You've probably heard of SmallMenu before. It's a free task manager and cascading program launcher for the Pocket PC. Just recently, it was updated to support Windows Mobile 5.0, so if you've experienced problems in the past getting it to play nicely with your new device, you might want to try the latest v3.18 release. Note, there is also a Plus version available at Handango, which offers a lot more features and costs $7.70. [Affiliate]
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In addition to considering SmallMenu, consider also the completely freeware GSPocketMagic++ v1.32.18. GSPocketMagic++ offers cascading menues for the Program Menu as well as the Settings without any push to upgrade as with SmallMenu. Eight of the sixteen features are only available in the Plus version of SmallMenu.