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IOS : iPhones & iPads

Apple IOS devices (iPhone, iPad, and iPod Touch) by nature have a good level of security. There will always be vulnerabilities to be found, though for someone who will not be actively paying attention to security issues and wants to install applications to simply enjoy using their device, IOS seems to be one of the best options.
With regards to surveillance, you’ve probably heard of programs or malicious apps that can watch where you go, read your emails, messages, and pretty much copy everything that you do on devices and computers. If you’re using an IOS device, in order for someone to do what I just described, your device would have to be jail-broken. Jail-breaking a device tends to be fun for the technologically inclined, as it gives them full control over what they can do with their device. They can install all sorts of third party apps and tweaks without having to download them from the Apple App Store, and they can access the full contents of the device’s memory and storage. The drawback of using a jail-broken device is that a malicious app can also access just about anything on the device.
If you are concerned with security and surveillance, then I would recommend that you NOT jail-break your device unless you really know what you’re doing. If your device is not jail-broken, then there are only a few ways that someone could be reading your information:
  1. If someone knows your iCloud password, then they could set up *your* iCloud account on another device or a Mac in order to get copies of all the iMessages that you send or receive. When someone (including you) sets up a new device with your iCloud account, you will be notified on your other devices. As of September 2014, iCloud can make use of strong authentication, which will require that you authorize any new access on one of your existing devices or enter a code that will be sent via text message. If you have not already enabled this, then I strongly suggest that you do so now.
  2. If someone knows your email password, then they could set up *your* email account on another device or computer in order to get copies of all the emails that you send or receive (this one isn’t specific to IOS devices, but we’re on the topic so I’m including it).
  3. If you have authorized someone in the Find My Friends app to look up your location (GPS coordinates), then they can find your device any time they want to.
  4. If you have another app such as Google+ Location (it used to be called Latitude) that identifies your location to people (those in the Circle authorized to view your location), then they can find your device any time they want to.
  5. If you have enabled an online application from your cellular service provider (such as Rogers One Number), then all of the text messages you send and receive (note that this applies to text messages and not iMessages), as well as call logs will be stored online and accessible by anyone who knows the password you use for your service provider’s portal.
There are a few simple things that everyone should do with their device, the first being setting a passcode. Provided that you’ve enabled a passcode (you have to type a password or code every time you turn on the device), the information on the device will be encrypted. Having a passcode is only the first of many steps to securing your device, so don’t stop reading just yet. Next is setting up an automatic wipe of the device after too many bad passcode attempts. If someone takes your device and tries to log in, it’s better to have the information deleted than to let them have it!
Find My iPhone/iPad is a great service that lets you log into the iCloud web site (or an App from another IOS Device) and see the current location (GPS coordinates on a map) of your device. If it’s ever lost or stolen, this is one option for finding it! Enabling iCloud on your device is another critical step, as once you’ve registered your device, if someone should steal it and try to erase it, they won’t (easily) be able to re-install it and use it until your iCloud password has been entered.
If you leave your device where someone else can take it, there are a few simple settings that will make it more difficult for them to access your information and applications. The setting for Auto-Lock will turn off your screen after a delay. I tend to like keeping this at 2 minutes for my iPad, and 1 minute for my iPhone. The setting for Grace Time will determine how long after the screen turns off will your passcode be required to use the device. I tend to leave this at 1 minute in my office (where I’m the only person with access), or immediately when elsewhere. If you set this option too high, then anyone who picks up your device within the grace period won’t need to unlock it when the screen lights up!
If you’ve used a computer, I’m sure the concept of backups has come up before. Backups are slightly different with IOS devices and can be separated into two categories: Backup of the device and its configuration / basic information, and backup of specific information on the device (files, photos, etc). To backup the device, including your configuration, the apps that you have installed, and the data in (most of) those apps, you can use iCloud. iCloud, by definition, is located in the cloud (on the internet) and you don’t have to do anything other than enable the option (and have enough space in your iCloud account for backups to complete). When your device is plugged in (charging) and connected to a WiFi network, it will backup automatically. Note that some information will not be backed up by default, specifically the passwords to your email accounts and private keys or certificates (unless you have Keychain sync enabled), and any information in an application that supports a feature called Data Protection (to encrypt the data belonging to that application).
The second option for backups is to use your computer running iTunes. iTunes can backup similar to iCloud, though if you have enabled the “Encryption” option then it will also automatically backup passwords, encrypted information, and everything else on your device. If you do make an encrypted backup, be sure that the password you use is a strong one, otherwise anyone who copies your backup file from your computer could gain access to everything on your device.
With regards to applications that you install, your information is only as secure as the application. IOS will sandbox applications, and prevent other applications from taking their information without permission (see the Privacy section under your device’s Settings for a list of which applications can access certain types of information), though if you put something confidential within an app, you have to trust that the app developer and the servers used by the app are secure. Apple has little to no power over the security of that information once you’ve stored it in an app. For example, we can look at common document editing applications. Most of them will support a cloud service (such as DropBox, Box, Drive, or others) and will synchronize automatically with any cloud service that you’ve set up. If you have a critically sensitive document in your email (you shouldn’t keep critically sensitive documents in email attachments, but that’s another debate altogether), and you open that document in an app, then that app may save it automatically to your cloud service account. If you have another 10 apps that are all authorized to access that same account, or your home computer (also set up to sync your account) is infected by malware, then that critically sensitive document that you thought you were simply viewing on your iPad could be compromised.
If you use a cloud storage service, there are solutions to secure the data and still make it available on your device. One interesting solution that I’ve come across is BoxCryptor. BoxCryptor can run on multiple platforms, and encrypts the contents (and file names if you use the paid version) of individual files. This makes it more efficient than using a full encrypted container that can be quite large where each individual file must be stored together. I’ll go into more detail on BoxCryptor and other encryption solutions on another page.
There are a lot of considerations on how best to secure your device based on your use cases (what you actually want to do with the device). If anyone wants to suggest a particular case, activity, or app, I’ll be happy to give my opinion of it.
With regards to government information accumulation (commonly refered to as, “the NSA spying on you”), Tim Cook wrote an open letter (posted to http://www.apple.com/privacy/ in mid September 2014) that stated the following, “Finally, I want to be absolutely clear that we have never worked with any government agency from any country to create a backdoor in any of our products or services. We have also never allowed access to our servers. And we never will.
This is somewhat misleading, as all companies located in the United States have legal requirements to cooperate with government / law enforcement. What Tim Cook wrote is that they have not created a backdoor for government agencies to read whatever they want, whenever they want, and however they want, and have not given access to their servers so that said agencies may read everything on the servers. What Tim Cook did not write was how they do cooperate with said agencies – as it’s commonly accepted that they do, though the technological details have not been made public.

