659: Email Ecosystems: Navigating Apple and Outlook

The hosts preview an upcoming Patreon episode about self-hosted, locally run AI for clients who want AI-powered editing without sending sensitive content to cloud services like ChatGPT, Gemini, or Claude. Jerry describes setting up a local AI system for a client to refresh medically based academic writings while keeping privacy, noting most of the solution was free aside from the computer, and contrasts this with internet-connected autonomous AI bots that require credentials and could be influenced by other bots online. The conversation broadens into Patreon topics about business operations, client attrition and return, and discussing sensitive client situations more freely.

They discuss hardware and product preferences, including choosing iPhone models (with repeated recommendations for an iPhone Pro), interest in a MacBook with built-in cellular to avoid carrier hotspot throttling, and debates about MacBook Pro battery life versus MacBook Air. Sam explains he switched work email to Outlook on Mac and iPhone due to Apple Mail reliability issues and to better separate work from personal notifications, while others compare Apple Mail smart mailboxes to Outlook’s saved searches and discuss organizing workflows with smart folders and flags.

Sam recounts testing whether an iPad could serve as a second travel workstation for a client who relies on an on-prem Mac server (SMB file sharing and FileMaker Server). They run into clunky SMB workflows in iPad Files/Word, inability to favorite deep SMB paths, OneDrive-first behavior in Word, and a FileMaker version mismatch where an older iPad (limited to iOS 16) can’t connect to the newer FileMaker server. They consider shortcuts like web clips but conclude a second MacBook would be simpler.

The episode also covers a bug on iOS/macOS 26 where Microsoft 365 accounts in Apple’s native Internet Accounts setup appear authenticated but don’t actually work, leading them to use Outlook as a workaround and consider resetting MFA/credentials. They close with a story about extending the usability of a 10-year-old MacBook Pro by installing Firefox ESR, and discuss typical Mac lifespan expectations and guidance for clients on replacement timelines.

00:00 Self‑Hosted AI Teaser: Keeping Client Content Private

02:20 Wild West AI Agents: Credentials, Bot Networks & Security Risks

03:34 On‑Prem vs Cloud (and Why VPN Matters)

05:19 Patreon Plug: Business Ops, Client Attrition & “Juicy Stories”

08:16 iPhone Upgrade Debate: Pro vs Air, Foldables & Pro Cameras

09:04 Dream MacBook Features: Built‑In Cellular, OLED & Battery Life

15:42 Switching Mail Clients: Outlook for Work, Sanity on iPhone

18:28 Email Overload & Smart Mailboxes: Apple Mail vs Outlook Searches

26:56 iPad as a Work Device? Real‑World Client Scenarios

29:02 Why the On‑Prem Mac Server Can’t Be Easily Replaced (SMB, Screen Sharing, FileMaker)

29:52 iPad + SMB Shares: VPN Access Works, But Favorites and Navigation Don’t

31:38 Editing Word Docs from a Server: Share Sheet Confusion & Save Behavior

32:25 OneDrive Defaults, Hazel Watch-Folder Ideas, and the “Just Use a MacBook Air” Moment

34:21 Shortcut Hack: Using Web Clips to Jump Straight to Deep Server Folders

36:13 The Dealbreaker: Old iPadOS vs New FileMaker Server Compatibility

37:43 Remote Setup via MDM + VPN Profile (and the Keyboard/Mouse Reality Check)

39:11 Multitasking Limits on iPadOS 16: Split View vs Modern Windowed Apps

41:32 Microsoft 365 Login Bug on iOS/macOS 26: No Password Prompt, Account Weirdness

46:04 Workarounds and Client Perception: “Just Use Outlook” (and Why That Stings)

47:53 Wrapping Up: Keeping Old Macs Alive (Firefox ESR) and How Long Apple Silicon Will Last

52:50 Final Thoughts & Sign-Off

658: From Command to Control: Stories of Digital Dilemmas

From Command to Control: Stories of Digital Dilemmas

The hosts discuss Apple Mail email signatures and discover that when a website URL lacks a prefix, Apple Mail defaults it to an insecure http link, which can trigger junk filtering; they also note cases where a displayed https link still points to http behind the scenes. They compare Apple Mail to Outlook in business environments, mention limitations around advanced signature management, and comment on Apple’s minimal transparency in service-status outage explanations. They cover Apple’s iOS 12 update extending certificates for services like iMessage, FaceTime, and device activation through January 2027, and then shift to opinions and speculation about Tim Cook’s political pandering possibly being tied to tariffs and CEO succession timing. Returning to tech, they explain Apple Pay’s security benefits—device-specific numbers and unique transaction codes—especially after a client’s credit card was repeatedly compromised, and discuss adding additional browser protection via Malwarebytes Browser Guard and Chrome/Safari extension deployment through MDM (Addigy), including using ChatGPT to generate a configuration profile. They also describe using ChatGPT to edit MailChimp newsletter HTML quickly, and explore AI-assisted app development ideas such as an iOS app that converts call logs into calendar entries, referencing a Steven Robles video about building an app with AI while noting potential security pitfalls like exposed credentials. Lgistics issue involving gear ordered for testing via an Amazon locker at Staples. When attempting pickup, the host discovers the locker has no keypad and relies on the Amazon app and NFC. Despite signing into the client’s Amazon account and enabling required app permissions (Bluetooth and device access), the locker cannot be accessed. Amazon customer service suggests the order data may be incomplete due to a third-party seller and issues immediate refunds or credits.

