diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index ce56db4b962f4..97bfa81630db2 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -21973,6 +21973,13 @@ namespace ts {
                     const arg = (<PrefixUnaryExpression>node).operand;
                     return op === SyntaxKind.MinusToken && (arg.kind === SyntaxKind.NumericLiteral || arg.kind === SyntaxKind.BigIntLiteral) ||
                         op === SyntaxKind.PlusToken && arg.kind === SyntaxKind.NumericLiteral;
+                case SyntaxKind.PropertyAccessExpression:
+                case SyntaxKind.ElementAccessExpression:
+                    const expr = (<PropertyAccessExpression | ElementAccessExpression>node).expression;
+                    if (isIdentifier(expr)) {
+                        const symbol = getSymbolAtLocation(expr);
+                        return !!(symbol && (symbol.flags & SymbolFlags.Enum) && getEnumKind(symbol) === EnumKind.Literal);
+                    }
             }
             return false;
         }
@@ -21981,7 +21988,7 @@ namespace ts {
             let exprType = checkExpression(expression, checkMode);
             if (isConstTypeReference(type)) {
                 if (!isValidConstAssertionArgument(expression)) {
-                    error(expression, Diagnostics.A_const_assertion_can_only_be_applied_to_a_string_number_boolean_array_or_object_literal);
+                    error(expression, Diagnostics.A_const_assertions_can_only_be_applied_to_references_to_enum_members_or_string_number_boolean_array_or_object_literals);
                 }
                 return getRegularTypeOfLiteralType(exprType);
             }
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index a78e89f42beb3..04d8213dacbc6 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -1031,7 +1031,7 @@
         "category": "Error",
         "code": 1354
     },
-    "A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.": {
+    "A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.": {
         "category": "Error",
         "code": 1355
     },
diff --git a/tests/baselines/reference/constAssertions.errors.txt b/tests/baselines/reference/constAssertions.errors.txt
index 24fce1599012a..8ecce1377e344 100644
--- a/tests/baselines/reference/constAssertions.errors.txt
+++ b/tests/baselines/reference/constAssertions.errors.txt
@@ -1,7 +1,7 @@
 tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(44,32): error TS2540: Cannot assign to 'x' because it is a read-only property.
-tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(61,10): error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
-tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(62,10): error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
-tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(63,10): error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
+tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(61,10): error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(62,10): error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(63,10): error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
 
 
 ==== tests/cases/conformance/expressions/typeAssertions/constAssertions.ts (4 errors) ====
@@ -69,11 +69,11 @@ tests/cases/conformance/expressions/typeAssertions/constAssertions.ts(63,10): er
     
     let e1 = v1 as const;  // Error
              ~~
-!!! error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
+!!! error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
     let e2 = (true ? 1 : 0) as const;  // Error
              ~~~~~~~~~~~~~~
-!!! error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
+!!! error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
     let e3 = id(1) as const;  // Error
              ~~~~~
-!!! error TS1355: A 'const' assertion can only be applied to a string, number, boolean, array, or object literal.
