Today you learned about Apple’s smart file dragging trick for macOS

Apple has made macOS very good at handling drag and drop. For example, I often drag an image directly from the Photos app or Safari and drop it into iMessage or Slack. One thing that has always slowed me down, though, is moving around more traditional files, like PDFs or other documents.

But then I learned that very few apps, including many built in, have a quick shortcut to the file you’re viewing. With this shortcut (officially called the proxy icon), you can easily do things like upload a PDF you opened in Preview to Google Drive without having to search for the file in Finder. Here’s how it works:

A Nary a Finder window has opened.
GIF of someone dragging a file from Preview into a Safari window using Google Drive.

The trick is to use the title bar, which is the area where Apple puts the window controls in traffic light style and the name of the file you’re opening as well as other buttons, depending on the app. If you hover over that file name for a second, you may notice a small icon appear to the left of it. (Some apps don’t require scrolling.) That’s what lets us do our magic. If you click and drag this icon, you will basically be clicking and dragging the actual file as if you were using a file manager.

To be clear, this is not a new feature of the latest macOS beta or anything else. I’m sure I learned about it when someone mentioned it in the context of features that have been around for so long that younger guys like me have never heard of them. So yeah, I’m a little late to the party here. But now that I finally know about it, I use it all the time.

One of the most common use cases is when I have to read a working PDF and then upload it to DocumentCloud so I can include it in an article. I used to do this by reducing the preview and then searching for the document on my busy desktop, using Quick Look (the thing that previews a document when I press the space bar) to make sure I didn’t load the wrong thing. Now, I can just drag and drop the thing I’m reading directly from the preview, like I do in the GIF above.

I have also found plenty of other ways to use this feature. If I have Finder in a certain mode, I can use it to quickly copy the folder path I’m using in Terminal. (Bonus tip: If you drag and drop a file or folder into Terminal, macOS will just enter the path to it.) I even used this feature in QuickTime to make the screen recorded in the GIF you were watching in this article.

Oh yeah, did you know you can just drag files to the default Choose File button?

While this won’t necessarily apply if you’re just using this feature to share files between apps, I have one word of caution if, like me, you’re thinking, “Wait, what happens if I drag the file from the address bar into a Finder window?” The answer is that he will moving file from anywhere currently to wherever you dropped it. This is a reasonable assumption, I suppose, but it might end up confusing if you assume it will copy and paste the file instead of cutting and pasting it.

Unfortunately, this is not something every app can do. I haven’t been able to find a way to get files from Obsidian or Photoshop, for example – although the latter isn’t entirely surprising. But there are quite a few apps I was able to use with it, including Pages, Blender, Logic Pro, Nova, and even Microsoft Word of all things. If there is an app where you search for files frequently, it is worth checking if it supports this feature; You never know when it will come in handy.

But wait, I’ve got one last extra tip if you’re hanging around the address bar – although if I’m being honest, that’s a bonus because I haven’t run into any situations where it comes in handy. In addition to being able to drag a file’s icon, you can also right-click on it to see what folder that file is in (and which folder who – which folder in, and so on). From there, you can use the menu to quickly open a Finder window that navigates to that folder.

Right-clicking on the file icon allows you to easily see where it is on the disk.

While discovering this system wasn’t a shocking revelation that my productivity increased 10x, it did help reduce the amount of time I spent searching for files I had already opened. And that’s great because having to do this can, ironically, be a real handicap.

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