How it works
pfSense has a captive portal service that will capture all packets unless you are authorized. It will capture any HTTP requests and redirect you to a special page served by pfSense (see pfsense/portal.php). However, this page simply uses pfSense functions to map your requesting IP to a MAC address. Then it takes this MAC address and the URL you were trying to go to, base64 encodes them, and passes that information to an App Engine app via redirect.
The App Engine app serves a page that lets members login for full access, or lets guests get a daypass or use the guest network. This app keeps this state for pfSense to check if you are authorized.
The way pfSense finds out if you are authorized is using a RADIUS server. This is the only workable option pfSense gives us. So we have a "fake" RADIUS server running on pfSense (see pfsense/bridge.py) that takes authorization packets and checks with the App Engine app if that MAC is authorized. It keeps a local cache and has a fail over mechanism, but otherwise it's just a bridge to let us do authorization with the App Engine app that has that state.
The App Engine app has some tricky logic that is worth pointing out. When you login as a member, it will authorize against Google Apps. This may return a captcha challenge, which we have to pass on to the user. If they successfully login, we create a Login record and a MacAddressMapping. Recall, the MAC address was passed in from the pfSense captive portal PHP page. The app actually stores this in a cookie for easy access later.
Now that there is a MacAddressMapping (and there can only be a limited number of mappings per member), when the RADIUS bridge asks if a MAC address is authorized, we lookup the MacAddressMapping, make sure the member is not suspended, then authorize by returning 200 and some configuration that's passed back to pfSense (namely bandwidth limitations).
The app handles guest logins slightly differently. When you connect as a guest, daypass or not, we do not use a MacAddressMapping, but a simple memcache key using the MAC address as the key. This makes it easy to expire and keeps member mappings separate from guest mappings. When a guest purchases a day pass, we set the value to signify they are a day pass user. Otherwise, we signify they are just a guest.
So when the RADIUS bridge asks the app if a MAC is authorized, it will first check memcache to see if they are a guest or day pass holder before checking for member MacAddressMappings. It will return appropriately depending on which they are, including their bandwidth limitations.
Lastly, regarding device limits, we limit you to a number of devices based on MAC address. If you login at your device limit, it will succeed, but the MacAddressMapping for your oldest device will be removed. This does not mean it will stop working! pfSense will continue to allow it until the session expires and it has to check RADIUS again. Sessions expire most likely after an idle timeout set in pfSense.
The DNS problem
Unfortunately, since our captive portal login page is out on the Internet, we need to let the captive portal always allow it. There is an Allowed IPs list and an Allowed Hostnames list in pfSense. Ideally, we'd just have hd-captiveportal.appspot.com in Allowed Hostnames, but last we checked, this new feature was not working.
We have to use an IP address for the App Engine app. The IP that App Engine apps resolve to can change, which makes it difficult to allow a known IP. So we first override the DNS provided by the router to force a known working IP for App Engine.
Now we've created a new problem. If the user is using custom DNS instead of DHCP assigned, they won't get this IP address. This breaks their Internet access because they can't get out but can't get to our captive portal page to authorize.
One possible solution is to set up a routing rule to route all DNS traffic to our DNS server provided by pfSense. However, in practice, these rules in pfSense happen after the captive portal. So they work when you're authorized, but don't seem to be in effect before you've authorized. That means this won't work.
The only remaining alternative is to just allow the IP of all known DNS servers that one might manually set their device to use. This is a reasonable approach because if people are setting their DNS manually, it's likely to a well-known IP like 184.108.40.206 or 220.127.116.11 ... so we allow these in our Allowed IPs list. Any time somebody can't access, we can ask them what manual DNS server they're using and add it to the list until we have decent coverage.
Resetting your device
If you logged in as a guest, you can just go to the root path (/) of the App Engine app and it will clear your cookie and its memcache record of you. If you are logged in as a member, you will have to use the App Engine admin to delete the MacAddressMapping record.
In either case, you will also have to remove a record from pfSense under Status > Captive Portal. Then you should be reset. You have to delete both the record in App Engine and pfSense for reset to happen correctly.