[RKearney]

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

[powvans]

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

[King-Aaron]

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

[manigandham]

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

https://aws.amazon.com/certificate-manager/

[dmitrymukhin]

It's Heroku for Stackshare: https://stackshare.io/stackshare/stackshare

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