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

679: New OS, Old Problems

In this episode of Command Control Power, the hosts discuss early experiences with the macOS 27 “Golden Gate” beta, noting it feels snappy and stable but breaks QuickBooks, leading one host to keep QuickBooks on a headless Mac mini running macOS 26. They cover upcoming Apple Intelligence features, including AI-assisted file renaming, Safari profiles and AI-suggested tab grouping, page-change notifications, and Apple Passwords’ potential to automate password changes (which appears incomplete in testing). The conversation compares Apple Passwords with 1Password, explains passkeys with client-friendly metaphors and technical points, and notes issues caused by multiple password tools. They also review AirPods Pro 3 fit and changes, discuss hearing-aid functionality on AirPods Pro 2/3, and share troubleshooting tips for Splashtop permissions and an Apple Mail send bug tied to “check spelling before sending.”

00:00 Show Kickoff

00:08 macOS Golden Gate Beta

01:47 Safari Tab Groups

06:18 Apple Intelligence Highlights

08:39 Passwords Auto Change

17:48 Passkeys Explained

24:01 Passkey Pitfalls

26:33 AirPods Pro 3 First Impressions

26:47 Better Fit Out of Box

27:07 Why Upgrade AirPods

28:08 Lost AirPod Find My

30:10 Sound Signature Debate

31:25 AirPods at Loud Venues

33:03 Hearing Aid Potential

37:00 Remote Setup iPhone Mirroring

42:08 Splashtop Permissions Trick

44:42 Fuzzy Mic Trend Rant

46:50 Apple Mail Send Bug Fix

49:17 Next Episode Teasers Wrap

676: OS 27 Support, Siri AI, and the New Backup Reality

The hosts discuss early impressions of iOS 27 on an iPhone 15 Pro Max and interest in Siri AI on newer iPhone hardware, plus Apple’s macOS 27 compatibility list ending Intel support while continuing support for 2020 M1 Macs, which they estimate could extend security updates to roughly 2029. They debate device lifespans for home and business, note iOS 27 supports iPhone 11, and consider how Siri AI’s on-device, voice-first, screen-aware approach could change form factors and competition. A cautionary story highlights lost Quicken 2016 data due to missing backups and limitations of iCloud Drive and Backblaze, including Backblaze’s cloud-sync folder controversy and retention/restore issues, while Carbon Copy Cloner’s option to temporarily download cloud-only files is raised. They recount multiple Migration Assistant failures resolved by re-wiping and redoing the migration, identify a client complaint as Stage Manager, and briefly cover testing the UniFi 5G Max cellular backup with AT&T and a low-income T-Mobile-based SIM option.

00:00 OS 27 First Impressions

01:13 macOS 27 Compatibility Shift

02:34 M1 Macs Longevity

05:34 Upgrade Cycles and Siri AI

08:30 Siri AI and Voice Future

10:50 AI Hardware Beyond Phones

13:05 Quicken File Lost

15:09 Backblaze Cloud Sync Fallout

23:24 Carbon Copy Cloner Workaround

26:54 Backup Strategy for Workstations

28:20 Migration Assistant Stalls

29:24 Migration Keeps Dropping

30:36 iCloud Backup Wish

31:25 Thunderbolt Reset Fix

32:55 Fallback Migration Options

33:59 Why Did It Fail

34:59 Sam’s Reboot Mystery

36:56 Backups and Backblaze Rant

40:21 Stage Manager Diagnosis

42:48 Settings Menu Weirdness

46:26 UniFi 5G Max Testing

50:18 Wrap Up and Goodbye

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

673: AI for IT Workflows, Solutions and Apple’s Slow Siri Rollout

In this episode of Command Control Power, the hosts discuss practical IT uses of AI, including improving client communications, speeding email migration due diligence via AI-generated PowerShell reporting (mailbox size, forwarding rules, aliases, naming pitfalls, licensing limits), and reducing billing friction by summarizing recorded RingCentral calls in Claude to log hours and generate detailed invoices, including for Ubiquiti camera projects. They debate risks such as blindly running AI-suggested commands, clients acting on AI advice, and data leakage when employees paste company information into public AI tools, emphasizing guardrails, policies, and potential local/private AI setups (e.g., Mac mini with Ollama). The conversation broadens to AI’s impact on IT business models, automation in ticketing, and Apple’s lackluster AI progress, delayed Siri features, privacy positioning, and reliance on partners like Google/Gemini.

00:00 Show Kickoff

00:02 New Studio Tour

00:31 Flag Outage Story

01:35 AI Migration Prep

03:26 PowerShell Due Diligence

05:36 Call Summaries Invoicing

07:31 Automating Call Logs

09:35 AI As Expert Helper

11:51 Safety With Commands

12:58 Clients Using AI

13:54 Data Privacy Guardrails

17:17 Industry Shift Fears

20:07 Auto Reply Ticketing

24:18 Local AI Knowledge Base

26:02 AI Eats Software

27:35 Future Of IT Services

29:04 AI Automation Ethics

30:06 Market Pressure On IT

31:03 Apple Intelligence Doubts

33:10 Privacy And Gemini

35:06 Apple Strategy And Mindshare

37:43 MDM Guardrails Needed

39:39 First Mover Myth

43:32 Ubiquity And AirPods AI

47:21 Beta Plans And Rollout

48:06 AI Policy And Profiles

51:32 Wrap Up And Outro

Best Of CCP - Interview With Dave Hamilton - CEO of BackBeat Media, Mac Geek Gab, Gig Gab, and Business Brain Podcasts

Topics:

-This week we welcome Dave Hamilton of Mac Geek Gab!

-Dave actually grew up a street away from our very own Joe Saponare.

-Dave has some knowledge on the music history in the area.

-Dave has known his co-host, John Braun since they were 15 years old.

-He remembers the days of NCSA Mosaic.

-The Mac Observer and BackBeat Media are just some of Dave’s major accomplishments.

-Wasn’t 2001 just a few years ago?

-Dave takes us down memory lane in the early days of The Mac Observer.

-His original plan was not to continue hosting Mac Geek Gab.

-Being persistent paid off as he reached out to Steve Jobs himself to be included in their new Podcast Directory.

-In both Texas and the northeast, Dave has a quite a technical background.

-Quick Tip from Joe - If the minimum brightness is too bright on your iPhone, you can Reduce White Point under Accessibility>Display & Text Size.

-We talk about listener burnout in the podcast world.

-Mac Geek Gab is on episode 941!

-A tip that Jerry heard on Dave’s show was about Tailscale, which makes a virtual network out of your devices, no matter where you are.

-Sam talks about some tips he learned on recent episodes of Mac Geek Gab.

-The simple stuff is why you get paid the “big bucks”.

-Business Brain - The Entrepreneurs' Podcast is another show Dave co-hosts with Shannon Jean.

-The 20 minute rule - keeping clients engaged every 20 minutes along the way.

-Besides his podcasts, you can find Dave at https://www.davethenerd.com or on Twitter @davehamilton