How to Take the Annoyance Out of Your Key Passwords and Passcodes

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We constantly say, “Use a password manager!” for good reason. Password managers make it easy to generate, store, and enter strong passwords. You don’t have to decide whether or not your password is strong or weak, remember it, and type it accurately every time you log in to a website. Seriously, just get 1Password or LastPass, or you could use Apple’s iCloud Keychain.

But what about those passwords you have to enter regularly, like your Mac’s login password, your Apple ID password, and the master password for your password manager? And the passcodes for your iPhone, iPad, and Apple Watch? Plus, it may also be helpful to be able to remember and type passwords for a few services that require you to enter the password into an app instead of a Web browser. (Of course, you can copy and paste the password from your password manager, but that’s fussy if you have to do it frequently.)

For such passcodes and passwords, you’ll want to come up with options that are strong, memorable, and easily entered. Here’s what we recommend for most people. (If you’re a target of a nation-state or regularly deal in highly confidential government or corporate information, you’ll need an even higher level of security.)

Passcodes

It’s essential that your iPhone, iPad, and Apple Watch have a passcode that can’t easily be guessed. Once someone can get into an iPhone or iPad, they could read all your email, look at all your photos, make purchases via Apple Pay, and impersonate you in conversations with others. And yet, many people use worthless passcodes like 111111 or 123456. Don’t do that! Also, don’t worry about making a passcode that’s easy to type—with Touch ID, Face ID, and Apple Watch unlocking, you don’t have to type your passcode all that frequently.

Since we’re talking about physical objects that can’t be accessed remotely and are most likely to be compromised by someone who knows you personally, the key is to think about what six digits you can remember but that even people who know you well couldn’t guess.

For instance, you might think of using 081995 if you were born in August 1995, but your birthdate is both widely known and easily discovered. A better pattern would be the dates of the month associated with the birthdays of your best friend from high school, your favorite cousin, and your late grandmother—132408 if they were born on May 13th, July 24th, and November 8th. No one will ever guess that.

You get the idea. Think of dates associated with people or events important to you but that even close friends or family members wouldn’t necessarily know. Then combine those days, months, or years in a way that makes sense to you. You’ll end up with a strong passcode that you’ll never forget.

One last point. Given the level to which data syncs between your iPhone, iPad, and Apple Watch, we don’t see any significant benefit in creating different passcodes for each. Come up with a secure passcode and use it on all three.

Mac Login Passwords

Much like an iPhone’s passcode, the primary vulnerability for your Mac’s login password is someone who has physical access. You don’t have to worry about remote brute force attacks (as long as you don’t have remote access enabled in System Preferences > Sharing) or password files being stolen, suggesting that the password doesn’t need to be insanely strong and equivalently hard to type.

That’s especially true for an M1-based Mac or Intel-based Mac with a T2 security chip, and even more so if you have enabled FileVault (which we recommend). But if it’s an older Intel-based Mac without a T2 chip, it’s conceivable that a thief could image the drive and use brute force attacks to find the password. A stronger password might make sense for such an older Mac.

Considering all this, we recommend coming up with a password that’s easy to type, memorable, and difficult to guess for even those who know you well. It doesn’t have to be strong enough to protect against serious cracking software unless you live in a Spy-vs.-Spy world. Consider taking a few words from a song lyric or movie quote you’ll never forget and jamming them together, such as “ettubrute” or “goestoeleven.”

If you unlock your Mac and apps using an Apple Watch or Touch ID most of the time, you can make the login password a bit stronger without the annoyance of having to type it so frequently.

Apple ID and Password Manager Passwords

When it comes to your Apple ID password, the master password for your password manager, and other passwords to online services you need to type, attacks will take place either remotely or be directed against a stolen password file. Plus, your Apple ID password and master password to your password manager literally hold the keys to your kingdom, so they must be extremely strong and resistant to automated cracking. It’s also essential that you won’t forget them and that you be able to enter them—on both a Mac keyboard and an iPhone keyboard—reasonably easily. What to do?

One possible solution is to create a long passphrase of random but easily remembered words, as suggested in the classic xkcd cartoon. Current advice suggests that a passphrase of five words—with at least 32 characters—is now necessary to resist modern cracking methods.

