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I am looking for a simple/fast, free solution that will allow me to get screenshots from different windows, crop areas that are interesting to me and adding some comments to them.

It's main use case would be to track UI changes in applications, so it would be a good idea to support layers.

On Windows I was using Paint.NET but this is not available on OS X. Also, do not recommend GIMP, it's free but not simple and loads really slowly.

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up vote 11 down vote accepted

Use Apple's built-in to capture screenshots, Apple's built-in to crop, and the open-source Inkscape to annotate the bitmap.

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You can annotate directly in – jm666 Jun 7 '11 at 10:04
Actually, you can do the whole process, not just annotate, right in preview. See my answer for details. – user137369 Aug 30 '15 at 13:49

If you prefer an all-in-one solution to the Grab + Preview combination, try Skitch.
The lite version is free and should be enough for your -described- needs.

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I definitely like Skitch's features (though it's workflow/usability is... frustrating, at least to me). Being able to make distinctly vivid arrows/lines, boxes, circles, or text within seconds is a great feature of Skitch. Emphasis on DISTINCTLY VIVID. Any neon (pastel?) color in a hurry, with distinct sizes and completely readable. – Jason Salaz Jun 8 '11 at 18:33

If you are interested in a portion of the screen, try Cmd+Shift+4, which turns the cursor to a crosshair; you can then select the portion of the screen and it will be captured to your desktop. By the way, Cmd+Shift+3 captures the whole screen. As far as annotation, you can follow jm666's suggestion and use Preview.

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i am using jing from techsmith for a long time now and enjoy it very much:

you can even record screencasts in the free version. and it's cross platform (windows and osx).

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You can do everything from OS X’s Preview app.

Under File you’ll find Take Screen Shot. After you take it, the image will open directly in preview, and you can use the Annotate options under Tools, and more that appear from Show Edit Toolbar under View.

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This might be better as an edit to the prominent / accepted answer as opposed to being buried at the end of the list. Your call, of course... – bmike Jun 4 '14 at 23:02

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