690: AI-Powered PowerShell, and Carrier Trade-In Traps

Joe and Jerry discuss using iPhone built-in Background Sounds (rain/white noise) and Joe’s reliable Shortcuts automation: when power connects, if the time is after 9:55 PM or before 6:15 AM and audio isn’t already playing (checked via the third-party Actions app), set rain sound and volume and enable it; Siri’s shortcut generation was buggy, while Gemini helped produce working logic. They swap notes on using white noise at home and while traveling, and Joe recounts encountering a bear at night and ideas for a “bear alert” automation. They note Apple Notes lacks version history/rollback and mention the Note Export app as a workaround. Jerry describes using Claude to guide PowerShell incident response for a Microsoft 365 phishing compromise, generating reports and adding an admin-enforced outbound wire-fraud notice. They also compare Gemini/Claude/ChatGPT (including an annoying ChatGPT “pet” hotkey conflict) and praise Duolingo’s habit features. Finally, Joe explains Verizon’s AI chat helped clarify phone unlocking and trade-in financing rules versus AT&T’s device-locking and poor chat results, influencing his upgrade decision.

00:00 Show Kickoff Banter

00:23 iPhone Rain Sounds

01:42 Automating Bedtime Audio

05:44 Actions App Trick

06:20 Bear Encounter Story

10:52 White Noise Sleep Habits

13:41 Notes History Missing

17:27 Yosemite Climbing Doc

20:03 Duolingo Streak Hacks

25:00 Gemini and ChatGPT Pet

27:30 Unforgetful Reminders App

30:17 Phished Microsoft 365

31:29 Global Admin Gone Wrong

32:32 Claude Powershell Cleanup

33:08 Wire Fraud Email Disclaimer

34:25 Conversation History Scam Tactics

35:54 Best Practice Admin Accounts

37:27 Building an Incident Checklist

42:08 Proactive Audits and MFA Training

44:58 Authenticator App Switching Pitfalls

49:16 Break Glass and Defender Layers

51:08 Verizon AI vs Carrier Lock-In

53:06 Trade In Math and Unlock Policies

01:01:56 Wrap Up and Show Milestones

689: Stitches, Switches, and Sketchy Devices: A Podcast Nose Dive

Jerry describes having basal cell carcinoma removed from his nose and urges regular dermatology checkups, then shares how iOS 27 repeatedly warned him before sharing a “sensitive” stitched-and-bloody photo, even suggesting he consult a “trusted adult.” Joe discusses costly RV maintenance and how machines (including hard drives) can fail when left idle, leading into Mac maintenance routines. They debate slang like “cooked,” then talk Apple’s new iPhone lineup, including Jerry’s iPhone 13 Pro Max purchase and their mixed expectations for the first-gen iPhone Duo (weight, outer-screen constraints, camera and battery compromises) alongside improvements like cooling, battery life, and a vapor chamber. They cover Apple Watch “always listening” features, citing Gruber’s privacy rationale, and discuss practical recording/summaries for medical visits. Jerry explains how Claude helps him solve technical issues, analyze security research, navigate health insurance decisions, and produce billable security reporting; they note macOS screen sharing bug fixes and mention keychain migration and safe mode articles. They tease upcoming Patreon topics about a move and walking away from a client.

