I’ve posted in Apple’s forums, sent them feedback, opened support requests, talked to people at the stores. Human beings I’ve been able to interface with directly all seem to understand my complaints and acknowledge it is an issue, yet years go by and nothing changes. I can only assume Apple is either not operated by humans, or simply doesn’t give a shit because the current system generates some financial benefit for them which my mediocre brain is not capable of envisioning.

Here is the issue. You have one Apple ID, it allows for the attachment of a single credit card. Every purchase you make goes through this card. Every service you subscribe to goes through this card. If you enable family sharing, every purchase made by an Apple ID who joins the family goes through this card.

Why is this the most poorly thought out billing system ever? Well, first and foremost, is because it PREVENTS the giving of more money to Apple that they’d otherwise be receiving. However, from my personal perspective, here’s my areas of pain:

• Impossible to separate employer vs personal purchases
• Impossible to easily reconcile family purchases
• Painful to reconcile any purchases for that matter
• Painful to temporarily change credit cards
• Painful to make use of gift cards
• Painful to make use of role accounts for security reasons

Let’s tackle those one at a time.

Impossible to separate employer vs personal purchases

If you are committed to the Apple ecosystem, chances are you have more than one Apple device. While it can be argued that a desktop device might facilitate the use of multiple Apple ID’s via different logins and fast user switching, this is not the case on mobile devices like phones and tablets. On those, it is extremely difficult to switch Apple ID’s, so it simply can’t be argued that you should just keep employer-related and personal purchases separate by way of using different Apple ID’s, unless you’re also willing to discard the security of fast user switching, and keep separate mobile devices for each type of use. If you don’t do that, then you’d have no way to purchase a book, podcast, subscription-based app, etc. on your work Apple ID and then make use of it on your mobile device.

The decision we’re now left with is what is least painful; having your employer card attached to your Apple ID and working around it for personal purchases, or having your personal card attached to your Apple ID and requesting reimbursement for all employer expenses. Thanks Apple; for your unknown personal reasons, I’m forced to decide which option wastes less of my time, or is even possible, as some employers allow only expenses via employer-issued credit / purchase card.

In my personal case, I have employer-paid iCloud for the sync’ing of documents between devices, app-based subscriptions, random app purchases as needed, a paid stream I have added into iTunes, and random podcasts as needed. Apple offers no method of consolidating regular charges on a common date or into a single charge. Before making use of family sharing and Apple Music, I found it to waste slightly less time having my employer card on there and purchasing gift cards to apply before making personal purchases. Once I desired to use those services, the balance of time waste shifted in the other direction, so now I have to audit and submit consolidated reimbursement requests every month.

What would solve the entire fucking problem? Oh here’s a mind blowing idea; allow an Apple ID to have two or more payment ‘roles’ and I simply pick which role charges go to when purchasing/subscribing. If I need to swap out a card later, doesn’t matter, that role’s charges keep going to the card set for that role. I could then have personal, work, family (since family purchases stupidly have to go to my card).

Impossible to easily reconcile family purchases

Oh yeah, this is easy. Want to ‘enjoy’ family sharing? Well, at least for children, you can force an approval of purchases via your manager account, so you can loosely track purchases by recording those yourself, but for other adult family members, those just get charged to your card on file; your ONE card on file. So, regardless of family sharing and having an employer card being mutually exclusive, it’s also a nightmare to reconcile because of how much of a pain it is to even view purchases, unless you simply don’t care what your family purchases, if it was intentional, if you run separate bank accounts / budgeting, if an account compromise has occurred and the purchase was unauthorized, etc.

Here’s how you do that. One of two painful methods. Use your phone, click settings, click your Apple ID, click iTunes and App Store (yes even for Books purchases), click your Apple ID again because that’s intuitive, click View Apple ID, authenticate, click Purchase History. Yes, seven different navigation steps, several that make no sense, allows you to finally see the purchases and then start your work of figuring out if they were legit.

On computer, iTunes, Account menu (since it’s not actually present in the iTunes GUI), View My Account, purchase history->see all. Each step is incredibly slow, so the phone is actually less painful even though it involves more clicking.

