OO5 has been in maintenance mode for so long I'm frankly shocked that an update was annouced, and that it contains new features.

https://9to5mac.com/2025/11/04/omnioutliner-6-will-be-a-huge-update-and-you-can-try-it-today/

Currently available for beta testing in TestFlight.

https://www.omnigroup.com/test/

You will be able to link to local documents, as well as work with files in iCloud Drive, Dropbox, Google Drive, Google Docs, and local servers. Using Apple's privacy-preserving AI on-device model, Omni's AI Tools will use Omni plugins to pull information from docs, emails, and webpages, turn it into outlines, and export those outlines into formats like blog posts or Obsidian entries. You can drag and drop between multiple windows (even of the same document, I think) and they're giving feature parity to iOS/iPadOS versions so you can finally edit filters there.

No word on pricing or if it's a free update to OO5 users, but I assume not.

I'll be delighted to pay for it. I've felt guilty being such a heavy user of OO5 for years without having to pay anything since the original purchase!

Glad to see Omni hasn't forgotten it, given how little publicity they've been giving it vs. their other products.

Indeed, good tho see signs of life. I hope the AI can be turned off.

Linking to files is nice. Better that it will open multiple views of a document.


It’s beta so this isn’t a gripe. There are UI issues in the present OO 6 release. I reported what I found. The production release will be polished.

[Warning: This is probably more off-topic than on.]

Around 2008 I decided to go back to Apple for my personal computing -- for the previous 13 years I used PCs, because that's what I had at work. But two Mac apps convinced me to return to Apple. Those were Scrivener and OmniOutliner. I was drawn to Scrivener because I thought it would help me write my novel. OmniOutliner seemed the nearest thing to the old DOS app I loved, GrandView. Oddly, I've never used either of those apps much. Scrivener because I don't really have a novel in me, I think. OmniOutliner, because... well I'm not sure, but I think a lot of it has to do with the fact that there is a lot of friction using it, and even back then there were more nimble outliners, even if they didn't pack the same features. Don't get me wrong, I admire OO -- and I think it is great to learn that a new version is in the works. I still have a copy on my current MacBook. I tried to use it the other day, but then thought that I would do better in Workflowy, where I can just bang out the outline. But it still seems the OO is the only local outliner with the ability to add columns for viewing meta data (remind me of others if I've forgotten any). That makes it special.

Thanks for the update!

Steve

I'm glad to see OmniOutliner is now a universal app. In the past it was a pain to get files back and forth from the desktop to the mobile app.

"Outliner" always seemed like a misnomer. It's really more for making fancy data tables.

OmniGroup so far is on the sidelines in the AI-integration hustle. Craft is in beta (for late November release) with some thoughtfully designed integration with Craft documents and artifacts like their "collection" figure (also a database-light concept).

This is the year OmniGroup has come alive again -- first with OmniFocus 4, then with betas for a new version of OmniGraffle (one of my favorite things), and now with OmniOutliner.

Paul Korm wrote:

"Outliner" always seemed like a misnomer. It's really more for making
fancy data tables.

Not for my use case. I do make use of columns for some things, but for me it's primarily an industrial-strength outliner, which I use to organize my life, but even more to store massive amounts of structured information in a hierarchically organized fashion. For example, I have an outline for each of my clients (I'm a web developer) storing account information, historical information regarding issues that I've had to resolve, esoteric information related to their setup, etc. (I store the outlines in highly encrypted containers for obvious reasons. There's no way I would trust an online solution.)

Bob Spies wrote:

Paul Korm wrote:

>"Outliner" always seemed like a misnomer. It's really more for making
>fancy data tables.

Not for my use case. I do make use of columns for some things, but for
me it's primarily an industrial-strength outliner,

Same.

Bob Spies wrote:

There's no way I would trust an online solution.

Hear, hear!

Local first for everything!

The latest build of OmniOutliner fixes user interface issues I found.

I haven't figured out the linked directories yet - I think that's for file links from OO. Experimentation will tell.