+!!! error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
     
\ No newline at end of file
diff --git a/tests/baselines/reference/constantEnumAssert.errors.txt b/tests/baselines/reference/constantEnumAssert.errors.txt
new file mode 100644
index 0000000000000..b384d3bd308e0
--- /dev/null
+++ b/tests/baselines/reference/constantEnumAssert.errors.txt
@@ -0,0 +1,59 @@
+tests/cases/compiler/constantEnumAssert.ts(45,20): error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+tests/cases/compiler/constantEnumAssert.ts(49,20): error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+
+
+==== tests/cases/compiler/constantEnumAssert.ts (2 errors) ====
+    enum E1 {
+        a,
+        b
+    }
+    
+    enum E2 {
+        a = 'a',
+        b = 'b'
+    }
+    
+    enum E3 {
+        a = 1,
+        b = a << 1,
+        c = a << 2,
+    }
+    
+    const enum E4 {
+        a,
+        b
+    }
+    
+    const E5 = {
+        a: 'a',
+        b: 'b'
+    }
+    
+    const foo1 = { a: E1.a }
+    
+    const foo2 = { a: E2.a }
+    
+    const foo3 = { a: E1.a } as const
+    
+    const foo4 = { a: E2.a } as const
+    
+    const foo5 = { a: E3.a } as const
+    
+    const foo6 = { a: E4.a } as const
+    
+    const foo7 = { a: E5.a } as const
+    
+    const foo8 = { a: E1.a as const }
+    
+    const foo9 = { a: E2.a as const }
+    
+    const foo10 = { a: E3.a as const }
+                       ~~~~
+!!! error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+    
+    const foo11 = { a: E4.a as const }
+    
+    const foo12 = { a: E5.a as const }
+                       ~~~~
+!!! error TS1355: A 'const' assertions can only be applied to references to enum members, or string, number, boolean, array, or object literals.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/constantEnumAssert.js b/tests/baselines/reference/constantEnumAssert.js
new file mode 100644
index 0000000000000..85f3db9d93a77
--- /dev/null
+++ b/tests/baselines/reference/constantEnumAssert.js
@@ -0,0 +1,85 @@
+//// [constantEnumAssert.ts]
+enum E1 {
+    a,
+    b
+}
+
+enum E2 {
+    a = 'a',
+    b = 'b'
+}
+
+enum E3 {
+    a = 1,
+    b = a << 1,
+    c = a << 2,
+}
+
+const enum E4 {
+    a,
+    b
+}
+
+const E5 = {
+    a: 'a',
+    b: 'b'
+}
+
+const foo1 = { a: E1.a }
+
+const foo2 = { a: E2.a }
+
+const foo3 = { a: E1.a } as const
+
+const foo4 = { a: E2.a } as const
+
+const foo5 = { a: E3.a } as const
+
+const foo6 = { a: E4.a } as const
+
+const foo7 = { a: E5.a } as const
+
+const foo8 = { a: E1.a as const }
+
+const foo9 = { a: E2.a as const }
+
+const foo10 = { a: E3.a as const }
+
+const foo11 = { a: E4.a as const }
+
+const foo12 = { a: E5.a as const }
+
+
+//// [constantEnumAssert.js]
+var E1;
+(function (E1) {
+    E1[E1["a"] = 0] = "a";
+    E1[E1["b"] = 1] = "b";
+})(E1 || (E1 = {}));
+var E2;
+(function (E2) {
+    E2["a"] = "a";
+    E2["b"] = "b";
+})(E2 || (E2 = {}));
+var E3;
+(function (E3) {
+    E3[E3["a"] = 1] = "a";
+    E3[E3["b"] = 2] = "b";
+    E3[E3["c"] = 4] = "c";
+})(E3 || (E3 = {}));
+var E5 = {
+    a: 'a',
+    b: 'b'
+};
+var foo1 = { a: E1.a };
+var foo2 = { a: E2.a };
+var foo3 = { a: E1.a };
