diff --git a/internal/checker/checker.go b/internal/checker/checker.go
index 020fe611931..5e23758e720 100644
--- a/internal/checker/checker.go
+++ b/internal/checker/checker.go
@@ -614,8 +614,10 @@ type Checker struct {
 	evaluate                                    evaluator.Evaluator
 	stringLiteralTypes                          map[string]*Type
 	numberLiteralTypes                          map[jsnum.Number]*Type
+	nanType                                     *Type
 	bigintLiteralTypes                          map[jsnum.PseudoBigInt]*Type
 	enumLiteralTypes                            map[EnumLiteralKey]*Type
+	enumNaNLiteralTypes                         map[*ast.Symbol]*Type
 	indexedAccessTypes                          map[CacheHashKey]*Type
 	templateLiteralTypes                        map[CacheHashKey]*Type
 	stringMappingTypes                          map[StringMappingKey]*Type
@@ -924,6 +926,7 @@ func NewChecker(program Program, tracer *Tracer) (*Checker, *sync.Mutex) {
 	c.numberLiteralTypes = make(map[jsnum.Number]*Type)
 	c.bigintLiteralTypes = make(map[jsnum.PseudoBigInt]*Type)
 	c.enumLiteralTypes = make(map[EnumLiteralKey]*Type)
+	c.enumNaNLiteralTypes = make(map[*ast.Symbol]*Type)
 	c.indexedAccessTypes = make(map[CacheHashKey]*Type)
 	c.templateLiteralTypes = make(map[CacheHashKey]*Type)
 	c.stringMappingTypes = make(map[StringMappingKey]*Type)
@@ -25152,6 +25155,14 @@ func (c *Checker) getStringLiteralType(value string) *Type {
 }
 
 func (c *Checker) getNumberLiteralType(value jsnum.Number) *Type {
+	// NaN cannot be used as a Go map key because NaN != NaN in IEEE 754,
+	// so Go map lookups for NaN always miss. Cache NaN type separately.
+	if value.IsNaN() {
+		if c.nanType == nil {
+			c.nanType = c.newLiteralType(TypeFlagsNumberLiteral, value, nil)
+		}
+		return c.nanType
+	}
 	t := c.numberLiteralTypes[value]
 	if t == nil {
 		t = c.newLiteralType(TypeFlagsNumberLiteral, value, nil)
@@ -25193,11 +25204,22 @@ func getBooleanLiteralValue(t *Type) bool {
 
 func (c *Checker) getEnumLiteralType(value any, enumSymbol *ast.Symbol, symbol *ast.Symbol) *Type {
 	var flags TypeFlags
-	switch value.(type) {
+	switch v := value.(type) {
 	case string:
 		flags = TypeFlagsEnumLiteral | TypeFlagsStringLiteral
 	case jsnum.Number:
 		flags = TypeFlagsEnumLiteral | TypeFlagsNumberLiteral
+		// NaN cannot be used as a Go map key because NaN != NaN in IEEE 754,
+		// so Go map lookups for NaN always miss. Cache NaN enum types separately by enum symbol.
+		if v.IsNaN() {
+			t := c.enumNaNLiteralTypes[enumSymbol]
+			if t == nil {
+				t = c.newLiteralType(flags, value, nil)
+				t.symbol = symbol
+				c.enumNaNLiteralTypes[enumSymbol] = t
+			}
+			return t
+		}
 	default:
 		panic("Unhandled case in getEnumLiteralType")
 	}
diff --git a/testdata/baselines/reference/compiler/enumAutoIncrementValue.types b/testdata/baselines/reference/compiler/enumAutoIncrementValue.types
index 900cfc8b844..dd23ea4453a 100644
--- a/testdata/baselines/reference/compiler/enumAutoIncrementValue.types
+++ b/testdata/baselines/reference/compiler/enumAutoIncrementValue.types
@@ -11,6 +11,6 @@ enum E {
 >0 : 0
 
