Ruby PDF generation with CombinePDF & StringIO removes "<" character

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I can't for the life of me figure out how to make < show up in pdf generation using CombinePDF & StringIO. > shows up fine in the generated pdf but not <. I can't easily change the software I'm using and would ideally escape "<" so that it still shows up in the pdf. I would post the code here but it's extensive across multiple files.

Anyone have an idea what I can try to get the symbol to show up in my pdf? Is there a way to choose an encoding type in CombinePDF or StringIO on ruby on rails.

Thank you in advance, sorry for a more broad question. I've been working on this for a day now and need any help you can provide.

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