The security of communications via iMessage has been a concern in the media recently. My understanding of the process for securing iMessage communications (presented in an over simplified manner) is that each device has a set of keys (one public and one private) that are associated to your iCloud account. When someone sends you an iMessage, their device will receive a copy of all of the public keys for all of your devices from the Apple servers, and will then encrypt the iMessage contents such that only your devices can read them. The encrypted messages are then sent to the Apple servers, where they are routed (via push notification) to your devices (IOS) or computers (OSX has a messaging app for iMessage). Being as Apple controls their own servers, it is technologically feasible that they can add an extra key to someone’s iCloud account without that person’s knowledge, so any messages sent to that person would also be encrypted using that key. If that key were to be given to a government agency, then said agency could read the contents of those messages. In the same manner, such a key could be used to give an agency access to your iCloud account and all its contents.

Please note that I am not aware if this is actually how Apple handles this issue – only that it is technologically possible and is likely the simplest method for Apple to conform to legal requirements for cooperation with government / law enforcement. If this is indeed how they cooperate with legal requirements (where a warrant or some such is signed by a judge), then it would be on a per-person or per-account basis, and would not be blanket access to all iMessages as many people seem to fear.

Another interpretation of, “We have also never allowed access to our servers.” is that while access to the actual servers has not been provided, there is no mention of the information in transit (travelling to or from their servers). There was an interesting technical document about key servers and man-in-the-middle attacks I read a few weeks ago (if I recall the URL I’ll post it here later) and someone else’s ideas about how these *could* apply to Apple servers.

In summary, if you’re a very bad person planning to do very bad things, iMessage is probably not going to give you 100% secure communications (nor will most other technologies). If however you’re like me – one of the rest of 99.99 (add a whole lot more 9’s) % of the population, your iMessage communications are more likely to be of interest to some random person out there who will be using social engineering, malware on your computer, or the theft of one of your devices to get your information for financial reasons than to a government agency – and you probably shouldn’t be storing nude photos in the cloud anyway.