Managing unpatched virtual machines

Usually I would look for change management , either manual or automatic patching

I have a customer who has pretty much performed no patching for 2 and a half years. For pretty much of all of their 100 virtual servers

Allied to this VMware tools , hardware versions aren't in line

Usually in my own experience, I would create test environment and apply patches there , a month behind MS Security Bulletin.

Now we're upgrading tools, hardware version currently 8, and the patches next week

Is there a best way to upgrade patches since June 2014?

I have flagged all this at the very start , that its not best practice etc to give them the outline, but I don't want to throw on a load of updates manually either (they have no WSUS, Shavlik ,or SCCM) etc

Any best way to do this? (its very frustrating as they lost 2 servers already that weren't patched, they just dont get it)
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Indie101Asked:
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Andrew Hancock (VMware vExpert / EE MVE^2)Connect With a Mentor VMware and Virtualization ConsultantCommented:
I would recommend, you look at a Patch Management solution, and we use and recommend Shavlik, which if you wish you can integrate with WSUS, but not necessary, scan the VMs, (make sure you have valid backups), and deploy patches.

and then create a deployment plan, of which servers you will rollout to, and scheduled out out of production hours to complete the patching, not patched since 2014, is going to be a lot of patches, e.g. circa 154.

So it's going to take some time, to apply them, but Shavlik will be your quickest solution, OR.... have you considered you could consolidate servers and replace them.
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Indie101Author Commented:
Thanks Andrew. I had asked you about best ways to patch VMs previously. I suggested Shavlik to them but they weren't interested. (I'm a contractor here 5.1 and 5.5 VCP- 3-4 years in VMware Support) They have a big environment but no ones being keeping an eye on it for some time

This time around I have to go with manual unfortunately, its a bit of a joke but thats the customer, they've been briefed etc on difficulties of this

With a manual download of updates since June 2014, any best plan? Its a file server so no dependent software involved, Windows 2008 R2 64 Bit

I haven't had to plan like this since I did desktop ago 7 years ago. I have explained its not VMware and that VMware will not support it etc but thats all I can do
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Indie101Author Commented:
No consolidation either, i had looked into that in my first week

Thanks I have a plan in mind just wanted to check this here

Go through security bulletins, highlight and download updates (no office\windows 10 etc) and take it from there, I have one or two test vms, but not a complete standalone vCenter with test vms etc so this is going to take time

Using this

https://technet.microsoft.com/en-us/security/hh778967.aspx
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
If they don't want to purchase software you are in luck as a Contractor, because they will just have to pay you more to do it.

To be honest with you rather than visiting every server, and downloading the same patches, I would recommend you stand up a WSUS server, install Windows 2012 R2, patch it, install WSUS, sync it with Microsoft, so you have ALL the patches required locally, this will speed up deployment.

and then create a new OU in Active Directory, Create a Group Policy, and move Servers into this Managed Folder.

and then on WSUS Approve Patches.

All this is going to add to the Project and keep you in beers!
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Indie101Author Commented:
Thanks Andrew, just wanted to confirm what was there. Shavlik or some other tool would be great here
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