I was missing a slash... :oops:
When I use session.SynchronizeDirectories I can copy a file from my local folder to a remote site without issue.
These are my folders:
Dim signalFolder As String = "e:\Signal"
Dim RemotePathSignal As String = "/Test/"
When I use session.putfiles with [signalFolder & "\*"] as local folder and the same remote path the file gets picked up but then I get: Copying files to remote side failed Access Denied"