diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 48bc0da113816..7bf615735312c 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -48564,6 +48564,15 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
     }
 
     function checkImportAttribute(node: ImportAttribute) {
+        // Validate that the value is a string literal before type checking
+        if (!isStringLiteral(node.value)) {
+            const parent = node.parent;
+            const diagnostic = parent.token === SyntaxKind.WithKeyword
+                ? Diagnostics.Import_attribute_values_must_be_string_literal_expressions
+                : Diagnostics.Import_assertion_values_must_be_string_literal_expressions;
+            error(node.value, diagnostic);
+            return errorType;
+        }
         return getRegularTypeOfLiteralType(checkExpressionCached(node.value));
     }
 
diff --git a/tests/baselines/reference/importAssertionNonstring.errors.txt b/tests/baselines/reference/importAssertionNonstring.errors.txt
index a220b1f213eaa..2112d47fd934a 100644
--- a/tests/baselines/reference/importAssertionNonstring.errors.txt
+++ b/tests/baselines/reference/importAssertionNonstring.errors.txt
@@ -1,37 +1,21 @@
 mod.mts(1,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-mod.mts(1,37): error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'number' is not assignable to type 'string'.
 mod.mts(1,52): error TS2837: Import assertion values must be string literal expressions.
 mod.mts(3,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
 mod.mts(3,52): error TS2837: Import assertion values must be string literal expressions.
 mod.mts(5,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-mod.mts(5,37): error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'RegExp' is not assignable to type 'string'.
 mod.mts(5,52): error TS2837: Import assertion values must be string literal expressions.
 mod.mts(7,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-mod.mts(7,37): error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'string[]' is not assignable to type 'string'.
 mod.mts(7,52): error TS2837: Import assertion values must be string literal expressions.
 mod.mts(9,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-mod.mts(9,37): error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type '{ a: number; }' is not assignable to type 'string'.
 mod.mts(9,52): error TS2837: Import assertion values must be string literal expressions.
 mod.mts(11,37): error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
 mod.mts(11,66): error TS2837: Import assertion values must be string literal expressions.
 
 
-==== mod.mts (16 errors) ====
+==== mod.mts (12 errors) ====
     import * as thing1 from "./mod.mjs" assert {field: 0};
                                         ~~~~~~
 !!! error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-                                        ~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'number' is not assignable to type 'string'.
                                                        ~
 !!! error TS2837: Import assertion values must be string literal expressions.
     
@@ -44,30 +28,18 @@ mod.mts(11,66): error TS2837: Import assertion values must be string literal exp
     import * as thing3 from "./mod.mjs" assert {field: /a/g};
                                         ~~~~~~
 !!! error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-                                        ~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'RegExp' is not assignable to type 'string'.
                                                        ~~~~
 !!! error TS2837: Import assertion values must be string literal expressions.
     
     import * as thing4 from "./mod.mjs" assert {field: ["a"]};
                                         ~~~~~~
 !!! error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-                                        ~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'string[]' is not assignable to type 'string'.
                                                        ~~~~~
 !!! error TS2837: Import assertion values must be string literal expressions.
     
