diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 75be36474222f..d9efc284f1b88 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -40789,6 +40789,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 if (checkForDisallowedESSymbolOperand(operator)) {
                     leftType = getBaseTypeOfLiteralTypeForComparison(checkNonNullType(leftType, left));
                     rightType = getBaseTypeOfLiteralTypeForComparison(checkNonNullType(rightType, right));
+                    if (leftType.flags === TypeFlags.String && rightType.flags === TypeFlags.String) {
+                        error(errorNode, Diagnostics.Cannot_compare_strings);
+                    }
                     reportOperatorErrorUnless((left, right) => {
                         if (isTypeAny(left) || isTypeAny(right)) {
                             return true;
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index 0e60926c93d50..4e2ef2c651fd9 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -8519,5 +8519,9 @@
     "'{0}' is not a valid meta-property for keyword 'import'. Did you mean 'meta' or 'defer'?": {
         "category": "Error",
         "code": 18061
+    },
+    "Cannot compare strings": {
+        "category": "Error",
+        "code": 18062
     }
 }
diff --git a/tests/baselines/reference/stringComp.js b/tests/baselines/reference/stringComp.js
new file mode 100644
index 0000000000000..f636152889758
--- /dev/null
+++ b/tests/baselines/reference/stringComp.js
@@ -0,0 +1,6 @@
+//// [tests/cases/compiler/stringComp.ts] ////
+
+//// [stringComp.ts]
+
+
+//// [stringComp.js]
diff --git a/tests/baselines/reference/stringComp.symbols b/tests/baselines/reference/stringComp.symbols
new file mode 100644
index 0000000000000..5b2186d07237d
--- /dev/null
+++ b/tests/baselines/reference/stringComp.symbols
@@ -0,0 +1,4 @@
+//// [tests/cases/compiler/stringComp.ts] ////
+
+=== stringComp.ts ===
+
diff --git a/tests/baselines/reference/stringComp.types b/tests/baselines/reference/stringComp.types
new file mode 100644
index 0000000000000..5b2186d07237d
--- /dev/null
+++ b/tests/baselines/reference/stringComp.types
@@ -0,0 +1,4 @@
+//// [tests/cases/compiler/stringComp.ts] ////
+
+=== stringComp.ts ===
+
diff --git a/tests/cases/compiler/stringComp.ts b/tests/cases/compiler/stringComp.ts
new file mode 100644
index 0000000000000..b0de87196ff6a
--- /dev/null
+++ b/tests/cases/compiler/stringComp.ts
@@ -0,0 +1,3 @@
+if ("bar" <= "foo") {
+  console.log("Really?")
+}
\ No newline at end of file