Stephen Hackett returns to the show to help me make sense of a problem that is hard even to describe, let alone solve, regarding Apple One, family sharing, a separate Media & Purchasing account, and iCloud storage space. Also: what we’re expecting from WWDC 2026.

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Transcripts: Unofficial but surprisingly good.

Links:

Cross Forward — David Smith’s suite of iOS apps, where Stephen is now managing director.
512 Pixels.
Connected — The weekly podcast Stephen co-hosts with Myke Hurley and Federico Viticci.
Apple Support:
- Migrate purchases from one Apple Account to another Apple Account.
- What happens to your iCloud storage when you sign up for Apple One.
Stephen’s post on the restrictions around Apple Account migration.

This episode of The Talk Show was edited by Caleb Sexton.