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The world of Mac software development

I was recently sent an offer to beta test a new service. The service is interesting – it is a subscription service for applications on the Mac operating system. Let me digress for a moment. Selling applications on the Mac, or any desktop operating system, has become more difficult in recent years. In the case of the Mac, this is partly Apple’s fault.

The App Store

Apple introduced the App Store for the iPhone back in 2008, and it completely turned the traditional software business on its head. Many companies made a lot of money from the App Store, and others went out of business. It messed with existing business models, and the reverberations in the software industry are still being felt. My own company, Command Speech, was founded shortly before the launch of the App Store, and it had severe effects on our business.

The App Store today
The App Store today

One of the big effects of the App Store was the race to the bottom. Traditionally, software companies had to spend money to market their applications – through magazines, newspapers, and online. There were also distribution costs. In the old days you had to pay for the media it was distributed on, whether a floppy disk or a CD-ROM, and the printed manual and box as well. You had to keep inventory. You needed to ship products, or put them in retail stores where it cost a lot of money to get shelf space. That meant you couldn’t charge too little for your app, or your acquisition cost for that customer would be more than you were getting paid. Some smaller developers could charge less, especially when the Internet brought down distribution costs, but it was still hard to get the word out. The App Store as a searchable marketplace for apps solved this problem, and allowed developers to charge less for their applications since their distribution was handled by Apple, and anyone could find their applications in the App Store. Add to that viral marketing on social networking sites, and you had the perfect storm to lower the price of software.

If you look back to the days of the Palm Pilot or Psion, the software prices were not that different than desktop software. A bit less maybe, but still in the double digits. With the App Store and viral marketing, the most common price for apps shot quickly to the lowest possible price, $0.99, if not free. It’s rare to find software in the App Store more than $9.99, and the only software I’ve seen in that category are apps that work with expensive desktop apps or with hardware, and can charge $14.99 or $19.99 because if you’re a captive user of their other product, you will pay to have a compatible mobile app.

The best example of this that I’ve seen was when Nuvo introduced a mobile app for their home music system. Nuvo has a great system that distributes music to multiple rooms, offers in-wall touch-screen controllers, and has a music server that can stream audio from its hard drive or from various online streaming services. Besides the in-wall touch screen controllers, they also offered a wireless touchscreen remote for hundreds of dollars. When they introduced their iPhone app, they knew they would be cannibalizing the sales of their touchscreen remote, so they priced the app at a price that probably made them more money than the remote – $99. I don’t know how long they kept the price that high, but I can tell you that they now give the app away for free. In fact, the great majority of apps in the App Store are free. Instead of selling the apps upfront, most developers have come up with other business models, such as in-app advertising. Advertising on the desktop has never been very popular, however, so apps on the Mac needed a different model.

The Mac App Store

In 2011, Apple launched the Mac App Store, bringing the same model of app sales to the desktop, except with one major difference. On iOS, Apple controlled all apps that were made available on the device. The only way to get your software on an iPhone or iPad was through the Apple-controlled App Store (without hacking the phone which most people would not do). On the Mac, Apple didn’t close access to the computer, so developers could choose to continue selling directly, could switch to the Mac App Store, or could try some combination.

The Mac App Store today
The Mac App Store today

At first, the Mac App Store seemed great to developers, particularly smaller developers. Basically free distribution, people could find you by doing a search, and updates were automatically pushed out to users. Of course there was a 30% cut for Apple, but other distribution methods were not free, and meant dealing with credit cards, refunds, issuing serial numbers, etc. The App Store simplified everything. At the beginning the App Store was missing a few things, but developers figured Apple would get around to fixing the missing features. One missing feature was a way to do a paid upgrade. Upgrades are the lifeblood of the software industry. You get a customer, they like your software, you spend time to improve the software, and you get paid for that work. Except for reasons that are still not clear, Apple’s decision not to include an upgrade route was not a missing feature, it was by design. Another missing capability for most developers was a way to do a free trial. Developers can of course create another version that users can download from their web site, but that kind of defeats the purpose of selling through the App Store.

