If can't sign in to your Outlook. Go to the Outlook. Check the Keep me signed in box if you want to go straight to Outlook. If you're having trouble signing in to your Microsoft account, there could be a few different reasons for that - like you can't remember your password or have two-step verification turned on. Your account hasn't been inactive for more than days. To keep your Outlook. After days of inactivity, your email will be deleted and cannot be recovered.