diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index c646224ba5..9b2e3286ac 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -588,7 +588,7 @@ export const webviewMessageHandler = async (
 			break
 		}
 		case "addToWhitelist": {
-			// Handle adding a command pattern to the whitelist without running it
+			// Handle adding a command pattern to the whitelist and then running it
 			if (message.pattern) {
 				// Get current allowed commands
 				const currentAllowedCommands = getGlobalState("allowedCommands") || []
@@ -608,6 +608,9 @@ export const webviewMessageHandler = async (
 					// Post state update to webview
 					await provider.postStateToWebview()
 				}
+
+				// After whitelisting, approve the pending command execution
+				provider.getCurrentCline()?.handleWebviewAskResponse("yesButtonClicked")
 			}
 			break
 		}
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index c18d64bf9c..176f3e1ce3 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -1659,7 +1659,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 								<>
 									{/* Command approval with auto-approve pattern */}
 									{clineAsk === "command" && !isStreaming ? (
-										<div className="flex flex-col gap-[6px]">
+										<div className="flex flex-col gap-[6px] mb-[10px]">
 											{/* Top row: Run Command and Reject */}
 											<div className="flex gap-[6px]">
 												<StandardTooltip content={t("chat:runCommand.tooltip")}>