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Oct 5 at 7:10 comment added Thomas well, yes, but that's why I gave it a static route for this: 10.212.69.3 255.255.255.255 10.0.0.97
Oct 4 at 8:31 comment added vidarlo Because it has no idea of how to reach 10.212.69.3 on a local interface. Remember that IP packets doesn't contain routing information; they contain source and destination address. Look up the IP header; it doesn't have a Next hop-option; it has src and dst IP.
Oct 4 at 8:29 comment added Thomas "Every machine is a router." My thoughts exactly: One Windows box -> one router - MY router ;-) I gave it plenty of info how to route the package (through two hops, all on the same Windows machine). I fully agree that one route is suffcient and technically works, but I still don't quite see why giving it two hops should confuse it so much that it rather sends it to the default gateway instead.
Oct 4 at 8:00 comment added vidarlo Every machine is a router. It may be routing only for packets originating from itself, but it uses the routing table to look up where to send them. Source routing was a thing, but security implications basically killed it a long time ago.
Oct 3 at 22:09 comment added Thomas Geeeesh... that worked. "You can only specify the next hop, you can't instruct upstream routers what to do." was the key - but I still don't quite understand that. I mean, that package needs to get to 10.212.69.3 so I gave MY Windows a route from 100.102.0.0/28 to 10.212.69.3 and also told MY Windows that packages to 10.212.69.3 must be sent through 10.0.0.97. Doing it your way (the right way!) makes this even simpler, but I would have thought that passing data through two routes on a single Windows machine should work, too... I didn't (and still don't) see MY Windows box as being two routers.
Oct 3 at 21:50 vote accept Thomas
Oct 3 at 18:51 history edited vidarlo CC BY-SA 4.0
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Oct 3 at 18:46 history answered vidarlo CC BY-SA 4.0