Mac Geek Gab — Apple Tips, Tricks, and Troubleshooting

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.

00:00:00 Mac Geek Gab 1156 for Monday, August 24th, 2026

August 24th: National Waffle Day

MGG Monthly Giveaway – Win a license to Yoink, Screenfloat, Transloader, or DeskMat from Eternal Storms

Quick Tips

00:00:01 Clifton-QT-Delete Stale Unsent Messages

00:05:08 Jim-QT-Move the Dock between displays with your mouse

Disable Click on Desktop to Expose

00:10:00 Pete-Customize Location Sharing in iOS 27

00:13:54 Aron-QT-1149-Save iMessage Videos with Click-and-drag

00:14:32 Bruce-QT-1148-Setup TextExpander Snippets for Pasting as Text

Sponsors

00:19:13 SPONSOR: Gusto. Get three months free when you run your first payroll when you start at https://gusto.com/MGG

00:20:47 SPONSOR: Hims is changing men’s healthcare by providing convenient, quality care, 100% online. Start your free online visit today at https://Hims.com/MGG.

Your Questions Answered – feedback@macgeekgab.com

00:22:29 Bruce-Troubleshooting a slow passwords database

Base to open sqlite database

SQLite Browser

00:35:03 Jim-How do I get my Recents folder to behave?

00:42:35 Harvey-How to deal with TextExpander stopping expansion

00:48:44 Eric-MacUpdater replacement options?

Updatest

CleanMyMac’s Application Updater

00:56:25 Heidi-How can I get OneNote to stop crashing without losing all my data?

Obsidian

01:06:02 Roy-What are your long-term storage plans?

Cloud Backups – BackBlaze, iDrive E2, iCloud

Local Storage – Drobo (RIP), Synology (Adam has DS423+)

Hyper Backup and Arq Backup

New SuperDuper 4

01:20:30 MGG 1156 Outtro

MGG Monthly Giveaway

Bandwidth Provided by CacheFly

Pilot Pete’s Aviation Podcast: So There I Was (for Aviation Enthusiasts)

The Debut Film Podcast – Adam’s new podcast!

Dave’s Business Brain (for Entrepreneurs) and Gig Gab (for Working Musicians) Podcasts

MGG Merch is Available!

Mac Geek Gab iOS app

Mac Geek Gab YouTube Page

Mac Geek Gab Live Calendar

This Week’s MGG Premium Contributors

MGG Apple Podcasts Reviews

feedback@macgeekgab.com

224-888-GEEK

Active MGG Sponsors and Coupon Codes List

BackBeat Media Podcast Network

Command+Comma jumps you straight into any well-coded Mac app’s settings, no menu-hunting required, and Option+Return reveals the formula in any Numbers cell (Command+Return puts the result back). If your cross-platform Logitech keyboard has its Command and Option keys backwards, hold Fn+Shift+O for three seconds to flip the firmware into Mac mode — Fn+Shift+P sends it back to PC. While you’re at it, download the PDF manual for every new piece of gear today and stash it in Books so it syncs everywhere, because that manual won’t be on the manufacturer’s site three years from now. You’ll also hear why Siri AI in the iOS 27 betas is genuinely iterative: you can follow up, edit, and append without starting over. Plus the best quick tip anyone’s sent in: go listen to the old episodes.

Then you’re into your questions. Skipping Tahoe on your way to Golden Gate? You pay the re-indexing tax either way, so make the one jump instead of two. You’ll get the cable-bag answer (mesh zipper pouches you can see through, plus a slim organizer case that slides in next to your laptop), the 4K travel monitor that earns its space, and how one listener had Claude Cowork build an exhaustive Mac migration checklist.

You’ll hear why consolidating into a single password manager makes your next nuke-and-pave dramatically less painful, and whether an app that vets every link before you click it could actually exist, because knowing where a link really goes is how you Don’t Get Caught. Plus: build and sideload your own single-use iOS apps for free with your Xcode personal team (AltStore and Sideloadly make it stick), why Messages keeps splitting your family group thread and what actually works, and a long-overdue robot mower update covering stereo vision versus LiDAR, all-wheel drive, and what your yard size really costs you.

00:00:00 Mac Geek Gab 1155 for Monday, August 17th, 2026

August 17th: Black Cat Appreciation Day

MGG Monthly Giveaway – Win a license to Yoink, Screenfloat, Transloader, or DeskMat from Eternal Storms

The MGG Merch Store is Live!

