diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 56c4d8a2114c9..b0ea7ea9ffb04 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -967,6 +967,7 @@ import {
     skipParentheses,
     skipTrivia,
     skipTypeChecking,
+    skipTypeParentheses,
     some,
     SourceFile,
     SpreadAssignment,
@@ -18490,7 +18491,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return constraint && (isGenericObjectType(constraint) || isGenericIndexType(constraint)) ? cloneTypeParameter(p) : p;
     }
 
-    function isSimpleTupleType(node: TypeNode) {
+    function isSimpleTupleType(node: TypeNode): boolean {
         return isTupleTypeNode(node) && length(node.elements) > 0 &&
             !some(node.elements, e => isOptionalTypeNode(e) || isRestTypeNode(e) || isNamedTupleMember(e) && !!(e.questionToken || e.dotDotDotToken));
     }
@@ -18521,11 +18522,13 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             if (checkType === wildcardType || extendsType === wildcardType) {
                 return wildcardType;
             }
+            const checkTypeNode = skipTypeParentheses(root.node.checkType);
+            const extendsTypeNode = skipTypeParentheses(root.node.extendsType);
             // When the check and extends types are simple tuple types of the same arity, we defer resolution of the
             // conditional type when any tuple elements are generic. This is such that non-distributable conditional
             // types can be written `[X] extends [Y] ? ...` and be deferred similarly to `X extends Y ? ...`.
-            const checkTuples = isSimpleTupleType(root.node.checkType) && isSimpleTupleType(root.node.extendsType) &&
-                length((root.node.checkType as TupleTypeNode).elements) === length((root.node.extendsType as TupleTypeNode).elements);
+            const checkTuples = isSimpleTupleType(checkTypeNode) && isSimpleTupleType(extendsTypeNode) &&
+                length((checkTypeNode as TupleTypeNode).elements) === length((extendsTypeNode as TupleTypeNode).elements);
             const checkTypeDeferred = isDeferredType(checkType, checkTuples);
             let combinedMapper: TypeMapper | undefined;
             if (root.inferTypeParameters) {
diff --git a/tests/baselines/reference/deferredConditionalTypes2.symbols b/tests/baselines/reference/deferredConditionalTypes2.symbols
new file mode 100644
index 0000000000000..b3abb1b74ba1a
--- /dev/null
+++ b/tests/baselines/reference/deferredConditionalTypes2.symbols
@@ -0,0 +1,117 @@
+//// [tests/cases/compiler/deferredConditionalTypes2.ts] ////
+
+=== deferredConditionalTypes2.ts ===
+// https://github.com/microsoft/TypeScript/issues/56270
+
+type PositiveInfinity = 1e999;
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+type NegativeInfinity = -1e999;
+>NegativeInfinity : Symbol(NegativeInfinity, Decl(deferredConditionalTypes2.ts, 2, 30))
+
+export type IsEqual<A, B> = (<G>() => G extends A ? 1 : 2) extends <
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 5, 20))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 5, 22))
+>G : Symbol(G, Decl(deferredConditionalTypes2.ts, 5, 30))
+>G : Symbol(G, Decl(deferredConditionalTypes2.ts, 5, 30))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 5, 20))
+
+  G,
+>G : Symbol(G, Decl(deferredConditionalTypes2.ts, 5, 68))
+
+>() => G extends B ? 1 : 2
+>G : Symbol(G, Decl(deferredConditionalTypes2.ts, 5, 68))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 5, 22))
+
+  ? true
+  : false;
+
+export type Add<A extends number, B extends number> = [
+>Add : Symbol(Add, Decl(deferredConditionalTypes2.ts, 9, 10))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 11, 16))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 11, 33))
+
+  IsEqual<A, PositiveInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 11, 16))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+  IsEqual<A, NegativeInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 11, 16))
+>NegativeInfinity : Symbol(NegativeInfinity, Decl(deferredConditionalTypes2.ts, 2, 30))
+
+  IsEqual<B, PositiveInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 11, 33))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+  IsEqual<B, NegativeInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 11, 33))
+>NegativeInfinity : Symbol(NegativeInfinity, Decl(deferredConditionalTypes2.ts, 2, 30))
+
+] extends infer R extends [boolean, boolean, boolean, boolean]
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 16, 15))
+
+  ? [true, false] extends ([R[0], R[3]])
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 16, 15))
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 16, 15))
+
+    ? PositiveInfinity
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+    : "failed"
+  : never;
+
+export type AddWithoutParentheses<A extends number, B extends number> = [
+>AddWithoutParentheses : Symbol(AddWithoutParentheses, Decl(deferredConditionalTypes2.ts, 20, 10))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 22, 34))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 22, 51))
+