     import * as thing5 from "./mod.mjs" assert {field: { a: 0 }};
                                         ~~~~~~
 !!! error TS2880: Import assertions have been replaced by import attributes. Use 'with' instead of 'assert'.
-                                        ~~~~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type '{ a: number; }' is not assignable to type 'string'.
                                                        ~~~~~~~~
 !!! error TS2837: Import assertion values must be string literal expressions.
     
diff --git a/tests/baselines/reference/importAttributes6(module=node18).errors.txt b/tests/baselines/reference/importAttributes6(module=node18).errors.txt
index f2f160a4bd0e1..18fa0ba6b693d 100644
--- a/tests/baselines/reference/importAttributes6(module=node18).errors.txt
+++ b/tests/baselines/reference/importAttributes6(module=node18).errors.txt
@@ -1,53 +1,25 @@
-mod.mts(1,37): error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'number' is not assignable to type 'string'.
 mod.mts(1,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(2,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(3,37): error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'RegExp' is not assignable to type 'string'.
 mod.mts(3,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(4,37): error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'string[]' is not assignable to type 'string'.
 mod.mts(4,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(5,37): error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type '{ a: number; }' is not assignable to type 'string'.
 mod.mts(5,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(6,65): error TS2858: Import attribute values must be string literal expressions.
 
 
-==== mod.mts (10 errors) ====
+==== mod.mts (6 errors) ====
     import * as thing1 from "./mod.mjs" with { field: 0 };
-                                        ~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'number' is not assignable to type 'string'.
                                                       ~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing2 from "./mod.mjs" with { field: `a` };
                                                       ~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing3 from "./mod.mjs" with { field: /a/g };
-                                        ~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'RegExp' is not assignable to type 'string'.
                                                       ~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing4 from "./mod.mjs" with { field: ["a"] };
-                                        ~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'string[]' is not assignable to type 'string'.
                                                       ~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing5 from "./mod.mjs" with { field: { a: 0 } };
-                                        ~~~~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type '{ a: number; }' is not assignable to type 'string'.
                                                       ~~~~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing6 from "./mod.mjs" with { type: "json", field: 0..toString() };
diff --git a/tests/baselines/reference/importAttributes6(module=node20).errors.txt b/tests/baselines/reference/importAttributes6(module=node20).errors.txt
index f2f160a4bd0e1..18fa0ba6b693d 100644
--- a/tests/baselines/reference/importAttributes6(module=node20).errors.txt
+++ b/tests/baselines/reference/importAttributes6(module=node20).errors.txt
@@ -1,53 +1,25 @@
-mod.mts(1,37): error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'number' is not assignable to type 'string'.
 mod.mts(1,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(2,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(3,37): error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'RegExp' is not assignable to type 'string'.
 mod.mts(3,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(4,37): error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'string[]' is not assignable to type 'string'.
 mod.mts(4,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(5,37): error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type '{ a: number; }' is not assignable to type 'string'.
 mod.mts(5,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(6,65): error TS2858: Import attribute values must be string literal expressions.
 
