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What exactly happens when you try to send files? Do you get any error message? You are unable to send files to any device or just one device? Does the list of device show your device? There may be an issues with the device, use the FIXIT option in the link http://windows.microsoft.com/en-US/windows-vista/Troubleshoot-problems-with-Bluetooth-enabled-devices You can also try the following:

(A) Update the drivers and software for the Bluetooth from the system manufacturer website.
(B) Disable antivirus temporarily.
(C) Re-pair the Bluetooth device.
(D) Try to send other small file and see if it works.
(E) If you have another profile in your syste, login with the other profile and see if the transfer works.
(F) Check the settings of the device if it detects your system or if it is blocking incoming request.

Here’s to Good Karma