_, Decl(nondistributiveConditionalTypeInfer.ts, 0, 33))
+>R : Symbol(R, Decl(nondistributiveConditionalTypeInfer.ts, 0, 41))
+>R : Symbol(R, Decl(nondistributiveConditionalTypeInfer.ts, 0, 41))
+
+type _E<T> = [T] extends [{ _E: () => infer E }] ? E : never;
+>_E : Symbol(_E, Decl(nondistributiveConditionalTypeInfer.ts, 0, 68))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 1, 8))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 1, 8))
+>_E : Symbol(_E, Decl(nondistributiveConditionalTypeInfer.ts, 1, 27))
+>E : Symbol(E, Decl(nondistributiveConditionalTypeInfer.ts, 1, 43))
+>E : Symbol(E, Decl(nondistributiveConditionalTypeInfer.ts, 1, 43))
+
+type _A<T> = [T] extends [{ _A: () => infer A }] ? A : never;
+>_A : Symbol(_A, Decl(nondistributiveConditionalTypeInfer.ts, 1, 61))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 2, 8))
+>T : Symbol(T, Decl(nondistributiveConditionalTypeInfer.ts, 2, 8))
+>_A : Symbol(_A, Decl(nondistributiveConditionalTypeInfer.ts, 2, 27))
+>A : Symbol(A, Decl(nondistributiveConditionalTypeInfer.ts, 2, 43))
+>A : Symbol(A, Decl(nondistributiveConditionalTypeInfer.ts, 2, 43))
+
+interface Sync<R, E, A> {
+>Sync : Symbol(Sync, Decl(nondistributiveConditionalTypeInfer.ts, 2, 61))
+>R : Symbol(R, Decl(nondistributiveConditionalTypeInfer.ts, 4, 15))
+>E : Symbol(E, Decl(nondistributiveConditionalTypeInfer.ts, 4, 17))
+>A : Symbol(A, Decl(nondistributiveConditionalTypeInfer.ts, 4, 20))
+
+  _R: (_: R) => void;
+>_R : Symbol(Sync._R, Decl(nondistributiveConditionalTypeInfer.ts, 4, 25))
+>_ : Symbol(_, Decl(nondistributiveConditionalTypeInfer.ts, 5, 7))
+>R : Symbol(R, Decl(nondistributiveConditionalTypeInfer.ts, 4, 15))
+
+  _E: () => E;
+>_E : Symbol(Sync._E, Decl(nondistributiveConditionalTypeInfer.ts, 5, 21))
+>E : Symbol(E, Decl(nondistributiveConditionalTypeInfer.ts, 4, 17))
+
+  _A: () => A;
+>_A : Symbol(Sync._A, Decl(nondistributiveConditionalTypeInfer.ts, 6, 14))
+>A : Symbol(A, Decl(nondistributiveConditionalTypeInfer.ts, 4, 20))
+}
+
+type R = _R<Sync<number, string, void>>;
+>R : Symbol(R, Decl(nondistributiveConditionalTypeInfer.ts, 8, 1))
+>_R : Symbol(_R, Decl(nondistributiveConditionalTypeInfer.ts, 0, 0))
+>Sync : Symbol(Sync, Decl(nondistributiveConditionalTypeInfer.ts, 2, 61))
+
+type E = _E<Sync<number, string, void>>;
+>E : Symbol(E, Decl(nondistributiveConditionalTypeInfer.ts, 10, 40))
+>_E : Symbol(_E, Decl(nondistributiveConditionalTypeInfer.ts, 0, 68))
+>Sync : Symbol(Sync, Decl(nondistributiveConditionalTypeInfer.ts, 2, 61))
+
+type A = _A<Sync<number, string, void>>;
+>A : Symbol(A, Decl(nondistributiveConditionalTypeInfer.ts, 11, 40))
+>_A : Symbol(_A, Decl(nondistributiveConditionalTypeInfer.ts, 1, 61))
+>Sync : Symbol(Sync, Decl(nondistributiveConditionalTypeInfer.ts, 2, 61))
+
diff --git a/tests/baselines/reference/nondistributiveConditionalTypeInfer.types b/tests/baselines/reference/nondistributiveConditionalTypeInfer.types
new file mode 100644
index 00000000000..ec301cfb344
--- /dev/null
+++ b/tests/baselines/reference/nondistributiveConditionalTypeInfer.types
@@ -0,0 +1,35 @@
+=== tests/cases/compiler/nondistributiveConditionalTypeInfer.ts ===
+type _R<T> = [T] extends [{ _R: (_: infer R) => void }] ? R : never;
+>_R : _R<T>
+>_R : (_: infer R) => void
+>_ : R
+
+type _E<T> = [T] extends [{ _E: () => infer E }] ? E : never;
+>_E : _E<T>
+>_E : () => infer E
+
+type _A<T> = [T] extends [{ _A: () => infer A }] ? A : never;
+>_A : _A<T>
+>_A : () => infer A
+
+interface Sync<R, E, A> {
+  _R: (_: R) => void;
+>_R : (_: R) => void
+>_ : R
+
+  _E: () => E;
+>_E : () => E
+
+  _A: () => A;
+>_A : () => A
+}
+
+type R = _R<Sync<number, string, void>>;
+>R : number
+
+type E = _E<Sync<number, string, void>>;
+>E : string
+
+type A = _A<Sync<number, string, void>>;
+>A : void
+
diff --git a/tests/cases/compiler/nondistributiveConditionalTypeInfer.ts b/tests/cases/compiler/nondistributiveConditionalTypeInfer.ts
new file mode 100644
index 00000000000..01d70af644b
--- /dev/null
+++ b/tests/cases/compiler/nondistributiveConditionalTypeInfer.ts
@@ -0,0 +1,13 @@
+type _R<T> = [T] extends [{ _R: (_: infer R) => void }] ? R : never;
+type _E<T> = [T] extends [{ _E: () => infer E }] ? E : never;
+type _A<T> = [T] extends [{ _A: () => infer A }] ? A : never;
+
+interface Sync<R, E, A> {
+  _R: (_: R) => void;
+  _E: () => E;
+  _A: () => A;
+}
+
+type R = _R<Sync<number, string, void>>;
+type E = _E<Sync<number, string, void>>;
+type A = _A<Sync<number, string, void>>;
\ No newline at end of file