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Not sure whether this should be asked in Super User or here.
How does Chrome distinguish between a Wi-Fi access point intercepting with a captive portal and a man-in-the-middle attack on HTTPS?
Are they using a preloaded list of redirect targets when checking against sites with HSTS or what?
About Chrome
According to https://www.google.com/chrome/browser/privacy/whitepaper.html
In the event that Chrome detects SSL connection timeouts, certificate errors, or other network issues that might be caused by a captive portal (a hotel's WiFi network, for instance), Chrome will make a cookieless request to http://www.gstatic.com/generate_204 and check the response code. If that request is redirected, Chrome will open the redirect target in a new tab on the assumption that it's a login page. Requests to the captive portal detection page are not logged.
You can disable navigation error tips by unchecking the box in the "Privacy" section of Google Chrome's options.
About Chromium OS
https://www.chromium.org/chromium-os/chromiumos-design-docs/network-portal-detection explains :
Shill, the connection manager for Chromium OS, attempts to detect services that are within a captive portal whenever a service transitions to the ready state. This determination of being in a captive portal or being online is done by attempting to retrieve the webpage http://clients3.google.com/generate_204. This well known URL is known to return an empty page with an HTTP status 204. If for any reason the web page is not returned, or an HTTP response other than 204 is received, then shill marks the service as being in the portal state.
Many, or perhaps most, captive portals found in Hotels, Coffee Shops, Airports, etc, either run their own DNS server which returns IP address for all queries which point to their webserver, or they intercept all HTTP web traffic and return a 302 (redirect) response. The captive portal detection works very reliably with these types of portal to indicate that the service is not fully online.
