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Ever fire off a text that never actually sent? You’ll learn how to clear those stale unsent iMessages out of the More menu, move your Dock between displays using nothing but your cursor, and set exactly how long you share your location with iOS 27 (anywhere from 15 minutes to 30 days), plus a quiet hide that doesn’t tip the other person off. You’ll also grab videos out of Messages with a simple click-and-drag, and build a TextExpander snippet that pastes as plain text into those maddening web forms that block Command-V in the name of “security.”

Then it’s your questions. Why does the Passwords app crawl on one Mac while syncing fine on everything else? And how do you safely peek inside its SQLite database without breaking it? You’ll find out how to get your Recents folder to actually reflect recent, what’s really happening when an app disables TextExpander expansion, where to turn now that MacUpdater’s databases have gone stale, and what your options are when OneNote crashes on launch and holds years of research hostage. Stick around for all three of us on long-term storage: Synology, cloud archives, and the two-layer approach that keeps your irreplaceable stuff off-site. Adam’s the cautionary tale: a migration he was sure he’d finished, a Drobo powered off for a year, and files that aren’t where he swore he put them. Don’t get caught assuming your backup ran. Go check.

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