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.

6 thoughts on “The User-Unfriendly Feature and Pricing Structure of OmniOutliner

  1. That’s exactly why I stopped using Omni software at all – after more than a decade. Their upgrade paths are confusing and the prices are way too high now, at least for my taste.

    What I also don’t accept is when developers cripple-down the feature set of a purchased app afterwards – like Airmail is doing right now. They are blocking many features you already paid for, trying to pull you over to a subscription model. I find that pretty shady.

    There are better ways to keep customers paying. I do like the pricing model of Agenda, for instance. When you buy Premium, you’re getting any new features for 1 year. After that period all existing features are permanently unlocked. Forever. Even if you decide to not renew the subscription. If you renew, you’re getting all upcoming new features for the next 12 months. Those will be permanently unlocked, too. And so on.

    That’s pretty fair I think. If you’e happy with what you have, fine. If you want more bells and whistles, great – go pay for another year. You can do that any time, so there is no pressure.

    I hope more developers are going to adopt those pricing models, because they are cool for both, them and us.

    • Yes, there are lots of apps that have moved to a freemium model. I’m not sure I like it in general, but, as you say with Agenda, it works. I use Bear for notes, and it has the same model. With the free version you can do things, but not as much as if you pay.

      What complicates OmniOutliner is that it functions as a free viewer on iOS, so it can read my document just fine, but I can’t make any edits without paying. And, again, the fact that there are two different apps under the same name is problematic. I don’t think this is the case with OmniFocus, but I have the Standard version both for the Mac and iOS.

  2. Outlinely basically copies the UI of, which itself came into being when it seemed that wasn’t being developed (or quickly). Dynalist is actually a great service, the free version offers a lot for users, and there’s an iOS app (which is kind of meh, to be honest). Unfortunately it and Workflowy (and are all basically online services with moderately expensive yearly subscriptions for full unlock. Dynalist is something like $90/yr (although they usually offer a big discount around Black Friday).

    Outlinely also has very slow development for most of the year, and it picks up in the spring/summer, which makes me wonder if the dev is a student. At the least, this is a side-business.

    I own OO Pro on the Mac and too was blindsided when I considered getting the pro iOS version. Seems like they’re milking it and not expecting to give it much dev love going forward. Indeed, if you look at the forums 90% of discussions are about OmniFocus (which years ago started out based on OO), followed by Omnigraffle, and smatterings of discussions about all other products.

  3. Kirk – I like OO, but understand your point. If you want to go back and forth between mind mapping and outlining, MindNode is worth a look. If you want to explore a less structered kind of laying things out for a Scrivener file, you ought to take a look at Scapple, a fine and powerful application that, alas, doesn’t yet exist in iOS – the developer of Scrivener when through such nightmares getting that app ported over to iOS that he’s reluctant to take a shot at doing this again with Scapple.

    The best outliner of all, according to some sources, is Tinderbox, but it’s expensive, has a steep learning curve, and doesn’t have the export options that OO offers.



    • I long used mind-mapping software (starting with Inspiration, back in the MacOS 9 days), but I shifted to OO because it offered me a lot for flexibility in text mode. I’m really not interested in going back to mind mapping, especially because it’s not really ideal on a handheld device.

      Ah, Tinderbox… I recall trying that out some 15 years ago, and being flummoxed by its features. I’m sure it’s still about the same, and, if there are no export options, then I can’t use it.

  4. This is a great article, I am in the same boat, I already own pro on my Mac and just want to make a few edits. I almost bought the essentials version and then read your article. $50 is a lot to spend just to make a few changes on the iPad.

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