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Mail Attempting to Sync Previous Recipients Despite Setting

5 August 2026 at 22:11

Jeff Johnson (Hacker News):

Nonetheless, when I send an email in Mail app, from a non-iCloud account to an non-iCloud account, Mail immediately triggers an iCloud connection, as revealed by Little Snitch.

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What could Mail be querying and saving in CloudKit when I’ve disabled Mail in iCloud?

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As you can see in my screenshot at the beginning of this blog post, I have Contacts turned off in iCloud settings, so my Previous Recipients list should not be synced to iCloud. Nonetheless, I followed the commenter’s suggestion of logging in Terminal. I saw log messages that referred to com.apple.mail.recents, which might indicate Previous Recipients and would certainly explain why this happens when I send an email.

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I do object to notifying Apple that I’ve just sent an email. That in itself seems like a violation of my privacy.

The settings are confusing, even more so than with System Preferences. If you go to System Settings β€£ Apple Account, it shows a round rect that says Mail and shows the Mail icon. If you click this, it lets you uncheck Sync this Mac for iCloud Mail. This mirrors the iCloud Mail checkbox that you get when you click See All to see the full list of apps. I don’t like how the top-level name and icon suggest that you’re going to a settings sheet for the Mail app, but then it actually gives you iCloud settings.

Importantly, there’s also another Mail checkbox in that list. It’s easy to miss because, first, why would you expect to see two Mail checkboxes?

And, second, it’s not obvious that there are actually three lists: a bunch of β€œfavorite” system apps, in non-alphabetical order, for some reason including lesser ones like Freeform and Image Playground; followed by a second list of system apps in alphabetical order; and then a third list of alphabetical third-party apps.

Mail is in the second list, along with (to me) other top-tier apps like Books and Maps. Anyway, this second Mail checkbox controls the syncing of non-mail Mail data such as rules and smart mailboxes. But not, apparently, according to Apple, the previous recipients.

Previously:

Confidential Apple Files in iCloud

4 August 2026 at 19:59

Juli Clover:

The way Apple combines work and personal iCloud accounts left some employees able to access confidential documents after departing the company, reports The Information. The site spoke to more than half a dozen former Apple employees who were unknowingly left with access to sensitive content.

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Apple told The Information that the OpenAI lawsuit is unrelated to any files left available on iCloud and that it does not pursue legal claims against former employees who accidentally have Apple documents in their personal iCloud accounts.

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In a now-settled legal dispute, chip company Rivos claimed Apple intentionally lets former employees retain access to files β€œas part of a planned effort to generate a pretextual basis to sue the employees and their new employer for β€˜stealing’ Apple material.” In the Rivos case, an employee was targeted for keeping work files in his personal iCloud account.

Andrew Orr:

The documents included confidential material such as plans for product launch events. The former employees said they made no effort to retain access and unexpectedly found the files mixed with their personal iCloud data.

The problem reportedly grew from Apple’s practice of encouraging employees to connect their personal Apple IDs to company-funded iCloud storage.

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Apple also relied heavily on iMessage for workplace conversations and file sharing before rolling out Slack around 2019. Former employees could retain old iMessage conversations and attachments, while Apple could terminate their Slack access when they left.

John Gruber (Mastodon):

If you use your personal Apple ID, you get a magic β€œApple Work” folder in iCloud Drive. When you leave Apple, that β€œApple Work” folder disappears. But any other files or folders that were shared with you that were outside that magic folder are still in your iCloud Drive, because it’s still your personal iCloud account.

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You still have the same Apple ID account, even though you no longer have an employee @apple.com email account. Overall, this is a humane way of dealing with digital identity. Your Apple ID account is you, the person, not β€œexample@icloud.com”, one specific unique email address. And you, the person, may well have multiple email addresses — all of which can be associated with your one Apple ID account. That makes Apple IDs more nuanced and complicated than a simple mapping of one email address = one account. And it obviously makes access restrictions more complicated.

Yesterday, OpenAI released messages to show that Apple employees (with permission) retained access to the departing employee’s personal iCloud account so that they could access work files that were stored there. It’s just a mess that both the software and corporate policy encourage mixing everything in one account.

Eric Schwarz:

As many things I know about Apple, this whole thing both makes perfect sense and feels absolutely bonkers.

Previously:

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