not sure office == work place, but most workplaces have policies around intentionally bypassing network security/firewall rules. If your workplace has any kind of security operations/threat detection, you could find yourself explaining why exactly your host is reaching out over suspiciously encrypted channels?

Specifically, https://en.wikipedia.org/wiki/Egress_filtering. If the OP's company has restrictive firewalling and filtering already, they also probably have egress filtering and monitoring as well.

I agree with you, this will surely raise a red flag in our administrators panel and this isn't my intention. I'm mainly interested on the technical side of things.

I know that most ports and traffic types are already blocked. What about outgoing https traffic, this is encrypted and should be allowed to pass...something like an https tunnel.

Just note that doing that is probably a fireable offense.

Definitely agree! Irrespective of motive it would raise questions about integrity! You don’t want to be going there!!

Fully agree with you, this is something that needs to be treated seriously especially in a professional business environment. I'm mainly interested on the technical side of things and on what is feasible, not on ways to bypass security for illegal purposes.