Hi

> If the server is running on a private IP, how can you expect it to know
anything except the private IP?

Administrators that make SFTP-Servers available to the public internet, NEED
to be aware of that problems and as such NEED to configure the server
accordingly. Otherwise they are not doing their jobs. SFTP-Servers do have
configuration options for this. (Like -P <ip> for pure-ftpd for example.)

You wrote:
> Given the discussion below, we need a solution that allows 
> the user to force an override for the IP address used for 
> passive connections.

I wrote:
> If at all, give the use a change to optionally overwrite used IPs.

Which matches... And solves the problem without introducing broken logic.
If you are ONLY connecting to that server, don't ask at all. You know how to
connect.

Regards,
  Steffen

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