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I have a server with Win2008R2 and a synology NAS. On the Nas there are 6 iSCSI partitions which are mounted on the windows server. The windows server is virtualized under Hyper-V.

After rebooting the client machine, two of the 6 partitions do not remount and I have to manually remount them... every time.

Each one has a similar configuration and has been configured with CHAP authentication. All 6 appear in the favourites list.

Event log shows no errors regarding iSCSI. The other 4 partitions mount without problems.

Any suggestions for further debugging?

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Have you checked the logs on the NAS? – Joseph Kern Oct 26 '11 at 1:03
Good thinking, I hadn't checked that. However, it doesn't say anything. The log is almost empty. – Ian Oct 26 '11 at 11:06
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Apart from Favourites list have you checked if the volumes are listed in Volumes and Devices tab in iSCSI initiator properties? And are they set to Auto Configure?

This should (in theory) make sure that all volumes are initialized.

Auto Configure Volumes

Source

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This list is empty on this server and every other server I have using iSCSI. Any idea what purpose this serves as against the favourite targets. They appear to do the same. Favourites are reopened after rebooting, and so are what appears in this list. Saying that, I've just tried out the 'auto configure' button and it has added drives in the form D:\, E:\, etc and not as appears in your screenshot above. Odd, no? I seem to remember trying this in the past and not finding it useful. – Ian Oct 26 '11 at 10:43
According to the second paragraph in the dialog, you should have your initiator in the Favorites, and your individual devices in the Volumes and Devices. You could try removing all of the devices, then add them back in via the Auto Configure button. – Joseph Kern Oct 26 '11 at 14:47
Thanks for the visual aid ;). Much appreciated. I too think clearing the devices and readding them back via Auto Configure could help. – LukeP Oct 26 '11 at 21:28
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