+  IsEqual<A, PositiveInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 22, 34))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+  IsEqual<A, NegativeInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>A : Symbol(A, Decl(deferredConditionalTypes2.ts, 22, 34))
+>NegativeInfinity : Symbol(NegativeInfinity, Decl(deferredConditionalTypes2.ts, 2, 30))
+
+  IsEqual<B, PositiveInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 22, 51))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+  IsEqual<B, NegativeInfinity>,
+>IsEqual : Symbol(IsEqual, Decl(deferredConditionalTypes2.ts, 3, 31))
+>B : Symbol(B, Decl(deferredConditionalTypes2.ts, 22, 51))
+>NegativeInfinity : Symbol(NegativeInfinity, Decl(deferredConditionalTypes2.ts, 2, 30))
+
+] extends infer R extends [boolean, boolean, boolean, boolean]
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 27, 15))
+
+  ? [true, false] extends [R[0], R[3]]
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 27, 15))
+>R : Symbol(R, Decl(deferredConditionalTypes2.ts, 27, 15))
+
+    ? PositiveInfinity
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+    : "failed"
+  : never;
+
+type AddTest0 = Add<PositiveInfinity, PositiveInfinity>;
+>AddTest0 : Symbol(AddTest0, Decl(deferredConditionalTypes2.ts, 31, 10))
+>Add : Symbol(Add, Decl(deferredConditionalTypes2.ts, 9, 10))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
+type AddTest1 = AddWithoutParentheses<PositiveInfinity, PositiveInfinity>;
+>AddTest1 : Symbol(AddTest1, Decl(deferredConditionalTypes2.ts, 33, 56))
+>AddWithoutParentheses : Symbol(AddWithoutParentheses, Decl(deferredConditionalTypes2.ts, 20, 10))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+>PositiveInfinity : Symbol(PositiveInfinity, Decl(deferredConditionalTypes2.ts, 0, 0))
+
diff --git a/tests/baselines/reference/deferredConditionalTypes2.types b/tests/baselines/reference/deferredConditionalTypes2.types
new file mode 100644
index 0000000000000..a14eb9574aa16
--- /dev/null
+++ b/tests/baselines/reference/deferredConditionalTypes2.types
@@ -0,0 +1,62 @@
+//// [tests/cases/compiler/deferredConditionalTypes2.ts] ////
+
+=== deferredConditionalTypes2.ts ===
+// https://github.com/microsoft/TypeScript/issues/56270
+
+type PositiveInfinity = 1e999;
+>PositiveInfinity : Infinity
+
+type NegativeInfinity = -1e999;
+>NegativeInfinity : -Infinity
+>-1e999 : -Infinity
+>1e999 : Infinity
+
+export type IsEqual<A, B> = (<G>() => G extends A ? 1 : 2) extends <
+>IsEqual : IsEqual<A, B>
+
+  G,
+>() => G extends B ? 1 : 2
+  ? true
+>true : true
+
+  : false;
+>false : false
+
+export type Add<A extends number, B extends number> = [
+>Add : [true, false] extends [IsEqual<A, Infinity>, IsEqual<B, -Infinity>] ? Infinity : "failed"
+
+  IsEqual<A, PositiveInfinity>,
+  IsEqual<A, NegativeInfinity>,
+  IsEqual<B, PositiveInfinity>,
+  IsEqual<B, NegativeInfinity>,
+] extends infer R extends [boolean, boolean, boolean, boolean]
+  ? [true, false] extends ([R[0], R[3]])
+>true : true
+>false : false
+
+    ? PositiveInfinity
+    : "failed"
+  : never;
+
+export type AddWithoutParentheses<A extends number, B extends number> = [
+>AddWithoutParentheses : [true, false] extends [IsEqual<A, Infinity>, IsEqual<B, -Infinity>] ? Infinity : "failed"
+
+  IsEqual<A, PositiveInfinity>,
+  IsEqual<A, NegativeInfinity>,
+  IsEqual<B, PositiveInfinity>,
+  IsEqual<B, NegativeInfinity>,
+] extends infer R extends [boolean, boolean, boolean, boolean]
+  ? [true, false] extends [R[0], R[3]]
+>true : true
+>false : false
+
+    ? PositiveInfinity
+    : "failed"
+  : never;
+
+type AddTest0 = Add<PositiveInfinity, PositiveInfinity>;
+>AddTest0 : Infinity
+
+type AddTest1 = AddWithoutParentheses<PositiveInfinity, PositiveInfinity>;
+>AddTest1 : Infinity
+
diff --git a/tests/cases/compiler/deferredConditionalTypes2.ts b/tests/cases/compiler/deferredConditionalTypes2.ts
new file mode 100644
index 0000000000000..e1f4f57a2673b
--- /dev/null
+++ b/tests/cases/compiler/deferredConditionalTypes2.ts
@@ -0,0 +1,38 @@
+// @strict: true
+// @noEmit: true
+
+// https://github.com/microsoft/TypeScript/issues/56270
+
+type PositiveInfinity = 1e999;
+type NegativeInfinity = -1e999;
+
+export type IsEqual<A, B> = (<G>() => G extends A ? 1 : 2) extends <
+  G,
+>() => G extends B ? 1 : 2
+  ? true
+  : false;
+
+export type Add<A extends number, B extends number> = [
+  IsEqual<A, PositiveInfinity>,
+  IsEqual<A, NegativeInfinity>,
+  IsEqual<B, PositiveInfinity>,
+  IsEqual<B, NegativeInfinity>,
+] extends infer R extends [boolean, boolean, boolean, boolean]
+  ? [true, false] extends ([R[0], R[3]])
+    ? PositiveInfinity
+    : "failed"
+  : never;
+
+export type AddWithoutParentheses<A extends number, B extends number> = [
+  IsEqual<A, PositiveInfinity>,
+  IsEqual<A, NegativeInfinity>,
+  IsEqual<B, PositiveInfinity>,
+  IsEqual<B, NegativeInfinity>,
+] extends infer R extends [boolean, boolean, boolean, boolean]
+  ? [true, false] extends [R[0], R[3]]
+    ? PositiveInfinity
+    : "failed"
+  : never;
+
+type AddTest0 = Add<PositiveInfinity, PositiveInfinity>;
+type AddTest1 = AddWithoutParentheses<PositiveInfinity, PositiveInfinity>;