How to use Apple’s Messages in iCloud for iOS, Mac

Messages in iCloud is secure enough for most of us, but it opens a new attack vector for enterprise users.

Apple, iOS, Mac, Mac OS, SMS, iMessage, Messages in iCloud
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Along with key HomePod improvements, Apple introduced Messages in iCloud with iOS 11.4. It’s a useful feature designed to store your Messages and attachments in iCloud, but enterprise users should think twice before enabling it.

Security is everything

I’m not saying iCloud is not secure — so long as you use a six- or more digit passcode or (better, but more awkward) an alphanumeric passcode, it’s highly secure. I’m reasonably confident a strong password, Apple’s own systems. and its insistence you use two-factor authentication is enough for most of us.

However, when it comes to valuable enterprise or government data, I am concerned that determined cyber criminals will use phishing, man-in-the-middle, and a range of other complex attacks to get inside accounts if the value of the data they want to access justifies the effort.

What is Messages in iCloud?

When you begin using Messages in iCloud, you’ll find that all your messages (both iMessage and SMS) received across all your devices will be stored on Apple’s servers. A message deleted on one device will be reliably deleted on all of them, and you’ll save lots of space because those communications won’t need to be stored locally.

When you set up a new device, you’ll gain access to all your messages. The bad side of this exchange is that those messages count against your iCloud storage allowance, even though Apple offers a pathetic 5GB of space for free. Messages are still sent and received in encrypted form, so they can’t (easily) be accessed on their journey.

One more thing: Once you offload messages from your devices to iCloud you’ll find the size of the device back-ups you create will be smaller, as they won’t need to include all those messages.

The good things are ...

When your messages are stored on Apple’s servers, you’ll always be able to find or download the ones you need, including attachments and images. When you delete a message on one device, it will be deleted across all your devices, disappearing from the cloud. Incoming messages will be made available across all your Apple products, even if they happen to be switched off when they were originally received. This works across iOS and Mac.

The bad things might be ...

The fact that these messages exist online may be a problem for enterprise users who need to follow strict data security protocols.

While I’m certain most larger enterprises now archive their iMessage sessions (particularly those sent using Business Chat), I’m not convinced they want that data to leak into the public cloud.

The problem is that enterprise information shared via personal messages may now be made available via iCloud. This could become a brand-new attack vector for cyber criminals hoping to undermine company security.

Another risk might be what happens to enterprise data in the event a rogue nation’s security services use local law to demand access to employee iCloud accounts, giving them the chance to explore messages held there.

What I think Apple thinks

Apple attracted a lot of heat in 2016 when it refused to create a way to unlock a work iPhone used by one of the San Bernardino murderers. It argued that if you create a way to unlock one device, then security across the entire platform suffers. This kind of designer insecurity threatens not just personal privacy, but enterprise and infrastructure security.

Apple didn’t say this because it didn’t want to help. Its Privacy - Transparency Reports show it will happily share information with law enforcement when permitted by the courts.

With Messages in iCloud, Apple has figured out a compromise. It provides rock-solid protection for law-abiding individuals, while making it possible to provide authorities with information about criminals on receipt of a valid warrant to access iCloud data.

(It still collects way less data than competitors).

How to set up and use Messages in iCloud

Setting up and using Messages in iCloud is a breeze. You’ll need to go through the following process on each device you want to use with the service:

  • Install the latest OS on all your Apple products.
  • Use the same Apple ID to sign into all your devices.
  • Enable two-factor authentication.
  • On iOS, open Settings>iCloud and toggle Messages to On(Green).
  • On a Mac, open Messages>Preferences and check the Messages in iCloud.
  • The amount of time it will take for all your messages to reach iCloud varies depending on how many messages you have to upload.

You switch off this feature using the same checkboxes. When you do so, you can choose to turn off Messages in iCloud for just that device or all of your devices.

More information?

Here is Apple’s tech support article concerning Messages in iCloud.

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