Unfortunately, the mobile app is pretty trash for this. I have had issues with that multi-address toggle disappearing constantly. Its basically a desktop-only feature because the mobile UI is so limited. Honestly, just log in on a real browser and hit the Desktop Site button. It is way more reliable for bulk orders. Just make sure items are all sold by Amazon or it might glitch again tho.

^ This. Also, you gotta be really careful about how you toggle those addresses on mobile because it is so easy to accidentally ship everything to your default address. I've been there, and let me tell you, returning five identical items just to re-order them is a total nightmare. Honestly, I'm usually pretty happy with how the desktop site handles it... it just feels more reliable and stable when you're dealing with multiple recipients and different names. One big warning tho: watch out for the gift options specifically. Sometimes when you split the order into different addresses, the 'this is a gift' checkmark resets for some of the items. If that happens, your friends get the items with no note and maybe even a packing slip with the price on it, which is kind of a vibe killer for bridesmaid gifts. I always do a final pass on the review page to make sure every single name and message is attached correctly to the right person. No complaints once you get that part locked in! If the app is still giving you grief and you're worried about mistakes, I've used a simple tool for share Amazon cart before and it honestly makes the whole coordination part way less stressful. It's a solid way to double-check your list before diving into the actual checkout chaos. Just make sure you check if items are Prime eligible too. If they arent, shipping costs can get weirdly high when you start splitting things up. Better to catch that before you click pay!

Regarding what #3 said about "^ This. Also, you gotta be really careful..." - man, he is not kidding. I've spent way too many hours on the phone with support because a multi-ship order accidentally went to my house instead of the recipients. I've tried many ways to do this over the years and honestly, the app is just not built for it. The code for that multi-address toggle is legacy stuff that barely works on modern mobile browsers. In my experience, here is how to keep it reliable:

• Use a real computer and clear your cookies before you start. Sometimes old cart data gunks up the shipping options and hides the toggle.
• Make sure every single item is actually in stock. If one thing is backordered, it can grey out the ship-to-multiple option entirely.
• Since you are buying 5 of everything, definitely check this free price tracker before you hit buy. Prices on those giftable items fluctuate like crazy and you might save a ton. Basically, just stay off the phone for this one. The desktop site gives you a much better overview of who is getting what. Better to spend ten minutes on a laptop than two hours fixing a wrong delivery... trust me.

You're totally right that the mobile app hides these advanced logistics features! It's actually because the mobile checkout flow is optimized for single-tap purchases, which is super annoying when you're trying to be efficient with bridesmaid gifts. I've managed dozens of bulk orders for events and the technical backend for multi-shipping is way more robust on the full site.

• First, move everything to your cart on a computer browser. The Ship to multiple addresses link only populates once you've reached the final Review your order screen, not the initial cart page.
• Second, click that tiny blue link right above your default shipping address. It opens a fantastic grid where you can assign a different friend to every single item in your cart!
• Don't forget to check the This is a gift box for each one. This ensures they get a nice packing slip without the price listed, plus you can write individual messages. It's seriously amazing how much time this saves once you get into the desktop workflow. If you're still seeing shipping costs, try to bundle items for each friend into sets or use Prime to get that sweet free shipping on every single gift. It's gonna save you a ton of money compared to five separate transactions tho. I usually just use Cart To Link to send my PC builds to friends; much easier than copy-pasting ten different product links.