What is the main difference (may be pro/con list) between buying a custom SSL certificate and getting one from Free certificate provided by Let's Encrypt. This is all about just having simple https in our Web Application
P.S I believe you understand what I am trying to do.
The main practical difference is to be trusted in all browsers and third party systems, for example Android, iOS or Windows.
Lets encrypt has taken this restriction into account and has proposed a solution that you can read on its website https://letsencrypt.org/certificates/
That is, in fact, their certificates are signed by a trusted 'usual' CA. So in practice there is no difference
Take a look at letsencrypt's own web certificate, it is signed by
DST Root CA X3
(IdenTrust)I have checked if CA is present in some keystore:
Full list here: https://letsencrypt.org/docs/certificate-compatibility/