[jzelinskie]

TailScale is great -- I've met the founders and use it for my own personal network.

At it's core, ShareWith is more about being able to take anything that supports OIDC and adding the ability to dynamically request access in the login flow. OAuth2Proxy, which is a popular way to protect generic HTTP resources, is one convenient way to demonstrate that functionality, but you could leverage that same functionality in a completely different way native to your application if you don't want to have to build that same workflow for your app.

For the borderless network use case, an access request workflow really changes how you use protected resources because getting access to something becomes simple and routine. In a VPN setup, you're unlikely to share with users outside of your organization because of the overhead from provisioning and setup. Consider how you can easily share a Google doc with an outside contractor, but it's not worth the effort to give them access to a JIRA ticket.