Windows iSCSI dynamic disk does not reconnect after reboot

It’s not possible;

Dynamic disks (applies to Windows 2000 and Windows Server 2003): Configuring volumes on iSCSI disks as Dynamic disk volumes using the Microsoft software iSCSI initiator is not currently supported. It has been observed that timing issues may prevent dynamic disk volumes on iSCSI disks from being reactivated at system startup.

Dynamic disks are also unsupported in the Windows 2000 Advanced Server and Windows Server 2003 cluster services.

Now, if you’ve upgraded your disks from basic to dynamic, you’ve probably read that you can’t go the other way—from dynamic to basic. However, this tidbit isn’t 100 percent true. You can revert back to a basic disk at any time…with a little pain. Here are the basic steps:

  1. Start the Disk Management tool.
  2. Move data off all volumes housed on dynamic disks. If you’re running services that are dependent on files located on the volume, stop those services first.
  3. Delete all volumes from the dynamic disk
  4. Right-click the dynamic disk and choose Revert to Basic Disk.
  5. Recreate the volumes as partitions on the new basic disk.
  6. Move the original data back.

Of course, if you have data on any of the volumes located on a dynamic disk, you need to back that data up before you delete the volume.