Application to device requires reboot to install

We've imported a handheld device, we have distributed files directly to
the device. However, when we distribute an application (.cab files OR
just a test text file), they do not appear on the device until the
device's workstation is rebooted. Even if we activate scan now, or
refresh, or any other setting that should resend it to the device, files
do not appear or installation begin until the device's workstation is
rebooted. Is this correct behaviour? We were expecting to send files
(text or .cabs) directly to the device and they appear or install
immediately without rebooting the attached workstation. Wrong assumption?
thanks