[throw0101b]

> I have a work laptop (government) that hates captive portals. It has a security system that won't let it connect using the local DNS.

Does the OS not pay attention to DHCP option 114:

    This document describes a DHCP option (and a Router Advertisement
    (RA) extension) to inform clients that they are behind some sort of
    captive-portal device and that they will need to authenticate to get
    Internet access.  It is not a full solution to address all of the
    issues that clients may have with captive portals; it is designed to
    be used in larger solutions.  The method of authenticating to and
    interacting with the captive portal is out of scope for this
    document.

* https://datatracker.ietf.org/doc/html/rfc8910

* https://developer.apple.com/news/?id=q78sq5rv

[sandworm101]

It is more layered than that. The work machine initiates a VPN automatically at login. Once that VPN is up, all traffic goes through the VPN, including DNS. It will actively ignore/block anything that isn't coming from the VPN. So we do tricks to get to the hotel splash page before the VPN software wakes up. These are corporately-managed windows machines. The boot/login process isn't exactly quick.

[jemmyw]

Why do you try to solve the problem at all? Wouldn't it be better to say "sorry I can't do any work from this location because of our IT policy" and let your organisation sort it out if they need you to work from a hotel?