Passphrases are highly secure, but they can be tedious to type and may not work well for an Apple ID password. Apple requires that Apple ID passwords have upper and lowercase letters and include at least one number. But don’t make it longer than 32 characters; some have reported problems with longer passwords.

For a compromise approach, consider a password built using the following rules:

  • It starts with an uppercase letter. That satisfies Apple’s requirement and means you don’t have to switch between upper and lowercase keyboards on an iPhone more than once.
  • That letter and subsequent lowercase letters come from the initials of unrelated people, movie titles, the first few letters of a saying or product name, or something similar that you’ll have no trouble remembering.
  • It includes several punctuation characters accessible from the iPhone’s numeric keyboard that don’t require the use of the Shift key on the Mac keyboard.
  • It ends with digits developed along the lines of the passcode above—this keeps you on the iPhone’s numeric keyboard. (You could also swap the order of the punctuation and digits.)
  • Overall, it has at least 13 characters, preferably more.

(As an aside, does having two-factor authentication (2FA) turned on for any account where you’re creating a memorable password let you make a weaker password? Yes, in the sense that your overall security is much higher with 2FA because someone would have to hack your password and compromise the 2FA system in some way. But no, if your password is so weak that it’s trivially crackable, such that 2FA becomes the only protection. Don’t overthink it—stick with strong passwords.)

As an example, consider this possibility for a LastPass master password: Tpmbialas/.19851955. It’s not entirely random, but it’s close and doesn’t use obvious patterns that cracking software could exploit. Let’s break it down:

  • Tpmbialas comes from the first letter of the words in the movie The Phantom Menace and the Dire Straits album Brothers in Arms, plus the first three letters of LastPass.
  • /. plays on the name of the tech news site Slashdot to be memorable, and the characters are easily typed on both the iPhone and Mac keyboards.
  • 19851955 will be easily remembered by fans of the movie Back to the Future, whose characters travel in time from 1985 back to 1955.

It’s highly secure—the How Secure Is My Password? site says it would take 1 quintillion years to crack, and there’s no way that even someone who knew your taste in movies and music could guess it (as long as you don’t tell them about your pattern).

One last thing to consider: is your password fun to type? Some key combinations probably roll off your fingers, whereas others will be prone to typos. Test your proposed password on both a Mac keyboard and your iPhone. If you hate typing it, tweak the characters until it’s better.

When you’re developing your own unique passwords that you must be able to remember and type, a strategy along these lines should serve you well. Just make sure to avoid dictionary words, repeated characters, and any password under 13 characters in length, all of which make passwords easier for cracking software to guess.

(Featured image by iStock.com/peshkov)

Share Files, Photos, and other Data between Apple Devices with AirDrop

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It’s common to want to share files, photos, and other data between your devices—or with friends and family. When the desired person or device isn’t nearby, it’s easiest to use Messages or Mail. But what if you want to move a file between two of your Macs, from your iPhone to your Mac, or to your friend who’s across the table? For transfers within immediate proximity, Apple provides AirDrop, a quick and easy way to move data between devices.

Make Sure AirDrop Is Ready to Go

First off, AirDrop requires both Wi-Fi and Bluetooth, so make sure both are enabled. If you use wired Ethernet on your Mac, enable Wi-Fi as well, but put the Wi-Fi service beneath the Ethernet service in System Preferences > Network (click the down-pointing arrow under the list and choose Set Service Order).

Next, make sure other devices can discover you. On the Mac, choose Go > AirDrop and, near the bottom of the Finder window that appears, choose Everyone from the pop-up menu. (If you’re out in public and random people keep trying to send you files, which would be weird, choose Contacts Only instead.) On an iPhone or iPad, go to Settings > General > AirDrop and select Everyone.

Send a File or Photo via AirDrop

Apple has integrated AirDrop into the standard sharing mechanism in macOS, iOS, and iPadOS, so sharing via AirDrop works the same as sharing via most other apps.

In the Finder on the Mac, the easiest approach may be to select AirDrop in a Finder window’s sidebar and then drag files to the icon representing the destination device (below left). You can also select one or more files and choose File > Share > AirDrop or Control-click them and choose Share > AirDrop, both of which present a dialog from which you can select the destination (below right). The right-hand dialog is also what you’ll see if you use the Share option in Photos or any other app.