Apple has still not added the ability to do a real upgrade. Some companies have gotten creative, by introducing a new app with a new version number, and offering it for less for the first few weeks to allow people to ‘upgrade’ and then raising the price before publicizing the software. This is an imperfect solution to be sure. The worst part is that if a user doesn’t upgrade in the set period, they cannot get the upgrade price in the future. Other developers have come up with more sophisticated solutions.

Omni Group, a long-time Mac developer, has created a way to do both free trials and upgrades, although it’s a bit complicated. They’ve started to make their apps free on the store, enabling for a free trial. After a couple of weeks, features in the app are disabled unless you purchase them through an in-app purchase. If you want to upgrade, you can find the old version of the app on your hard drive, and it will verify that it’s a valid version of the app, and then show you less expensive in-app purchases to get the same features. Not particularly elegant, but still workable.

There were other problems with the App Store, including additional security features (sandboxing in particular) which prevented some developers from selling through the App Store. Other developers found the effort too complicated, and reduced their interaction with their customers, and so abandoned it. Even so, the world for Mac software was changed. Prices had come down and they were not going back up just because an app was not in the App Store.

Loss of Marketing Avenues

In the old days there were magazines and web sites focused on the Mac, but even the web sites slowly started shutting down. Back in 1997, MacUser magazine in the US merged into MacWorld Magazine. MacWorld shut down its printed magazine in 2014. MacUser UK closed down its magazine in 2015. The MacMinute web site, a popular mac news site shut down in 2008 after the death of its owner., the web site of MacLife magazine merged into the generic TechRadar site in 2015. Is there still a magazine? I have no idea. MacNN, another popular Mac news site shut down in 2016.


In 2006, a new style of software marketing was introduced – the bundle. MacHeist pioneered this marketing scheme, where multiple software products were bundled together and sold for a low price. The site gamified the process, adding challenges that could get the user additional software. The site also raised money for charity at the same time.

The original MacHeist in December 2006

Controversial at the time, since relatively little money went to the developers themselves, the developers looked at it a bit differently. They looked at it as a way to gain new customers, who they would get more money from through future upgrades. MacHeist marketing its bundle as a limited time event, generating lots of sales over a short period of time. This model was copied by many other companies, generating all kinds of bundle sites such as BundleHunt, BundleFox, StackSocial, FairBundle, and more. Many sites came and went, such as Bundleecious, MacBundleBox, TheMacBundles, etc. How many bundle sites could operate at the same time?

Deal Sites

Another variation on the short-term deal are the individual deal sites. They offer a discount on one or more apps separately for a day or a week. Some sites of note include MacZOT and MacUpdate Promos, which is a directory of Mac software that also offer deals on a regular basis.

MacZot today

Besides the lack of immediate payback from bundle sites, another downside is that it precludes selling through the Mac App Store. Of course, not every developer wants to sell through the Mac App Store, but if you could properly promote your app, even at a big discount, it would help your rankings in the store, and make your app more visible, which would bring in more sales, etc. A beneficial cycle. One site that targets this opportunity is Two Dollar Tuesday, a site that promotes discounts on apps, but which sends you to the Mac App Store to make those purchases.

Two Dollar Tuesday today

Two Dollar Tuesday markets the discount (if an app is normally $9.99 then they market it as 80% off) to their subscribers and the developer lowers the price of the app in the app store for the period of the discount (up to a week usually). Like MacZot, the site is essentially a large mailing list that allows software publishers to reach a large number of targeted customers. Another site that follows a similar model is MacAppStoreSale.

A Subscription Model

So back to the beta service. The service is called SetApp, and offers a large number of Mac applications (currently 60 and new ones have been added over time) for a set monthly subscription price of $9.99/month. I was sent an invite from a software publisher whose application I’ve already paid for, whose application is one of the applications in the subscription. Of course, that’s a bit of the problem. I already own many of the applications I like in the subscription.