00:00 Welcome In: Time, the Clock Tower, and “Running Out of Time”

00:46 Client Referral Follow-Up: When People Go Radio Silent

01:39 Apple Mail Link Gotcha: Why Your Clean URL Becomes HTTP

04:13 Hidden Signature Code: Displayed HTTPS, Actual HTTP (and Spam Filters)

05:45 Why Apple Should Default to HTTPS (Google Already Does)

08:34 Signature Tools & Workflows: WiseStamp, Outlook, and What Clients Actually Use

10:37 Apple Still Updating Old iOS: Certificate Expiration and 2027 Cutoff

11:40 Tim Cook, Politics, and the CEO Succession Theory

15:06 Bully-Pulpit News Cycle: Waiting for the Next Outrage

16:08 Epstein Files & Accountability: Why Consequences Aren’t Landing in the U.S.

18:16 From Past Scandals to Today: How the Bar Moved (Back to Tech)

19:00 Merch & Sponsorship Shoutouts (The Command Control Power Mug)

19:47 Apple Services Outages & the Vague Status Page Problem

21:14 Why Apple Pay Is Safer After a Card Gets Compromised

23:40 Dashlane vs Malwarebytes Browser Guard: Phishing/Scam Blocking Extensions

28:19 Layered Web Protection: Safari Safe Browsing, DNS Filtering, and Extension Risks

31:36 ChatGPT for Real Work: Fixing a Mailchimp Newsletter with HTML

33:06 AI-Assisted App Idea: Turn Call Logs into Calendar Entries (and Vibe Coding)

37:59 Security Caveats + Wrap-Up Quip About AI Summaries

Best of CCP - 469: Past Performance Is No Guarantee Of Future Results

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Sam Valencia, Jerry Zigmont and Joe Saponare discuss working with Apple technology and clients. Drawn from their combined experience of over 20 years in the Apple Consultants Network, thaey discuss technical support issues both with the technology and working with clients.

653: We Don't Need No Stinkin’ Deferrals

In this episode of Command Control Power, the hosts humorously discuss their tech-related frustrations and the nuances of tech support. They struggle with audio issues at the beginning, but then delve into the timing issues with Apple's OS updates and deferrals, highlighting the challenges of managing these updates for clients. There's a light-hearted recount of personal tech issues, such as using HomePods and streaming music services. They also share the complexities of dealing with ISPs, particularly with switching providers and maintaining service quality. The episode concludes with a quirky story about a tech support session interrupted by a client's unexpected firing.

00:00 Introduction and Banter

01:12 Technical Difficulties and Setup

06:17 ISP Experiences and Switching to Frontier

08:07 Nostalgia and Local References

11:57 Dealing with ISPs and Customer Service

19:46 Frontier Fiber and Recommendations

23:05 Awkward Client Interaction

24:47 Tahoe Deferrals Explained

26:15 Apple's 90-Day Update Policy

29:04 Challenges with OS Updates

32:25 Client Management Strategies

36:49 The Frustrations of Tech Updates

50:45 Humorous Client Stories

52:20 Closing Remarks and Announcements

646: Navigating Tech Updates and Client Communications

In this episode of Command Control Power, the hosts welcome listeners to their December show, tease upcoming Patreon episodes discussing managed service offerings, designing flyers using Canva and ChatGPT, and all-inclusive pricing with Tim Pearson. The episode touches on experiences with a Canva PDF rendering issue using the Preview app in MacOS, including troubleshooting steps with Adobe PDF engines. The hosts share client communication challenges about service rate negotiations and discuss the intricacies of pricing models and plan structures. Additional technical topics include a significant bug with Microsoft Auto Update renaming apps erratically, strategies for managing OnePassword memory prompts and passkey enrollments, and a tip-off from listeners about Backblaze's change in policy for iCloud Drive backups. They wrap up with amusing anecdotes from client interactions and discuss the complexities of web browsers and user understanding of tech terms.

00:00 Opening Banter and Introductions

00:25 Welcome to Command Control Power

01:40 Patreon Teasers and Managed Service Offerings

02:33 PDF Rendering Issues with Canva

07:53 Client Negotiations and Pricing Strategies

28:02 Reselling Services and Client Retention

30:53 Microsoft Auto Update Issues

34:04 Microsoft Auto Update Issues

34:42 Identifying the Problem

35:08 Known Issues and Workarounds

36:29 Installer Process and Conflicts

37:59 Disabling Auto Update

38:19 Microsoft's Response

39:04 Apple's Role in the Issue

39:43 Temporary Solutions

44:08 One Password Tips

53:32 Backup Solutions and Listener Feedback

01:01:20 Concluding Thoughts and Listener Stories

Best of CCP - 427: Guest Host - Tim Pearson of CreativeTechs

This week we welcome long time supporter of the show, Tim Pearson of Creative Techs.

Tim joins us as a co-host.

He talks about traveling on the ferry to do onsite work.

The group discusses the wildfires out west.

Tim shares a story about the time he made a mistake of wearing a Star Wars shirt, causing his meeting to go way overtime.

The group helps Tim with approaching a mistake he made in his business.

Jerry’s talks about the “Screwdriver Effect”

Getting fired by a client is a great opportunity to take another look at how you do things.

Everyone discusses MSP and contracts with clients.

How are the group members finding new work throughout the pandemic?

Sam explains how he started getting referrals from the Apple stores.

The group talks about the Apple Consultants Network program and its benefits.

What is everyone seeing regarding to employees coming back to the offices?

Some people work better in offices and some at home.

Do you have employees or paid friends?