diff --git a/tests/gateway.rs b/tests/gateway.rs
index 7c15bf6..86cf947 100644
--- a/tests/gateway.rs
+++ b/tests/gateway.rs
@@ -1,7 +1,9 @@
 mod common;
 
+use std::sync::{Arc, RwLock};
+
 use chorus::gateway::*;
-use chorus::types::{self, ChannelModifySchema};
+use chorus::types::{self, ChannelModifySchema, RoleCreateModifySchema, RoleObject};
 
 #[tokio::test]
 /// Tests establishing a connection (hello and heartbeats) on the local gateway;
@@ -62,6 +64,48 @@ async fn test_self_updating_structs() {
 #[tokio::test]
 async fn test_recursive_self_updating_structs() {
     // Setup
-    let bundle = common::setup().await;
+    let mut bundle = common::setup().await;
+    let guild = bundle.guild.clone();
+    // Observe Guild, make sure it has no channels
+    let guild = bundle.user.gateway.observe(guild.clone()).await;
+    let inner_guild = guild.read().unwrap().clone();
+    assert!(inner_guild.roles.is_none());
+    // Create Role
+    let permissions = types::PermissionFlags::CONNECT | types::PermissionFlags::MANAGE_EVENTS;
+    let permissions = Some(permissions.to_string());
+    let mut role_create_schema: types::RoleCreateModifySchema = RoleCreateModifySchema {
+        name: Some("cool person".to_string()),
+        permissions,
+        hoist: Some(true),
+        icon: None,
+        unicode_emoji: Some("".to_string()),
+        mentionable: Some(true),
+        position: None,
+        color: None,
+    };
+    let guild_id = inner_guild.id;
+    let role = RoleObject::create(&mut bundle.user, guild_id, role_create_schema.clone())
+        .await
+        .unwrap();
+    // Watch role;
+    bundle
+        .user
+        .gateway
+        .observe(Arc::new(RwLock::new(role.clone())))
+        .await;
+    // Update Guild and check for Guild
+    let guild = bundle.user.gateway.observe(guild.clone()).await;
+    let inner_guild = guild.read().unwrap().clone();
+    assert!(inner_guild.roles.is_some());
+    // Update the Role
+    role_create_schema.name = Some("yippieee".to_string());
+    RoleObject::modify(&mut bundle.user, guild_id, role.id, role_create_schema)
+        .await
+        .unwrap();
+    // Check if the change propagated
+    let guild_roles = guild.read().unwrap().clone().roles;
+    let guild_role = guild_roles.unwrap();
+    let guild_role_inner = guild_role.get(0).unwrap().read().unwrap().clone();
+    assert_eq!(guild_role_inner.name, "yippieee".to_string());
     common::teardown(bundle).await;
 }