+var foo4 = { a: E2.a };
+var foo5 = { a: E3.a };
+var foo6 = { a: 0 /* a */ };
+var foo7 = { a: E5.a };
+var foo8 = { a: E1.a };
+var foo9 = { a: E2.a };
+var foo10 = { a: E3.a };
+var foo11 = { a: 0 /* a */ };
+var foo12 = { a: E5.a };
diff --git a/tests/baselines/reference/constantEnumAssert.symbols b/tests/baselines/reference/constantEnumAssert.symbols
new file mode 100644
index 0000000000000..3249dbe61ccaa
--- /dev/null
+++ b/tests/baselines/reference/constantEnumAssert.symbols
@@ -0,0 +1,140 @@
+=== tests/cases/compiler/constantEnumAssert.ts ===
+enum E1 {
+>E1 : Symbol(E1, Decl(constantEnumAssert.ts, 0, 0))
+
+    a,
+>a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+
+    b
+>b : Symbol(E1.b, Decl(constantEnumAssert.ts, 1, 6))
+}
+
+enum E2 {
+>E2 : Symbol(E2, Decl(constantEnumAssert.ts, 3, 1))
+
+    a = 'a',
+>a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+
+    b = 'b'
+>b : Symbol(E2.b, Decl(constantEnumAssert.ts, 6, 12))
+}
+
+enum E3 {
+>E3 : Symbol(E3, Decl(constantEnumAssert.ts, 8, 1))
+
+    a = 1,
+>a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+
+    b = a << 1,
+>b : Symbol(E3.b, Decl(constantEnumAssert.ts, 11, 10))
+>a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+
+    c = a << 2,
+>c : Symbol(E3.c, Decl(constantEnumAssert.ts, 12, 15))
+>a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+}
+
+const enum E4 {
+>E4 : Symbol(E4, Decl(constantEnumAssert.ts, 14, 1))
+
+    a,
+>a : Symbol(E4.a, Decl(constantEnumAssert.ts, 16, 15))
+
+    b
+>b : Symbol(E4.b, Decl(constantEnumAssert.ts, 17, 6))
+}
+
+const E5 = {
+>E5 : Symbol(E5, Decl(constantEnumAssert.ts, 21, 5))
+
+    a: 'a',
+>a : Symbol(a, Decl(constantEnumAssert.ts, 21, 12))
+
+    b: 'b'
+>b : Symbol(b, Decl(constantEnumAssert.ts, 22, 11))
+}
+
+const foo1 = { a: E1.a }
+>foo1 : Symbol(foo1, Decl(constantEnumAssert.ts, 26, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 26, 14))
+>E1.a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+>E1 : Symbol(E1, Decl(constantEnumAssert.ts, 0, 0))
+>a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+
+const foo2 = { a: E2.a }
+>foo2 : Symbol(foo2, Decl(constantEnumAssert.ts, 28, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 28, 14))
+>E2.a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+>E2 : Symbol(E2, Decl(constantEnumAssert.ts, 3, 1))
+>a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+
+const foo3 = { a: E1.a } as const
+>foo3 : Symbol(foo3, Decl(constantEnumAssert.ts, 30, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 30, 14))
+>E1.a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+>E1 : Symbol(E1, Decl(constantEnumAssert.ts, 0, 0))
+>a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+
+const foo4 = { a: E2.a } as const
+>foo4 : Symbol(foo4, Decl(constantEnumAssert.ts, 32, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 32, 14))
+>E2.a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+>E2 : Symbol(E2, Decl(constantEnumAssert.ts, 3, 1))
+>a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+
+const foo5 = { a: E3.a } as const
+>foo5 : Symbol(foo5, Decl(constantEnumAssert.ts, 34, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 34, 14))
