Hi, I haven’t looked deeply into this, but there was a reported issue with OCSP stapling with Nginx between the LibreSSL portable releases 2.9.0 and 2.9.1 (which would have been between December 15th, 2018 and April 21st, 2019)
Reposting here for visibility: https://github.com/libressl-portable/portable/issues/532#issuecomment-501828392 <https://github.com/libressl-portable/portable/issues/532#issuecomment-501828392> - Brent