Open Tools | Developer Tools from Chome menu. Switch to Network tab there. Keep that window open, browse as usual. Once you see that phenomenon again, go to that Developer tools window, and see which file was not loaded properly and why. It could be a DNS issue, or some transparent proxy acting up, or some other problem.
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The problem is that after the captive portal redirects, I'll have also a HTTPS redirect and Chrome remembers the certificate and to use only HTTPS. So I cannot use the same site twice (in a session). A well-known public HTTP only site will resolve this. Well-known sites usually work, causing less debugging of the Wi-Fi connection. google-chrome.
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Now, when you open that file you’ll see information about the websites you've visited directly or indirectly. To get rid of this, just type the command ipconfig /flushdns and your DNS cache will be cleared. Angel Luis has written a nice tutorial and script on this topic, I suggest you read it.
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