The User-Unfriendly Feature and Pricing Structure of OmniOutliner

I use a wide range of apps in my work. From Apple apps that are included with the operating systems I use – Mail, Messages, Pages, Numbers, etc. – to third-party productivity apps, as well as apps across many categories. In addition, as a journalist and reviewer, I test many apps. So I have a very good understanding of the different ways apps are marketed and sold.

One company stands out for its odd structure of features and pricing: The OmniGroup. At some point – I don’t recall exactly when – they made the decision to offer two versions of many of their apps. On the Mac, for OmniFocus, there is a Standard version ($50) and a Pro version ($100); for OmnOutliner, there is an Essentials version ($20) and a Pro version ($100); and for OmniGraffle, there is a Standard version ($150) and a Pro version ($250). (iOS pricing is $50; $75 for OmniFocus and $20 and $50 for OmniOutliner; and $60 and $120 for OmniGraffle.)

I’m a long-time user of the first two apps. I bought OmniFocus when it was first released, and used it extensively at the time, because I was involved in managing some fairly complex writing projects. For many years, I didn’t need it, but I have recently started using it again to organize the tasks I need to do for my work. And bought I OmniOutliner many years ago – perhaps not when the first version was released – and have used it to outline all my books since then. I don’t use OmniOutliner for anything else, but I’ve written enough books that I want a powerful outliner to help me in the planning stage.

I’m currently working on a new book proposal, and, as in the past, I’ve created an outline on my Mac in the Pro version of OmniOutliner. I’m pretty sure that I bought the first version, but the oldest serial number record I can find is from 2009. In my accounting, I find two recent purchases for the Pro versions, one for $50 in 2015, and another for $30 in 2017, and each of these was a discounted upgrade because I owned a previous version.

As I said, I’m working on a new book proposal. I’ve created the outline on my Mac, and I wanted to be able to edit the outline a bit on my iPad. But it seemed overkill to pay $50 for the equivalent Pro version, for what would really just be a handful of edits. So I decided to buy the Essentials version for $20, figuring that I didn’t need the “Pro” features if I was just editing an outline. When I opened the document on my iPad, I was greeted with a warning:


The warning talked about “with all features intact,” without saying what would be lost, and I did not want to lose anything in my outline, so I did not make the change. I was extremely upset by this: if it told me what I would lose, such as specific formatting, I could go ahead, and reformat my outline back on my Mac, but it didn’t say anything at all. In addition, there were no options to change the font size in new outlines; I have a great deal of contempt for app developers who assume that everyone has good eyesight like they do, and not having a font size option is a deal-breaker. (Frankly, shipping an outliner with no font, size, and style options is downright hostile.)

So I went to the Report a Problem section in my Purchased list and requested a refund, which Apple issued quickly.

I am very irked by this confusion. First of all, having two different versions of the same app is not common; unless you’re Microsoft. (Yes, there are some exceptions, but it’s rare.) In most cases, you don’t get access to certain features with a free or low-priced version of an app, but it’s always clear what the features are. But in this case, I couldn’t see what was going to happen to my outline.

I’m not bothered by The OmniGroup’s choice of charging what seem to be high prices for their apps. These apps are rock-solid, feature-rich tools, and the company does not issue frequent major version upgrades; I think that when I last upgraded OmniFocus, it had been seven years since the previous paid upgrades. However, I did have two upgrades for OmniOutliner in a relatively short period (2015 and 2017).

What bothers me is the confusion between versions. With OmniFocus, the Pro versions only add a few features, and, aside from AppleScript support, it seems a bit ridiculous that you have to pay $50 extra for custom perspectives (views), or a customizable sidebar. (There are exactly four features added in the Pro version of OmniFocus.) For OmniOutliner, the $50 bump on the Mac gives you access to a small set of tweaks, such as “column width improvements,” (which is vague), and “style preview.” These features seem like they should be in all versions of the app.

But with OmniOutliner, it’s even more confusing, because apparently they are different apps. As I was told when The OmniGroup’s support got around to replying to me:

The Essentials edition is a much more radically simplified version of the app (much different than the Standard/Pro split in prior versions), which is intended for people that are brand new to OmniOutliner (and potentially outlining apps in general).

While OmniOutliner is a really great tool, this whole experience has caused me a lot of annoyance. I spent a lot of time over the weekend trying to understand why I couldn’t easily work on my outline on my iPad, and then having to request a refund, and I will now look for an outlining tool that has both Mac and iOS versions that are compatible. Users should never be confused by pricing models, or by feature sets, and if the versions of an app are that different, then they should have different names (i.e., not just be in-app purchases within the same app).

There is a strange mindset at The OmniGroup about both the feature sets and pricing models that just adds too much friction to my work. I shouldn’t have to think about these things. And my guess is that it costs them a fair amount of sales, as people with less experience with apps may be put off by not understanding why two versions of an app can be so different in price with the addition of only a few features.

And worst of all, having two versions of an app where files you create are incompatible is simply wrong. It’s confusing enough at times when features are different on the Mac and on iOS – which is often the case – but when there are multiple versions of an app on each platform, that’s just user-unfriendly.

Do you use an outliner? Do you have any recommendations for an app that has both Mac and iOS versions, and is flexible enough regarding styles? I recently moved my note archive from Evernote to Bear, and I find the latter much better for notes, and wish it had an outline feature. But I do want an outliner that can export in OPML format, so I can import my finished outline into Scrivener, when I start writing my book. (And, no, I’d rather not outline in Scrivener.)

Outlinely looks good, but while the Mac app is a one-time purchase, the iOS app is a subscription. This is an even more frustrating pricing model. Also, the Mac app has some weird display bugs, and there are hardly any options for formatting outlines.