Remote "seems to work but not ios app"

Server Version#: 1.26.0.5715
Player Version#: Web

So, I recently got upgraded my mac mini server from mojave to catalina (yes it is older one..) and at the same time I also replaced my pihole dns with adguard home instead..
I have everything backup and running, except for plex remote access..
Well, yes, initially it does show red but it will eventually turn green and remote access works, tested from outside. BUT the ios app keeps showing offline :confused:
I suspect it has to do with the certificates as this is in the logs:

May 15, 2022 19:53:25.304	ERROR	CERT: Error acquiring new certificate: Failed to upload CSR: 429,
May 15, 2022 19:51:24.171	INFO	[CERT/OCSP] Successfully retrieved response from cache.
May 15, 2022 19:51:24.165	ERROR	CERT: Error acquiring new certificate: Failed to retrieve cert from plex.tv: 429,
May 15, 2022 19:49:21.280	INFO	[CERT/OCSP] Successfully retrieved response from cache.
May 15, 2022 19:49:21.275	ERROR	CERT: Error acquiring new certificate: Failed to retrieve cert from plex.tv: 429,

repeatedly (even with remote access disabled)
I cannot find any cert in the plex directories and from the error code it seems to be declining the connection due to initial spam when I was still configuring things.
Can staff please reset the cert?
thanks

EDIT: Canyouseeme works and can see the manual port forward etc..

update, since the last pms update everything seems to be working as it should