Quick Tips

00:00:01 Christopher-QT-Command+Comma gets to App Settings NOW!

00:03:50 Wayne-QT-1151-Option+Return in Numbers shows Formula for current cell

00:05:21 Jimmy-QT-Use Fn+O to switch a Logitech Keyboard into Mac mode

Bonus Quick Tip: System Settings > Keyboard > Keyboard Shortcuts… > Modifier

Bonus Bonus QT: Download PDFs of your user manuals and save them in Books (which syncs!)

00:11:26 Paul-Siri AI is transformative and iterative, even with local apps

00:15:16 Pilot Pete-If you’re on the iOS 27 Betas: Settings > Siri > Try Siri AI Beta

00:21:47 Joe-QT-The Best Quick Tip Ever…Listen to old episodes!

Sponsors

00:24:09 SPONSOR: Helix Sleep makes premium mattresses and bedding that are customized to fit your personal needs, and conveniently shipped to your door. Go to https://helixsleep.com/MGG for 27% Off Sitewide.

00:25:50 SPONSOR: Shopify. If you’re ready to stop putting off your business and start selling, sign up for your free trial and start selling today at https://Shopify.com/MGG

Your Questions Answered – feedback@macgeekgab.com

00:27:18 Harvey-Long Jump to Golden Gate or Tahoe First?

00:30:48 Rod-Which cable organizer bags do you use?

Mesh Zipper Pouches

Cable organizer travel case

ViewSonic VX1655-4K

00:40:15 Alexander-Using Claude Cowork to build a Mac migration checklist

00:42:58 Patrick-QT-1154-Using a password manager makes Nuke-and-Pave simpler

00:48:14 Clif-What about an app that checks every link I click?

00:53:57 Joe-Can I create my own single-use iOS apps without paying for a developer account?

00:58:59 Kim-Why Messages is Splitting Groups and What to do about it?

Cool Stuff Found

01:05:48 ATC-Altstore or Sideloadly

AltStore

Sideloadly

01:09:24 Robot Mowers Revisited

eufy Robot Mower e15 – $1,199.99

Segway Navimow i215 LiDAR Robot Mower – $1,599

Mammotion LUBA mini 2 AWD – $1,799.00

Navimow X4 Robotic Lawn Mower – $2,499.00

01:24:26 MGG 1155 Outtro

MGG Monthly Giveaway

Bandwidth Provided by CacheFly

Pilot Pete’s Aviation Podcast: So There I Was (for Aviation Enthusiasts)

The Debut Film Podcast – Adam’s new podcast!

Dave’s Business Brain (for Entrepreneurs) and Gig Gab (for Working Musicians) Podcasts

MGG Merch is Available!

Mac Geek Gab iOS app

Mac Geek Gab YouTube Page

Mac Geek Gab Live Calendar

This Week’s MGG Premium Contributors

MGG Apple Podcasts Reviews

feedback@macgeekgab.com

224-888-GEEK

Active MGG Sponsors and Coupon Codes List

BackBeat Media Podcast Network

You’ll start with a travel charger that swallows 200-plus countries into one brick, then find out that macOS Tahoe 26.6 is quietly rebuilding your Spotlight index to get ready for macOS 27…and hear the theory on why Apple wants that churn finished before you upgrade. You’ll get talked into finally looking at Raycast (with a nostalgia lap through Quicksilver, LaunchBar, and Alfred), meet Brett Terpstra’s TerminalWidget as the GeekTool replacement you’ve been waiting a decade for, and learn how Paperless-ngx in Docker can run your entire paperless workflow off a Mac or a Synology. There’s Type Switch for anyone living in two keyboard layouts, LibraryThing for the book hoarders, Nixbook for putting an operating system with guardrails on an old Mac, wallet tracker cards that double as digital business cards, and Tailscale Grants so the family you added to your tailnet can’t go wandering your whole network. You’ll also stop fighting the Sonos app and just AirPlay to your speakers, and pick up the Siri fix that ends the “did you mean” death spiral: answer “the first one,” not by repeating yourself.

Then it gets real. You’ll sit in on the question every geek eventually faces: Migration Assistant or nuke and pave? You’ll hear why a half-fresh install is the worst of both worlds, how keeping the old machine alive on your network turns a scary afternoon into a safe one, and where to log in and reclaim those third-party licenses when you hit your device limit. You’ll learn what those “free credit monitoring after a breach” offers are actually worth, why freezing your credit at all three bureaus costs nothing by law no matter how hard they upsell you, and the surprise bonus that a credit lock also blocks buy-now-pay-later signups. And when your Synology Assistant app goes Intel-only, finds.synology.com finds your NAS from the browser. Five new things, minimum, so whatever this week throws at you, don’t get caught.

