diff --git a/src/index.ts b/src/index.ts
index cea8f69..c908d63 100755
--- a/src/index.ts
+++ b/src/index.ts
@@ -8,7 +8,7 @@ import type { AgentProvenance } from "./agent/create";
 import { LETTA_CLOUD_API_URL } from "./auth/oauth";
 import { permissionMode } from "./permissions/mode";
 import { settingsManager } from "./settings-manager";
-import { loadTools, upsertToolsToServer } from "./tools/manager";
+import { loadTools, upsertToolsIfNeeded } from "./tools/manager";
 
 function printHelp() {
   // Keep this plaintext (no colors) so output pipes cleanly
@@ -431,7 +431,7 @@ async function main() {
     );
     await loadTools(modelForTools);
     const client = await getClient();
-    await upsertToolsToServer(client);
+    await upsertToolsIfNeeded(client, baseURL);
 
     const { handleHeadlessCommand } = await import("./headless");
     await handleHeadlessCommand(process.argv, specifiedModel, skillsDirectory);
@@ -573,7 +573,7 @@ async function main() {
         }
 
         setLoadingState("upserting");
-        await upsertToolsToServer(client);
+        await upsertToolsIfNeeded(client, baseURL);
 
         // Handle --link/--unlink after upserting tools
         if (shouldLink || shouldUnlink) {
diff --git a/src/settings-manager.ts b/src/settings-manager.ts
index a80600d..7e376a8 100644
--- a/src/settings-manager.ts
+++ b/src/settings-manager.ts
@@ -19,6 +19,8 @@ export interface Settings {
   refreshToken?: string;
   tokenExpiresAt?: number; // Unix timestamp in milliseconds
   deviceId?: string;
+  // Tool upsert cache: maps serverUrl -> hash of upserted tools
+  toolUpsertHashes?: Record<string, string>;
 }
 
 export interface ProjectSettings {
diff --git a/src/tools/manager.ts b/src/tools/manager.ts
index d74684a..9bd96e6 100644
--- a/src/tools/manager.ts
+++ b/src/tools/manager.ts
@@ -1,3 +1,4 @@
+import { createHash } from "node:crypto";
 import type Letta from "@letta-ai/letta-client";
 import {
   AuthenticationError,
@@ -586,6 +587,58 @@ export async function upsertToolsToServer(client: Letta): Promise<void> {
   await attemptUpsert();
 }
 
+/**
+ * Compute a hash of all currently loaded tools for cache invalidation.
+ * Includes tool names and schemas to detect any changes.
+ */
+export function computeToolsHash(): string {
+  const toolData = Array.from(toolRegistry.entries())
+    .sort(([a], [b]) => a.localeCompare(b)) // deterministic order
+    .map(([name, tool]) => ({
+      name,
+      serverName: getServerToolName(name),
+      schema: tool.schema,
+    }));
+
+  return createHash("sha256")
+    .update(JSON.stringify(toolData))
+    .digest("hex")
+    .slice(0, 16); // short hash is sufficient
+}
+
+/**
+ * Upserts tools only if the tool definitions have changed since last upsert.
+ * Uses a hash of loaded tools cached in settings to skip redundant upserts.
+ *
+ * @param client - Letta client instance
+ * @param serverUrl - The server URL (used as cache key)
+ * @returns true if upsert was performed, false if skipped
+ */
+export async function upsertToolsIfNeeded(
+  client: Letta,
+  serverUrl: string,
+): Promise<boolean> {
+  const currentHash = computeToolsHash();
+
+  const { settingsManager } = await import("../settings-manager");
+  const cachedHashes = settingsManager.getSetting("toolUpsertHashes") || {};
+
+  if (cachedHashes[serverUrl] === currentHash) {
+    // Tools unchanged, skip upsert
+    return false;
+  }
+
+  // Perform upsert
+  await upsertToolsToServer(client);
+
+  // Save new hash
+  settingsManager.updateSettings({
+    toolUpsertHashes: { ...cachedHashes, [serverUrl]: currentHash },
+  });
+
+  return true;
+}
+
 /**
  * Helper to clip tool return text to a reasonable display size
  * Used by UI components to truncate long responses for display