+>E3.a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+>E3 : Symbol(E3, Decl(constantEnumAssert.ts, 8, 1))
+>a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+
+const foo6 = { a: E4.a } as const
+>foo6 : Symbol(foo6, Decl(constantEnumAssert.ts, 36, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 36, 14))
+>E4.a : Symbol(E4.a, Decl(constantEnumAssert.ts, 16, 15))
+>E4 : Symbol(E4, Decl(constantEnumAssert.ts, 14, 1))
+>a : Symbol(E4.a, Decl(constantEnumAssert.ts, 16, 15))
+
+const foo7 = { a: E5.a } as const
+>foo7 : Symbol(foo7, Decl(constantEnumAssert.ts, 38, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 38, 14))
+>E5.a : Symbol(a, Decl(constantEnumAssert.ts, 21, 12))
+>E5 : Symbol(E5, Decl(constantEnumAssert.ts, 21, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 21, 12))
+
+const foo8 = { a: E1.a as const }
+>foo8 : Symbol(foo8, Decl(constantEnumAssert.ts, 40, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 40, 14))
+>E1.a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+>E1 : Symbol(E1, Decl(constantEnumAssert.ts, 0, 0))
+>a : Symbol(E1.a, Decl(constantEnumAssert.ts, 0, 9))
+
+const foo9 = { a: E2.a as const }
+>foo9 : Symbol(foo9, Decl(constantEnumAssert.ts, 42, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 42, 14))
+>E2.a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+>E2 : Symbol(E2, Decl(constantEnumAssert.ts, 3, 1))
+>a : Symbol(E2.a, Decl(constantEnumAssert.ts, 5, 9))
+
+const foo10 = { a: E3.a as const }
+>foo10 : Symbol(foo10, Decl(constantEnumAssert.ts, 44, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 44, 15))
+>E3.a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+>E3 : Symbol(E3, Decl(constantEnumAssert.ts, 8, 1))
+>a : Symbol(E3.a, Decl(constantEnumAssert.ts, 10, 9))
+
+const foo11 = { a: E4.a as const }
+>foo11 : Symbol(foo11, Decl(constantEnumAssert.ts, 46, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 46, 15))
+>E4.a : Symbol(E4.a, Decl(constantEnumAssert.ts, 16, 15))
+>E4 : Symbol(E4, Decl(constantEnumAssert.ts, 14, 1))
+>a : Symbol(E4.a, Decl(constantEnumAssert.ts, 16, 15))
+
+const foo12 = { a: E5.a as const }
+>foo12 : Symbol(foo12, Decl(constantEnumAssert.ts, 48, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 48, 15))
+>E5.a : Symbol(a, Decl(constantEnumAssert.ts, 21, 12))
+>E5 : Symbol(E5, Decl(constantEnumAssert.ts, 21, 5))
+>a : Symbol(a, Decl(constantEnumAssert.ts, 21, 12))
+
diff --git a/tests/baselines/reference/constantEnumAssert.types b/tests/baselines/reference/constantEnumAssert.types
new file mode 100644
index 0000000000000..36d4f7f3abcd4
--- /dev/null
+++ b/tests/baselines/reference/constantEnumAssert.types
@@ -0,0 +1,172 @@
+=== tests/cases/compiler/constantEnumAssert.ts ===
+enum E1 {
+>E1 : E1
+
+    a,
+>a : E1.a
+
+    b
+>b : E1.b
+}
+
+enum E2 {
+>E2 : E2
+
+    a = 'a',
+>a : E2.a
+>'a' : "a"
+
+    b = 'b'
+>b : E2.b
+>'b' : "b"
+}
+
+enum E3 {
+>E3 : E3
+
+    a = 1,
+>a : E3
+>1 : 1
+
+    b = a << 1,
+>b : E3
+>a << 1 : number
+>a : E3
+>1 : 1
+
+    c = a << 2,
+>c : E3
+>a << 2 : number
+>a : E3
+>2 : 2
+}
+
+const enum E4 {
+>E4 : E4
+
+    a,
+>a : E4.a
+
+    b
+>b : E4.b
+}
+
+const E5 = {
+>E5 : { a: string; b: string; }
