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In finder, I can cntrl + click on a file and click "compress"... Sometimes. It seems that randomly the option just won't show up and I have to open a new finder window, or duplicate the folder first, or something ridiculous like that.

Is this a bug, or is compress only supposed to show up under certain circumstances?

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This might help:

Apple discussions

It says that you can't compress certain folders like smart folders that are created in the 'All My Files' and 'Recents' box.

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If you have any zip files in the selection, you are unable to compress these and the option will be removed from the context menu. Deselect any zip files from your current selection and try again.

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    The option disappears only if all the selected files cannot be compressed. Selecting one ZIP file and something else still shows the "Compress" option. – Matteo Jan 23 '15 at 20:38

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