diff --git a/crates-tauri/yaak-app/src/lib.rs b/crates-tauri/yaak-app/src/lib.rs
index 23da70a3..966c692b 100644
--- a/crates-tauri/yaak-app/src/lib.rs
+++ b/crates-tauri/yaak-app/src/lib.rs
@@ -1383,13 +1383,12 @@ async fn cmd_reload_plugins<R: Runtime>(
     app_handle: AppHandle<R>,
     window: WebviewWindow<R>,
     plugin_manager: State<'_, PluginManager>,
-) -> YaakResult<()> {
+) -> YaakResult<Vec<(String, String)>> {
     let plugins = app_handle.db().list_plugins()?;
     let plugin_context =
         PluginContext::new(Some(window.label().to_string()), window.workspace_id());
-    let _errors = plugin_manager.initialize_all_plugins(plugins, &plugin_context).await;
-    // Note: errors are returned but we don't show toasts here since this is a manual reload
-    Ok(())
+    let errors = plugin_manager.initialize_all_plugins(plugins, &plugin_context).await;
+    Ok(errors)
 }
 
 #[tauri::command]
@@ -1731,6 +1730,7 @@ pub fn run() {
             git_ext::cmd_git_rm_remote,
             //
             // Plugin commands
+            plugins_ext::cmd_plugin_init_errors,
             plugins_ext::cmd_plugins_install_from_directory,
             plugins_ext::cmd_plugins_search,
             plugins_ext::cmd_plugins_install,
diff --git a/crates-tauri/yaak-app/src/plugins_ext.rs b/crates-tauri/yaak-app/src/plugins_ext.rs
index 143ae769..714d7948 100644
--- a/crates-tauri/yaak-app/src/plugins_ext.rs
+++ b/crates-tauri/yaak-app/src/plugins_ext.rs
@@ -198,6 +198,13 @@ pub async fn cmd_plugins_uninstall<R: Runtime>(
     Ok(delete_and_uninstall(plugin_manager, &query_manager, &plugin_context, plugin_id).await?)
 }
 
+#[command]
+pub async fn cmd_plugin_init_errors(
+    plugin_manager: State<'_, PluginManager>,
+) -> Result<Vec<(String, String)>> {
+    Ok(plugin_manager.take_init_errors().await)
+}
+
 #[command]
 pub async fn cmd_plugins_updates<R: Runtime>(
     app_handle: AppHandle<R>,
@@ -306,7 +313,7 @@ pub fn init<R: Runtime>() -> TauriPlugin<R> {
                     dev_mode,
                 )
                 .await
-                .expect("Failed to initialize plugins");
+                .expect("Failed to start plugin runtime");
 
                 app_handle_clone.manage(manager);
             });
diff --git a/crates/yaak-plugins/src/manager.rs b/crates/yaak-plugins/src/manager.rs
index 26400e63..91d02a59 100644
--- a/crates/yaak-plugins/src/manager.rs
+++ b/crates/yaak-plugins/src/manager.rs
@@ -50,6 +50,8 @@ pub struct PluginManager {
     vendored_plugin_dir: PathBuf,
     pub(crate) installed_plugin_dir: PathBuf,
     dev_mode: bool,
+    /// Errors from plugin initialization, retrievable once via `take_init_errors`.
+    init_errors: Arc<Mutex<Vec<(String, String)>>>,
 }
 
 /// Callback for plugin initialization events (e.g., toast notifications)
@@ -93,6 +95,7 @@ impl PluginManager {
             vendored_plugin_dir,
             installed_plugin_dir,
             dev_mode,
+            init_errors: Default::default(),
         };
 
         // Forward events to subscribers
@@ -183,17 +186,21 @@ impl PluginManager {
 
         let init_errors = plugin_manager.initialize_all_plugins(plugins, plugin_context).await;
         if !init_errors.is_empty() {
-            let joined = init_errors
-                .into_iter()
-                .map(|(dir, err)| format!("{dir}: {err}"))
-                .collect::<Vec<_>>()
-                .join("; ");
-            return Err(PluginErr(format!("Failed to initialize plugin(s): {joined}")));
+            for (dir, err) in &init_errors {
+                warn!("Plugin failed to initialize: {dir}: {err}");
+            }
+            *plugin_manager.init_errors.lock().await = init_errors;
         }
 
         Ok(plugin_manager)
     }
 
+    /// Take any initialization errors, clearing them from the manager.
+    /// Returns a list of `(plugin_directory, error_message)` pairs.
+    pub async fn take_init_errors(&self) -> Vec<(String, String)> {
+        std::mem::take(&mut *self.init_errors.lock().await)
+    }
+
     /// Get the vendored plugin directory path (resolves dev mode path if applicable)
     pub fn get_plugins_dir(&self) -> PathBuf {
         if self.dev_mode {
diff --git a/src-web/lib/initGlobalListeners.tsx b/src-web/lib/initGlobalListeners.tsx
index 796c4234..1df5d723 100644
--- a/src-web/lib/initGlobalListeners.tsx
+++ b/src-web/lib/initGlobalListeners.tsx
@@ -123,6 +123,39 @@ export function initGlobalListeners() {
     console.log('Got plugin updates event', payload);
     showPluginUpdatesToast(payload);
   });
+
+  // Check for plugin initialization errors
+  invokeCmd<[string, string][]>('cmd_plugin_init_errors').then((errors) => {
+    for (const [dir, message] of errors) {
+      const dirBasename = dir.split('/').pop() ?? dir;
+      showToast({
+        id: `plugin-init-error-${dirBasename}`,
+        color: 'warning',
+        timeout: null,
+        message: (
+          <VStack>
+            <h2 className="font-semibold">Plugin failed to load</h2>
+            <p className="text-text-subtle text-sm">
+              {dirBasename}: {message}
+            </p>
+          </VStack>
+        ),
+        action: ({ hide }) => (
+          <Button
+            size="xs"
+            color="warning"
+            variant="border"
+            onClick={() => {
+              hide();
+              openSettings.mutate('plugins:installed');
+            }}
+          >
+            View Plugins
+          </Button>
+        ),
+      });
+    }
+  });
 }
 
 function showUpdateInstalledToast(version: string) {
diff --git a/src-web/lib/tauri.ts b/src-web/lib/tauri.ts
index b8946752..df37d0d1 100644
--- a/src-web/lib/tauri.ts
+++ b/src-web/lib/tauri.ts
@@ -42,6 +42,7 @@ type TauriCmd =
   | 'cmd_new_child_window'
   | 'cmd_new_main_window'
   | 'cmd_plugin_info'
+  | 'cmd_plugin_init_errors'
   | 'cmd_reload_plugins'
   | 'cmd_render_template'
   | 'cmd_save_response'