00:00 Show Kickoff Banter

00:21 Nose Surgery Story

02:30 iOS Sensitive Image Warning

04:43 Scar Care And Skin Checks

05:19 RV Maintenance Costs

06:57 Idle Vehicles And Backup Drives

07:51 Mac Maintenance Cycles

08:57 New Slang Cooked Debate

10:32 New iPhone Pro Purchase

11:09 iPhone Duo First Impressions

13:59 Upgrading From 16 Pro

15:52 Carrier Handoff And eSIM Switching

17:56 Duo Software And Fold Durability

19:26 Foldable Display Durability

20:54 Watch Always Listening Debate

23:24 Trusted Device Privacy Logic

25:53 Real World Recording Use Cases

27:43 Claude as IT Copilot

31:33 AI Summarizes Security Research

34:49 Health Insurance With Claude

39:25 Billable Security Reporting

41:45 macOS VNC Bug Takeaways

43:00 Keychain Migration Confusion

45:33 Safe Mode and Show Wrap

46:19 Patreon Tease and Goodbye

684: Resetting AirTags, Beta Bugs, and Vibe-Coded Mac Health Checks

Resetting AirTags, Beta Bugs, and Vibe-Coded Mac Health Checks

The hosts discuss how to reset an Apple AirTag by inserting and removing the battery five times until a different sound plays, noting newer AirTags may require pressing down. They share issues seen on iOS 27 and macOS betas, including missing app icons in search, slow contact searching, Contacts app odd behavior, Apple Configurator on iPhone failing to enroll devices until using a non-beta phone, and a Control Center white-noise toggle bug requiring reboots. They debate installing macOS 27 “Golden Gate” on production machines, restarting habits, and workflow clutter from Safari tabs, Finder windows, and messy desktops, with Sam recommending an analog black glass dry-erase desktop board. They also note a Safari private browsing/profile issue showing history and Microsoft 365 credential problems. Jerry describes using Claude to “vibe code” an unsigned “MacWorks Health Check” app that collects Mac discovery info and uploads reports to Dropbox via API keys to replace a costly subscription tool.

00:00 Show Kickoff and Setup

00:26 Resetting an AirTag

02:33 iOS Beta Bugs and Contacts Glitches

04:20 Configurator Beta Breakage

07:41 White Noise and Beta Quirks

08:33 Should You Install macOS Betas

13:53 Restarting and Workflow Friction

15:06 Tabs Desktops and Finder Chaos

21:37 Analog To Do Board and Vig Talk

23:19 Vigorish Explained

23:45 Desktop Whiteboard Find

25:12 Madden Movie Tangent

25:55 Safari Private Mode Bug

29:53 Analog Workflow Systems

33:14 Notion For Solo Work

36:26 Vibe Coded Health Check

41:19 Sizing Storage Needs

50:55 Tool Ideas And Wrap

680: Microsoft Retires SMS/Voice MFA, Salesforce SSO Headaches, and SOC 2 Realities

Sam and Joe discuss Microsoft’s plan to retire Microsoft-provided SMS and voice calls for MFA, with key dates of Sept 1, 2026 (users on SMS/voice are automatically enabled for passkeys and nudged to register) and Feb 1, 2027 (blocking enforcement for users whose only MFA is SMS/voice, no opt-out), noting paid/customer-managed telecom options and the need to warn clients, address legacy per-user MFA vs conditional access, and handle shared accounts via shared mailboxes or passkey-sharing tools. Sam recounts a prolonged Salesforce SSO/MFA issue worsened by poor vendor documentation and misleading AI guidance, ultimately tied to a Microsoft KB update. They then cover partnering with Fuji for client SOC 2 compliance support, emphasizing evidence, audits, costs, and ongoing maintenance, plus how cyber-insurance questionnaires drive security improvements. The episode also touches on residential support cases, Vision Pro support challenges with DRM blocking screen mirroring, and show wrap-up.

