Error uploading ios application to itunesconnect "failed to open ssh session (16)"

According to the log, you don't have network connectivity to Apple's servers, so all of your connection attempts are timing out.

[2014-06-09 11:12:22 CEST] <main> DBG-X:   testing host/port: vgr105.apple.com/33001[2014-06-09 11:13:38 CEST] <aspera.util.SelectThread> ERROR: The session's status is FAILED and the error description is 'failed to open ssh session. (16)'[2014-06-09 11:23:07 CEST] <Transport Protocol Seeker> DEBUG: Transfer warning: Unable to connect to sgr403.apple.com:44001: Failed to connect    at com.signiant.interactivetransfer.engine.TransferEngine$5.run(TransferEngine.java:3617)Caused by: Transfer error: Failed to connect    at com.signiant.interactivetransfer.engine.TransferInstance.newControlPort(TransferInstance.java:367)    at com.signiant.interactivetransfer.engine.ControlStream.<init>(ControlStream.java:894)    at com.signiant.interactivetransfer.engine.TransferEngine$Connector.run(TransferEngine.java:3185)Caused by: java.io.IOException: java.io.IOException: connection timeout    at com.signiant.mobilize.ddsclient.connection.Tcp.<init>(Tcp.java:47)    at com.signiant.interactivetransfer.engine.TransferInstance.newControlPort(TransferInstance.java:361)    ... 2 moreCaused by: java.io.IOException: connection timeout    at com.signiant.mobilize.ddsclient.connection.Tcp.<init>(Tcp.java:42)    ... 3 more

The simplest explanation is that you're being blocked by a firewall within your local network. If that is the case, then you need to contact your network administrators to open up the ports needed for the transporter to work.

The iTunes Connect Transporter Quick Start Guide lists the ports that have to be opened in order for the transporter to work. You can get the document from the iTunes developer site, or I found a copy online here.

You can also try the answer here:

itunesconnect using application loader behind a firewall

In short, change Application Loader's Advanced preferences so that it only uses the DAV transfer protocol.

If anyone comes across this issue again and cant find a resolution. I had to re download the application loader and after the IPA has been created open up the application loader you just downloaded.