00:00:00 Mac Geek Gab 1154 for Monday, August 10th, 2026

August 10th: National Spoil Your Dog Day

MGG Monthly Giveaway – Win a license to Yoink, Screenfloat, Transloader, or DeskMat from Eternal Storms

Cool Stuff Found

00:00:01 John-CSF-Anker Nano Travel Plug Adapter for over 200 Countries

00:02:27 Hey there, Pilot Pete!

00:03:28 Allen-CSF-Raycast is the best app launcher, and it’s free!

Alfred

QuickSilver

00:07:11 macOS Tahoe 26.6 optimizes the Spotlight index to prepare for macOS 27

00:12:26 Jessi-CSF-TerminalWidget to replace GeekTool

00:14:58 Max-CSM-Type Switch for people who regularly type in more than one language

00:16:15 Paul-CSF-Paperless-NGX runs in a docker container

00:18:43 Mike-CSF-Pause Take9

00:19:57 Also…beware of recurring in-app purchases from scammy apps.

00:22:58 KingKelson-CSF-1130-LibraryThing for organizing books (and Kevin, too)

00:23:53 Don’t sleep on Sonos with AirPlay

00:28:02 Does Siri on HomePod get smarter with Apple Intelligence?

00:30:22 You can tell Siri AI “the first one” or “the third one” when it gives you an audible list of options for its (potential) translation of your commands

00:33:33 Siri AI is still misgendering people despite the update to their Contact record

00:35:42 Joel-CSF-Ridge Wallet Tracker Card

Rolling Square AirCard

00:38:44 CSF-TOS 7.0 for TNAS— Full Native AI NAS OS (leveraging OpenClaw)

00:44:36 WillRun4Fun-CSF-Nixbook for putting linux on older Macs

00:47:04 Jonathan-Tailscale Grants allows you to control what your family can do

Sponsor

00:50:13 SPONSOR: CleanMyMac. Get Tidy Today! Try 7 days free and use our code MACGEEK for 20% off at https://clnmy.com/MACGEEK

Your Questions Answered – feedback@macgeekgab.com

00:52:29 Mark-Nuke and Pave vs. Partial Migration?

01:06:46 Andy-Should I take the credit monitoring service offers?

PIlot Pete says: freeze your credit bureau accounts

TransUnion Freeze

Equifax Freeze

Experian Freeze

01:13:21 Joe-How do I find my Synology server?

01:17:40 MacPaw and Liquid AI bring On-Device AI to Millions of Mac Users

01:18:48 iNET App for local scanning

01:19:47 MGG 1154 Outtro

MGG Monthly Giveaway

Bandwidth Provided by CacheFly

Pilot Pete’s Aviation Podcast: So There I Was (for Aviation Enthusiasts)

The Debut Film Podcast – Adam’s new podcast!

Dave’s Business Brain (for Entrepreneurs) and Gig Gab (for Working Musicians) Podcasts

MGG Merch is Available!

Mac Geek Gab iOS app

Mac Geek Gab YouTube Page

Mac Geek Gab Live Calendar

This Week’s MGG Premium Contributors

MGG Apple Podcasts Reviews

feedback@macgeekgab.com

224-888-GEEK

Active MGG Sponsors and Coupon Codes List

BackBeat Media Podcast Network

Your quick tips run deep this week. Learn why snapping a throwaway photo is the fastest route to every picture you’ve ever taken at that spot, then rediscover Libby for free ebooks and audiobooks from your public library. You’ll find the hidden Attachments Browser in Notes (Command-3) that filters your notes by scans, documents, maps, and websites — plus a reminder that tagging still beats foldering. Drag the items in the Messages plus menu into the order you actually use them, right-click your Activity Monitor column headers to surface the data you’re missing, and open two windows on the same Excel or FileMaker document so building formulas stops feeling like guesswork. Scott explains why he left Mint Mobile for US Mobile and put his two lines on two different networks, and Ron shows you how VoiceOver can read the date the moment your iPhone wakes. Don’t Get Caught assuming your QR scans are saved: the Code Scanner app throws away your link history when you close it, so use the Camera app or tap through to Safari.