On an iPhone or iPad, when you’re viewing the item you want to share, tap the Share button to bring up the Share sheet. You may be able to tap the AirDrop icon for the desired destination directly in the top row, but if it doesn’t show what you want, tap the general AirDrop icon in the second row to display the AirDrop screen with icons for all available destinations. Either way, tap the destination to send the file.

Receive Data via AirDrop

On the receiving side, AirDrop is utterly simple, particularly when transferring files between your devices, though the experience varies a little depending on the direction and file type.

  • Receiving on a Mac: If you’re transferring between your own devices, you don’t need to do anything; the file will appear in the Downloads folder of the destination Mac. Files sent from other people will appear there too, but you’ll get a prompt asking you to accept or decline the file, and if you accept, an option to open it in the appropriate app.
  • Receiving on an iPhone/iPad: Receiving on an iPhone or iPad is similar, with one additional step. Unless iOS/iPadOS knows where the file should go (images always import into Photos automatically, for instance), it prompts you with a list of apps that can open the file. Files you transfer between your own devices are accepted automatically; for files from other people, you must tap the Accept button first.

Troubleshooting

AirDrop has been around since Mac OS X 10.7 Lion in 2011 and has seen significant updates since then. So if you had trouble getting AirDrop to work years ago, it’s worth revisiting the feature. That said, problems can still crop up:

  • If a Mac doesn’t appear as an AirDrop destination, make sure it has Wi-Fi active. Ethernet is not sufficient. Also, if the Mac’s firewall is active, check that it allows incoming connections. Open System Preferences > Security & Privacy > Firewall > Firewall Options and deselect “Block all incoming connections.”
  • If an iPhone doesn’t appear as an AirDrop destination, make sure Personal Hotspot is turned off in Settings > Personal Hotspot.
  • Because AirDrop relies on Bluetooth and Wi-Fi, interference with either, or a separation between devices of more than 30 feet (9 meters), can cause performance and reliability to suffer.
  • For best results, make sure you’re using recent Apple hardware running the latest versions of macOS, iOS, and iPadOS. Apple has improved AirDrop over the years, and it works significantly better than it did years ago. Technically, AirDrop requires a Mac introduced in 2012 (excluding the 2012 Mac Pro) or later running OS X 10.10 Yosemite or later. On the mobile device side, the iPhone, iPad, or iPod touch must be running at least iOS 7.
  • If you’re prompted to accept transfers between your own devices, that’s an indication that the devices aren’t logged in to the same iCloud account.
  • Although AirDrop has no explicit size limit, very large files (over 500 MB) will take a long time to transfer and are more likely to fail due to network issues during the transfer.
  • If you can’t find a transferred file in the destination Mac’s Downloads folder, remember that it retains its original creation and modification dates, so it might be sorting differently than you expect.

Next time you need to move data between nearby Apple devices, give AirDrop a try!

(Featured image by iStock.com/jroballo)

Ransomware Is on the Rise: Learn How to Protect Your Macs

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In cybercriminal circles, ransomware is all the rage. Once it has infected a computer, it encrypts all the files and then presents a ransom demand—pay up to get the decryption software necessary to recover the data.

Ransomware has been in the news all year, with the Colonial Pipeline attack in particular spending weeks in the headlines. Attacks rose 485% in 2020 and show no signs of abating. The amounts demanded by the attackers are increasing, too, with PC manufacturer Acer and Apple supplier Quanta both hit with $50 million demands. Worse, some ransomware attackers are adding an extortion component where they threaten to reveal confidential data if the victim doesn’t pay. It’s scary, we know.

First, the good news. Although there are several examples of ransomware that target the Mac, none of them have been particularly well done or (as far as we know) successful. Right now, the chances of Macs falling prey to ransomware are very low, and there’s no reason to panic.

However, complacency is dangerous. There’s a trend toward “ransomware as a service” (RaaS). The RaaS operators maintain the ransomware malware, offer a payment portal for victims, and provide “customer service” for victims who don’t know how to pay with Bitcoin or other cryptocurrencies. Affiliates spread the ransomware and split the revenues with the operators. It’s a tidy little cybercriminal enterprise, and separating the malware development and network penetration tasks has made it significantly easier for more criminals to leverage ransomware. It’s only a matter of time before they turn their attention to Macs.

