diff --git a/tsc/internal/checker/checker.go b/tsc/internal/checker/checker.go
index 4464564837b8a..3a0e0b2558acd 100644
--- a/tsc/internal/checker/checker.go
+++ b/tsc/internal/checker/checker.go
@@ -3368,7 +3368,9 @@ func (c *Checker) checkTemplateLiteralType(node *ast.Node) {
 func (c *Checker) checkImportType(node *ast.Node) {
 	c.checkSourceElement(node.AsImportTypeNode().Argument)
 	if attributes := node.AsImportTypeNode().Attributes; attributes != nil {
-		c.getResolutionModeOverride(attributes.AsImportAttributes(), true /*reportErrors*/)
+		importAttributes := attributes.AsImportAttributes()
+		c.checkGrammarImportAttributeValues(importAttributes)
+		c.getResolutionModeOverride(importAttributes, true /*reportErrors*/)
 	}
 	c.checkTypeReferenceOrImport(node)
 	c.checkImportAttributes(node)
@@ -5492,14 +5494,9 @@ func (c *Checker) checkExternalImportOrExportDeclaration(node *ast.Node) bool {
 	if !ast.IsImportEqualsDeclaration(node) {
 		attributes := ast.GetImportAttributes(node)
 		if attributes != nil {
-			hasError := false
-			for _, attr := range attributes.AsImportAttributes().Attributes.Nodes {
-				if !ast.IsStringLiteral(attr.AsImportAttribute().Value) {
-					hasError = true
-					c.error(attr.AsImportAttribute().Value, diagnostics.Import_attribute_values_must_be_string_literal_expressions)
-				}
+			if c.checkGrammarImportAttributeValues(attributes.AsImportAttributes()) {
+				return false
 			}
-			return !hasError
 		}
 	}
 	return true
diff --git a/tsc/internal/checker/grammarchecks.go b/tsc/internal/checker/grammarchecks.go
index a942d0381aac2..cc274d8b2fd4d 100644
--- a/tsc/internal/checker/grammarchecks.go
+++ b/tsc/internal/checker/grammarchecks.go
@@ -2120,6 +2120,19 @@ func (c *Checker) checkGrammarImportClause(node *ast.ImportClause) bool {
 	return false
 }
 
+func (c *Checker) checkGrammarImportAttributeValues(node *ast.ImportAttributes) bool {
+	hasError := false
+	for _, attribute := range node.Attributes.Nodes {
+		value := attribute.AsImportAttribute().Value
+		if ast.IsStringLiteral(value) {
+			continue
+		}
+		hasError = true
+		c.error(value, diagnostics.Import_attribute_values_must_be_string_literal_expressions)
+	}
+	return hasError
+}
+
 func (c *Checker) checkGrammarTypeOnlyNamedImportsOrExports(namedBindings *ast.Node) bool {
 	nodeList := namedBindings.ElementList()
 	for _, specifier := range nodeList.Nodes {
diff --git a/tsc/testdata/baselines/reference/conformance/importAttributes12.errors.txt b/tsc/testdata/baselines/reference/conformance/importAttributes12.errors.txt
new file mode 100644
index 0000000000000..0e1c8f0e4524a
--- /dev/null
+++ b/tsc/testdata/baselines/reference/conformance/importAttributes12.errors.txt
@@ -0,0 +1,55 @@
+importAttributes12.ts(10,12): error TS2858: Import attribute values must be string literal expressions.
+importAttributes12.ts(16,28): error TS2858: Import attribute values must be string literal expressions.
+importAttributes12.ts(21,11): error TS2322: Type '{ "resolution-mode": 0; }' is not assignable to type 'ImportAttributes'.
+  Property 'resolution-mode' is incompatible with index signature.
+    Type 'number' is not assignable to type 'string'.
+importAttributes12.ts(22,28): error TS2858: Import attribute values must be string literal expressions.
+importAttributes12.ts(28,28): error TS2858: Import attribute values must be string literal expressions.
+
+
+==== importAttributes12.ts (5 errors) ====
+    declare module "dependency" {
+        export interface Type {}
+    }
+    
+    type T1 = typeof import("dependency", { with: { "resolution-mode": "import" } });
+    type T2 = import("dependency", { with: { "resolution-mode": "require" } }).Type;
+    
+    type T3 = typeof import("dependency", {
+        with: {
+            a: (() => "value")(),
+               ~~~~~~~~~~~~~~~~~
+!!! error TS2858: Import attribute values must be string literal expressions.
+        },
+    });
+    
+    type T4 = import("dependency", {
+        with: {
+            "resolution-mode": (() => "import")(),
+                               ~~~~~~~~~~~~~~~~~~
+!!! error TS2858: Import attribute values must be string literal expressions.
+        },
+    }).Type;
+    
+    type T5 = import("dependency", {
+        with: {
+              ~
+            "resolution-mode": 0,
+    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+                               ~
+!!! error TS2858: Import attribute values must be string literal expressions.
+        },
+    ~~~~~
+!!! error TS2322: Type '{ "resolution-mode": 0; }' is not assignable to type 'ImportAttributes'.
+!!! error TS2322:   Property 'resolution-mode' is incompatible with index signature.
+!!! error TS2322:     Type 'number' is not assignable to type 'string'.
+    }).Type;
+    
+    type T6 = import("dependency", {
+        with: {
+            "resolution-mode": `import`,
+                               ~~~~~~~~
+!!! error TS2858: Import attribute values must be string literal expressions.
+        },
+    }).Type;
+    
\ No newline at end of file
diff --git a/tsc/testdata/tests/cases/conformance/importAttributes/importAttributes12.ts b/tsc/testdata/tests/cases/conformance/importAttributes/importAttributes12.ts
new file mode 100644
index 0000000000000..b4d8e6a29f34f
--- /dev/null
+++ b/tsc/testdata/tests/cases/conformance/importAttributes/importAttributes12.ts
@@ -0,0 +1,35 @@
+// @target: esnext
+// @module: esnext
+// @noEmit: true
+// @noTypesAndSymbols: true
+
+declare module "dependency" {
+    export interface Type {}
+}
+
+type T1 = typeof import("dependency", { with: { "resolution-mode": "import" } });
+type T2 = import("dependency", { with: { "resolution-mode": "require" } }).Type;
+
+type T3 = typeof import("dependency", {
+    with: {
+        a: (() => "value")(),
+    },
+});
+
+type T4 = import("dependency", {
+    with: {
+        "resolution-mode": (() => "import")(),
+    },
+}).Type;
+
+type T5 = import("dependency", {
+    with: {
+        "resolution-mode": 0,
+    },
+}).Type;
+
+type T6 = import("dependency", {
+    with: {
+        "resolution-mode": `import`,
+    },
+}).Type;