+>{    a: 'a',    b: 'b'} : { a: string; b: string; }
+
+    a: 'a',
+>a : string
+>'a' : "a"
+
+    b: 'b'
+>b : string
+>'b' : "b"
+}
+
+const foo1 = { a: E1.a }
+>foo1 : { a: E1; }
+>{ a: E1.a } : { a: E1; }
+>a : E1
+>E1.a : E1.a
+>E1 : typeof E1
+>a : E1.a
+
+const foo2 = { a: E2.a }
+>foo2 : { a: E2; }
+>{ a: E2.a } : { a: E2; }
+>a : E2
+>E2.a : E2.a
+>E2 : typeof E2
+>a : E2.a
+
+const foo3 = { a: E1.a } as const
+>foo3 : { readonly a: E1.a; }
+>{ a: E1.a } as const : { readonly a: E1.a; }
+>{ a: E1.a } : { readonly a: E1.a; }
+>a : E1.a
+>E1.a : E1.a
+>E1 : typeof E1
+>a : E1.a
+
+const foo4 = { a: E2.a } as const
+>foo4 : { readonly a: E2.a; }
+>{ a: E2.a } as const : { readonly a: E2.a; }
+>{ a: E2.a } : { readonly a: E2.a; }
+>a : E2.a
+>E2.a : E2.a
+>E2 : typeof E2
+>a : E2.a
+
+const foo5 = { a: E3.a } as const
+>foo5 : { readonly a: E3; }
+>{ a: E3.a } as const : { readonly a: E3; }
+>{ a: E3.a } : { readonly a: E3; }
+>a : E3
+>E3.a : E3
+>E3 : typeof E3
+>a : E3
+
+const foo6 = { a: E4.a } as const
+>foo6 : { readonly a: E4.a; }
+>{ a: E4.a } as const : { readonly a: E4.a; }
+>{ a: E4.a } : { readonly a: E4.a; }
+>a : E4.a
+>E4.a : E4.a
+>E4 : typeof E4
+>a : E4.a
+
+const foo7 = { a: E5.a } as const
+>foo7 : { readonly a: string; }
+>{ a: E5.a } as const : { readonly a: string; }
+>{ a: E5.a } : { readonly a: string; }
+>a : string
+>E5.a : string
+>E5 : { a: string; b: string; }
+>a : string
+
+const foo8 = { a: E1.a as const }
+>foo8 : { a: E1.a; }
+>{ a: E1.a as const } : { a: E1.a; }
+>a : E1.a
+>E1.a as const : E1.a
+>E1.a : E1.a
+>E1 : typeof E1
+>a : E1.a
+
+const foo9 = { a: E2.a as const }
+>foo9 : { a: E2.a; }
+>{ a: E2.a as const } : { a: E2.a; }
+>a : E2.a
+>E2.a as const : E2.a
+>E2.a : E2.a
+>E2 : typeof E2
+>a : E2.a
+
+const foo10 = { a: E3.a as const }
+>foo10 : { a: E3; }
+>{ a: E3.a as const } : { a: E3; }
+>a : E3
+>E3.a as const : E3
+>E3.a : E3
+>E3 : typeof E3
+>a : E3
+
+const foo11 = { a: E4.a as const }
+>foo11 : { a: E4.a; }
+>{ a: E4.a as const } : { a: E4.a; }
+>a : E4.a
+>E4.a as const : E4.a
+>E4.a : E4.a
+>E4 : typeof E4
+>a : E4.a
+
+const foo12 = { a: E5.a as const }
+>foo12 : { a: string; }
+>{ a: E5.a as const } : { a: string; }
+>a : string
+>E5.a as const : string
+>E5.a : string
+>E5 : { a: string; b: string; }
+>a : string
+
diff --git a/tests/cases/compiler/constantEnumAssert.ts b/tests/cases/compiler/constantEnumAssert.ts
new file mode 100644
index 0000000000000..d57845a7edfdd
--- /dev/null
+++ b/tests/cases/compiler/constantEnumAssert.ts
@@ -0,0 +1,49 @@
+enum E1 {
+    a,
+    b
+}
+
+enum E2 {
+    a = 'a',
+    b = 'b'
+}
+
+enum E3 {
+    a = 1,
+    b = a << 1,
+    c = a << 2,
+}
+
+const enum E4 {
+    a,
+    b
+}
+
+const E5 = {
+    a: 'a',
+    b: 'b'
+}
+
+const foo1 = { a: E1.a }
+
+const foo2 = { a: E2.a }
+
+const foo3 = { a: E1.a } as const
+
+const foo4 = { a: E2.a } as const
+
+const foo5 = { a: E3.a } as const
+
+const foo6 = { a: E4.a } as const
+
+const foo7 = { a: E5.a } as const
+
+const foo8 = { a: E1.a as const }
+
+const foo9 = { a: E2.a as const }
+
+const foo10 = { a: E3.a as const }
+
+const foo11 = { a: E4.a as const }
+
+const foo12 = { a: E5.a as const }