     B,
->B : E.B
+>B : E.A
 }
 
diff --git a/testdata/baselines/reference/compiler/enumNaNValues.errors.txt b/testdata/baselines/reference/compiler/enumNaNValues.errors.txt
new file mode 100644
index 00000000000..10d8b638b29
--- /dev/null
+++ b/testdata/baselines/reference/compiler/enumNaNValues.errors.txt
@@ -0,0 +1,20 @@
+enumNaNValues.ts(13,7): error TS2322: Type 'F' is not assignable to type 'E'.
+
+
+==== enumNaNValues.ts (1 errors) ====
+    enum E {
+      A = NaN,
+      B = NaN,
+    }
+    
+    const a: E.A = E.B;
+    const b: E.B = E.A;
+    
+    enum F {
+      X = NaN,
+    }
+    
+    const c: E.A = F.X; // Error expected - different enums
+          ~
+!!! error TS2322: Type 'F' is not assignable to type 'E'.
+    
\ No newline at end of file
diff --git a/testdata/baselines/reference/compiler/enumNaNValues.js b/testdata/baselines/reference/compiler/enumNaNValues.js
new file mode 100644
index 00000000000..88ba034c4d5
--- /dev/null
+++ b/testdata/baselines/reference/compiler/enumNaNValues.js
@@ -0,0 +1,32 @@
+//// [tests/cases/compiler/enumNaNValues.ts] ////
+
+//// [enumNaNValues.ts]
+enum E {
+  A = NaN,
+  B = NaN,
+}
+
+const a: E.A = E.B;
+const b: E.B = E.A;
+
+enum F {
+  X = NaN,
+}
+
+const c: E.A = F.X; // Error expected - different enums
+
+
+//// [enumNaNValues.js]
+"use strict";
+var E;
+(function (E) {
+    E[E["A"] = NaN] = "A";
+    E[E["B"] = NaN] = "B";
+})(E || (E = {}));
+const a = E.B;
+const b = E.A;
+var F;
+(function (F) {
+    F[F["X"] = NaN] = "X";
+})(F || (F = {}));
+const c = F.X; // Error expected - different enums
diff --git a/testdata/baselines/reference/compiler/enumNaNValues.symbols b/testdata/baselines/reference/compiler/enumNaNValues.symbols
new file mode 100644
index 00000000000..0d3125bbb81
--- /dev/null
+++ b/testdata/baselines/reference/compiler/enumNaNValues.symbols
@@ -0,0 +1,47 @@
+//// [tests/cases/compiler/enumNaNValues.ts] ////
+
+=== enumNaNValues.ts ===
+enum E {
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+
+  A = NaN,
+>A : Symbol(E.A, Decl(enumNaNValues.ts, 0, 8))
+>NaN : Symbol(NaN, Decl(lib.es5.d.ts, --, --))
+
+  B = NaN,
+>B : Symbol(E.B, Decl(enumNaNValues.ts, 1, 10))
+>NaN : Symbol(NaN, Decl(lib.es5.d.ts, --, --))
+}
+
+const a: E.A = E.B;
+>a : Symbol(a, Decl(enumNaNValues.ts, 5, 5))
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+>A : Symbol(E.A, Decl(enumNaNValues.ts, 0, 8))
+>E.B : Symbol(E.B, Decl(enumNaNValues.ts, 1, 10))
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+>B : Symbol(E.B, Decl(enumNaNValues.ts, 1, 10))
+
+const b: E.B = E.A;
+>b : Symbol(b, Decl(enumNaNValues.ts, 6, 5))
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+>B : Symbol(E.B, Decl(enumNaNValues.ts, 1, 10))
+>E.A : Symbol(E.A, Decl(enumNaNValues.ts, 0, 8))
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+>A : Symbol(E.A, Decl(enumNaNValues.ts, 0, 8))
+
+enum F {
+>F : Symbol(F, Decl(enumNaNValues.ts, 6, 19))
+
+  X = NaN,
+>X : Symbol(F.X, Decl(enumNaNValues.ts, 8, 8))
+>NaN : Symbol(NaN, Decl(lib.es5.d.ts, --, --))
+}
+
+const c: E.A = F.X; // Error expected - different enums
+>c : Symbol(c, Decl(enumNaNValues.ts, 12, 5))
+>E : Symbol(E, Decl(enumNaNValues.ts, 0, 0))
+>A : Symbol(E.A, Decl(enumNaNValues.ts, 0, 8))
+>F.X : Symbol(F.X, Decl(enumNaNValues.ts, 8, 8))
+>F : Symbol(F, Decl(enumNaNValues.ts, 6, 19))
+>X : Symbol(F.X, Decl(enumNaNValues.ts, 8, 8))
+
diff --git a/testdata/baselines/reference/compiler/enumNaNValues.types b/testdata/baselines/reference/compiler/enumNaNValues.types
new file mode 100644
index 00000000000..5417c190e03
--- /dev/null
+++ b/testdata/baselines/reference/compiler/enumNaNValues.types
@@ -0,0 +1,44 @@
+//// [tests/cases/compiler/enumNaNValues.ts] ////
+
+=== enumNaNValues.ts ===
+enum E {
+>E : E
+
+  A = NaN,
+>A : E.A
+>NaN : number
+
+  B = NaN,
+>B : E.A
+>NaN : number
+}
+
+const a: E.A = E.B;
+>a : E
+>E : any
+>E.B : E
+>E : typeof E
+>B : E
+
+const b: E.B = E.A;
+>b : E
+>E : any
+>E.A : E
+>E : typeof E
+>A : E
+
+enum F {
+>F : F
+
+  X = NaN,
+>X : F.X
+>NaN : number
+}
+
+const c: E.A = F.X; // Error expected - different enums
+>c : E
+>E : any
+>F.X : F
+>F : typeof F
+>X : F
+
diff --git a/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types b/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types
index da805aefa1f..5bddfd98720 100644
--- a/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types
+++ b/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types
@@ -79,7 +79,7 @@ enum E5 {
 >0.0 : 0
 