Here are the 61 applications currently in the subscription:

Aeon Timeline Get Backup Pro Permute
Alternote Gifox Pixa
Archiver GoodTask Polarr
Base HazeOver RapidWeaver
Be Focused Home Inventory Remote Mouse
Blogo Hype Renamer
Capto iFlicks Screens
Chronicle Image2icon Shimo
ChronoSync Express iMazing Simon
CleanMyMac iStat Menus Sip
Cloud Outliner iThoughtsX SQLPro Studio
CodeRunner Jump Desktop Squash
Disk Drill Lacona Studies
Downie Manuscripts TaskPaper
Elmedia Player Marked Timing
Findings MoneyWiz Ulysses
Flume My Wonderful Days WiFi Explorer
Focused Numi XMind
Folx Pagico Yummy FTP Pro
Forecast Bar Paste
Gemini PDF Squeezer

The service installs a folder on your hard drive with all the applications, except they’re not really the applications. The first time you launch one of them, it shows a preview of the application with a screenshot and a description, and if you want to use it you then have it installed remotely. The next time you launch the application, it launches normally. It’s a nice solution that both gives you a way to find out about the applications, and removes the need to store applications on your hard drive that you’re not using.

For me, since I already own most of the applications I want to use, I need to calculate if the $120/year is worth it for the applications I don’t own. That depends on how many of those other applications I want to use. Sure, if I subscribe to the service I won’t have to pay upgrade fees for the applications I do own. That requires a more complicated cost/benefit calculation. In general I’m opposed to software subscriptions, such as Adobe Creative Cloud. I particularly don’t like the idea of software stopping to work when I stop paying, and I can’t stand the massive number of Internet calls these subscription apps seem to make back to their servers. Try installing a single Adobe CC app with a network monitoring tool such as Little Snitch, and you’ll be shocked how often and to how many servers that single app tries to phone home.

That’s the case where there are no other options. Adobe gets away with that because there are not many alternatives to many of their applications. There’s nothing yet to indicate that these software publishers are planning to use this subscription as their only means of distribution. I suspect that wouldn’t make sense for most of them. As such, as an additional option, it’s probably a good thing. Someone should probably put together a chart showing the cost of each of these applications, and the upgrade costs over the last few versions, to let someone see if they would be paying over $120/year in upgrade fees on the apps they want.

In a world where many of the most ubiquitous desktop applications are available through the web, such as office suites (Microsoft Office 365 and Google Docs) and photo editors (Adobe Photoshop Express, Fotor, Pixlr), it seems logical that even non-web-based applications would find a way to get into the subscription model. For SetApp, I suppose the big question is does their mix of applications appeal to enough people and provide a big enough payoff to the developers who include their applications in the subscription. The beta ends in March, and it will be interesting to see how many people make the shift to paying $9.99/month. I don’t expect they would be promoting their numbers, at least not right away, but I suppose a good proxy for that information will be if new developers continue to add their apps to the subscription in the months that follow.

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Circus Ponies Web Site

How not to upgrade software

Update 6 Jan 2016: A year and a half after this post was written, Daring Fireball is reporting that Circus Ponies, the company discussed in this post, is out of business. Not surprisingly, considering the odd customer service described below, customers were not a consideration in the closing of the company. The company simply disappeared, and posted a message that sending them an e-mail might get a response, but they wouldn’t guarantee it. Oddly they linked to a second web site with the same message in some kind of parody of Alphabet (old Google). I think creating a parody instead of some kind of customer-focused site on how to transition away from Notebook was not the best use of their time. Oh well.

I used to use a program called simply NoteBook on a fairly regular basis. It’s developed by a company called Circus Ponies Software. Its origin dates back before Mac OS X, to an application that ran on NeXTSTEP (the operating system that would go with Steve Jobs to Apple and become Mac OS X). In the early days of Mac OS X, NoteBook was extremely advanced and fairly unique. Over time other applications aped its user interface, and other organizational applications using different paradigms emerged that in some ways were better. I used NoteBook for a long time, but it seemed to be dying a slow death with infrequent and relatively minor updates. I do have several NoteBook documents I still use, if less frequently, so I run the app on occasion. If the application has an update, I usually install it.

Today I noticed on MacUpdate that there was a minor update (4.0.3) to NoteBook available. The odd thing is that the update was to a major upgrade (version 4) that I seem to have missed. Wondering what I missed I went to the company’s web site This is the top-of-fold view of the site:

Circus Ponies Web Site

Do you see the big announcement of a major new upgrade? I didn’t on first glance and went to their blog which announced the new version a little over a month ago, and linked to a list of changes. If you haven’t found it yet, it’s that red circle on the right side of the page, roughly in the middle – “New Version 4.0!”.

