My guess is something failed and did not terminate the process properly and although it may appear to be doing something it probably is not. A couple of things to try:
1) Does exporting to a ctx file work? This should tell us if it is something to do with the configurable model conversion or communicating with the device.
2) If possible get the site to export their datamodel and configurable model. We can test the ctx export with this.

To narrow down the root cause it may useful test if "Export to File" option works ok. You can then try to upload generated CTX file to the device using CyberTracker application itself.

If the problem is related to upload itself then we should ask Justin about this. Maybe he as aware about it.

here is the CA.

file:belXAYxxur5B3cdmr6bg7m

Rich - I had no problems exporting the configurable model or the data model to a ctx file. This leads me to believe the issue is likely with the communication between cybertracker the device. It might be worth following up with Justin, he may know of issues with Trimble/Windows Mobile.

I investigated the problem a bit and here are my findings:
1) I was able to export to ctx file without any problems
2) I was able to reproduce the issue from the first tile I tried to export to my android device
3) I created very simple configurable model and it exported without any issues, after that export for "June2015" was working fine as well. I was unable to reproduce the issue afterwards.
4) Issue is related to CyberTracker as the ct3.exe was still running after about 10 minutes (see processes_bug.png)

Several key thing about my configuration:
1) I had CT v3.386 on android device with some old apps installed
2) I had CT v3.390 on my PC

Note: I noticed that when we successfully execute /uploadpda ct3.exe launches 2 processes. Once occupies a bit less memory then the other and looks like one lunches the other. (see processes_ok.png)

We should address this question to Justin.
As I workaround I may suggest to kill ct3.exe process if upload is hanging for a long time and try to repeat it again.

I don't think Justin is a "user" on the SMART Assembla project. Can we add him so that he can be sent a link to this page?

Rich - anyone can view these tickets they do not need to be an assembla user. However if he needs to edit the ticket he does need an account. I believe Alexa is the one who has been setting up these accounts, so perhaps you can ask her.