Try this test on your Mac: Select a collection of ten image files in the Finder and open them in Photoshop. You can either double-click the files, or drag them together onto the Photoshop icon in your dock.

Do they open up in the order you expected? Do they open in alphanumeric or chronological order? Chances are Photoshop opens the images in a seemingly random order. How frustrating!

This annoyance isn’t limited to Photoshop. With a few notable exceptions, opening a list of files from the Mac OS X Finder results in a random order in most applications. In this tip we’ll describe 3 workarounds to solve this annoying behavior.

Workaround #1: Use Column View instead of List View in the Mac Finder.

The easiest way to avoid a random sort when opening multiple files from the Finder is to use column view instead of list view. In the Finder menu, choose View > as Columns, or click on the column view icon in the top of your Finder window.

Double-click on a collection of files in column view, and they’ll open in alphanumeric order in the final application.

Tip: Want to open all your files in a specific application? You can’t drag the file to an icon in the dock — that opens them with the same frustratingly random sort. Instead, right-click or control-click on the selected files and choose Open With from the pop-up menu.

Workaround #2: Select Multiple Files from the Open Dialog Box.

Another easy way to avoid the random sort is to simply select them all directly in your application’s Open dialog box. This works in Photoshop, and many other applications.

Workaround #3: Open Files using Adobe Bridge Instead.

Finally, you can avoid the Finder altogether. When you open a collection of files using Adobe Bridge, the correct sort order is maintained. Plus, when using Bridge, you have a greater number of sort options available when browsing your files (chose View > Sort from the main menu).

Editorial: Why is this still a problem?

The first public beta of Mac OS X was released in late 2000. We are currently using the fifth major release (Leopard 10.5). It seems inconceivable that this tip still needs to be written. Here is to hoping that in in the next release (Snow Leopard 10.6) we won’t still need these types of silly workarounds.

Source: This tip is inspired by a range of frustrated phone calls we’ve received about this issue over the years.