What is the deal with this? How can it be done! There has to be a way 2 years later!!!
Yeah, I agree, the situation really is ridiculous. All the UPS Plugin for Windows is is a special-purpose MIME handler; it looks for the MIME type indicating a Zebra "EPL" file and sends it directly to the Zebra printer. There's really no reason why UPS can't make their plugin for other platforms. In fact, someone wrote an open-source plugin for Linux, but it isn't being maintained. It's on SourceForge here:
http://sourceforge.net/projects/upsplugin/files/
My way around this mess is to download the label generated by UPS.com, then manually send it to my Zebra printer. This is preferable to copying the label image and printing it because you get full resolution, so the label looks nice and sharp.
The easy way to download the label is to use a download manager (I'm using Speed Download), and tell the DM to handle the MIME type "application/epl2". Now, every time Speed Download sees this type of file sent, it downloads it to my Mac. Once the file is on your Mac, you have to send it to the printer. So far, I do this on the command line. Just like other *nixes, you can use 'lp' to send the file. Or, if you have a network-attached Zebra, you can use NetCat to send the file: 'nc PRINTER_IP 9100 < /path/to/label/file' (substitute your Zebra's IP for "PRINTER_IP"). This technique works perfectly, though anyone shipping more than a few packages a week will find this cumbersome. Hopefully, UPS will write a Mac plugin, or better yet, someone will improve the open-source one.