448: ‘Twins Named John’, With Stephen Hackett

Stephen, you walked me through a wild Apple account mess, and it felt like magic even though you barely touched anything.

You pinged me about a classic dual‑Apple‑ID headache, where old iTunes purchases live on one login and iCloud life is on another, and that split still bites people like us.

My iCloud world runs on a mac dot com address with family sharing, but every app, movie, and subscription I’ve bought forever sits on my daringfireball dot net media account, which has thousands of dollars in movies alone.

Back then it was simple—buy music, sync the iPod—and now the legacy of that choice makes everything complicated.

Apple got better about supporting two accounts on new devices, though there used to be oddities like Game Center guessing the wrong ID.

Apple even built a purchase migration tool, but the fine print is brutal and, in my case, it failed with almost no feedback.

I’ve long thought it works as well as it does because many longtime Apple employees also have split accounts, so the pain was felt internally, but the real breakage for me started with Apple One.

Apple One is a solid bundle on price, but it blends media and iCloud in a way that clashes with two identities, and storage gets weird fast.

Do the math and Apple One Premiere is a bargain versus buying Music, TV, Arcade, News, Fitness, and two terabytes of iCloud a la carte; News+ alone covers my Wall Street Journal habit.

Same here—some services I barely touch, but the bundle still saves money.

We hit about one point nine out of two terabytes and I figured I’d just add more iCloud, but the docs quietly say the family member who bought Apple One must be the one to buy extra storage.

Because your media account owns Apple One, buying iCloud on your iCloud account creates a second bucket that doesn’t combine with the bundle’s two terabytes.

I even tried moving Apple One to my iCloud login so I could stack storage, but then family purchase sharing broke and my family instantly lost Apple Music at the gym, so I rolled it back and did a quick cleanup to buy time.

The workaround is to add your media‑purchases Apple ID as an actual member of your Family Sharing group, enable purchase sharing, and let that account buy the extra iCloud so it stacks with Apple One.

It costs you a family slot and some apps do not allow family sharing, so I re‑bought a few, and I renamed my old account “Legacy Stephen” so it’s clear what it is.

I hunted around and your 512 Pixels post was the only clear write‑up I found; I worried Apple would block adding myself twice, but it worked.

Once purchase sharing is on, it’s impressively transparent across devices, though some categories—like weather—often skip family sharing for cost reasons.

To actually buy iCloud on the media account, I signed that ID into iCloud on a spare iPhone, purchased two terabytes, assigned it to the family, and bam—four terabytes showed up everywhere while my media account uses basically no space.

I went further and made my iCloud account the only one I use daily, left the old media account in the family just for legacy purchases, and stopped buying anything new on it.

If Apple One isn’t offered where you live you won’t hit this exact snag, but Apple One’s special blend of media and iCloud is the root of this trap, and Apple could fix it by selling higher storage tiers inside Apple One.

That would have saved you a couple days of chasing ghosts.

Why not merge accounts? I avoided it because my setup worked, but also because the migration rules are strict and my media email is tied to tons of TestFlight apps.

I tried migrating and it still failed, and TestFlight, music libraries on both accounts, and other edge cases make it a slog that many developers won’t have time to help unwind.

So the ugly but reliable fix is adding my second self to the family and buying storage on that account, or dropping Apple One and paying more piecemeal; I now have a phantom John in Family Sharing.

There’s also the hard limit of six family members, and Apple’s back‑end feels ancient in places, a byproduct of starting from the iTunes store and layering on decades of systems.

That history is why things like upgrade pricing never fit the App Store model, and it’s how we ended up with Creator Studio and duplicate app IDs that let two “Numbers” live side by side on the Mac.

At least the old iWork icons still have a certain charm, even if their glow seems to run in reverse.

Anyway, after this detour into twenty‑five‑year‑old payment plumbing, the run‑up to WWDC feels unusually quiet, and Gurman’s big card—Apple leaning on Gemini—may already be on the table.

Google wants AI at your cursor everywhere, but I expect Apple to be choosier. Let me flip switches without breaking apps, because they usually design around features, not hype.

I do not want wall to wall AI. They should place it with intent, make the writing tools fast and useful when I select text, and let me turn them off cleanly; the cutesy image stuff never felt worth the focus.

Their restraint on deepfakes is good, though there is space between today’s weak output and anything creepy.

Honestly, they could skip photorealistic generators entirely; it is expensive and ethically messy. If they do it, it must be best in class, which clashes with a stance of keeping it tame, so I hope the keynote makes Apple Intelligence a headliner without swallowing the show.

They still have to push the platforms and first‑party apps forward. Last year they buried solid updates; this time I expect a tighter story that avoids big promises and feels more genuine.

On UI, I have been hard on macOS Tahoe, but I like the liquid direction on touch devices. The Watch did not need it, yet Apple can frame last year as the groundwork and now tune the details without saying they blew it.

That is exactly how they will pitch it. It sings on iPhone, and I bet macOS 27 looks cleaner in demos even if they do not call it out.

I loved that they openly fixed the Photos front page after feedback; people just wanted recents up front. If macOS 27 lands, I will explain why it is better; Photos was a universal win because almost everyone relies on it.

You cannot avoid it. The stock camera writes there, even if you sync elsewhere.

Plenty shoot with third‑party cameras and still manage in Photos, and the silence since the fix says it worked. I am optimistic about UI across the board; Alan Dye moving on invites reflection, not a purge, and under Craig everything now ships the same year even if iPhone leads.

We have seen that pattern before, like when iOS 7 modernized first and the Mac followed later.

Year one showed the limits and that the design was iPhone‑first, with iPad late and rough. Anything else before we wrap?

No, it is a fun stretch every year, more complex each time, and I am hopeful they nail this one.

Same here. AI is roaring, but the rules feel clearer now; operating systems still matter, and this is a step change we adapt to, not a replacement. All right.