With TradeManger 2008, you can send the same file to several contacts at the same time. The detailed steps are as follows:
1. Select contacts from your contacts list;
2. Right click "Send Files";

3. Find the file to be transferred and click "Open".

Or right click the file to be transferred in your computer and select "Send File via TradeManager".

On the pop up window, please select receivers and click "OK":