ssh wants passphrase and password if accessed via remote VPN login

[Petter Adsen]

On Thu, 19 May 2016 18:44:55 -0700
MR ZenWiz <mrzenwiz at gmail.com> wrote:

> My workstation is, let's say, DeskBox.  At work, I log onto DeskBox
> directly, and from there I use a terminal windows to ssh to the other
> development machine, let's call it DevBox.
> 
> When I work from home, I use the Win7 VM to PuTTY in to DeskBox, and
> from that pseudo-terminal window attempt to ssh into DevBox.  This is
> where the pass phrase and password demand occur.
> 
> The connection is always between DeskBox and DevBox.  The only
> difference is whether I am sitting at the desk and connected directly
> to DeskBox via its keyboard, mouse, monitors and terminal window, or I
> am logging into DeskBox remotely (via my Win7 VM and PuTTY).

Then I am guessing ssh-agent is behind this. On DeskBox ssh-agent is
probably running in the background, so the first time your passphrase
is used, it will be stored in memory by ssh-agent. OTOH, when you log
in from the Windows VM your session will not have an ssh-agent running,
so you will be asked for the passphrase every time.

https://wiki.archlinux.org/index.php/SSH_keys#SSH_agents

For a simple solution you might want to check out 'keychain'. There's
a quick guide to setting it up on the wiki page above.

Petter

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