diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 49c45384e6df5..8ac9aecfd13af 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -16750,7 +16750,7 @@ namespace ts {
                 // numeric enum literal type. This rule exists for backwards compatibility reasons because
                 // bit-flag enum types sometimes look like literal enum types with numeric literal values.
                 if (s & (TypeFlags.Number | TypeFlags.NumberLiteral) && !(s & TypeFlags.EnumLiteral) && (
-                    t & TypeFlags.Enum || t & TypeFlags.NumberLiteral && t & TypeFlags.EnumLiteral)) return true;
+                    t & TypeFlags.Enum || relation === assignableRelation && t & TypeFlags.NumberLiteral && t & TypeFlags.EnumLiteral)) return true;
             }
             return false;
         }
diff --git a/tests/baselines/reference/equalityWithEnumTypes.errors.txt b/tests/baselines/reference/equalityWithEnumTypes.errors.txt
new file mode 100644
index 0000000000000..ebe0b71982717
--- /dev/null
+++ b/tests/baselines/reference/equalityWithEnumTypes.errors.txt
@@ -0,0 +1,51 @@
+tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts(14,9): error TS2367: This condition will always return 'true' since the types 'E1' and '0' have no overlap.
+tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts(23,9): error TS2367: This condition will always return 'true' since the types 'E1' and '3' have no overlap.
+
+
+==== tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts (2 errors) ====
+    // Literal enum type
+    enum E1 {
+        a = 1,
+        b = 2,
+    }
+    
+    // Numeric enum type
+    enum E2 {
+        a = 1 << 0,
+        b = 1 << 1
+    }
+    
+    function f1(v: E1) {
+        if (v !== 0) {  // Error
+            ~~~~~~~
+!!! error TS2367: This condition will always return 'true' since the types 'E1' and '0' have no overlap.
+            v;
+        }
+        if (v !== 1) {
+            v;
+        }
+        if (v !== 2) {
+            v;
+        }
+        if (v !== 3) {  // Error
+            ~~~~~~~
+!!! error TS2367: This condition will always return 'true' since the types 'E1' and '3' have no overlap.
+            v;
+        }
+    }
+    
+    function f2(v: E2) {
+        if (v !== 0) {
+            v;
+        }
+        if (v !== 1) {
+            v;
+        }
+        if (v !== 2) {
+            v;
+        }
+        if (v !== 3) {
+            v;
+        }
+    }
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/equalityWithEnumTypes.js b/tests/baselines/reference/equalityWithEnumTypes.js
new file mode 100644
index 0000000000000..31e33c5bddad5
--- /dev/null
+++ b/tests/baselines/reference/equalityWithEnumTypes.js
@@ -0,0 +1,86 @@
+//// [equalityWithEnumTypes.ts]
+// Literal enum type
+enum E1 {
+    a = 1,
+    b = 2,
+}
+
+// Numeric enum type
+enum E2 {
+    a = 1 << 0,
+    b = 1 << 1
+}
+
+function f1(v: E1) {
+    if (v !== 0) {  // Error
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) {  // Error
+        v;
+    }
+}
+
+function f2(v: E2) {
+    if (v !== 0) {
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) {
+        v;
+    }
+}
+
+
+//// [equalityWithEnumTypes.js]
+"use strict";
+// Literal enum type
+var E1;
+(function (E1) {
+    E1[E1["a"] = 1] = "a";
+    E1[E1["b"] = 2] = "b";
+})(E1 || (E1 = {}));
+// Numeric enum type
+var E2;
+(function (E2) {
+    E2[E2["a"] = 1] = "a";
+    E2[E2["b"] = 2] = "b";
+})(E2 || (E2 = {}));
+function f1(v) {
+    if (v !== 0) { // Error
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) { // Error
+        v;
+    }
+}
+function f2(v) {
+    if (v !== 0) {
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) {
+        v;
+    }
+}
diff --git a/tests/baselines/reference/equalityWithEnumTypes.symbols b/tests/baselines/reference/equalityWithEnumTypes.symbols
new file mode 100644
index 0000000000000..e3fe037eb2bcd
--- /dev/null
+++ b/tests/baselines/reference/equalityWithEnumTypes.symbols