Surprised that as a long time customer I didn’t remember seeing any announcement, I searched through my old e-mails. Sure enough, no e-mail announcing the new version. I had received e-mails from the company as recently as November, so I’m certainly in their database, so why wasn’t I informed about their new version?

I then launched NoteBook to see if it was going to show there was an update. It actually did pop up an update message, but it turns out it was for a minor update to the version I was running (some update to version 3). After I installed that update, it told me I was up-to-date. No mention that version 4 was available.

Next I checked out their online store to see what the new version cost. This is what I found:


The price is ‘from’ $19.95. My first thought was that I remembered it being more expensive. I clicked through and got the following:

Circus Ponies Store

Note that it still highlights that the price is ‘from’ $19.95. It also, however, shows the price now at $49.95 (in smaller text than the $19.95 price) for a standard license. What’s the $19.95 price you ask? It’s for upgrading from the previous version. I suppose it’s debatable whether you should list a starting price for a software application that is only available to existing customers. I would probably show both starting prices to reduce confusion.

Remembering that the application was also available in the Mac App Store, I decided to check out the app there. I sometimes check when a new application is out on the Mac App Store since companies sometime offer upgrade pricing to everyone for a limited time. I don’t know if Circus Ponies offered such a deal to existing customers or not, since I never received an e-mail from them, but now more than a month later this is what I found:

NoteBook App Store Listing

I’m going to guess the reason Circus Ponies is charging $59.99 on the App Store, and $49.95 in their own store, is an attempt to recover the 30% they are required to pay to Apple for use of the App Store. That doesn’t recover the full amount, but it does recover most of it (they end up with about $42). In my experience, however, this is unusual. Some companies explain that they need to implement different features for the App Store version (such as support for iCloud) and thus charge more, but usually that is explained clearly. Most companies charge the exact same price in the App Store as in their own store, and eat the cost. In many cases this works out well as the company gets exposure they didn’t get before and more people buy the application.

So while I still look forward to seeing the new features in NoteBook 4, there are a few suggestions I’d like to make to Circus Ponies in particular, and all software publishers in general:

  1. When you come out with a new version, make sure to inform all of your existing users via e-mail. Track those e-mails and see who follows the links to your site to find out more. If you don’t get a response, send a second e-mail. If you do get a click, but not a purchase, e-mail them and ask them why – they might tell you.
  2. Your web site should look like Times Square showing there is a new version (especially if as in this case it has been 6 years since a major upgrade).
  3. Your application should inform your user that a new version is available. You can even hook into their system’s notification system and push notifications to them even when they’re not running the application (with their permission).
  4. In your own web store, be careful when using statements like ‘Pricing from…’ which don’t apply to all users.
  5. When using App Stores like Apple’s Mac App Store (or Microsoft’s Windows Store) price your apps the same as you sell them in your own store. It might cost you more to use that store, but think of it as a marketing expense.
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Leaving a WhatsApp Group

UX Note – Changing the admin of a WhatsApp group

WhatsApp has been in the news a lot for obvious reasons, and it has been praised for its focus and simplicity. Sometimes, however, simplicity is a crutch. Here’s one example.

Ever use groups on WhatsApp? It’s a great feature. You can set up up to 50 groups with up to 50 people in each group. I’ve used it spontaneously to organize get-togethers with friends, etc. and it is very useful. I am also part of a larger WhatsApp group used for more long-term coordination. I set it up not realizing a major limitation of WhatsApp groups.

The problem starts with only the admin being able to add people to groups. In order to add people, I of course had to have them in my address book with the same phone number they associate with their WhatsApp account. Okay, so I collected the phone numbers of the people I didn’t have. Not a problem. As the group grew I realized I didn’t want to manage it myself, so I figured I would add a second admin to help manage adding all the people. Except, like in Highlander, there can only be one. Then I figured I would switch the admin over to someone else and let them run the group instead. Except not only can’t you add a second admin, you can’t assign who becomes the next admin.