Then things get interesting. Dave walks through migrating to a new M4 mini without Migration Assistant, using Homebrew casks to reinstall apps cleanly instead of dragging years of cruft along. Adam reports from the iOS 27 public beta where the new Siri is finally delivering — except it keeps misgendering his kids based on their first names, and the fix might live in your contact records. Paul shares first impressions of the Golden Gate beta, and Ron’s question sparks a real conversation about whether a VPN or iCloud Private Relay deserves the spot on your device (spoiler: they don’t play nicely together). You’ll get honest advice on whether to buy the next iPhone or wait, plus clarity on encrypted drives, exFAT, and why moving to APFS is the safer bet: back up first, because you will lose data. Cool Stuff Found closes it out with Nib for fully on-device transcription and apfel, which gives you command-line access to the LLM already sitting on your Mac.

00:00:00 Mac Geek Gab 1153 for Monday, August 3rd, 2026

August 3rd: Big Forehead Day

MGG Monthly Giveaway – Win a license to Yoink, Screenfloat, Transloader, or DeskMat from Eternal Storms

The MGG Merch Store is Live!

MGG Monthly Giveaway

Quick Tips

00:00:01 Todd-QT-1150-Take a Photo to easily find past photos at the same location

00:05:13 Deborah-QT-1148-Don’t forget about Libby for free book rentals

Dungeon Crawler Carl

00:09:10 Adam-QT-Notes, View > Show Attachments Browser for a filtered look at your Notes data

And also don’t forget about #tagging your notes

00:11:48 Managing notes and tags and lists and reminders

00:14:54 Ron-QT-Rearrange iPhone Messages + menu

00:17:22 Ben-QT-1149-Right-Click Activity Monitor Headers to add columns

00:19:25 Todd-QT-Use Multiple Windows for the same document in Excel, FileMaker, and more

00:21:35 Scott-QT-1151-The reason I switched from Mint Mobile to US Mobile

00:25:09 Ron-QT-Setup your iPhone and iPad to read the date upon wake

00:26:19 Todd-DGC-1152-Code Scanner app doesn’t save link history

Sponsors

00:29:00 SPONSOR: OneSkin. Born from over a decade of longevity research, OneSkin’s OS-01 Peptide is proven to target the visible signs of aging. Get 15% off OneSkin with the code MGG at https://www.oneskin.co/MGG  #oneskinpod #ad

00:30:30 SPONSOR: Gusto. Get three months free when you run your first payroll when you start at https://gusto.com/MGG

00:31:55 SPONSOR: Hims is changing men’s healthcare by providing convenient, quality care, 100% online. Start your free online visit today at https://Hims.com/MacGeekGab.

Migrating without Migration Assistant

00:33:15 Dave-Migrating to a new M4 Mini: The benefits of installing your apps with homebrew

Updatest

Beta Thoughts

00:36:54 ATC-On the Public iOS 27 beta…with an issue?

Siri AI is beginning to live up to (at least some of!) the hype

Except (at least in the public beta) Siri keeps misgendering people based upon their first names

00:50:27 Paul-Initial thoughts on the Golden Gate beta

00:55:26 iOS 27 Liquid Glass Enhancements

Your Questions Answered and Tips Shared!

00:56:39 Ron-Should I use A VPN or Apple’s iCloud Private Relay?

PIAVPN.com/MGG

01:05:39 Wi-Fi incompatible with iCloud Private Relay

01:07:17 James-Seeking Advice and Opinions for Upcoming iPhone Upgrade

01:15:43 Galen-?-Clarification on HFS+ Encryption Support Dropping in 2027

Lexar 2TB Armor 700 SSD

Cool Stuff Found

01:20:55 Yuki-CSM-Nib – transcribe audio locally on your Mac

01:23:16 Todd-CSF-apfel uses your Mac’s free, local LLM

01:26:38 MGG 1153 Outtro

MGG Monthly Giveaway

Bandwidth Provided by CacheFly

Pilot Pete’s Aviation Podcast: So There I Was (for Aviation Enthusiasts)

The Debut Film Podcast – Adam’s new podcast!

Dave’s Business Brain (for Entrepreneurs) and Gig Gab (for Working Musicians) Podcasts

MGG Merch is Available!

