When should I upgrade to macOS 10.15 Catalina?

Apple’s new macOS 10.15 Catalina is upon us! Like all major operating system releases, Apple has been talking it up since it was introduced at the company’s Worldwide Developer Conference in June.

It will feature new Music, TV, and Podcasts apps to replace iTunes. Photos, Reminders, and Notes all get major upgrades. A new Mac Catalyst technology will make it easier for developers to make their iPad apps available for the Mac. Screen Time has migrated over from iOS. And Sidecar lets you use an iPad as a second screen or graphics tablet with an Apple Pencil. Sounds great, doesn’t it?

It will be… eventually. We are upgrading non-essential Macs right away so we can become more familiar with the ins and outs of Catalina, but our recommendation to our managed services clients right now, is simple:

Do not upgrade to Catalina until we give you the go-ahead.

(Based on the last couple of releases, we expect this to be sometime around January 2020.)

Even more than previous major macOS upgrades, Catalina is not something you should install right away. Aside from the usual bugs in any new version, with Catalina Apple changed macOS in some fundamental ways that could break your essential apps or workflows. Here are the issues that cause us to recommend delaying your upgrade:

32-bit apps don’t work in Catalina

Macs have had 64-bit processors since 2006, macOS has been gaining 64-bit support since 10.6 Snow Leopard, and Apple has been warning developers for years that 32-bit apps would stop being supported at some point. That point is Catalina.

To identify which apps won’t work in Catalina, download and run the free Go64 utility from St. Clair Software. If you recognize any of the software it identifies — pay special attention to Adobe apps — you’ll need a plan to address that.

Catalina uses a read-only system volume

To increase security and ensure that an attacker cannot modify macOS itself, Apple changed the disk structures under Catalina. Now, instead of having one main volume that contains both macOS and your apps and documents, Catalina runs in its own read-only volume. Some behind-the-scenes magic makes the Catalina boot volume and the main volume look like a single volume. This may cause scripts that access files stored in newly changed parts of the directory hierarchy to break, and is likely to have other consequences we’ll only discover the hard way. It also means backup apps like SuperDuper and Carbon Copy Cloner will require updates to be able to backup and restore data properly. Never upgrade before your backup app is 100% compatible!

Newly installed apps must be “notarized” by Apple

Notarization is an automated process that Apple uses to verify that an app distributed outside the Mac App Store is free of malware. It’s not optional—in one statement, Apple said, “Mac software distributed outside the Mac App Store must be notarized by Apple in order to run on macOS Catalina.” However, the company has also said that notarization requirements don’t apply to previously distributed software. It’s likely that older apps already on your Mac when you upgrade it will continue to work fine, but if you try to install an older, unnotarized app on a Mac running Catalina, that may not work.

Apps require more permissions than before

In the last few versions of macOS, you’ve probably seen apps asking for permission to do things like access data in Contacts, Calendars, Reminders, and Photos, or be able to use the camera or microphone. In Catalina, apps will have to ask for permission to access files in your Desktop and Documents folders, iCloud Drive, and external volumes. Plus, you’ll be prompted before any app can capture keyboard activity or a screenshot or screen recording. That’s good for security, but it’s possible that older software won’t know how to ask or won’t work properly if you deny its request.

Kernel extension installs require restarts

Kernel extensions are often necessary for third-party hardware peripherals or for apps that need particularly low-level access to the operating system. Installing one requires giving it permission in System Preferences > Security & Privacy > General even now in Mojave, and in Catalina, you’ll also have to restart your Mac. Coupled with the new read-only system volume, these new kernel extension changes are going to increase the typical delays involved with third-party developers each time a new macOS arrives.

