diff --git a/stdlib/tests/stdlib_tests.rs b/stdlib/tests/stdlib_tests.rs
index f7df969f..17e7e355 100644
--- a/stdlib/tests/stdlib_tests.rs
+++ b/stdlib/tests/stdlib_tests.rs
@@ -407,6 +407,82 @@ fn test_regex_operations() {
     assert_eq!(res.as_string(), Some("hello TechScript"));
 }
 
+#[test]
+fn test_web_module() {
+    use std::net::TcpListener;
+    use std::panic;
+
+    let registry = StdlibRegistry::new();
+    let web = registry.get_module("std.web").unwrap();
+
+    let mut caps = HashSet::new();
+    caps.insert(Capability::Network);
+    let mut ctx = RuntimeContext::new(RuntimeConfig {
+        strict_mode: false,
+        max_recursion_depth: 1000,
+        enable_assertions: true,
+        capabilities: caps,
+    });
+
+    let start = web.exports.get("start").unwrap();
+    let serve = web.exports.get("serve").unwrap();
+    let stop = web.exports.get("stop").unwrap();
+
+    // Bind a listener to a random port to ensure the port is taken
+    // Keep it alive to conflict
+    let listener = TcpListener::bind("0.0.0.0:0").unwrap();
+    let port = listener.local_addr().unwrap().port();
+
+    // Test panic on `start` when port is in use
+    let start_result = panic::catch_unwind(panic::AssertUnwindSafe(|| {
+        let mut caps = HashSet::new();
+        caps.insert(Capability::Network);
+        let mut ctx2 = RuntimeContext::new(RuntimeConfig {
+            strict_mode: false,
+            max_recursion_depth: 1000,
+            enable_assertions: true,
+            capabilities: caps,
+        });
+        let _ = start.call(
+            &mut ctx2,
+            vec![
+                RuntimeValue::Int(port as i64),
+                RuntimeValue::Str("<h1>Test</h1>".to_string()),
+            ],
+        );
+    }));
+
+    assert!(
+        start_result.is_err(),
+        "Expected `start` to panic due to port already in use"
+    );
+
+    // Make sure we stop the server and cleanup the global bool in case of weirdness,
+    // although the panic meant it wasn't started fully, but `SERVER_RUNNING` is true.
+    let _ = stop.call(&mut ctx, vec![]).unwrap();
+
+    // Test panic on `serve` when port is in use
+    let serve_result = panic::catch_unwind(panic::AssertUnwindSafe(|| {
+        let mut caps = HashSet::new();
+        caps.insert(Capability::Network);
+        let mut ctx3 = RuntimeContext::new(RuntimeConfig {
+            strict_mode: false,
+            max_recursion_depth: 1000,
+            enable_assertions: true,
+            capabilities: caps,
+        });
+        let _ = serve.call(&mut ctx3, vec![RuntimeValue::Int(port as i64)]);
+    }));
+
+    assert!(
+        serve_result.is_err(),
+        "Expected `serve` to panic due to port already in use"
+    );
+
+    // Reset `SERVER_RUNNING` so other tests aren't affected
+    let _ = stop.call(&mut ctx, vec![]).unwrap();
+}
+
 #[test]
 fn test_http_module() {
     use std::io::{Read, Write};