OmniOutliner 5 Pro

An outliner, who needs them these days with iOS apps that let you write anything from free text to outlines with a stylus? Well, if you’re someone who likes to get some order in the chaos of his mind, there’s more to outlining than adding words with a checkbox in front of, or indenting lines of text. In fact, if you’ve tried OmniOutliner Pro you’ll realise it can help you organise even relatively complex projects.

OmniOutliner must be the best outliner for the Mac — and I bet you’ll be hard pressed to find a better one in the Windows world as well. The newest version of OmniOutliner Pro is nothing short of awesome. As always, there are two versions of OmniOutliner 5, a Standard version and a Pro version. I was given the opportunity to test the Pro version.

I concentrated on the new features that I believe help you create and organise your thoughts, ideas, projects and — why not — shopping lists better than before.

The first new feature in that category is Filters. It allows you to quickly search for any keyword from the toolbar. In the Pro version, this becomes much more powerful with the ability to create and save complex filters based on status, column data, and boolean operations. The only thing that I found a bit awkward was the location where the icon lives to create such a “smart filter” — it’s a “plus” icon all the way down at the bottom of the sidebar. Another, mildly worrying thing, is that double-clicking the Filter tab’s icon generates a small green lock on it. That’s not explained anywhere — at least, I couldn’t find a reference to it.

Document statistics in the bottom status bar, make OmniOutliner 5 better suitable for writing that great British novel. There’s a Distraction-free mode as well, which is good, but not earth-shaking — the Typewriter mode, however, is brilliant. It centres the row you’re working on and is absolutely fabulous to avoid neck strain. Margins also don’t behave like they used to: the whole document now keeps to the middle of your app window, so that you can make it as narrow or large as you want without having to stretch.

One of the goofy new features is Dark Mode. It’s goofy because it doesn’t work by you switching it on, but by you darkening your document background colour to about 60% darkness. At about that point, it just flips on!

OmniOutliner Pro

Password Encryption is a Pro-only feature that’s been added in the new version. Must I say it’s useful? It is, and just to make sure you understand: if you’re using OmniOutliner Pro for anything even remotely sensitive, from business to private information, you can now at least make it a lot more difficult for nosy people to snoop around.

OK, this one is a bit overdue in my opinion: keyboard shortcuts that you can customise yourself.

The Pro version now also features something called Smarter Paste. If you have PopClip running on your Mac, this is what the “Paste =“ item does. It avoids copying everything from text you’re about to paste in OmniOutliner Pro. With Smart Paste, the styles get stripped from text that comes from outside sources, while retaining links and images. A new “Paste with Original Style” option lets you retain the styles from your source content in case you do want that.

The Pro version has a lot of other new tricks up its sleeve. For example, the “Side Margins” feature locks the outline column to a specific width and keeps your outline centred in the window with side margins. You can now also customise the colour of the margins on a document basis.

The Column Inspector now has an editable field for column width. The outline column can also be set to automatically resize with the window. OmniOutliner 5 Pro can also adjust the width to fit your content with the Resize to Fit button.

In version 5, columns can be resized by dragging anywhere — literally: in the middle of your text, if you like — on their right edges. Dragging the left-most edge also resizes the outline column.

The sidebar sections list now allows you to focus on command-clicked rows, which is quite handy, while a new Focus bar appears when you’re selecting parts of your document, that provides access to the button that extends your focus to the whole document again.

In version 5 Pro, you can now export to the Excel (xlsx) format. This is another feature I’ve been eager to have. PowerPoint export now places embedded images on corresponding slides. You’ll need to manually reposition them, though.


OmniOutliner 5 Pro is a great upgrade of a great application. It has become even more powerful and good-looking. The new version costs $59.99 for the Pro edition — money well spent if you ask me.