I had similar problems. Just figured Id turn to the ladies of BG to see if you had any helpful advice
"Well chase doesn't latch well at all so we've been using nipple shields and he just rips them right off. I've tried swaddling him and he just screams because he loves his hands. So I tried pumping into bottles and he was fine with that. I've been doing that the past two weeks and trying to feed him directly as well which rarely works. The worst part is waking up with clogged ducts every day. I do warm compresses and massaging them but I have a horrible one in my left side that literally hurts to even touch it. It's over all just so frustrating having to pump and then feed him then its already time to pump again haha. Plus he's tongue tied so he gets frustrated fast"
How Is he ripping off the shield? Maybe she needs to out her hand behind his head so he's not pulling it off.
Is she trying to open his mouth all the way and sandwiching her nipple in his mouth to get a good latch?
She can massage the clogged duct but really him nursing is the most efficient to get it out. Have her massage it while she's pumping and while in the shower. If she doesn't get it out it can cause a yeast Infextion or mastitis.