     e = NaN,
->e : E5.e
+>e : E5.d
 >NaN : number
 
     f = Infinity,
@@ -120,7 +120,7 @@ const enum E6 {
 >0.0 : 0
 
     e = NaN,
->e : E6.e
+>e : E6.d
 >NaN : number
 
     f = Infinity,
diff --git a/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types.diff b/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types.diff
deleted file mode 100644
index d7977f84248..00000000000
--- a/testdata/baselines/reference/submodule/conformance/enumConstantMembers.types.diff
+++ /dev/null
@@ -1,20 +0,0 @@
---- old.enumConstantMembers.types
-+++ new.enumConstantMembers.types
-@@= skipped -78, +78 lines =@@
- >0.0 : 0
-
-     e = NaN,
-->e : E5.d
-+>e : E5.e
- >NaN : number
-
-     f = Infinity,
-@@= skipped -41, +41 lines =@@
- >0.0 : 0
-
-     e = NaN,
-->e : E6.d
-+>e : E6.e
- >NaN : number
-
-     f = Infinity,
\ No newline at end of file
diff --git a/testdata/tests/cases/compiler/enumNaNValues.ts b/testdata/tests/cases/compiler/enumNaNValues.ts
new file mode 100644
index 00000000000..33c0d037412
--- /dev/null
+++ b/testdata/tests/cases/compiler/enumNaNValues.ts
@@ -0,0 +1,15 @@
+// @strict: true
+
+enum E {
+  A = NaN,
+  B = NaN,
+}
+
+const a: E.A = E.B;
+const b: E.B = E.A;
+
+enum F {
+  X = NaN,
+}
+
+const c: E.A = F.X; // Error expected - different enums