Should I Upgrade to the Latest OmniOultiner on Mac?

Hey All,
I run OmniOutliner 4 Pro on my Mac. I use it primarily for tracking projects and outlining for my law practice. I use OmniOutline as well.

There are some minor annoyances like the app crashing when I try to print and having to create a bunch of blank space at the bottom of the outline to keep the cursor centered. The spartan look of the app is also not a turn on.

I was just about to pull the trigger on updating to the latest version but a few things made me pause: (1) I can’t find my license key for OO4, (2) I know I can buy the upgrade outright but I see they have a subscription option that caused me to fire up the App Store as I like to keep all subscriptions tied to my Apple ID. The reviews on OO in the App Store are not what I expected. Quite poor, actually. Now I’m not sure what my move is.

Should I ride the OO4 horse until it dies, buy the upgrade outright, subscribe monthly, or find an alternative?

Any suggestions on what to do and where to look?

Note - I also use Obsidian heavily but I don’t feel it’s my solution for outlining.

1 Like

Omnioutliner is floating in developmental limbo. I still use it occasionally and it works well for me. Have you looked at other outliners? Is there something specific that omnioutliner does than other outliners can not do ?

OmniOutliner 5.0 was released in March 2017. Seven years is forever in software time. Considering you’re running software almost twice that age, it’s probably a good idea to consider updating the app, and OO5 is pretty stable by now. OmniGroup is very good about finding old licenses for you, as long as you have some idea what email address(es) you were using when you bought OO4.

I doubt many OO users are holding their breath waiting for OO6 to ever materialize. It’s taken OmniGroup years to get OF4 finished, and it’s still has a long way to go before “final” is written.


1 Like

I am a long-time user of OmniOutliner, starting with it because it shipped with my first PowerBook in 2002. I continue to use it, but lately I have started using a new outliner called Bike. It’s developed by Jesse Grossjean, who also writes an application called TaskPaper. Anyway, Bike feels very different from OmniOutliner in ways that I mostly really like. You might want to give it a try. It is under very active development and may not have everything you need, but I’ve found that it helps get me unstuck when I need to plan projects and lectures.


I don’t need anything super specific but would like easy text manipulation (drag and drop sections) and something that can handle multimedia (mostly pdfs).

Logseq is a credible outliner.


I use Logseq as well, but must caution that users have experienced data loss. Hasn’t happened to me, but I am maniacal about backing up. They’re redeveloping the backend database, which should be interesting. It’s a great app, but does take some getting used to.


Bike looks awesome but it doesn’t look like it can handle pdfs - unless I’m missing something?

I wouldn’t try to time a purchase based on it, but Ken dropped a hint that they are in the thinking stage of OmniOutliner 6. Omni support helps you find missing product licenses.

I think OO5 is solid but it’s definitely a product out of step with multiple zeitgeists since it’s not plain text based and it’s not a cool infinite outliner/graph search app. So middling reviews make sense.

1 Like

Zavala is a wonderful, free, open source outliner.


I don’t think so, but I do not know for sure.

Bike looks very easy to use and the “free movement” as well as “structured” entry looks really useful.

From the video and the manual, however, it doesn’t look like Bike can do columns - whcih OO can do.

Yes, OO can do columns. Bike can not. And that’s a big benefit of Bike … it’s focused, it’s fast, it’s really really good. When a person starts to need columns for an outline my first thought is “I think there’s a better tool for them.” … but if OO is what you love to use, then use it! I personally find it slow, clunky, and over the years it simply added features while diluting focus. It’s a shame as once it was a very good app.

… but Bike. Ah, such a lovely app.

1 Like

what happens when you dump a pdf into Bike?

Bike auto-creates a link to that file. You can name the link so you don’t have an uber long path name on your computer.

I’m not exactly sure how you want to do links, but linking in general in Bike is very good and flexible. Quite possible to link from one Bike item to another in a different Bike document.

I also use Hookmark a lot for links, but as far as I recall I haven’t used Hookmark for links within Bike. No particular reason, just the “need” hasn’t cropped up yet. All that said, Hookmark does a great job of “following” the PDF if it is moved to other locations on your computer. Bike doesn’t do any “following” of files … but in many cases that’s not needed.

However, if you want Bike to “show” or “preview” the PDF within Bike … that doesn’t work. I don’t know the need for that, but maybe it’s something you are looking for.


@MacDependent I made a few changes/additions to my post above. I don’t know if these changes provide you with any extra useful information, but they might.

1 Like

Super helpful, thanks! I use Hook too and like that it can “follow” a file after it’s moved. As long as Bike plays nicely with Hook, I’m in. I downloaded Bike last night and will have a look!


I would be interested to know what you have in mind for the better tool(s). What I often want to do is put in something like a source reference such as “X’s affidavit para. n”. The advantage being is it is nicely and clearly separated from the content of the “node” but linked with it.

1 Like

Sorry for a late reply, and also a very short one. We’ve had internet going down several times today … so I need to limit my time in answering this.

If you wanted to use Bike for this then they have a “note” style. It’s italicized light gray. And, like other things in Bike, you can add a link. That might work for you.

In terms of using other apps, it really depends on the case study. I know you’ve provided a bit of information, but the details would be really important in a case like yours and I’d only be making guesses (and likely bad guesses at that).

From your description it “seems” Bike would accomodate all your needs if you treated these added PDF links as Bike notes. Of course I may be wrong, but that’s what I’d try first. There are several other things that could handle this (required Obsidian plug … even though I don’t use it, and other notetaking apps). But it seems outlines fit your style/needs well.

I think the Bike approach using note styling may work for you: it’s clearly different from the other content under a specific heading. I know it’s not a different column, but it seems what you really want is easy and clear demarcation of important links versus main content.

Sorry for the brief reply.

Judging by the glacial dev speed of OF4. OO 6 should be available in 5 years :grin:.

1 Like