659: Email Ecosystems: Navigating Apple and Outlook

Sam and Jerry record an episode of Command and Control Power without Joe, briefly discussing hiking safety, then focus on Microsoft Exchange Web Services (EWS) deprecation affecting Apple Mail on macOS and the ethical question of proactively extending EWS via PowerShell for former clients; they extended it for a few Apple Mail–using customers but wouldn't change settings for non-clients. They describe difficult troubleshooting when business addresses were previously used for personal Microsoft 365 accounts, requiring Keychain resets and, for Apple Calendar sync issues, removing Apple Internet Accounts data. Sam notes quirks with Microsoft passkey QR logins leaving the phone camera active, shares an embarrassing "good Samaritan" story at JNUC, highlights Jamf's AI governance tool, and recounts fixing his own Jamf enrollment by disabling SIP and repairing configuration profile folders before re-enrolling. They also discuss syncing the macOS Downloads folder via iCloud, cautious AI permissions, and AI's usefulness and risks.

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.

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.

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.

Joe and Jerry chat about haircuts, travel plans to Yosemite via Reno and Lake Tahoe amid fires and crowds, and recent wildlife encounters. They discuss upgrading iPhones and frustrations about promised Apple Intelligence features, plus recurring complaints about changing chargers and Apple hardware quality, including deteriorating Apple cases and notoriously poor pre‑M1 MacBook Airs. Joe shares an anecdote about helping an elderly client set up a new Apple account on an M4 iMac while a clock loudly recited affirmations and the Lord's Prayer during an Apple support call. They cover "technical debt" ("Schedule the maintenance or the maintenance will schedule itself"), Mac pricing for RAM/storage, John Siracusa's choice to use an external SSD for a photo library, mixed experiences with M1 MacBook Air performance and batteries, and field benefits of newer Macs. The episode also reviews UniFi improvements (CGNAT alerts, channel optimization, rollback/Safe Ops), using Claude to analyze Wi‑Fi settings, and frustrations when AV installers build weak networks in high-end homes.