This would make sense. Even with wired ethernet ssh has to have succeeded once and accepted if the user will not be required to reply that “yes, the connection is legitimate, go ahead and connect”. If you can’t reply to that ssh question, then you cannot connect.
On ssh command line this is never a problem, it just asks in the same terminal you connect from…for a GUI, and for anything automated, you need a second set of software for the pop-up to make the asking of password prompt available…appropriately named via the SSH_ASKPASS environment variable. If your host has installed an askpass mechanism (multiple “brands” of this are available, depending on distribution, e.g., KDE has “ksshaskpass”, Ubuntu has “ssh-askpass”…but often these are not installed by default and must be explicitly added).
Examples for Fedora with KDE:
dnf search askpass
=============================================================== Name & Summary Matched: askpass ===
lxqt-openssh-askpass-l10n.noarch : Translations for lxqt-openssh-askpass
lxqt-openssh-askpass.x86_64 : Askpass openssh transition dialog for LXQt desktop suite
==================================================================== Name Matched: askpass ========
ksshaskpass.x86_64 : A ssh-add helper that uses kwallet and kpassworddialog
openssh-askpass.x86_64 : A passphrase dialog for OpenSSH and X
x11-ssh-askpass.x86_64 : A passphrase dialog for X and not only for OpenSSH
From a Jetson TX2 on R28.1 (some results intentionally removed as not relevant):
apt search askpass
ksshaskpass/xenial 4:5.5.5-0ubuntu1 arm64
interactively prompt users for a passphrase for ssh-add
lxqt-openssh-askpass/xenial 0.10.0-3 arm64
OpenSSH user/password GUI dialog for LXQt
razorqt-openssh-askpass/xenial 0.5.2-4build1 arm64
OpenSSH helper component for Razor-qt desktop environment
ssh-askpass/xenial 1:126.96.36.199-9 arm64
under X, asks user for a passphrase for ssh-add
ssh-askpass-fullscreen/xenial 0.3-3.1 arm64
Under Gnome2, asks user for a passphrase for ssh-add
ssh-askpass-gnome/xenial-updates 1:7.2p2-4ubuntu2.2 arm64
interactive X program to prompt users for a passphrase for ssh-add
But…this would be the same issue regardless of whether using WiFi or wired. It isn’t just a WiFi issue. On the other hand, this askpass must be accomplished once for every “name@host” used…if your Jetson is at 192.168.1.3, and you ssh to “firstname.lastname@example.org”, and if there is also an alias of “tegra-ubuntu” for “192.168.1.3”, then although this is the same connection askpass must be run on each one, and “ssh email@example.com” will be considered completely separate from “ssh name@tegra-ubuntu”.
Note that “~/.ssh/config” might not be able to override “/etc/ssh/ssh_config” to loosen restrictions…it can however always tighten restrictions. I suspet that if you want to loosen a restriction you need to test and see if it actually works. Since WiFi is not behind a router to block incoming unwanted networks you are at extreme risk to do this if you do not change passwords. Everyone knows the default install accounts and passwords for Ubuntu.