Make sure you have the most recent drivers for your soundcard installed.

In Options | Audio, try increasing the Buffers in Playback Queue setting by small amounts.

In Options | Audio | Advanced, try turning Enable Simultaneous Record and Playback off.. If it works with Simultaneous Record and Playback off but not on, there is
most likely a problem with the drivers for the soundcard and the manufacturer should be contacted.

The video setup of the computer can also cause these types of problems. Go to Control Panel | System | Performance | Graphics, and turn "Hardware acceleration"
down a couple of notches. If that doesn't help, try any or all of the following: Update the video driver from the manufacturer of the card, try the Windows provided
driver for your specific card (instead of the manufacturers), try the Standard VGA/SVGA drivers provided with Windows, and decrease the amount of colors and the
resolution being displayed.

Here are some additional items worth checking:
- Defrag all the hard disks in the computer.
- Disable screen savers
- Remove all programs from the Windows StartUp folder (Windows\Start Menu\Programs\StartUp)
- Open WIN.INI and if there is anything after the run= or load= lines, use a semi-colon to rem the line out.
- Disable any kind of virus scanning program that might be running in the background
- If Cakewalk's Auto Save feature is enabled, try to disable it.
- Make sure Cakewalk (and the Wavedata directory) is not installed on a compressed hard disk.