Hi @AA007 ,
Thanks for bringing this over from Inspire. I hope you are enjoying the conference!
My initial thoughts:
This is most likely a certificate trust issue, or a failure to negotiate a common cipher suit with the end server. Designer in general (including the download tool) will refuse to connect to services running with an non-trusted or invalid certificate. The connection can also fail if the service and Designer can't negotiate a cipher suit both are willing to use. If you want to see what is failing with the SSL negotiation you will need to use Wireshark or something similar . I would also connect to the service via a web browser and ensure the certificate the service is using is properly trusted.
I have also seen another scenario seen here: https://community.alteryx.com/t5/Alteryx-Designer-Discussions/SSL-Connect-Error-in-2019-1/td-p/41459...
Where the individual said that, "The user registry policy had todays date whilst the machine had a different date (yesterdays)." This would also be worth checking.
I hope this helps!
