If you use iCloud for email, calendar events, or contacts with any apps other than those made by Apple, and you haven’t upgraded the security on your account to use two-factor authentication (2FA), syncing and other interaction will fail starting June 15. That’s when Apple imposes a new security requirement that requires unique passwords for all third-party software that works with iCloud accounts. That includes apps like BusyContacts, Fantastical, and Thunderbird, to name a few of hundreds, as well as online services that sync with iCloud or retrieve email.

That sounds a lot more secure, but there’s less there than meets the eye. Apple’s method of allowing third-party access has significant flaws in containing abuse if one of these unique passwords gets discovered. There’s a better way with its own set of problems, but Apple doesn’t appear to be moving in that direction. (Here’s our how-to guide on setting up iCloud/Apple ID 2FA.)

Blocking easy account hijacking

2FA is a simple way to make it much more difficult for someone to access your account with just your password from anywhere in the world. Your first factor is a password, and with accounts that just require an account and that element, a hijacker can log in typically anywhere. (Some services, like Gmail, alert users to odd geographic login locations, or even block access without additional confirmation.)

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Apple’s 2FA system alerts you to new logins by rough location before proceeding to offer a code as a second factor.

The password is “something you know” in the authentication rubric. Add something you are, like a fingerprint, or something you have, like an authentication app on a smartphone, and someone has to either gain physical access to you or your devices or remotely hack that equipment through malware. A code sent via SMS is also an option for most 2FA systems, including Apple’s, but SMS isn’t as secure: it can be intercepted, a phone number can be transferred to another device, and SMS doesn’t require special software or an account to receive. SMS texts also appear by default on locked screens unless you reconfigure iOS and Android options.

The problem with 2FA is that it typically works only within an ecosystem run by the company that makes the services. So you can use Apple’s 2FA with iOS, macOS, iCloud.com, iTunes, and other Apple websites and services. But what if you want to use third-party software for the limited elements Apple exposes?

In that case, as with other 2FA systems, you have the option to create an app-specific password. With some systems, you can crank the limit further. For example, with Fastmail, you can specify that a password only allows SMTP (outgoing email). For Apple and Google, these passwords can be broadly used for email, calendar events, and contacts with zero limitations. Here’s my brief guide to setting up app-specific passwords with an Apple ID.

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An app-specific password provides access to several iCloud services, and can be revoked (as I did for this one).

That means your weakest link for those critical parts of your life—your most private information that you haven’t taken extra effort to encrypt—can be accessed and changed by anyone who acquires any of your app-specific passwords. They can reset passwords at other services and intercept the incoming email with the reset link, spam all your contacts, and so forth. (iCloud Keychain isn’t affected by this. Third parties can’t gain access, and Apple developed a robust encryption and confirmation process for it.)

The solution for avoiding this app-specific password weakness is OAuth, a standard used broadly by websites like Facebook, Twitter, and Google to allow third-party services limited access to features and data within those companies’ silos on behalf of a user.



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