diff --git a/tsc/internal/checker/checker.go b/tsc/internal/checker/checker.go
index 9b52a55d92310..5419f32d3846d 100644
--- a/tsc/internal/checker/checker.go
+++ b/tsc/internal/checker/checker.go
@@ -139,6 +139,8 @@ const (
 	CachedTypeKindDecoratorContextStatic
 	CachedTypeKindDecoratorContextPrivate
 	CachedTypeKindDecoratorContextPrivateStatic
+	CachedTypeKindSimplifiedConditionalTypeForReading
+	CachedTypeKindSimplifiedConditionalTypeForWriting
 )
 
 // CachedTypeKey
@@ -28507,6 +28509,16 @@ func (c *Checker) distributeIndexOverObjectType(objectType *Type, indexType *Typ
 }
 
 func (c *Checker) getSimplifiedConditionalType(t *Type, writing bool) *Type {
+	key := CachedTypeKey{kind: core.IfElse(writing, CachedTypeKindSimplifiedConditionalTypeForWriting, CachedTypeKindSimplifiedConditionalTypeForReading), typeId: t.id}
+	if cached, ok := c.cachedTypes[key]; ok {
+		return cached
+	}
+	result := c.getSimplifiedConditionalTypeWorker(t, writing)
+	c.cachedTypes[key] = result
+	return result
+}
+
+func (c *Checker) getSimplifiedConditionalTypeWorker(t *Type, writing bool) *Type {
 	checkType := t.AsConditionalType().checkType
 	extendsType := t.AsConditionalType().extendsType
 	trueType := c.getTrueTypeFromConditionalType(t)
diff --git a/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.errors.txt b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.errors.txt
new file mode 100644
index 0000000000000..9ed906581b180
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.errors.txt
@@ -0,0 +1,21 @@
+simplifiedConditionalTypeWritingCache.ts(7,9): error TS2322: Type 'T["a"]' is not assignable to type 'Value<T>'.
+  Type 'string' is not assignable to type 'T["a"] & T["b"]'.
+    Type 'string' is not assignable to type 'T["b"]'.
+      'T["b"]' could be instantiated with an arbitrary type which could be unrelated to 'string'.
+
+
+==== simplifiedConditionalTypeWritingCache.ts (1 errors) ====
+    type Value<T extends { a: string; b: number }> = T["a" | "b"] extends unknown
+      ? T["a" | "b"]
+      : never;
+    
+    function test<T extends { a: string; b: number }>(value: Value<T>, a: T["a"]) {
+      const read: T["a"] | T["b"] = value;
+      const write: Value<T> = a;
+            ~~~~~
+!!! error TS2322: Type 'T["a"]' is not assignable to type 'Value<T>'.
+!!! error TS2322:   Type 'string' is not assignable to type 'T["a"] & T["b"]'.
+!!! error TS2322:     Type 'string' is not assignable to type 'T["b"]'.
+!!! error TS2322:       'T["b"]' could be instantiated with an arbitrary type which could be unrelated to 'string'.
+    }
+    
\ No newline at end of file
diff --git a/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.js b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.js
new file mode 100644
index 0000000000000..b69d342f0a6cd
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.js
@@ -0,0 +1,19 @@
+//// [tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts] ////
+
+//// [simplifiedConditionalTypeWritingCache.ts]
+type Value<T extends { a: string; b: number }> = T["a" | "b"] extends unknown
+  ? T["a" | "b"]
+  : never;
+
+function test<T extends { a: string; b: number }>(value: Value<T>, a: T["a"]) {
+  const read: T["a"] | T["b"] = value;
+  const write: Value<T> = a;
+}
+
+
+//// [simplifiedConditionalTypeWritingCache.js]
+"use strict";
+function test(value, a) {
+    const read = value;
+    const write = a;
+}
diff --git a/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.symbols b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.symbols
new file mode 100644
index 0000000000000..cc30f57fa2753
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.symbols
@@ -0,0 +1,39 @@
+//// [tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts] ////
+
+=== simplifiedConditionalTypeWritingCache.ts ===
+type Value<T extends { a: string; b: number }> = T["a" | "b"] extends unknown
+>Value : Symbol(Value, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 0))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 11))
+>a : Symbol(a, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 22))
+>b : Symbol(b, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 33))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 11))
+
+  ? T["a" | "b"]
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 11))
+
+  : never;
+
+function test<T extends { a: string; b: number }>(value: Value<T>, a: T["a"]) {
+>test : Symbol(test, Decl(simplifiedConditionalTypeWritingCache.ts, 2, 10))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+>a : Symbol(a, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 25))
+>b : Symbol(b, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 36))
+>value : Symbol(value, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 50))
+>Value : Symbol(Value, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 0))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+>a : Symbol(a, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 66))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+
+  const read: T["a"] | T["b"] = value;
+>read : Symbol(read, Decl(simplifiedConditionalTypeWritingCache.ts, 5, 7))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+>value : Symbol(value, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 50))
+
+  const write: Value<T> = a;
+>write : Symbol(write, Decl(simplifiedConditionalTypeWritingCache.ts, 6, 7))
+>Value : Symbol(Value, Decl(simplifiedConditionalTypeWritingCache.ts, 0, 0))
+>T : Symbol(T, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 14))
+>a : Symbol(a, Decl(simplifiedConditionalTypeWritingCache.ts, 4, 66))
+}
+
diff --git a/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.types b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.types
new file mode 100644
index 0000000000000..8e77eb17868ec
--- /dev/null
+++ b/tsc/testdata/baselines/reference/compiler/simplifiedConditionalTypeWritingCache.types
@@ -0,0 +1,27 @@
+//// [tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts] ////
+
+=== simplifiedConditionalTypeWritingCache.ts ===
+type Value<T extends { a: string; b: number }> = T["a" | "b"] extends unknown
+>Value : Value<T>
+>a : string
+>b : number
+
+  ? T["a" | "b"]
+  : never;
+
+function test<T extends { a: string; b: number }>(value: Value<T>, a: T["a"]) {
+>test : <T extends { a: string; b: number; }>(value: Value<T>, a: T["a"]) => void
+>a : string
+>b : number
+>value : Value<T>
+>a : T["a"]
+
+  const read: T["a"] | T["b"] = value;
+>read : T["a"] | T["b"]
+>value : Value<T>
+
+  const write: Value<T> = a;
+>write : Value<T>
+>a : T["a"]
+}
+
diff --git a/tsc/testdata/tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts b/tsc/testdata/tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts
new file mode 100644
index 0000000000000..457405a3b05d9
--- /dev/null
+++ b/tsc/testdata/tests/cases/compiler/simplifiedConditionalTypeWritingCache.ts
@@ -0,0 +1,8 @@
+type Value<T extends { a: string; b: number }> = T["a" | "b"] extends unknown
+  ? T["a" | "b"]
+  : never;
+
+function test<T extends { a: string; b: number }>(value: Value<T>, a: T["a"]) {
+  const read: T["a"] | T["b"] = value;
+  const write: Value<T> = a;
+}