diff --git a/crates/native-sidecar/src/language_execution.rs b/crates/native-sidecar/src/language_execution.rs
index 46810a4362..5d0bb0d481 100644
--- a/crates/native-sidecar/src/language_execution.rs
+++ b/crates/native-sidecar/src/language_execution.rs
@@ -35,6 +35,7 @@ const TTY_ENV: &str = "AGENTOS_EXEC_TTY";
 const TTY_COLS_ENV: &str = "AGENTOS_EXEC_TTY_COLS";
 const TTY_ROWS_ENV: &str = "AGENTOS_EXEC_TTY_ROWS";
 const RETAIN_LANGUAGE_CONTEXT_ENV: &str = "AGENTOS_RETAIN_LANGUAGE_CONTEXT";
+const GUEST_ENTRYPOINT_MODULE_MODE_ENV: &str = "AGENTOS_GUEST_ENTRYPOINT_MODULE_MODE";
 const INLINE_FILE_PATH_ENV: &str = "AGENTOS_INLINE_FILE_PATH";
 const USE_BUNDLED_TYPESCRIPT_ENV: &str = "AGENTOS_USE_BUNDLED_TYPESCRIPT";
 const SEMANTIC_RESULT_PATH_PREFIX: &str = "/tmp/.agentos-semantic-result-";
@@ -336,14 +337,6 @@ fn transpile_typescript(
     transform_source(source, file_path, true, common_js)
 }
 
-fn transform_retained_javascript_module(
-    source: &str,
-    file_path: &str,
-) -> Result<String, SidecarError> {
-    let source = rewrite_static_imports(source, file_path, false)?;
-    transform_source(&source, file_path, false, true)
-}
-
 fn transform_retained_typescript_module(
     source: &str,
     file_path: &str,
@@ -528,16 +521,19 @@ fn lower_operation(payload: RequestPayload) -> Result<LoweredOperation, SidecarE
             let module = payload.format == Some(JavaScriptModuleFormat::Module);
             let mut source = inline_inputs_prefix(payload.inputs, false);
             source.push_str(&payload.source);
-            if module {
-                source = transform_retained_javascript_module(&source, &file_path)?;
-            }
             let retained_source = source.clone();
             let mut operation =
                 lowered_process(payload.process, "node", vec![String::from("-e"), source]);
             operation.retained_language = Some(RetainedExecutionLanguage::JavaScript);
             operation.retained_source = Some(retained_source);
             operation.retained_file_path = Some(file_path.clone());
-            operation.retained_module = false;
+            operation.retained_module = module;
+            if module {
+                operation.env.insert(
+                    String::from(GUEST_ENTRYPOINT_MODULE_MODE_ENV),
+                    String::from("1"),
+                );
+            }
             operation
                 .env
                 .insert(String::from(INLINE_FILE_PATH_ENV), file_path);
@@ -556,15 +552,18 @@ fn lower_operation(payload: RequestPayload) -> Result<LoweredOperation, SidecarE
                 serde_json::to_string(&result_path)
                     .expect("semantic result path serialization cannot fail")
             ));
-            if module {
-                source = transform_retained_javascript_module(&source, &file_path)?;
-            }
             let mut operation =
                 lowered_process(payload.process, "node", vec![String::from("-e"), source]);
             operation.retained_language = Some(RetainedExecutionLanguage::JavaScript);
             operation.retained_source = operation.args.get(1).cloned();
             operation.retained_file_path = Some(file_path.clone());
-            operation.retained_module = false;
+            operation.retained_module = module;
+            if module {
+                operation.env.insert(
+                    String::from(GUEST_ENTRYPOINT_MODULE_MODE_ENV),
+                    String::from("1"),
+                );
+            }
             operation
                 .env
                 .insert(String::from(INLINE_FILE_PATH_ENV), file_path);
diff --git a/crates/native-sidecar/tests/language_execution.rs b/crates/native-sidecar/tests/language_execution.rs
index ccdc2f57cc..7c1ad245e1 100644
--- a/crates/native-sidecar/tests/language_execution.rs
+++ b/crates/native-sidecar/tests/language_execution.rs
@@ -559,9 +559,9 @@ fn javascript_execution_reuses_retained_context() {
             wire::RequestPayload::JavaScriptExecutionRequest(wire::JavaScriptExecutionRequest {
                 process: context_process_options("test-execution"),
                 source: String::from(
-                    "import { sep } from 'node:path'; let retainedAnswer = sep === '/' ? 41 : 0;",
+                    "const { sep } = require('node:path'); let retainedAnswer = sep === '/' ? 41 : 0;",
                 ),
-                format: Some(wire::JavaScriptModuleFormat::Module),
+                format: Some(wire::JavaScriptModuleFormat::CommonJs),
                 file_path: None,
                 inputs: None,
             }),
@@ -637,7 +637,7 @@ fn javascript_execution_reuses_retained_context() {
             wire::RequestPayload::JavaScriptEvaluationRequest(wire::JavaScriptEvaluationRequest {
                 process: context_process_options(&execution_id),
                 expression: String::from("typedAnswer"),
-                format: Some(wire::JavaScriptModuleFormat::Module),
+                format: Some(wire::JavaScriptModuleFormat::CommonJs),
                 file_path: None,
                 inputs: None,
             }),
@@ -664,6 +664,62 @@ fn javascript_execution_reuses_retained_context() {
     dispose_vm_and_close_session_wire(&mut sidecar, &connection_id, &session_id, &vm_id);
 }
 
+#[test]
+fn javascript_module_execution_accepts_inline_exports_in_a_context() {
+    let mut sidecar = new_sidecar("language-execution-inline-esm");
+    let connection_id = authenticate_wire(&mut sidecar, "language-execution-inline-esm");
+    let session_id = open_session_wire(&mut sidecar, 2, &connection_id);
+    let cwd = temp_dir("language-execution-inline-esm-cwd");
+    let (vm_id, _) = create_vm_wire(
+        &mut sidecar,
+        3,
+        &connection_id,
+        &session_id,
+        wire::GuestRuntimeKind::JavaScript,
+        &cwd,
+    );
+    create_context(
+        &mut sidecar,
+        &connection_id,
+        &session_id,
+        &vm_id,
+        "module-context",
+    );
+
+    let started = sidecar
+        .dispatch_wire_blocking(wire_request(
+            4,
+            wire_vm(&connection_id, &session_id, &vm_id),
+            wire::RequestPayload::JavaScriptExecutionRequest(wire::JavaScriptExecutionRequest {
+                process: context_process_options("module-context"),
+                source: String::from("export const y = 1;"),
+                format: Some(wire::JavaScriptModuleFormat::Module),
+                file_path: None,
+                inputs: None,
+            }),
+        ))
+        .expect("start inline ES module");
+    let execution_id = accepted_execution_id(started);
+    let result = wait_for_execution(
+        &mut sidecar,
+        &connection_id,
+        &session_id,
+        &vm_id,
+        &execution_id,
+    );
+    assert_eq!(result.outcome, wire::ExecutionOutcome::Succeeded);
+    assert_eq!(result.exit_code, Some(0));
+
+    reset_execution(
+        &mut sidecar,
+        &connection_id,
+        &session_id,
+        &vm_id,
+        &execution_id,
+    );
+    dispose_vm_and_close_session_wire(&mut sidecar, &connection_id, &session_id, &vm_id);
+}
+
 #[test]
 fn typescript_check_reports_semantic_diagnostics() {
     let mut sidecar = new_sidecar("language-execution-typescript-check");