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Not sure if you’ve solved this but for the sake of anyone else who comes across this, I had the same issue and just figured it out.
If you use order_by on a field in Haystack and Whoosh is your back-end, the field you are ordering by must exist on ALL of your indexes. Not just the one you’re interested in. Filter doesn’t suffer from this same requirement, which is why that query goes through.
Source:stackexchange.com