Apple’s OS release schedule has been… troubled this year

There’s one final reason that Catalina doesn’t give us warm fuzzy feelings. In recent years, Apple has shipped all its operating systems on the same day, or at least without significant delay. This year, in less than two weeks, Apple has released iOS 13.0, 13.1, 13.1.1, and 13.1.2; iPadOS 13.1, 13.1.1, and 13.1.2; and watchOS 6.0 and 6.0.1 for the Apple Watch Series 3, Series 4, and Series 5; along with tvOS 13. For devices that can’t update to iOS 13, Apple also pushed out iOS 12.4.2, and for the Apple Watch Series 1 and Series 2, which won’t get watchOS 6 until later this fall, Apple released watchOS 5.3.2. Plus, HomePods are still using iOS 12.4 and even iOS 13.1.2 and iPadOS 13.1.2 still lack some promised features. Finally, the new Reminders app can’t share data with older versions after you upgrade its database, which means that you can’t take advantage of its new features until you upgrade everything to iOS 13 or later and Catalina or later.

We understand and appreciate the need to update software, but even for us, this has been a lot.

Traditionally, we’ve waited until the .1 or .2 update of macOS before recommending an upgrade. With all the trouble Apple has had shipping this year’s crop of operating systems, and all the problems that Catalina’s changes could cause for you, we are likely to wait for the 10.15.3 or 10.15.4 update. By then, Apple should have a stable release, and we’ll have a good handle on how to work around whatever of these issues you might encounter.

And as always, for our managed services clients, we’ll reach out to make sure you are upgraded on the right schedule with the right plan in place.

(Featured image by Apple)


Transfer Everything from Your Old iPhone to Your New One with Quick Start

Apple is making the migration from an old phone to a new one even easier this time around with Quick Start. All you have to do is turn on the new iPhone and place it next to a current iPhone running iOS 12.4 or later.

When you see the prompt asking if you want to set up a new iPhone, tap Continue and scan the animation on the new iPhone using the current iPhone’s camera. Then you have to enter your current passcode on the new iPhone (and optionally set up Touch ID or Face ID), and tap Transfer from iPhone. Next, just wait a while for all the data to transfer.

(If you don’t see this Transfer Your Data screen for some reason, you’ll still be able to restore all your data from an iCloud or iTunes backup the old fashioned way.)

Read more about it on Apple’s support site here:
Use Quick Start to transfer data from your previous iOS device to your new iPhone, iPad, or iPod touch

(Featured image by Adam Engst)


Ask Adam loves 1Password.

Everybody needs a password manager — whether we like it or not, we all have dozens (and some of us have hundreds) of passwords to keep track of. Without a secure place to write them down, most people do very dangerous things like using the same password again and again, or putting their passwords into a text file, their address book, or a Google doc. In the best case, you’re spending a lot of time looking them up and keeping them up to date. At worst, your password may already be in the hands of those who wish to cause trouble, either for money or just for their amusement.

If you’re not already using a password manager, 1Password is the best choice. It costs $3 per month for an individual or $5 per month for a family, and offers team and business accounts as well. If you’re the DIY sort, 1Password offers a lot of great documentation to help you get started. If you’d prefer to work with an expert, you can make an appointment with Ask Adam to get going.


Everybody needs backup. The easiest way to back up your Mac right now is to sign up with Backblaze. You can begin backing up in seconds, without even sharing your credit card info. I use Backblaze on all my Macs and almost all of my clients do too.

You can get started with Backblaze by clicking the “Get Backblaze” button below. Make sure you use a strong password when you sign up, and make sure you keep that password in a safe place!

You Should Be Using a Password Manager

We often recommend using a password manager, but we’ve gotten a few questions asking why we’re so adamant about this. Lots of people think that all they need to do to keep their online accounts secure is create a single password with some numbers, often switching a lowercase L with a 1 and a capital E with a 3. And that’s for accounts people care about—for those that they don’t see as important, they’re likely to use a simple password like their child’s or pet’s name. Plus, most people don’t think they have much to protect or that they would be targeted by hackers, so they reuse the same password across multiple sites.

Guess what? Such an approach is extremely dangerous on today’s Internet. First off, no one is explicitly targeted. The bad guys get passwords by stealing millions at a time from Web sites with lax security. Then they use sophisticated hardware that can test over 350 billion passwords per second to decrypt as many of the stolen passwords as possible. All passwords shorter than 13 characters are easily cracked by such hardware.