Mac Geek Gab iOS app

Mac Geek Gab YouTube Page

Mac Geek Gab Live Calendar

This Week’s MGG Premium Contributors

MGG Apple Podcasts Reviews

feedback@macgeekgab.com

224-888-GEEK

Active MGG Sponsors and Coupon Codes List

BackBeat Media Podcast Network

Your Quick Tip arsenal gets a serious upgrade this week: use the Live Text button to make scanning QR codes easier, resurrect Apple Mail’s Predicted Mailbox when it mysteriously grays out, and run softwareupdate –history in Terminal to see every macOS update your Mac has ever installed. You’ll also hear how one listener’s Shortcuts automation fixes AirPods auto-play, why BBEdit is your secret weapon for editing Excel formulas and tailing log files, and how Safari’s Show Reader option strips the junk from cluttered pages — plus a bonus riff on the real trade-offs between convenience, privacy, and the content you actually want. And yes, Siri AI in the iOS 27 betas is finally impressing people, with real-world examples to prove it.

Then Dave Hamilton and Adam Christianson dig into your questions: why Safari drops website connections (and how ping helps you diagnose it), whether those archive drives sitting in your drawer need regular care (spoiler: don’t get caught trusting a single backup you never spin up), and the smartest path for migrating your custom email domain from Google Workspace to iCloud. You’ll also get the scoop on replacing the aging Paperless app before Rosetta vanishes with macOS 28, and a challenge worth taking: get your AI out of the chat window and into doing actual work for you. Press play, take notes, and Don’t Get Caught.

00:00:00 Mac Geek Gab 1152 for Monday, July 27th, 2026

July 27th: Gary Gygax Day

MGG Monthly Giveaway – Win a license to Mole

Quick Tips

00:00:01 Todd-QT-Use the Live Text button to make QR codes easier

00:06:43 Steve-QT-Using Apple Mail’s Predicted Mailbox

Bonus QT: Connect your inbox to your favorite LLM (via an MCP Connector?) and ask it “please tell me the ten most important emails requiring my action today.”

00:09:55 Stephen-Some of Siri AI’s improvements in the iOS 27 betas

00:17:54 Mike-QT-1151-Solve AirPods auto-play issues with Shortcuts

00:19:15 Craig-QT-Use ‘softwareupdate –history’ to see every macOS update your Mac’s ever done.

Adam’s Safe Download Version for XProtect

00:22:41 Mike-QT-You can still buy StyleWriter II cartridges at Staples!

00:24:11 Todd-QT-1151-Edit Excel Formulas in BBEdit

00:25:47 Kiwi Graham-QT-View log tails with BBEdit

00:29:01 Andy-QT-Use Safari’s “Show Reader” option to force reader view

And a bonus conversation about the balance between convenience, privacy, and the entertainment we want

Sponsors

00:38:18 SPONSOR: Private Internet Access VPN – Save 83% off your VPN service PLUS four free months with a two-year plan at https://PIAVPN.com/mgg.

00:39:32 SPONSOR: Decagon. Ready to transform your customer support? Decagon helps companies create personalized, concierge-style customer experiences with AI agents across chat, email, voice, and SMS. Go to https://decagon.ai/MGG to get a personalized demo and see what Decagon can do for your team.

00:40:59 SPONSOR: BBEdit, the power tool for text from Bare Bones Software; now with integrated Notebooks and extended language support. https://www.barebones.com/products/bbedit/

Your Questions Answered and Tips Shared!

00:42:17 David-Why does Safari drop website connections?

ping -t 5 website.com

00:51:44 Using location to help deliver content

00:54:15 GW-Do I need to care for my archive drives?

01:02:30 Jonathan-How do I migrate my email domain from GSuite to iCloud?

01:09:45 Kim-Which Paperless replacement and migration path are you using?

macOS loses Rosetta in 2027 with macOS 28

softwareupdate –install-rosetta

01:16:03 Get out of Chat with your AI

01:18:51 MGG 1152 Outtro

MGG Monthly Giveaway

Bandwidth Provided by CacheFly

Pilot Pete’s Aviation Podcast: So There I Was (for Aviation Enthusiasts)

The Debut Film Podcast – Adam’s new podcast!

Dave’s Business Brain (for Entrepreneurs) and Gig Gab (for Working Musicians) Podcasts

MGG Merch is Available!

Mac Geek Gab iOS app

Mac Geek Gab YouTube Page

Mac Geek Gab Live Calendar

This Week’s MGG Premium Contributors

MGG Apple Podcasts Reviews

feedback@macgeekgab.com

224-888-GEEK

Active MGG Sponsors and Coupon Codes List

BackBeat Media Podcast Network