 
-==== mod.mts (10 errors) ====
+==== mod.mts (6 errors) ====
     import * as thing1 from "./mod.mjs" with { field: 0 };
-                                        ~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'number' is not assignable to type 'string'.
                                                       ~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing2 from "./mod.mjs" with { field: `a` };
                                                       ~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing3 from "./mod.mjs" with { field: /a/g };
-                                        ~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'RegExp' is not assignable to type 'string'.
                                                       ~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing4 from "./mod.mjs" with { field: ["a"] };
-                                        ~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'string[]' is not assignable to type 'string'.
                                                       ~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing5 from "./mod.mjs" with { field: { a: 0 } };
-                                        ~~~~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type '{ a: number; }' is not assignable to type 'string'.
                                                       ~~~~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing6 from "./mod.mjs" with { type: "json", field: 0..toString() };
diff --git a/tests/baselines/reference/importAttributes6(module=nodenext).errors.txt b/tests/baselines/reference/importAttributes6(module=nodenext).errors.txt
index f2f160a4bd0e1..18fa0ba6b693d 100644
--- a/tests/baselines/reference/importAttributes6(module=nodenext).errors.txt
+++ b/tests/baselines/reference/importAttributes6(module=nodenext).errors.txt
@@ -1,53 +1,25 @@
-mod.mts(1,37): error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'number' is not assignable to type 'string'.
 mod.mts(1,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(2,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(3,37): error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'RegExp' is not assignable to type 'string'.
 mod.mts(3,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(4,37): error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type 'string[]' is not assignable to type 'string'.
 mod.mts(4,51): error TS2858: Import attribute values must be string literal expressions.
-mod.mts(5,37): error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-  Property 'field' is incompatible with index signature.
-    Type '{ a: number; }' is not assignable to type 'string'.
 mod.mts(5,51): error TS2858: Import attribute values must be string literal expressions.
 mod.mts(6,65): error TS2858: Import attribute values must be string literal expressions.
 
 
-==== mod.mts (10 errors) ====
+==== mod.mts (6 errors) ====
     import * as thing1 from "./mod.mjs" with { field: 0 };
-                                        ~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: 0; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'number' is not assignable to type 'string'.
                                                       ~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing2 from "./mod.mjs" with { field: `a` };
                                                       ~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing3 from "./mod.mjs" with { field: /a/g };
-                                        ~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: RegExp; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'RegExp' is not assignable to type 'string'.
                                                       ~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing4 from "./mod.mjs" with { field: ["a"] };
-                                        ~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: string[]; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type 'string[]' is not assignable to type 'string'.
                                                       ~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing5 from "./mod.mjs" with { field: { a: 0 } };
-                                        ~~~~~~~~~~~~~~~~~~~~~~~~
-!!! error TS2322: Type '{ field: { a: number; }; }' is not assignable to type 'ImportAttributes'.
-!!! error TS2322:   Property 'field' is incompatible with index signature.
-!!! error TS2322:     Type '{ a: number; }' is not assignable to type 'string'.
                                                       ~~~~~~~~
 !!! error TS2858: Import attribute values must be string literal expressions.
     import * as thing6 from "./mod.mjs" with { type: "json", field: 0..toString() };
diff --git a/tests/baselines/reference/importTypeAttributesNonString.js b/tests/baselines/reference/importTypeAttributesNonString.js
new file mode 100644
index 0000000000000..590497bcee25e
--- /dev/null
+++ b/tests/baselines/reference/importTypeAttributesNonString.js
@@ -0,0 +1,65 @@
+//// [tests/cases/compiler/importTypeAttributesNonString.ts] ////
+
+//// [wat.mts]
+export const x = 1;
+
+//// [mod.mts]
+// Import type with function expression (should error)
+type T1 = typeof import("./wat.mjs", {