00:00 Show Kickoff

00:17 Microsoft MFA SMS Retirement

00:44 Key Dates and User Impact

03:28 Authenticator Backups and PSAs

04:40 Legacy MFA Cleanup Challenges

07:36 Conditional Access Licensing Risks

10:12 Shared Accounts and Passkeys

12:21 Salesforce MFA SSO Headaches

13:25 AI Missteps and Vendor Docs

17:50 SOC 2 Help from Fuji

21:23 SOC 2 Costs and Maintenance

22:49 Easy Buttons and Real Audits

26:27 Cyber Insurance Questionnaires

27:53 Partnering for Expertise

29:07 Cyber Insurance Foot in Door

30:31 Apple Store Referral Win

31:01 Lightroom Migration Pitfalls

34:31 Blocked Contacts Mystery

38:04 Email Search and User Training

40:02 Supporting Vision Pro Clients

47:28 Amazon Returns and Exceptions

50:24 Wrap Up and Callouts

674: Champing at the Bit for iOS 27 and Ghostly Hackers

The hosts discuss Jerry installing iOS 27 beta on an iPhone 15 Pro Max and watch, reporting strong stability, snappy performance, and minor reported edge-case crashes, while noting Siri AI requires newer hardware due to RAM constraints and that others find the new Siri improved. Joe shares a fresh issue deploying an MDM configuration profile to disable Siri: users still received “unable to use Siri” prompts because “Listen for ‘Hey Siri’” could remain enabled, requiring removing the profile, turning it off locally, and reapplying; Apple Intelligence also wasn’t fully disabled. Sam describes improving client offboarding by building a monday.com form that feeds Zendesk tickets, and the group compares running lean teams, using subcontractors and Foundation as pay-as-you-go helpdesk support (including an optional branded phone line). They also cover business uncertainty, tax-law changes affecting S-corps, and handling time-consuming “I’ve been hacked” client calls.

00:00 Show Kickoff Banter

00:35 iOS 27 Beta First Impressions

01:42 Installing Live and Siri AI Limits

04:40 MDM Glitch Disabling Siri

07:52 Advising Clients on Apple AI

10:16 Offboarding Workflow in Monday

12:25 Solo Juggling Without the Team

15:49 Jerry Business and Tax Updates

19:05 Hacked Device Panic Call

20:51 Explaining Normal iOS Mac Features

22:46 Clean Bill of Health Limits

24:07 Lean Teams and Overhead

28:51 Using Outsourced Helpdesk

29:58 Onboarding Big Client While Away

34:56 Pricing and Custom Phone Line

37:57 How to End Free Calls

41:56 Defining Success and Boundaries

45:23 Wrap Up and Outro

672: Apple TV Picks, Disclosure Theories, and Practical macOS Admin Tips

The hosts discuss Apple TV shows they were late to, including The Morning Show and For All Mankind, and talk about Hail Mary Project, comparing the film’s “E.T.-esque” choices to Andy Weir’s book. They segue into UFO/alien “disclosure” chatter, mentioning Spielberg’s upcoming Disclosure Day, the film Age of Disclosure, alleged legacy programs, and the idea that disclosure could distract from other news. The conversation returns to Apple and IT topics: an Apple fix for managed login window settings not resetting, a Family Sharing change allowing adult members to use their own payment methods, and why hidden Wi‑Fi networks trigger Apple security warnings. They share productivity tips, including a Shortcut to sort Contacts by creation date, NFC tag uses, remapping Safari’s Quit shortcut, menu bar icon spacing via defaults write, Finder column auto-sizing, and Boring Notch. Jerry describes building a client podcast studio around the RØDECaster Video S and Rode support, then they explain using Adigy DDM to automate macOS updates and upgrades with policies, scheduling, and monitoring alerts.

00:00 Show Kickoff Banter

00:18 Apple TV Catch Up

02:12 Hail Mary Debate

04:25 Disclosure Day Talk

07:32 Mac Login Banner Bug

09:47 Family Sharing Payments

10:50 Hidden WiFi Warning

13:25 Contacts Sort Shortcut

17:47 NFC Shortcut Ideas

20:38 Safari Quit Remap

24:00 Menu Bar Icon Tools

24:56 Menu Bar App Trust

26:16 Declutter Menu Bar

27:09 Shrink Icon Spacing

29:04 Finder Column Autosize

30:28 Boring Notch Tricks

32:10 Building Podcast Studio

33:17 RodeCaster Video S

39:27 Video Podcasts Debate

41:51 DDM Updates Workflow

49:20 DDM Policies and Alerts

55:32 Wrap Up and Patreon