WhatsApp made some very good decisions in designing their app, but I wonder how they came up with the group admin handling. What is the only way to switch the admin of a group to another person in the group? Here’s the description in the WhatsApp FAQ:

Leaving a WhatsApp Group

That’s right, the only way to switch admin of the group to another group member is to remove yourself from the group. Then, the best part, the admin role is randomly assigned to another group member. Of course, if you want back in the group, you need the admin (whoever that may be) to add you back into the group.

How do you figure out who the new admin is? I guess you need to ask someone you know is in the group to look at the group info, see who the new admin is, and then contact the new admin about being added back…

I looked online and some people have struggled to find a workaround for this. What do they do? They delete everyone from the group except who they want to be the new admin, leave the group which automatically assigns the group admin role to the one person left, and then send a list of all the people who had been in the group to the new admin to be added back to the group. Crazy.

Perhaps the idea behind not allowing multiple admins, or reassigning the admin role, was to maintain simplicity, but in the end it has created incredibly complex workarounds.

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Will Remove Apps

UX Note – Removing Apps from an iDevice

Will Remove Apps
Designating apps to be removed in iTunes

Apple is great at making things ‘just work’ which is why when things go wrong with Apple, it’s that much worse. This is just a quick note on a user experience (UX) issue that bothers me about how Apple syncs iDevices. I’ll preface this by saying that since Apple liberated their iDevices from the tether of iTunes, I think they’ve put a lot less focus into improving the iTunes experience. This issue, however, I believe long pre-dates Apple eliminating the need for iTunes.

If your iDevice is full, you need to remove data from the device to make room for new photos, videos, etc. Sometimes you can just offload your photos and videos to make room for more, but sometimes you want clear out more space, so you need to remove apps. There are a few ways to do this:

  1. Hold down an app in the Springboard view (aka the Home Page) until it starts jiggling. Press the ⓧ in the corner of the app icon, and approve it’s deletion. Find other apps to delete and continue the process. Upside, can be fairly quick. Downside, no way to know which apps take up the most room.
  2. Go to Settings > General > Usage and see what is taking up space on your iDevice, sorted by what is taking up the most space. Upside, you know which apps take up the most space so you don’t need to waste time deleting apps that might not make much of a difference. Downside, it can be infuriatingly slow to calculate your usage and display the space used by everything.
  3. Connect your iDevice to your computer, and delete the apps in the Apps panel of the iDevice in iTunes. Downside, does not immediately delete anything. Upside, can quickly and easily sort apps by size, name, kind, category and date – making it very easy to figure out which apps to delete.

It’s the last one I’m focused on here. While not immediate, it is the easiest way to go through your apps and figure out which ones to delete. However, there one really dumb thing about the way this works. Let’s throw out some numbers. Let’s say you only have 50mb of space on your iPhone. You’ve added 200mb of music to sync on your computer. Simple math shows you need 150mb of space on your iPhone for this to work. So you go to the Apps tab and tell it to remove 500mb of apps from your iPhone. Should work right? No, not really. It’s pretty simple, Apple should try deleting things before copying new things to your iDevice. Unfortunately, it doesn’t. Instead it tells you there isn’t enough room on your iDevice to finish syncing.

Why? I have no idea. Syncing isn’t a new concept. Apple has been syncing from the Mac to cell phones since long before the iPhone (remember iSync?). It seems pretty logical to me that if one of your sync steps is to remove data from a device, that that should be done first. Instead, you’re forced to go with option one or two above, just to make room for the sync to happen.


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UX Note: I see dead people…on WhatsApp.

I See Dead People
“I see dead people”

How and why WhatsApp grew at the rate it did in the years it has been in existence is a topic of much discussion. Most people attribute it to the fact that WhatsApp got rid of the concept of a ‘buddy list’ and just used the person’s address book in their phone to connect them to other WhatsApp users. I feel like the side-effects of this system haven’t been discussed in detail.

Multiple SIM Cards

One topic I have seen discussed is the problem people run into when they use multiple SIM cards, such as switching cards when traveling. I recall traveling last year and was surprised when I loaded a different SIM that WhatsApp recognized the phone was operating on a new number, and asked if I wanted to switch to the new number. At the time I didn’t realize the significance of the switch. When you change numbers, anyone who has your other number in their address book becomes disconnected from you (unless they also have the new number).