+  assert: {
+    a: (() => {
+      console.log("why can you write js here????");
+    })(),
+  }
+});
+
+// Import type with number literal (should error)
+type T2 = typeof import("./wat.mjs", {
+  assert: { field: 0 }
+});
+
+// Import type with template literal (should error)
+type T3 = typeof import("./wat.mjs", {
+  assert: { field: `a` }
+});
+
+// Import type with regex (should error)
+type T4 = typeof import("./wat.mjs", {
+  assert: { field: /a/g }
+});
+
+// Import type with array (should error)
+type T5 = typeof import("./wat.mjs", {
+  assert: { field: ["a"] }
+});
+
+// Import type with object (should error)
+type T6 = typeof import("./wat.mjs", {
+  assert: { field: { a: 0 } }
+});
+
+// Import type with method call (should error)
+type T7 = typeof import("./wat.mjs", {
+  assert: { field: 0..toString() }
+});
+
+// Import type with valid string literal (should work)
+type T8 = typeof import("./wat.mjs", {
+  assert: { type: "json" }
+});
+
+// Import type with 'with' keyword and valid string (should work)
+type T9 = typeof import("./wat.mjs", {
+  with: { type: "json" }
+});
+
+// Import type with 'with' keyword and invalid expression (should error)
+type T10 = typeof import("./wat.mjs", {
+  with: { field: 123 }
+});
+
+
+//// [wat.mjs]
+export const x = 1;
+//// [mod.mjs]
+export {};
diff --git a/tests/baselines/reference/importTypeAttributesNonString.symbols b/tests/baselines/reference/importTypeAttributesNonString.symbols
new file mode 100644
index 0000000000000..409b19a529c2d
--- /dev/null
+++ b/tests/baselines/reference/importTypeAttributesNonString.symbols
@@ -0,0 +1,90 @@
+//// [tests/cases/compiler/importTypeAttributesNonString.ts] ////
+
+=== wat.mts ===
+export const x = 1;
+>x : Symbol(x, Decl(wat.mts, 0, 12))
+
+=== mod.mts ===
+// Import type with function expression (should error)
+type T1 = typeof import("./wat.mjs", {
+>T1 : Symbol(T1, Decl(mod.mts, 0, 0))
+
+  assert: {
+    a: (() => {
+      console.log("why can you write js here????");
+>console.log : Symbol(Console.log, Decl(lib.dom.d.ts, --, --))
+>console : Symbol(console, Decl(lib.dom.d.ts, --, --))
+>log : Symbol(Console.log, Decl(lib.dom.d.ts, --, --))
+
+    })(),
+  }
+});
+
+// Import type with number literal (should error)
+type T2 = typeof import("./wat.mjs", {
+>T2 : Symbol(T2, Decl(mod.mts, 7, 3))
+
+  assert: { field: 0 }
+});
+
+// Import type with template literal (should error)
+type T3 = typeof import("./wat.mjs", {
+>T3 : Symbol(T3, Decl(mod.mts, 12, 3))
+
+  assert: { field: `a` }
+});
+
+// Import type with regex (should error)
+type T4 = typeof import("./wat.mjs", {
+>T4 : Symbol(T4, Decl(mod.mts, 17, 3))
+
+  assert: { field: /a/g }
+});
+
+// Import type with array (should error)
+type T5 = typeof import("./wat.mjs", {
+>T5 : Symbol(T5, Decl(mod.mts, 22, 3))
+
+  assert: { field: ["a"] }
+});
+
+// Import type with object (should error)
+type T6 = typeof import("./wat.mjs", {
+>T6 : Symbol(T6, Decl(mod.mts, 27, 3))
+
+  assert: { field: { a: 0 } }
+>a : Symbol(a, Decl(mod.mts, 31, 20))
+
+});
+
+// Import type with method call (should error)
+type T7 = typeof import("./wat.mjs", {
+>T7 : Symbol(T7, Decl(mod.mts, 32, 3))
+
+  assert: { field: 0..toString() }
+>0..toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+>toString : Symbol(Number.toString, Decl(lib.es5.d.ts, --, --))
+
+});
+
+// Import type with valid string literal (should work)
+type T8 = typeof import("./wat.mjs", {
+>T8 : Symbol(T8, Decl(mod.mts, 37, 3))
+
+  assert: { type: "json" }
+});
+
+// Import type with 'with' keyword and valid string (should work)
+type T9 = typeof import("./wat.mjs", {
+>T9 : Symbol(T9, Decl(mod.mts, 42, 3))
+
+  with: { type: "json" }
+});
+
+// Import type with 'with' keyword and invalid expression (should error)
+type T10 = typeof import("./wat.mjs", {
+>T10 : Symbol(T10, Decl(mod.mts, 47, 3))
+
+  with: { field: 123 }
+});
+
diff --git a/tests/baselines/reference/importTypeAttributesNonString.types b/tests/baselines/reference/importTypeAttributesNonString.types
new file mode 100644
index 0000000000000..28ab29153f16f
--- /dev/null
+++ b/tests/baselines/reference/importTypeAttributesNonString.types
@@ -0,0 +1,151 @@
+//// [tests/cases/compiler/importTypeAttributesNonString.ts] ////
+
+=== wat.mts ===
+export const x = 1;
+>x : 1
+>  : ^
+>1 : 1
+>  : ^
+
+=== mod.mts ===
+// Import type with function expression (should error)
+type T1 = typeof import("./wat.mjs", {
+>T1 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: {
+    a: (() => {
+>a : error
+>(() => {      console.log("why can you write js here????");    })() : void
+>                                                                    : ^^^^
+>(() => {      console.log("why can you write js here????");    }) : () => void
+>                                                                  : ^^^^^^^^^^
+>() => {      console.log("why can you write js here????");    } : () => void
+>                                                                : ^^^^^^^^^^
+
+      console.log("why can you write js here????");
+>console.log("why can you write js here????") : void
+>                                             : ^^^^
+>console.log : (...data: any[]) => void
+>            : ^^^^    ^^     ^^^^^    
