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Since you can't ssh from PagodaBox (the binary isn't installed), you can't rsync or scp between servers. Thus you need to copy them locally and then upload back up

1. Enable ssh in PB for both servers.
2. SSH to the first server and tar the uploads dir: tar -cvf uploads.tar shared/public/uploads. Not bothering with zipping causing it would take along time and it's all binary so I don't expect much compression help.
3. Download the uploads.tar file to your comp.
4. Delete uploads.tar file from server.
5. Upload uploads.tar file to the root of second server.
6. Connect to second server via SSH
7. Uncompress it: tar -xvf uploads.tar
8. Delete uploads.tar file from the second server