Why is it that a single WhatsApp account can’t be connected to more than one phone number/device? It seems a silly limitation. Changing the number from the WhatsApp perspective seems to be based on the consideration that a person might change their phone number. With number portability, it seems to me more likely that people switch SIMs to get service in different places, such as cheaper service in other countries.

In the developing world it’s very common for people to carry more than one SIM card with them, and some phones even support multiple SIM cards. Even Samsung makes dual-SIM models of its Galaxy S phone line, although those phones are not available (directly) outside of Asia.

Dead People

So what does that have to do with dead people? My current address book on my iPhone has entries that date back to my Pilot 5000 (that was a first generation Palm device released in 1996). That address book was eventually synced with my Mac Address Book, and then to my iPhone. The oldest entries in my address book don’t have cell numbers in them, as in 1996 not everyone had one. Among the people whose cell numbers I have, if they changed their numbers before number portability became common, and then later joined WhatsApp with their new numbers, obviously I wouldn’t know they were on WhatsApp. However, consider what happens when someone in your address book passes away. Unfortunately, this has happened. After enough time this happens to everyone. What happens to that person’s phone numbers? Generally they’re released back into the pool of available numbers and assigned to new subscribers. What happens when those people sign up to WhatsApp and register their phones with their new number? That’s right. Dead people from your address book show up in WhatsApp. I’ve had this happen a couple of times that I’ve noticed.

Flipping Through My Contacts

As I was writing the above I flipped through my WhatsApp address book. What I found was interesting. One dead person. Several people with multiple listings, where one was clearly their current number and others their older numbers. Sometimes I have more than one cell number for people who had more than one phone and then they dropped others, without removing the ones that were dropped. I noticed one of my friends with one account which appeared to be him, and another with a status written in Arabic. While it’s possible my friend learned Arabic, I’m guessing it’s more likely he got rid of one phone and that someone else who speaks Arabic now has that number. Lots of people I am no longer in touch with, or at least not in touch with via phone (Hi Facebook Friends), show up with WhatsApp accounts but are clearly not them either. Other than the status message, one can tell by the profile image as well. When I have a male friend and a female photo shows up, it’s a good chance it’s not the right person.

Arabic Status
Two WhatsApp accounts from the same address book entry

Another sub-category of incorrect listings in WhatsApp are travel numbers. I live in Israel and when people come here from the US to visit they frequently rent a phone or SIM for their visit. I add their temporary number to their address book entry in my phone, and rarely remember to remove them after they leave. All those people who have visited from abroad over the years, whose phone number have over the years ended up on other people’s phones here in Israel, show up among my WhatsApp contacts.

I even show up in my WhatsApp contacts, and can message myself. That’s pretty funny.

These problems are not unique to WhatsApp. I’ve seen them with Viber as well. I would think all of the mobile-first messaging apps that have linked to the phone’s address book have similar problems. These are not insurmountable problems, and I’m sure they will be resolved in the future. Hopefully one day I won’t have to worry about dead people showing up in my messaging apps.

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UX Note: Apple needs to get in sync

Apple IIe (Wikimedia Commons)
Apple IIe (Wikimedia Commons)

The first computer I used was an Apple II in a computer lab in my elementary school. My first computer was an Apple IIe. I am forever thankful to my father who convinced me that replacing it with a Mac SE was the smarter move than getting the Apple IIgs. Except for a few companies that had me working on Windows machines, and some development on Linux boxes, I’ve been using Macs ever since. I’ve been on the iPhone since the first one in 2007. I love Apple and most of their products (the Mac Portable should never have come out, and the Pippin…let’s not go there).

I love that their products ‘just work’ and are consistent in design (due to their ‘Human Interface Guidelines‘). That’s why it pains me when they don’t work. Some things should work better, and just don’t (and don’t get fixed). In particular, I’ve found that Apple has a problem keeping things in sync with their iTunes/iCloud services.