+>console : Console
+>        : ^^^^^^^
+>log : (...data: any[]) => void
+>    : ^^^^    ^^     ^^^^^    
+>"why can you write js here????" : "why can you write js here????"
+>                                : ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+    })(),
+  }
+});
+
+// Import type with number literal (should error)
+type T2 = typeof import("./wat.mjs", {
+>T2 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: 0 }
+>field : error
+
+});
+
+// Import type with template literal (should error)
+type T3 = typeof import("./wat.mjs", {
+>T3 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: `a` }
+>field : error
+
+});
+
+// Import type with regex (should error)
+type T4 = typeof import("./wat.mjs", {
+>T4 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: /a/g }
+>field : error
+>/a/g : RegExp
+>     : ^^^^^^
+
+});
+
+// Import type with array (should error)
+type T5 = typeof import("./wat.mjs", {
+>T5 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: ["a"] }
+>field : error
+>["a"] : string[]
+>      : ^^^^^^^^
+>"a" : "a"
+>    : ^^^
+
+});
+
+// Import type with object (should error)
+type T6 = typeof import("./wat.mjs", {
+>T6 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: { a: 0 } }
+>field : error
+>{ a: 0 } : { a: number; }
+>         : ^^^^^^^^^^^^^^
+>a : number
+>  : ^^^^^^
+>0 : 0
+>  : ^
+
+});
+
+// Import type with method call (should error)
+type T7 = typeof import("./wat.mjs", {
+>T7 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { field: 0..toString() }
+>field : error
+>0..toString() : string
+>              : ^^^^^^
+>0..toString : (radix?: number) => string
+>            : ^     ^^^      ^^^^^      
+>0. : 0
+>   : ^
+>toString : (radix?: number) => string
+>         : ^     ^^^      ^^^^^      
+
+});
+
+// Import type with valid string literal (should work)
+type T8 = typeof import("./wat.mjs", {
+>T8 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  assert: { type: "json" }
+>type : error
+
+});
+
+// Import type with 'with' keyword and valid string (should work)
+type T9 = typeof import("./wat.mjs", {
+>T9 : typeof import("wat")
+>   : ^^^^^^^^^^^^^^^^^^^^
+
+  with: { type: "json" }
+>type : error
+
+});
+
+// Import type with 'with' keyword and invalid expression (should error)
+type T10 = typeof import("./wat.mjs", {
+>T10 : typeof import("wat")
+>    : ^^^^^^^^^^^^^^^^^^^^
+
+  with: { field: 123 }
+>field : error
+
+});
+
diff --git a/tests/cases/compiler/importTypeAttributesNonString.ts b/tests/cases/compiler/importTypeAttributesNonString.ts
new file mode 100644
index 0000000000000..bc117956e78af
--- /dev/null
+++ b/tests/cases/compiler/importTypeAttributesNonString.ts
@@ -0,0 +1,59 @@
+// @module: nodenext
+// @filename: wat.mts
+export const x = 1;
+
+// @filename: mod.mts
+
+// Import type with function expression (should error)
+type T1 = typeof import("./wat.mjs", {
+  assert: {
+    a: (() => {
+      console.log("why can you write js here????");
+    })(),
+  }
+});
+
+// Import type with number literal (should error)
+type T2 = typeof import("./wat.mjs", {
+  assert: { field: 0 }
+});
+
+// Import type with template literal (should error)
+type T3 = typeof import("./wat.mjs", {
+  assert: { field: `a` }
+});
+
+// Import type with regex (should error)
+type T4 = typeof import("./wat.mjs", {
+  assert: { field: /a/g }
+});
+
+// Import type with array (should error)
+type T5 = typeof import("./wat.mjs", {
+  assert: { field: ["a"] }
+});
+
+// Import type with object (should error)
+type T6 = typeof import("./wat.mjs", {
+  assert: { field: { a: 0 } }
+});
+
+// Import type with method call (should error)
+type T7 = typeof import("./wat.mjs", {
+  assert: { field: 0..toString() }
+});
+
+// Import type with valid string literal (should work)
+type T8 = typeof import("./wat.mjs", {
+  assert: { type: "json" }
+});
+
+// Import type with 'with' keyword and valid string (should work)
+type T9 = typeof import("./wat.mjs", {
+  with: { type: "json" }
+});
+
+// Import type with 'with' keyword and invalid expression (should error)
+type T10 = typeof import("./wat.mjs", {
+  with: { field: 123 }
+});
diff --git a/tests/cases/fourslash/organizeImportsAttributes4.ts b/tests/cases/fourslash/organizeImportsAttributes4.ts
index bded70d338c6b..a04661551ec3c 100644
--- a/tests/cases/fourslash/organizeImportsAttributes4.ts
+++ b/tests/cases/fourslash/organizeImportsAttributes4.ts
@@ -6,16 +6,14 @@
 ////import { E } from "./a" assert { foo: 'bar', bar: "foo" };
 ////import { C } from "./a" assert { foo: "bar", bar: "foo" };
 ////import { F } from "./a" assert { foo: "42" };
-////import { Y } from "./a" assert { foo: 42 };
 ////import { Z } from "./a" assert { foo: "42" };
 ////
-////export type G = A | B | C | D | E | F | Y | Z;
+////export type G = A | B | C | D | E | F | Z;
 
 
 verify.organizeImports(
 `import { A, B } from "./a" assert { foo: "foo", bar: "bar" };
 import { C, D, E } from "./a" assert { bar: "foo", foo: "bar" };
 import { F, Z } from "./a" assert { foo: "42" };
-import { Y } from "./a" assert { foo: 42 };
 
-export type G = A | B | C | D | E | F | Y | Z;`);
\ No newline at end of file
+export type G = A | B | C | D | E | F | Z;`);
\ No newline at end of file