When a particular USB device is connected to a virtual machine for the first time, the host detects it as a new device named VMware USB Device and installs the appropriate VMware driver.

On a Windows Server 2003 host, User confirmation is required in the Found New Hardware Wizard. Select the default action — Install the software automatically. Once the software is installed, the guest operating system detects the USB device and searches for a suitable driver.

When you are synchronizing a PDA, such as a Palm handheld or Handspring Visor, to a virtual machine for the first time, the total time required to load the VMware USB device driver in the host and the PDA driver in the guest may exceed the device's connection timeout value. This causes the device to disconnect itself from the computer before the guest can synchronize with it. If this occurs, let the guest finish installing the PDA driver, dismiss any connection error warnings, then try synchronizing the PDA again. The second attempt should succeed.