Let me just preface this with saying technically there are no iTunes accounts and iCloud accounts, there are really just Apple IDs that are associated with iTunes or iCloud. I understand this, but we use these IDs in general for two reasons, for iTunes and iCloud. For that reason I call them iTunes accounts and iCloud accounts.

Here are a few examples of these problems:

De-Authorizing Computers

You probably know you can link up to five computers to a single iTunes account. In a small family these can get used up fairly quickly. Especially with tech-heavy families, where one or more parents might work in high-tech and have 2-3 computers they’re using themselves. More importantly, you need to de-authorize computers you no longer are using. If you still have the computer you no longer want to use, you can de-authorize the computer from within iTunes on that computer. What happens if you don’t have that computer? Like if the computer died and you replaced it? Certainly there must be a way to de-authorize a computer you no longer have, right? Well no, not directly. The only way to de-authorize a computer you no longer have is to de-authorize ALL your computers at once. There’s also a catch. You can only de-authorize all your computers once a year.

Doesn’t it make sense that you’d be able to see all your computer that are authorized on your iTunes account and could de-authorize specific ones whenever you want? Apparently not, according to Apple.

Using iTunes and iCloud on the Same Account

If you are a single person and pay for your own service, then this probably never occurred to you. Most people when they set up iCloud set it up with their existing iTunes account. Makes sense. That is, it makes sense as long as you have complete trust in everyone with whom you’re sharing. For example, let’s say you want to share your iTunes account with your children. Great. Save some money. However, it also means your children can now log in on, read your e-mails, check your calendar, read your notes, check out your Pages, Numbers and Keynote documents, locate your devices on a map, etc.

The solution is simple – don’t use your iTunes account as an iCloud account. However, if you’ve already done so, is there a way to shift your identity from one iCloud account to another? Certainly no simple way.

Multiple iTunes Accounts

iTunes was revolutionary in allowing users to share bought music among multiple computers and devices. When the App Store was launched, this spread to apps as well. Finally, a family could buy an app once, and use it on all their devices. Some developers hated this idea, but most embraced it (even if reluctantly). For those with a single account, this works pretty well. As someone who lives straddled between two countries, I can attest that when you have two accounts, not so much. I am required to have two accounts, because some apps are only available in one store or the other. For example, many transportation apps are different or only available in one country or another, and thus are not available in both.

In general, there is no problem with running apps from multiple accounts on the same phone. What happens is that you need to log into the correct store and purchase the app you need. It downloads and is linked to the device. Your single device is just taking up slots in two different iTunes accounts, not a real problem. Where things start to go wrong is when you are updating apps, particularly on the desktop. When downloading apps on your desktop in iTunes, it gets tripped up by the fact that there are apps from multiple accounts. It stops and makes you log in to the different account. Why? Why not allow one to be connected to more than one account? Just like you can have multiple e-mail accounts in Mail, you should be able to have multiple iTunes accounts in iTunes. Sure, one needs to be Primary, so it knows which store to show you, but when downloading apps you should not be made to switch back and forth. It’s inane and definitely cannot be described as ‘just works’.

While I was writing this I came across an even stranger occurrence. I had a mix of apps from both stores in my update queue, but if I clicked on apps from store A, it told me I was logged into store B, and needed to switch to store A. If I clicked on apps from store B, it told me I was logged into store A, and needed to switch to store B. Basically damned if you do, damned if you don’t. What was going on? I have no idea. I rebooted and everything updated quickly without having to switch stores at all. This kind of impossible problem is not something I’ve run across too much with Apple products, and it is therefore that much more disappointing.

Multiple iCloud Accounts

While multiple iTunes accounts might seem a minor issue that only afflicts people who spend significant time in more than one country, the issue of multiple iCloud accounts is a much more widespread problem. While a couple or family might share an iTunes account to share apps and music, they can’t share an iCloud account. Which iCloud account you’re connected to determines the identity of your phone in reference to iMessage, FaceTime, your calendar, your e-mail, etc. If a couple shared their iCloud account, they wouldn’t be able to message each other.

