1. Why is it that the order has to be marked completed manually in order to send an email to the recipient? I’ve had a few purchases on my site which after the purchase didn’t send an email to the recipient. Even though I had an appropriate setting checked in the PW gift card settings.

By default, the gift card number is generated and emailed once the order status is Complete. The PW Gift Card product type is flagged as “Virtual” in WooCommerce so the order should be completed as soon as payment has been received.

It sounds like your payment gateway plugin might not be marking the order as complete once the payment has been received. Take a screenshot of the Order in the admin area (along with the Order Notes section) and send it to us@pimwick.com along with a WooCommerce System Report. Reference this thread.

2. I accidentally marked a few gift card orders completed while I had the “Use the WooCommerce Transactional Email System” setting checked which didn’t send emails to the recipient. But after I found out unchecking the setting solves the problem of emails not sending, I’m not able to send gift card emails since marking it completed again will only send an email to the sender

If you are using PW Gift Cards Pro, you can resend the gift card email by going to Pimwick Plugins > PW Gift Cards > Balances > Send Email button next to the gift card.

If you have the free version, there isn’t an option to resend the gift card number so you will need to email the recipient directly with their gift card number.