For the most part, protecting your Macs from ransomware is no different than protecting against any number of other security problems. Follow this core advice:

  • Keep Macs and apps up to date: Always install macOS and security updates, and keep other apps up to date. With every update, Apple addresses numerous security vulnerabilities, fixing the vast majority of them before attackers can exploit them with malware. Every so often, however, Apple’s security notes include this sentence: “Apple is aware of a report that this issue may have been actively exploited.” That means there may be malware that targets that vulnerability; install such updates immediately!
  • Use strong passwords with a password manager: You’ve heard it from us before, and you’ll hear it again, but it’s essential that everyone in your organization use strong, unique passwords through a password manager like 1Password, LastPass, or even Apple’s iCloud Keychain. Just one weak password could allow attackers to infiltrate a computer or server and install ransomware.
  • Be suspicious of links and attachments: Ensure that everyone in your organization is careful about opening attachments or clicking links in email messages from unknown people or that seem off in some way. Phishing attacks are one of the primary ways of distributing malware. (If your group needs training in phishing awareness, contact us.)
  • Never download pirated software! Even aside from the fact that it’s ethically problematic, the most recent piece of Mac ransomware—ThiefQuest—was initially found in a malicious installer purporting to be for the LittleSnitch network security utility (ironic, eh?). Get apps only from the developers’ official sites or the Mac App Store.
  • Make frequent backups: Backups are essential so, even if you do fall prey to ransomware, you can restore data from before the infection point. The caveat is that some of your backups must be isolated from the Macs in question—some ransomware intentionally tries to encrypt or delete connected backups.
  • Monitor for ransomware: Although ransomware usually tries to stay below the radar while it’s encrypting files, the free RansomWhere utility can identify processes that quickly create encrypted files. It will likely incorrectly flag some legitimate behavior too (like in the screenshot below), but it’s still a helpful tool.
  • Have anti-malware software: For the most part, if you’re careful about following the advice above, you’ll be fine. But it’s a good idea to have a current anti-malware app around and run it occasionally—if you don’t already have one, try the free version of Malwarebytes. If you—or your users—aren’t good about the basic precautions, you might want to run anti-malware software all the time or set up broader network protections.
  • Have a disaster management plan: Every business should think about how it would react to a fire, flood, earthquake, or other disaster. When building a disaster management plan, be sure to include ransomware. How would you shut down infected systems, rebuild them from scratch, and restore uninfected files?

Setting up a backup strategy that protects against ransomware requires a little more thought. As noted, ransomware often tries to render backups useless in one way or another. You need to have versioned backups that allow you to restore from before the ransomware infection, and those backups need to be isolated from the computers and network being backed up. Techniques that help include:

  • Isolate backup drives: Rotate multiple Time Machine drives, with at least one that’s always disconnected. However, this strategy assumes you’ll detect a ransomware infection before you’ve rotated all the drives. Ransomware could lie undetected for weeks or months before activating. Manually run current anti-malware software before connecting any backup drive.
  • Use Internet backup: Set up an Internet backup system that will maintain versions of backed-up files, such as Backblaze with its Extended Version History feature. Retrospect 18 also supports object locking on cloud storage systems, which provides immutable storage. It ensures that no one—even someone who acquires root credentials—can delete the backups during the retention period.
  • Consider tape backups: Long ago, tape backups were the go-to solution for network backups, but as the price-per-gigabyte of hard drives dropped precipitously and Internet backups became feasible, tape has largely fallen by the wayside. But tape backups are still an option. They can hold a lot of data and are easily kept offline in a separate location. Plus, some tape drives can even operate in a write-once, read-many (WORM) mode that guarantees data can’t be erased or overwritten. Tape requires more human interaction than other backup methods, but it’s still a cost-effective way to protect hundreds of terabytes of data against ransomware.

Again, there’s no reason to panic about ransomware, but if it could significantly damage your business, you should take steps to reduce the chance of getting hit and ensure that you could restore your data if your computers were to get infected. There is no single approach that’s ideal for everyone, but we can help you think about what’s involved and develop a strategy that balances protection, cost, and effort.

(Featured image by iStock.com/chainatp)