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Can you please take a decent screenshot using the system tools?
Is there still a path in that counter or not?
This should not happen, but also you should not need to outline the text just for printing.
If there is still a path, then try and open the Attributes panel and set the fill rule to even-odd.
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Please use Printscreen
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OK, there is no path.
You could try: Object > Flatten transparency (check "Outline text")
Maybe it does it differently.
If that does not work. Draw the counter. And then after outlining the text, use the pathfinders to punch it from the text
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Thank you so much the first suggestion worked. Amazing.
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Glad you could solve this.
If you have an option to contact the font designer, you should do it, because Outline Text should not work like what you experience.