Right now what I see is OO 5 plus multiple windows. A very welcome feature. With file linking, worth an upgrade. Those not using AI - all three of us - the difference between 5 and 6 may be just a few refinements.

Here's hoping OO development is on the ascension.

It looks like one use for the linked directories (connected folders?) is to replace the OmniSync service. Another use would be collaboration support.

Amontillado wrote:

I haven't figured out the linked directories yet - I think that's for
file links from OO. Experimentation will tell.

Paul Korm wrote:

It looks like one use for the linked directories (connected folders?) is
to replace the OmniSync service. Another use would be collaboration
support.

You may be right. The beta version doesn't include help files or documentation. My guesswork came up a little differently.

OO now supports OmniLinks, which as far as I can tell are what everyone else calls links. They link to specific nodes in the OO file. There's a catch, though.

In order to copy a link the outline has to be stored in a connected folder. As best I can tell, subdirectories of a connected folder work, too. I'm not sure what would be wrong with making your whole hard drive a connected folder.

For the moment, I'll leave that to others!

for whomever it may concern, Joan Westenberg recently droped an interview with Ken Case, CEO of OmniGroup.

https://www.joanwestenberg.com/p/interview-ken-case-omnifocus


I've been following Westenberg site since Satis posted here a link to a provocative post tittled 'I Deleted My Second Brain' :

https://www.outlinersoftware.com/messages/viewm/46583

I've been playing with a certain workflow using OmniOutliner.

The idea is to see the outline entries for a single chapter plus background notes that have global reach.

Something like this.

In Chapter 1, Scene 1, Jack and Jill climb a hill. There is a drought, and everyone's thirsty. Scene two hints Jack's brother is secretly hitting on Jill.

When I'm looking at Chapter 1 in the outline, I want to see the story points and I also want to see and take notes for background information. In this case, I know Jack's brother's wandering eyes are going to be important later.

Sure enough, in Chapter 20 Jack's flip-flops are sabotaged and he falls, breaking his crown. The Chapter 20 view of the outline shows this plus the same notes I took in Chapter 1 about Jill's dalliance with Jack's brother.

OmniOutliner isn't bad for this sort of thing. Here are some expanded thoughts - https://thirdreef.wordpress.com/2025/11/21/a-breakthrough-of-the-obvious/

I know. I'm overposting. I'll try to do limit myself.

But in the meantime, I've finally taken a look at Omni-Automation for OmniOutliner. The automation is based on Javascript.

Very, very, cool. You can enter single statements in a console window and see results in real time.

The outlining/cross reference idea in my last post was my first target for automation.

Here's what I ended up with after a few hours experimentation.

Notes go under a Research topic.

A column called "xref" (for cross reference) gets space or line delimited tokens. Basically tags identifying topics.

I can click in an outline topic and run my new automation.

It focuses the outline on the topic I chose, which means I see that topic plus its descendants.

Then it adds every topic it finds under Research containing any of the tags found in the focused segment of the outline.

For instance, click on the Chapter 3 topic in the outline and run the automation. You see chapter 3 and its subordinate topics. Underneath that, assuming your Reseach topic was below your story outline, you see every relevant note.

If I set the background color of the Research topic to something different than my proper outline, new rows added under Research use the new background. New rows added in the outline retain their default color. That nicely differentiates Research from Outline.

You can almost do that with filtering, but not quite. Also, you don't have to maintain any stored filters. Write your outline, keep your notes, tag everything as appropriate, and then just choose a topic and run the automation to get a fresh look based on current tagging.

The only oddity I've found is that if a Research topic matches my tag search and if it has child topics, the child topics appear. That's because focusing on a topic also displays child rows.

I think I'm OK with that. It's sort of of like child rows inherit tags from parents. If the parent's tags match, I see its sub-tree. If only a child's tags match, I just see the child.

That's probably what I want, anyway.

Very happy. Time will tell if it's actually useful, but I think it will be.