diff --git a/src/everything/server/index.ts b/src/everything/server/index.ts
index 6293245c..2471c6e8 100644
--- a/src/everything/server/index.ts
+++ b/src/everything/server/index.ts
@@ -7,6 +7,7 @@ import { registerConditionalTools, registerTools } from "../tools/index.js";
 import { registerResources, readInstructions } from "../resources/index.js";
 import { registerPrompts } from "../prompts/index.js";
 import { stopSimulatedLogging } from "./logging.js";
+import { syncRoots } from "./roots.js";
 
 // Server Factory response
 export type ServerFactoryResponse = {
@@ -68,8 +69,18 @@ export const createServer: () => ServerFactoryResponse = () => {
   // Set resource subscription handlers
   setSubscriptionHandlers(server);
 
-  // Register conditional tools until client capabilities are known
-  server.server.oninitialized = () => registerConditionalTools(server);
+  // Perform post-initialization operations
+  server.server.oninitialized = async () => {
+    // Register conditional tools now that client capabilities are known.
+    // This finishes before the `notifications/initialized` handler finishes.
+    registerConditionalTools(server);
+
+    // Sync roots if the client supports them.
+    // This is delayed until after the `notifications/initialized` handler finishes,
+    // otherwise, the request gets lost.
+    const sessionId = server.server.transport?.sessionId;
+    setTimeout(() => syncRoots(server, sessionId), 350);
+  };
 
   // Return the ServerFactoryResponse
   return {
diff --git a/src/everything/server/roots.ts b/src/everything/server/roots.ts
index 05a6f90f..e09f0601 100644
--- a/src/everything/server/roots.ts
+++ b/src/everything/server/roots.ts
@@ -11,11 +11,17 @@ export const roots: Map<string | undefined, Root[]> = new Map<
 >();
 
 /**
- * Sync the root directories from the client by requesting and updating the roots list for
- * the specified session.
+ * Get the latest the client roots list for the session.
  *
- * Also sets up a notification handler to listen for changes in the roots list, ensuring that
- * updates are automatically fetched and handled in real-time.
+ * - Request and cache the roots list for the session if it has not been fetched before.
+ * - Return the cached roots list for the session if it exists.
+ *
+ * When requesting the roots list for a session, it also sets up a `roots/list_changed`
+ * notification handler. This ensures that updates are automatically fetched and handled
+ * in real-time.
+ *
+ * Therefore, calls to this function should only request roots from the client once per
+ * session, but the cache will always be up to date after that first call.
  *
  * @param {McpServer} server - An instance of the MCP server used to communicate with the client.
  * @param {string} [sessionId] - An optional session id used to associate the roots list with a specific client session.
@@ -23,7 +29,6 @@ export const roots: Map<string | undefined, Root[]> = new Map<
  * @throws {Error} In case of a failure to request the roots from the client, an error log message is sent.
  */
 export const syncRoots = async (server: McpServer, sessionId?: string) => {
-
   const clientCapabilities = server.server.getClientCapabilities() || {};
   const clientSupportsRoots: boolean = clientCapabilities.roots !== undefined;
 
@@ -71,14 +76,19 @@ export const syncRoots = async (server: McpServer, sessionId?: string) => {
       }
     };
 
-    // Set the list changed notification handler
-    server.server.setNotificationHandler(
-      RootsListChangedNotificationSchema,
-      requestRoots
-    );
+    // If the roots have not been synced for this client,
+    // set notification handler and request initial roots
+    if (!roots.has(sessionId)) {
+      // Set the list changed notification handler
+      server.server.setNotificationHandler(
+        RootsListChangedNotificationSchema,
+        requestRoots
+      );
 
-    // Request initial roots list immediatelys
-    await requestRoots();
+      // Request the initial roots list immediately
+      await requestRoots();
+      console.log(roots.get(sessionId));
+    }
 
     // Return the roots list for this client
     return roots.get(sessionId);
diff --git a/src/everything/tools/get-roots-list.ts b/src/everything/tools/get-roots-list.ts
index 24369070..62363da2 100644
--- a/src/everything/tools/get-roots-list.ts
+++ b/src/everything/tools/get-roots-list.ts
@@ -40,7 +40,7 @@ export const registerGetRootsListTool = (server: McpServer) => {
       config,
       async (args, extra): Promise<CallToolResult> => {
         // Get the current rootsFetch the current roots list from the client if need be
-        const currentRoots =  await syncRoots(server, extra.sessionId);
+        const currentRoots = await syncRoots(server, extra.sessionId);
 
         // Respond if client supports roots but doesn't have any configured
         if (
diff --git a/src/everything/tools/index.ts b/src/everything/tools/index.ts
index f1bab0fa..d3bd2aaf 100644
--- a/src/everything/tools/index.ts
+++ b/src/everything/tools/index.ts
@@ -39,7 +39,6 @@ export const registerTools = (server: McpServer) => {
  * These must be registered conditionally, after initialization.
  */
 export const registerConditionalTools = (server: McpServer) => {
-  console.log("Registering conditional tools...");
   registerGetRootsListTool(server);
   registerTriggerElicitationRequestTool(server);
   registerTriggerSamplingRequestTool(server);
diff --git a/src/everything/tools/trigger-elicitation-request.ts b/src/everything/tools/trigger-elicitation-request.ts
index 260c805d..6281c87d 100644
--- a/src/everything/tools/trigger-elicitation-request.ts
+++ b/src/everything/tools/trigger-elicitation-request.ts
@@ -131,9 +131,9 @@ export const registerTriggerElicitationRequestTool = (server: McpServer) => {
                     title: "Titled Single Select Enum",
                     description: "Choose your favorite hero",
                     oneOf: [
-                      {const: "hero-1", title: "Superman"},
-                      {const: "hero-2", title: "Green Lantern"},
-                      {const: "hero-3", title: "Wonder Woman"},
+                      { const: "hero-1", title: "Superman" },
+                      { const: "hero-2", title: "Green Lantern" },
+                      { const: "hero-3", title: "Wonder Woman" },
                     ],
                     default: "hero-1",
                   },
@@ -145,9 +145,9 @@ export const registerTriggerElicitationRequestTool = (server: McpServer) => {
                     maxItems: 3,
                     items: {
                       anyOf: [
-                        {const: "fish-1", title: "Tuna"},
-                        {const: "fish-2", title: "Salmon"},
-                        {const: "fish-3", title: "Trout"},
+                        { const: "fish-1", title: "Tuna" },
+                        { const: "fish-2", title: "Salmon" },
+                        { const: "fish-3", title: "Trout" },
                       ],
                     },
                     default: ["fish-1"],
@@ -166,7 +166,7 @@ export const registerTriggerElicitationRequestTool = (server: McpServer) => {
             },
           },
           ElicitResultSchema,
-          {timeout: 10 * 60 * 1000 /* 10 minutes */}
+          { timeout: 10 * 60 * 1000 /* 10 minutes */ }
         );
 
         // Handle different response actions
@@ -220,7 +220,7 @@ export const registerTriggerElicitationRequestTool = (server: McpServer) => {
           text: `\nRaw result: ${JSON.stringify(elicitationResult, null, 2)}`,
         });
 
-        return {content};
+        return { content };
       }
     );
   }