diff --git a/package-lock.json b/package-lock.json
index 3941462d2..19eb2d6fa 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,12 +1,12 @@
 {
     "name": "sillytavern",
-    "version": "1.10.5",
+    "version": "1.10.6",
     "lockfileVersion": 3,
     "requires": true,
     "packages": {
         "": {
             "name": "sillytavern",
-            "version": "1.10.5",
+            "version": "1.10.6",
             "hasInstallScript": true,
             "license": "AGPL-3.0",
             "dependencies": {
diff --git a/package.json b/package.json
index d2c9b7dd3..185af0b1d 100644
--- a/package.json
+++ b/package.json
@@ -47,7 +47,7 @@
         "type": "git",
         "url": "https://github.com/SillyTavern/SillyTavern.git"
     },
-    "version": "1.10.5",
+    "version": "1.10.6",
     "scripts": {
         "start": "node server.js",
         "start-multi": "node server.js --disableCsrf",
diff --git a/public/script.js b/public/script.js
index 06374aa02..dc718241d 100644
--- a/public/script.js
+++ b/public/script.js
@@ -339,6 +339,7 @@ export let isChatSaving = false;
 let chat_create_date = 0;
 let firstRun = false;
 let settingsReady = false;
+let currentVersion = "0.0.0";
 
 const default_ch_mes = "Hello";
 let count_view_mes = 0;
@@ -537,6 +538,7 @@ async function getClientVersion() {
         const data = await response.json();
         CLIENT_VERSION = data.agent;
         let displayVersion = `SillyTavern ${data.pkgVersion}`;
+        currentVersion = data.pkgVersion;
 
         if (data.gitRevision && data.gitBranch) {
             displayVersion += ` '${data.gitBranch}' (${data.gitRevision})`;
@@ -5045,7 +5047,8 @@ async function getSettings(type) {
         selected_button = settings.selected_button;
 
         if (data.enable_extensions) {
-            await loadExtensionSettings(settings);
+            const isVersionChanged = settings.currentVersion !== currentVersion;
+            await loadExtensionSettings(settings, isVersionChanged);
             eventSource.emit(event_types.EXTENSION_SETTINGS_LOADED);
         }
     }
@@ -5071,6 +5074,7 @@ async function saveSettings(type) {
         url: "/savesettings",
         data: JSON.stringify({
             firstRun: firstRun,
+            currentVersion: currentVersion,
             username: name1,
             active_character: active_character,
             active_group: active_group,
diff --git a/public/scripts/extensions.js b/public/scripts/extensions.js
index c62a24e5c..76c3c2b64 100644
--- a/public/scripts/extensions.js
+++ b/public/scripts/extensions.js
@@ -609,6 +609,15 @@ async function showExtensionsDetails() {
  */
 async function onUpdateClick() {
     const extensionName = $(this).data('name');
+    await updateExtension(extensionName, false);
+}
+
+/**
+ * Updates a third-party extension via the API.
+ * @param {string} extensionName Extension folder name
+ * @param {boolean} quiet If true, don't show a success message
+ */
+async function updateExtension(extensionName, quiet) {
     try {
         const response = await fetch('/api/extensions/update', {
             method: 'POST',
@@ -618,15 +627,20 @@ async function onUpdateClick() {
 
         const data = await response.json();
         if (data.isUpToDate) {
-            toastr.success('Extension is already up to date');
+            if (!quiet) {
+                toastr.success('Extension is already up to date');
+            }
         } else {
-            toastr.success(`Extension updated to ${data.shortCommitHash}`);
+            toastr.success(`Extension ${extensionName} updated to ${data.shortCommitHash}`);
+        }
+
+        if (!quiet) {
+            showExtensionsDetails();
         }
-        showExtensionsDetails();
     } catch (error) {
         console.error('Error:', error);
     }
-};
+}
 
 /**
  * Handles the click event for the delete button of an extension.
@@ -706,11 +720,16 @@ export async function installExtension(url) {
     const response = await request.json();
     toastr.success(`Extension "${response.display_name}" by ${response.author} (version ${response.version}) has been imported successfully!`, 'Extension import successful');
     console.debug(`Extension "${response.display_name}" has been imported successfully at ${response.extensionPath}`);
-    await loadExtensionSettings({});
+    await loadExtensionSettings({}, false);
     eventSource.emit(event_types.EXTENSION_SETTINGS_LOADED);
 }
 
-async function loadExtensionSettings(settings) {
+/**
+ * Loads extension settings from the app settings.
+ * @param {object} settings App Settings
+ * @param {boolean} versionChanged Is this a version change?
+ */
+async function loadExtensionSettings(settings, versionChanged) {
     if (settings.extension_settings) {
         Object.assign(extension_settings, settings.extension_settings);
     }
@@ -723,10 +742,25 @@ async function loadExtensionSettings(settings) {
     eventSource.emit(event_types.EXTENSIONS_FIRST_LOAD);
     extensionNames = await discoverExtensions();
     manifests = await getManifests(extensionNames)
+
+    if (versionChanged) {
+        await autoUpdateExtensions();
+    }
+
     await activateExtensions();
     if (extension_settings.autoConnect && extension_settings.apiUrl) {
         connectToApi(extension_settings.apiUrl);
     }
+
+}
+
+async function autoUpdateExtensions() {
+    for (const [id, manifest] of Object.entries(manifests)) {
+        if (manifest.auto_update && id.startsWith('third-party')) {
+            console.debug(`Auto-updating 3rd-party extension: ${manifest.display_name} (${id})`);
+            await updateExtension(id.replace('third-party', ''), true);
+        }
+    }
 }
 
 async function runGenerationInterceptors(chat, contextSize) {