Unable to print on compliment slip

[myhorsebox]

This is the third printer I've tried and still cannot figure out the correct settings...

Currently using a mac, word and Epson ET-2850

Word setup - Page Setup: Paper Size - Other 210 by 99 mm & Orientation: Portrait (although on screen it looks landscape because the page is wider than it is high)

Printer set up: Paper size 210 wide by 99 high

When I place the comp slip into the printer with the wide edge first, it spits it back out blank.
If I place it in short edge first, it prints small writing in the middle of the slip (but if you were to hold it the right way up, the text is rotated 90)

I have tried switching the page setup to landscape in word, but can't figure out how to get the text to rotate.

I'm all out of other ideas

 

[oemsetup.inf]

Did you also create the custom page size in the Driver and use it for the 'Print Size'?

Otherwise it will convert to the size set in the Driver regardless of Application or Device settings.