Yes, you can schedule two automatic recurring payments per month if you meet specific eligibility requirements. You can always schedule one automatic recurring payment per month plus as many manual payments per month as you like (more information here), there are no eligibility requirements to do this.
In order to be eligible to schedule two automatic recurring payments per month, your account must be current, and you must login to schedule the payments at least 15 days before your next due date to access this feature.
Bi-monthly automatic recurring payments can be scheduled up to 30 days apart, but you may not schedule payments more than 15 days past your due date, and payments cannot be fewer than 5 days apart. These two payments will repeat on the same days every month.
To schedule bi-monthly automatic recurring payments, login to your Upstart account and click on "Add/Edit a Recurring Payment." Then select the "Bi-monthly Recurring Payment" option to schedule recurring payments. If you do not see this feature, you may not be eligible to use this payment preference at this time.