I see this quiet a bit with routeros, when using the Hotspot. I've been able to work around this for years, by simply telling people to clear their browser cache, but as I"m setting up another client, it's really not an option. Perhaps I have been missing something simple all these years.

Basically when a user first logs onto the network, tries to navigate to example.com the first time, the hotspot login comes up and they log on normally. After logging off, assuming they don't clear their browser, which most people don't every time they use the internet. When they come back to log in, and navigate to example.com they are not directed to the login page, simply get a "website not available" or network not available, etc.

Only if they try to navigate to a page they've not been to, or clear their cache are they directed to the login window.

I've dealt with this over the years by simply telling people to do just that, but I'm wondering is their a way for this to actually work properly?

I have cookies turned off in the hotspot settings by the way. I want/need people to log in after every time they log out.

Is this repeatable with every browser on every client OS?

It's consistent across clients/os. And only for specific websites. For example, surfing to hotmail brings up the login window every time. Facebook results in "Safari can't open page" or "secure connection failed" in Firefox or "website not available" in chrome.

It may have something to do with htpps pages?

That's a possibility. If the user has the site in their history and they start typing it, the address bar will complete to the actual site [eg https://hotmail.com] whereas if they haven't visited it, the browser is going to assume HTTP and take them to http://hotmail.com, which can then be redirected to the hotspot login page. This would certainly be consistent with how Firefox behaves, anyway. I assume that when users are advised to empty their cache, they're probably deleting their history as well.