More Intelligent "Double-Click" to open documents in DT

This is purely a “it would be nice to have” feature request…

In DT Preferences > General > Interface, you can choose “Double-click opens documents externally”. Pretty self-evident … when unchecked, a double-click opens the document in DT (e.g. to edit an RTF file), when checked, a double-click opens the document in its native app (e.g. TextEdit for an RTF file).

However, in my workflow I have a lot of notes authored within DT (as RTF or markdown), but an equal number of documents authored externally (e.g. Word docs, OmniGraffle drawings etc). This means, for some items, I want to open the document internally, for others, externally. And yes, I can (and do) use the toolbar buttons for this, but even after all this time (using DT many hours every day) I routinely double-click on the wrong document type, and get it opened externally when I want it internally (or vice-versa).

I’m sure you can see where I’m going with this. It would be VERY helpful to have an “exception list” for the double-click setting, based on file type/extension, that basically reverses the setting for documents of that type. So, I could setup DT to open all documents externally on a double-click except RTF and markdown documents (or others I choose by file extension). (Or the other way around of course, open everything internally except the exception list).

This is purely a “nice to have” but it would sure help my workflow … I could just double-click and have stuff open exactly where I want it based on document type (with, perhaps, an override such as holding the Option key to flip it around the other way).

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Would it be an option to assign DT to certain document types in the OS?

That’s kind of the opposite … that would try to open the document in DT if double-clicked in the Finder. What I want is to open the document in its appropriate app (which IS controlled by Finder) when double-clicked in DT. Which of course you can do now, but its an all-or-nothing thing for ALL documents, regardless of type.

Only if you think inside the box :wink: You were quite specific in the files types you mentioned in your first post:

If that actually reflects what you are doing, and was not just a random example, then assigning RTF to DT would mean that if you opened an RTF “externally” in DT, it would open in DT by default. Sure, the same would happen if you opened an RTF from Finder; depending on how you work, that may or may not be a problem (in my case, all my files are in DT, so I don’t open things from Finder anyway…).

Why don’t you disable the preference and just use Shift-Command-O when you want to open documents externally?

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Oh, as I said, its just a convenience thing. My “muscle memory” is to double-click an item in DT to open it (after all, we do that in Finder all the time). When opening an RTF or markdown note, I want this to open the item internally to DT (rather than externally in TextEdit etc). But when opening (say) a diagram to edit, double-clicking it opens a preview view in DT … I have to remember to manually tell DT to open the item externally.

What I’m basically saying is that it would be nice to have DT be smart, and consult a list of files types/extensions to figure out if, when opened, the item should open inside DT or launch the appropriate external app. At the moment, I can set double-click to do one or the other, but only for ALL items

Perhaps I wasn’t clear enough. All the documents (notes, documents, diagrams) are stored inside a DT database. The point is, I want to be able to double-click an RTF note within DT and have it open inside DT, but double-click (say) a diagram within DT and have it open externally in the associated application. That way, a simple double-click always takes me to the correct edit context based on the document type/extension.

Na, I still think you are not reading what I am writing :see_no_evil: If you want an RTF within DT to open in DT if you double-click it, then why not assign RTF to DT in the OS? That way, in DT the open externally command will open the RTF externally in… DT.

The request is noted, with no promises, as always :slight_smile:


Ah yes, you’re right I missed that. Yeah, that would work, assuming, of course I did want to open all RTF documents in DT. It also might be a bit odd, as I have no idea how DT would (or even if it could) handle such a request from macOS.

Actually, setting DEVONthink as the default app should import the file.

I don’t have a test rig* (and whilst I will use my test database to test things for others here, as a matter of principle I’m not changing OS settings) available; if the file is already in DT (i.e. it is an imported record) then would DT not simply open the record?

* so is that the excuse I need to buy an M1 Mac…?

I can think of several reasons why you NEED an M1 Mac :slight_smile:

And while @cgrunenberg would need to weigh in on the feasibility of changing any of this behavior, setting DEVONthink as the Open With application for file types will invoke an import of said file.

  • If the file is already in the destination database, it will be skipped (and logged).

  • If you import to another database, the file will actually be moved from the internals of the current database to the other, leaving you with a missing file message.


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Well @drtimhill, I’m sorry my solution appears not to be a solution.

Feasible is almost everything :slight_smile: But at least currently it’s not yet planned to change this.

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Adding to this thread just to say that I am in the same situation and would really like the solution proposed by the OP.

Also, my recollection is that the previous version of Devonthink (version 2) did this stuff automatically. That is, when double-clicking, somehow it knew to open Word documents in Word while opening notes taken in text or RTF, as well as PDFs, internally. I don’t know how it did that or whether my recollection is entirely correct. But I do know that I never had a problem with how DT behaved in this regard until I installed the current version.