When the host machine I'm connecting to is currently on both the docked (ethernet) and wireless version of our network, which one does RDP default to when I initiate Remote Assistance?
2 Answers
It is connecting to the IP address the hostname resolves to, and therefore to the adapter that has that particular IP address.
You can verify the fact using netstat
on the command line, it shows the open TCP connections and the addresses on both ends.

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Does a laptop on Ethernet and Wi-Fi have two IP addresses assigned simultaneously in a DHCP environment? – WakeDemons3 Feb 27 '18 at 21:19
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Yes, both will have a separate IP address. Only if they are in the same L2 bridge, they can share an IP address, but that is very rare. You can check the IP addresses with `ipconfig` on the command line. – Tero Kilkanen Feb 27 '18 at 21:29
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So this doesn't really answer the question then. When one hostname resolves to two IP addresses, which one is RDP defaulting to? – WakeDemons3 Feb 27 '18 at 21:47
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It does answer the question as it was written. The answer you were seeking cannot be given with the information you provided in the question. – Tero Kilkanen Feb 28 '18 at 07:45
This isn't a function of RDP. It's a function of DNS. Whichever A record is returned first in the order in the DNS query answer is the ip address that RDP will use to connect to. More specifically, this is a function of the Round Robin feature of DNS.
In the two captures below taken while querying for the A record of my desktop computer from two different computers you'll see that my DNS server has used Round Robin to re-order the answer to each client. The first client gets one A record first and the other client gets the other A record first.

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