The Telnet/SSH button uses the Telnet or SSH client you have specified in the Options > Setup > Misc tab.
It doesn't actually use to CatTools Telnet/SSH client or test the credentials you have configured for the device.
With regards to the 'Failed to connect...' error in the CatTools info-log; it tends to suggest that maybe the SSH credentials have not been added for the device correctly in CatTools.
Can you check the following:
1) Device type: Cisco.Switch.IOS (the other Cisco.Switch.1900 is for real old 1900 devices).
2) In the 'Passwords' tab of the device set-up ensure the correct SSH credentials have been added in the fields:
- SSH Username
- SSH Password
It appears that in all the changes that I was making to get it working something wiped out the credentials in the device setup. Thanks for the help.