Painful to reconcile any purchases for that matter

Expanding on the above; while you can’t select payment information, you also have no way to tag a purchase in any meaningful way. I purchase all kinds of things via App Store, Book Store, etc. Each month I have to go through the purchase history and carefully examine each item to figure out if it was work or personal, then write up the reimbursement request. If I could simply tag each purchase as ‘work’, and then purchase history let you filter, problem solved; print screen and I’m done.

Painful to temporarily change credit cards

This one is actually painful for reasons other than what you might have initially assumed I’d be complaining about. Yes, it is a pain to actually change your Apple ID’s associated card; click through a multitude of menus and finally get to the place where you can alter it. However, the problem here is actually caused by Apple’s rare attempt at being helpful in relation to accidental purchases. If you make purchases from App Store, Books, etc. generally there’s a short window of time you can undo it; and during that period of time, those purchases will be in a “Pending” state from a charge perspective. Different types of purchases may have different sets of criteria defining how long they’ll be pending. So, while you can change your card to try and route purchases to a work or personal card, now you also have to plan what you purchase, when you purchase it, and if any other charges may hit your one payment method at an inopportune time.

For example, I bought an app today, for personal use, that will likely be pending for a few days. If I were still making mostly work purchases, I’d have my work credit card attached to my Apple ID. If I knew my iCloud storage charge was going to hit tomorrow, I’d need to postpone my personal purchase until after that because I will have no clue when my app purchase will go from pending to funds collected, and I’d need to ensure the right card were in place. How f’ing stupid is this system?!?!?!

Painful to make use of gift cards

A frequent suggestion in Apple community forums for solving all the above problems is to make use of gift cards. These suggestions of course come from Apple fanboys that would kill their own children before they’d blaspheme Apple.

Here’s how gift cards work in reality. Unlike Amazon who delivers gift card purchases almost instantly, when you purchase an Apple gift card through their site, they state the recipient should receive the code within one to four HOURS. I’ve found it is rare to receive the processed gift card link in less than 20 minutes. So, first things first, urgent purchases just became impossible.

Next up, the way gift cards work, any balance associated with the application of a gift card is consumed before the card on file is charged again. So, you are now prevented from simply maintaining a gift balance for use with purchases that are inappropriate for the card on file. I can’t maintain a family balance that I route family purchases through while having an employer card on file. This means you’re forced to purchase gift cards in the exact amount you need for an upcoming purchase, and incur the annoying delay each time.

Finally, expanding on the ‘pending’ purchase concept I complained about in the prior section, it applies here as well. I need $20.97 worth of gift card to make a $20.97 purchase, but different components of the purchase are going to go from pending to charged at different times, then here comes my monthly iCloud, iTunes, etc. scheduled charge in between; now something that should have gone to card got deducted from gift balance instead, and something that should have gone to gift balance went to the card. It is SO STUPID.

Painful to make use of role accounts for security reasons

This last section relates solely to Apple TV. I’m security conscious. No, I don’t want my iCloud ID inhabiting the stupid piece of hardware that sits under my TV and lets anyone in my home watch Netflix or Youtube TV. How do I know what is or isn’t running on that device, or what can be extracted from it or my iCloud? I want to use a role account specific to my Apple TV’s.

Once again, you must give up convenience to achieve the goal the Apple way. Browsing and purchasing movies is dramatically easier to do from my tablet versus swiping around endlessly on the little Apple TV remote. Well, I can’t shop as my Apple TV role account on anything but a device running Apple’s blessed apps that is logged into the same Apple ID as the Apple TV. There goes the tablet idea. The only way around that is to now enroll the Apple TV role account in family sharing; then I can purchase on my primary ID on my other devices and it’s auto shared to the role account.

Well, that doesn’t work too bad, but of course involves all the problems outlined above, and one additional. Enrolling a role account in family sharing requires a device other than an Apple TV. So now you have to figure out which device you’re going to log your own Apple ID out of, and deal with that hassle, so you can log in as the role account, add to family, then flip back, all so your Apple TV can join the family.