diff --git a/src/ClaudeDev.ts b/src/ClaudeDev.ts
index afd77be..c425e72 100644
--- a/src/ClaudeDev.ts
+++ b/src/ClaudeDev.ts
@@ -168,10 +168,6 @@ export class ClaudeDev {
 		this.client = new Anthropic({ apiKey })
 		this.maxRequestsPerTask = maxRequestsPerTask ?? DEFAULT_MAX_REQUESTS_PER_TASK
 
-        // conversationHistory (for API) and claudeMessages (for webview) need to be in sync
-        // if the extension process were killed, then on restart the claudeMessages might not be empty, so we need to set it to [] when we create a new ClaudeDev client (otherwise webview would show stale messages from previous session)
-        this.providerRef.deref()?.setClaudeMessages([])
-
         this.startTask(task)
 	}
 
@@ -206,6 +202,11 @@ export class ClaudeDev {
 	}
 
 	private async startTask(task: string): Promise<void> {
+		// conversationHistory (for API) and claudeMessages (for webview) need to be in sync
+        // if the extension process were killed, then on restart the claudeMessages might not be empty, so we need to set it to [] when we create a new ClaudeDev client (otherwise webview would show stale messages from previous session)
+		await this.providerRef.deref()?.setClaudeMessages([])
+		await this.providerRef.deref()?.postStateToWebview()
+		
 		// Get all relevant context for the task
 		const filesInCurrentDir = await this.listFiles()
 
diff --git a/src/extension.ts b/src/extension.ts
index 3f079ae..06ad0d0 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -34,10 +34,12 @@ export function activate(context: vscode.ExtensionContext) {
 	context.subscriptions.push(vscode.window.registerWebviewViewProvider(SidebarProvider.viewType, provider))
 
 	context.subscriptions.push(
-		vscode.commands.registerCommand("claude-dev.plusButtonTapped", () => {
+		vscode.commands.registerCommand("claude-dev.plusButtonTapped", async () => {
 			const message = "claude-dev.plusButtonTapped!"
-			vscode.window.showInformationMessage(message)
-			provider.postMessageToWebview({ type: "action", action: "plusButtonTapped"})
+			//vscode.window.showInformationMessage(message)
+			await provider.resetTask()
+			await provider.postStateToWebview()
+			await provider.postMessageToWebview({ type: "action", action: "plusButtonTapped"})
 		})
 	)
 
diff --git a/src/providers/SidebarProvider.ts b/src/providers/SidebarProvider.ts
index 5e49529..c7f8356 100644
--- a/src/providers/SidebarProvider.ts
+++ b/src/providers/SidebarProvider.ts
@@ -13,7 +13,7 @@ https://github.com/KumarVariable/vscode-extension-sidebar-html/blob/master/src/c
 
 type ExtensionSecretKey = "apiKey"
 type ExtensionGlobalStateKey = "didOpenOnce" | "maxRequestsPerTask"
-type ExtensionWorkspaceStateKey = "claudeMessages" | "apiConversationHistory"
+type ExtensionWorkspaceStateKey = "claudeMessages"
 
 export class SidebarProvider implements vscode.WebviewViewProvider {
 	public static readonly viewType = "claude-dev.SidebarProvider"
@@ -40,6 +40,9 @@ export class SidebarProvider implements vscode.WebviewViewProvider {
 		// Sets up an event listener to listen for messages passed from the webview view context
 		// and executes code based on the message that is recieved
 		this.setWebviewMessageListener(webviewView.webview)
+
+		// if the extension is starting a new session, clear previous task state
+		this.resetTask()
 	}
 
 	async tryToInitClaudeDevWithTask(task: string) {
@@ -199,6 +202,11 @@ export class SidebarProvider implements vscode.WebviewViewProvider {
 			state: { didOpenOnce: !!didOpenOnce, apiKey, maxRequestsPerTask, claudeMessages },
 		})
 	}
+
+	async resetTask() {
+		this.claudeDev = undefined
+		await this.setClaudeMessages([])
+	}
 	
 	// client messages
 
@@ -220,21 +228,21 @@ export class SidebarProvider implements vscode.WebviewViewProvider {
 
 	// api conversation history
 
-	async getApiConversationHistory(): Promise<ClaudeMessage[]> {
-		const messages = (await this.getWorkspaceState("apiConversationHistory")) as ClaudeMessage[]
-		return messages || []
-	}
+	// async getApiConversationHistory(): Promise<ClaudeMessage[]> {
+	// 	const messages = (await this.getWorkspaceState("apiConversationHistory")) as ClaudeMessage[]
+	// 	return messages || []
+	// }
 
-	async setApiConversationHistory(messages: ClaudeMessage[] | undefined) {
-		await this.updateWorkspaceState("apiConversationHistory", messages)
-	}
+	// async setApiConversationHistory(messages: ClaudeMessage[] | undefined) {
+	// 	await this.updateWorkspaceState("apiConversationHistory", messages)
+	// }
 
-	async addMessageToApiConversationHistory(message: ClaudeMessage): Promise<ClaudeMessage[]> {
-		const messages = await this.getClaudeMessages()
-		messages.push(message)
-		await this.setClaudeMessages(messages)
-		return messages
-	}
+	// async addMessageToApiConversationHistory(message: ClaudeMessage): Promise<ClaudeMessage[]> {
+	// 	const messages = await this.getClaudeMessages()
+	// 	messages.push(message)
+	// 	await this.setClaudeMessages(messages)
+	// 	return messages
+	// }
 
 	/*
 	Storage