A pretty common problem, so you’d think there would be an elegant solution to managing your identities on your iOS devices and Mac OS X computers. No so much. That a single account can be both an iTunes account and an iCloud account is possibly the root of the problem. It would be nice if there was a way to associate multiple iCloud accounts as sub-accounts to your iTunes accounts, allowing them access to your apps, music, books, etc. but not accessing your personal data.

The iBooks Conundrum

iBooks and iCloud

I have my computer and iDevice set up with my iTunes/iCloud account. My wife has her computer and iDevice set up with my iTunes account and her iCloud account. This is how it’s supposed to work. We share apps, and that works great. I wanted to share iBooks as well, and here’s what happened.

I added some books manually to my iBooks on my Mac. These were books in epub format. I created several Collections to divide the books. In theory the books should then sync my my iPhone, and my wife’s Mac and iPhone. Right? No. Here’s what happens. The Collections, which are essentially folders, sync everywhere. What was in them, not at all. So I find empty Collections spread all over the place. If I delete the empty Collection on my wife’s computer, it deletes it on mine (and all my books get thrown into the general ‘Books’ section).

You might be thinking that I need to set ‘All Books’ in the Books section of iTunes on my Mac. You’d be right, partially. I went into iTunes and realized that only a few books were set to sync (from a previous attempt to use iBooks no doubt) and I set it this time to ‘All Books’. I synced and lo and behold all my books were on my iDevice. Great. Well, sort of. The first thing I noticed was that while I had ordered the books in their Collections a specific way manually on my Mac, they were not ordered that way on the iDevice. You can re-order them again on the iDevice, but why if you took the trouble to order them on your Mac should you have to do it again on your iDevice?

So they’re on my iDevice. What about my wife’s? No, of course not, because iTunes manages the connection to your specific devices. My wife has her own iTunes and iDevices. So why do the Collections sync over? Of course Apple let’s you sync books that you bought through the iTunes between devices. If I had bought the books via iTunes they’d show up happily everywhere. Since I didn’t but them via iTunes, they’re not ‘in the cloud’ and thus do not sync. Why can’t books you add yourself be synced to the cloud? You can pay for extra iCloud storage, but Apple’s own iBooks won’t store those books in your iCloud storage space?

Keep in mind, this is how Apple advertises iCloud on their site:


I guess the emphasis is on ‘Your’ and not on ‘everywhere’. Perhaps there should be a footnote to the above that reads:

“As long as your music, movies, apps and books were purchased through the iTunes Store. Any content added directly to your device using the supported features in iTunes or iBooks will not be synced through iCloud, but must be manually moved to each device”

Not as sexy as ‘just works’.

Consolidation of iMessage and FaceTime

Not so long ago, you could chat using text and video with your friends using Apple’s AIM-compatible iChat client. iChat went even further and allowed screen-sharing in a very simple way. When Apple started deploying it’s own messaging and video solutions to the iPhone, it left iChat behind and created iMessage system (using the Messages app) and FaceTime for video (and later audio) conversations.

As Apple sought to bring the Mac in line with what is was doing with iOS, it dropped iChat altogether, and replaced it with a Mac version of Messages. It appears that Messages does have some of the legacy support of iChat, including support for video chat with AIM members, and screen-sharing, although I’ve had trouble getting my AIM account working in Messages. I can log in using the web to my account, but not via Messages. No idea why.

It also brought FaceTime to the Mac, but like on iOS, as a separate app that shared only its identity points (your phone number, e-mail address, etc.). If you’re video chatting with a friend through FaceTime, you can’t automatically send them a text message (such as a link to a web site) without opening another application altogether.

This is frankly just silly. Why have two apps that link to the same identities, but not work together? Why have two apps that do video chat? It’s a bit absurd. I understand that Apple’s initial goal was to built these features as system-level features. FaceTime was actually working like that on the iPhone initially, but eventually they went back on that and added an actual FaceTime app. Apple needs to work to bring all of the text/audio/video chat technology under one spot, and let it all work together. If I’m on FaceTime, why can’t I initiate a screen share? or send a link? Why can I initiate a FaceTime audio call from my iPhone but not my computer? These inconsistencies need to be resolved.

So what are your thoughts on iTunes, iCloud, and using them with multiple people, accounts, devices, etc.? What works for you and what doesn’t?

The end