People who use their Macs to back up or sync their iPhones and iPads have discovered they must enter their device passcode for every connection. What’s up with that?!? Adam Engst explains: it’s Apple’s ham-handed response to a security vulnerability.

Apple has updated all of its operating systems, adding the Freeform digital whiteboard app, support for Advanced Data Protection for iCloud, Apple Music Sing, Stage Manager on external displays, and various smaller improvements. A fix for a serious security vulnerability encourages updating soon.

Apple has announced Advanced Data Protection, an optional switch that enables end-to-end encryption for more types of iCloud data, including iCloud Backups, iCloud Drive, Photos, Notes, Reminders, and more.

Many Mac user groups have dissolved or are a shadow of their former selves. Not so the Naples MacFriends User Group, which has embraced the Internet and attracted hundreds of members from around the world. Adam Engst shares more on that, plus recommends Howard Oakley’s work at the Eclectic Light Company blog and provides an update on iCloud delivery problems for TidBITS subscribers.

TidBITS Talk readers shared an insightful essay that nicely describes the motivation of many TidBITS members in supporting us and a tip that the Gmail app now supports non-Gmail accounts.

Want to rely on iCloud Mail as your email provider but use a custom domain for your email address rather than icloud.com, me.com, or mac.com? Apple has now opened up that feature for testing. Here’s what you need to know.

A perfect storm of errors led to Dustin Curtis being locked out of many Apple services, with no easy way to get help from Apple. We try to tease out how this happened.

Apple has expanded its stable of subscription services with the addition of Apple Fitness+, an integrated “workout experience” that relies on multiple Apple devices and an ever-changing collection of workout classes. Plus, the company will soon offer bundles of services under the Apple One name.

After being warned by both iCloud and Gmail that he was running low on storage space, Adam Engst embarked on a mission to free up cloud space rather than pay for more than he needs. If your clouds are filling up too, follow along to avoid missing email, failing file syncs, and more.

Logging into a new Apple device may result in a prompt that asks you for the passcode or password of another one of your devices. Glenn Fleishman explains why this happens and why it’s a good idea.