On-Site Mac & iPad Mail Help - 18/09/2025 14:49 EDT

I’m a senior who lives just a short walk from Volunteer Park and my trusty Mac Pro has started to feel anything but friendly. Mail shows more than 6,000 messages I thought I’d already purged, my custom mailboxes refuse to stay organized, and the Favorites bar keeps forgetting what I pin.

I also want to read the same mail on my iPad but can’t even add the account—iPadOS rejects every attempt. To round things out, I’d like to start using passkeys yet I can’t get the Mac to generate one in the first place.

Here’s what I need, calmly and step-by-step:
• Permanently delete the backlog of messages and confirm they stay gone
• Re-organize my mailboxes so I can actually find things
• Make sure Favorites save correctly and persist after a restart
• Add my email account to the iPad and verify it syncs
• Walk me through creating and storing passkeys so I’m comfortable using them later

I do better with a patient teacher—preferably, though not necessarily, a woman—and I’m hoping you can come to my home tomorrow at 9:30 a.m. If that’s too soon, next Wednesday, Thursday, or Friday work as well.

You should be comfortable with Apple Mail on macOS, iPadOS settings, and iCloud Keychain or similar passkey managers. Once everything works, please leave me with simple written notes so I can keep things tidy on my own.

If a calm, in-person Apple support session sounds like your thing, I’d love to hear from you.