@@ -0,0 +1,85 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts ===
+// Literal enum type
+enum E1 {
+>E1 : Symbol(E1, Decl(equalityWithEnumTypes.ts, 0, 0))
+
+    a = 1,
+>a : Symbol(E1.a, Decl(equalityWithEnumTypes.ts, 1, 9))
+
+    b = 2,
+>b : Symbol(E1.b, Decl(equalityWithEnumTypes.ts, 2, 10))
+}
+
+// Numeric enum type
+enum E2 {
+>E2 : Symbol(E2, Decl(equalityWithEnumTypes.ts, 4, 1))
+
+    a = 1 << 0,
+>a : Symbol(E2.a, Decl(equalityWithEnumTypes.ts, 7, 9))
+
+    b = 1 << 1
+>b : Symbol(E2.b, Decl(equalityWithEnumTypes.ts, 8, 15))
+}
+
+function f1(v: E1) {
+>f1 : Symbol(f1, Decl(equalityWithEnumTypes.ts, 10, 1))
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+>E1 : Symbol(E1, Decl(equalityWithEnumTypes.ts, 0, 0))
+
+    if (v !== 0) {  // Error
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+    }
+    if (v !== 1) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+    }
+    if (v !== 2) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+    }
+    if (v !== 3) {  // Error
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 12, 12))
+    }
+}
+
+function f2(v: E2) {
+>f2 : Symbol(f2, Decl(equalityWithEnumTypes.ts, 25, 1))
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+>E2 : Symbol(E2, Decl(equalityWithEnumTypes.ts, 4, 1))
+
+    if (v !== 0) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+    }
+    if (v !== 1) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+    }
+    if (v !== 2) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+    }
+    if (v !== 3) {
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+
+        v;
+>v : Symbol(v, Decl(equalityWithEnumTypes.ts, 27, 12))
+    }
+}
+
diff --git a/tests/baselines/reference/equalityWithEnumTypes.types b/tests/baselines/reference/equalityWithEnumTypes.types
new file mode 100644
index 0000000000000..935989418df22
--- /dev/null
+++ b/tests/baselines/reference/equalityWithEnumTypes.types
@@ -0,0 +1,107 @@
+=== tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts ===
+// Literal enum type
+enum E1 {
+>E1 : E1
+
+    a = 1,
+>a : E1.a
+>1 : 1
+
+    b = 2,
+>b : E1.b
+>2 : 2
+}
+
+// Numeric enum type
+enum E2 {
+>E2 : E2
+
+    a = 1 << 0,
+>a : E2
+>1 << 0 : number
+>1 : 1
+>0 : 0
+
+    b = 1 << 1
+>b : E2
+>1 << 1 : number
+>1 : 1
+>1 : 1
+}
+
+function f1(v: E1) {
+>f1 : (v: E1) => void
+>v : E1
+
+    if (v !== 0) {  // Error
+>v !== 0 : boolean
+>v : E1
+>0 : 0
+
+        v;
+>v : E1
+    }
+    if (v !== 1) {
+>v !== 1 : boolean
+>v : E1
+>1 : 1
+
+        v;
+>v : E1.b
+    }
+    if (v !== 2) {
+>v !== 2 : boolean
+>v : E1
+>2 : 2
+
+        v;
+>v : E1.a
+    }
+    if (v !== 3) {  // Error
+>v !== 3 : boolean
+>v : E1
+>3 : 3
+
+        v;
+>v : E1
+    }
+}
+
+function f2(v: E2) {
+>f2 : (v: E2) => void
+>v : E2
+
+    if (v !== 0) {
+>v !== 0 : boolean
+>v : E2
+>0 : 0
+
+        v;
+>v : E2
+    }
+    if (v !== 1) {
+>v !== 1 : boolean
+>v : E2
+>1 : 1
+
+        v;
+>v : E2
+    }
+    if (v !== 2) {
+>v !== 2 : boolean
+>v : E2
+>2 : 2
+
+        v;
+>v : E2
+    }
+    if (v !== 3) {
+>v !== 3 : boolean
+>v : E2
+>3 : 3
+
+        v;
+>v : E2
+    }
+}
+
diff --git a/tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts b/tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts
new file mode 100644
index 0000000000000..31a902049e202
--- /dev/null
+++ b/tests/cases/conformance/types/typeRelationships/comparable/equalityWithEnumTypes.ts
@@ -0,0 +1,43 @@
+// @strict: true
+
+// Literal enum type
+enum E1 {
+    a = 1,
+    b = 2,
+}
+
+// Numeric enum type
+enum E2 {
+    a = 1 << 0,
+    b = 1 << 1
+}
+
+function f1(v: E1) {
+    if (v !== 0) {  // Error
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) {  // Error
+        v;
+    }
+}
+
+function f2(v: E2) {
+    if (v !== 0) {
+        v;
+    }
+    if (v !== 1) {
+        v;
+    }
+    if (v !== 2) {
+        v;
+    }
+    if (v !== 3) {
+        v;
+    }
+}