Imagine you have an account on a shopping site whose passwords are stolen. The attackers can log in to that site, change your shipping address, and order items with your stored credit card. But they won’t stop there. They’ll use automated software to try that username and password combination on lots of other high-profile sites: Google, Apple, Amazon, eBay, Facebook, many banks, and so on. If they can get in anywhere, they’ll take over the account and exploit it in any way they can, which could involve stealing money, ordering goods, or using it to reset passwords and lock you out of other accounts. It can get ugly fast.

Use a password manager to generate, store, and enter strong passwords, different for each site, and you’ll never have any of these problems. A sufficiently strong password (go for 20 characters or more) will withstand cracking efforts for centuries, and by using a unique password for every site, even one password being compromised won’t expose any of your other accounts to abuse.

Here then are five reasons for using a password manager:

  1. Generate strong passwords: A password should be random, or it should be a long collection of words (think 30+ characters). Password managers can generate such passwords for you, so it’s easy to make a new one for each Web site.
  2. Store passwords securely: If you’re going to put all your eggs in one basket, you want that basket to be well protected. Password managers employ their own strong encryption and various other techniques to ensure that your passwords are safe.
  3. Enter passwords for you: No one can remember and type long, random passwords, but having a password manager enter the password for you is even easier than typing a weak password. Log in faster than ever before!
  4. Audit existing accounts: Password managers learn the credentials you use for existing accounts, and they can tell you which passwords are weak and which have been reused.
  5. Access passwords on all your devices: It’s even harder to type passwords on an iPhone or iPad, but good password managers have apps for mobile devices that sync with your password archive so all your passwords are available whenever you need them.

There are many different password managers, but for most people, there are three main choices. If you use only Safari on the Mac and in iOS, Apple’s built-in iCloud Keychain feature may be sufficient.

If you’re an Apple user but you prefer browsing with Chrome or Firefox, or if you want to share some passwords with family members or your workgroup, 1Password is the best choice. It costs $3 per month for an individual or $5 per month for a family, with team and business accounts as well.

If you need help choosing a password manager or setting one up, particularly in the context of a small business, get in touch with us. And if you’d like us to write more about each of these options, just drop us a note and we’ll see what we can do.

(Featured image by CMDR Shane on Unsplash)

Can’t Remember When Your Warranty Expires? iOS 12.2 Can

With luck, you should never need to check your iPhone’s or iPad’s warranty status. But bad things do happen to good devices. In iOS 12.2, Apple made it easy to see if your device is still under warranty or covered by AppleCare+. Go to Settings > General > About, where you’ll find a new entry that’s either called Limited Warranty (the basic Apple warranty) or AppleCare+ (the extended warranty you can buy).

This entry shows the expiration date, and tapping it provides more details on the Coverage screen. If your iPhone or iPad doesn’t have AppleCare+ but is eligible for it, you can even buy it from this screen. (You won’t see anything if your device is out of warranty and no longer eligible for AppleCare+.)

“2. Ensure that Apple products last as long as possible”

[Lisa Jackson, vice president of Environment, Policy, and Social Initiatives] said Apple now strives to design and build durable products that last as long as possible. That means long-lasting hardware coupled with long-lasting software. She pointed out that iOS 12 runs even on iPhone 5S, now five years old. Because iPhones last longer, you can keep using them or pass them on to someone who will continue to use them after you upgrade.

She said that “keeping iPhones in use” is the best thing for the planet.

At this point in the presentation I wondered if everyone would rush out of the room and call their broker to sell Apple shares.

My thoughtful take on yesterday’s Apple’s news is that the Series 4 Apple Watch was the most important announcement by far. Writing at Asymco, Horace Dediu has an even more thoughtful take, noting that Apple made an incredibly public repudiation of planned obsolescence: Asymco: Lasts Longer

Apple Should Own The Term “Warrant Proof”

It is not only well within Apple’s rights to produce a product that happens to be warrant-proof, but it’s actually Apple’s responsibility to create a product that’s capable of enforcing the highest level of security permitted by our country’s laws… not the lowest. Apple is well within not only their rights, but in practices that support and place appropriate locks consistent with the levels of privacy our country recognizes. These products protect everyone – diplomats, doctors, journalists, as well as all of us. Of course they should be this secure.

Jonathan Zdziarski: Apple Should Own The Term “Warrant Proof”