diff --git a/eslint.config.mjs b/eslint.config.mjs
index 0f7fb55..d8270b3 100644
--- a/eslint.config.mjs
+++ b/eslint.config.mjs
@@ -81,6 +81,7 @@ export default tseslint.config(
         menuMemoryCheck: "writable",
         menuProvider: "writable",
         menuReload: "writable",
+        menuReloadSkills: "writable",
         menuSessions: "writable",
         menuSettings: "writable",
         menuSkills: "writable",
diff --git a/media/dom.js b/media/dom.js
index b07ba02..7753e11 100644
--- a/media/dom.js
+++ b/media/dom.js
@@ -34,6 +34,7 @@ const menuDelegationCheck = document.getElementById("menu-delegation-check");
 const menuMemory = document.getElementById("menu-memory");
 const menuMemoryCheck = document.getElementById("menu-memory-check");
 const menuMcp = document.getElementById("menu-mcp");
+const menuReloadSkills = document.getElementById("menu-reload-skills");
 const menuReload = document.getElementById("menu-reload");
 const menuSettings = document.getElementById("menu-settings");
 const statusDot = document.getElementById("status-dot");
diff --git a/media/menu.js b/media/menu.js
index dfd1fe0..9e8cdb8 100644
--- a/media/menu.js
+++ b/media/menu.js
@@ -25,6 +25,7 @@ onMenuClick(menuSkills, () => vscode.postMessage({ type: "toggleSkills", next: !
 onMenuClick(menuDelegation, () => vscode.postMessage({ type: "toggleDelegation", next: !delegationEnabled }));
 onMenuClick(menuMemory, () => vscode.postMessage({ type: "toggleMemory", next: !memoryEnabled }));
 onMenuClick(menuMcp, () => vscode.postMessage({ type: "manageMcpServers" }));
+onMenuClick(menuReloadSkills, () => vscode.postMessage({ type: "reloadSkills" }));
 onMenuClick(menuReload, () => vscode.postMessage({ type: "reload" }));
 onMenuClick(menuSettings, () => vscode.postMessage({ type: "openSettings" }));
 
diff --git a/src/core-client/process-args.ts b/src/core-client/process-args.ts
index e16debe..b760de3 100644
--- a/src/core-client/process-args.ts
+++ b/src/core-client/process-args.ts
@@ -8,6 +8,7 @@ export interface ServeArgsOptions {
   workspace: boolean;
   autoApprove: boolean;
   mcpServers: string[];
+  skillsRefresh?: boolean;
   resolveSetting: (value: string) => string;
 }
 
@@ -26,6 +27,9 @@ export function buildServeArgs(options: ServeArgsOptions): string[] {
   if (!options.skills) {
     args.push("--no-skills");
   }
+  if (options.skillsRefresh) {
+    args.push("--skills-refresh");
+  }
   if (options.delegation) {
     args.push("--delegate");
   }
diff --git a/src/features/chat/chat.controller.ts b/src/features/chat/chat.controller.ts
index 4723aff..259b116 100644
--- a/src/features/chat/chat.controller.ts
+++ b/src/features/chat/chat.controller.ts
@@ -16,6 +16,7 @@ import { FORWARDED_NOTIFICATIONS, PostMessage, ResolveSetting } from "./chat.typ
 
 export class ChatController {
   private client: RpcClient | undefined;
+  private pendingSkillsRefresh = false;
 
   constructor(
     private readonly context: vscode.ExtensionContext,
@@ -30,10 +31,12 @@ export class ChatController {
 
   async startConnection(): Promise<void> {
     if (!readSettings().provider) {
+      this.pendingSkillsRefresh = false;
       this.post({ type: "needsSetup" });
       return;
     }
     if (!(await this.hasCli())) {
+      this.pendingSkillsRefresh = false;
       this.post({ type: "cliMissing", command: this.resolveSetting(readSettings().command) });
       return;
     }
@@ -158,8 +161,10 @@ export class ChatController {
       workspace: settings.workspace,
       autoApprove: settings.autoApprove,
       mcpServers: settings.mcpServers,
+      skillsRefresh: this.pendingSkillsRefresh,
       resolveSetting: (value) => this.resolveSetting(value),
     });
+    this.pendingSkillsRefresh = false;
     const apiKey = await this.context.secrets.get(API_KEY_SECRET);
     const auth = this.readAuthFor(settings.provider);
     const env = spawnEnvForApiKey(apiKey, providerApiKeyEnvNames(auth));
@@ -227,4 +232,9 @@ export class ChatController {
     this.dispose();
     void this.startConnection();
   }
+
+  reloadSkills(): void {
+    this.pendingSkillsRefresh = true;
+    this.reload();
+  }
 }
diff --git a/src/vscode/sidebar/chatSidebarProvider.ts b/src/vscode/sidebar/chatSidebarProvider.ts
index 124047a..206365c 100644
--- a/src/vscode/sidebar/chatSidebarProvider.ts
+++ b/src/vscode/sidebar/chatSidebarProvider.ts
@@ -141,6 +141,9 @@ export class ChatViewProvider implements vscode.WebviewViewProvider {
       case "reload":
         this.chat.reload();
         break;
+      case "reloadSkills":
+        this.chat.reloadSkills();
+        break;
       case "installCli":
         this.chat.installCli();
         break;
diff --git a/src/vscode/webview/html.ts b/src/vscode/webview/html.ts
index 38f6983..835d071 100644
--- a/src/vscode/webview/html.ts
+++ b/src/vscode/webview/html.ts
@@ -51,6 +51,7 @@ export function renderChatHtml(options: ChatHtmlOptions): string {
             <span id="menu-memory-check" class="check-box"></span> Project memory
           </button>
           <button id="menu-mcp" class="menu-item">MCP Servers</button>
+          <button id="menu-reload-skills" class="menu-item">Reload Skills</button>
           <button id="menu-reload" class="menu-item">Reload Connection</button>
           <button id="menu-settings" class="menu-item">Open Settings</button>
         </div>
diff --git a/src/vscode/webview/messages.ts b/src/vscode/webview/messages.ts
index 498bed0..b72fe4c 100644
--- a/src/vscode/webview/messages.ts
+++ b/src/vscode/webview/messages.ts
@@ -20,6 +20,7 @@ export type WebviewMessage =
   | { type: "toggleMemory"; next: boolean }
   | { type: "manageMcpServers" }
   | { type: "reload" }
+  | { type: "reloadSkills" }
   | { type: "installCli" }
   | { type: "updateCli" }
   | { type: "openSettings" }