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It's a wildcard certificate, which isn't supported by Let's Encrypt yet.

Site appears to be hosted in AWS. Lots of free SSL goodness to be had from Amazon as well.

It's stretching into off-topic land here, but could you suggest any AWS SSL resources that are worth investigating?

AWS has Certificate Manager which provisions free certificates and manages renewals automatically. Usable across ELB, Cloudfront, etc.

Uploadcare does not have issues with certificates and we're indeed going to switch to ACM for some of the endpoints.