Issue with 3 vms not rebooting correct

We have 3 vms which are running 2008 R2 and for some reason after about a week or so, when trying to reboot the servers, they hang on the way down and never fully reboot. We have to power them off via the vctr to get them to go down..
These same servers when applying updates and when they go to reboot, they hang the same way going down..
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
I was going to mention Updates, Windows Updates can be very Disk I/O intensive, do you have datastore contention issues?

you have also checked for snapshots e.g. the VM are not writing to snapshot delta disks ?
vmichAuthor Commented:
well we found the issue when applying updates that the server would hang at server shutting down. But we found out that it does the same thing even if we do a reboot and then it hangs at server shutting down.
There are no snapshots on any of the 3 vms and we have like 40 other vms which don't have the same issue..
Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
When they are shutting down, are they applying updates ?

We've had exactly the same thing, and when moving to faster datastores the issue resolved it self, and also when we had VMs, with many updates, e.g. not just last months. (VMs not managed by us!)

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vmichAuthor Commented:
No they do it even when just telling them to restart guest.. Whats even more strange is  that sometimes they will go for a week or so and reboot just fine they start to hang again..
vmichAuthor Commented:
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