448: ‘Twins Named John’, With Stephen Hackett

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.