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Pillow seems to break TrueType loading
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Was just about to post this issue.
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Posted anyway, because I wanted to post the error it was throwing and I didn't want to delete my already-written post.
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I forgot that I had patched PIL to make that work, should be easy to use the same technique in Pillow.
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Great! looking forward to it.
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Quick workaround:
import _font_cache font_name = 'Helvetica' font = ImageFont.truetype(_font_cache.get_font_path(font_name))