Windows updates on Server 2008 r2

I have discovered that our Windows Server 2008 r2 has not downloaded and installed windows updates for two years. Is it safe to install them? Can I manually choose updates to install and do it in stages?
howardlAsked:
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JohnBusiness Consultant (Owner)Commented:
If Windows Update is working, allow it to update. If it wishes to exclude an update until later, it will do so.

You are looking a two to four hours to update and at least one restart. It could take longer on your connection.

Two years is a very long time not to look at updates.
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becraigCommented:
I would suggest you manually update as soon as possible.

There are so many security holes patched over the past two years.

You can do it in stages, but I would just proceed to manually apply all since all except for this patch Tuesday's releases have been out there in the working world for a while.
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howardlAuthor Commented:
It is one of a number of Servers and for some reason it had been set to not download and install updates and has been overlooked. There are 10Gb free on drive C. Will this present a problem? I am scared.
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JohnBusiness Consultant (Owner)Commented:
10Gb may be barely enough space. Patch Tuesday saw my Windows 8.1 disk usage climb by nearly 10Gb. That is patching, system volume information and winsxs. It all adds up.

I would free up some space if you can because you could run so short the server will stop operating.
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becraigCommented:
I agree with John here, two years of missed patches will devour your 10GB in little or no time and cripple your OS.

Do some housekeeping, if you don't mind me asking what is the capacity of your OS drive ?
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howardlAuthor Commented:
Do you think I should do progressive installs and watch the disk space. The partition size for drive C is something like 40Gb. What can I safely remove to gain some space? How much do you think I should need? Sorry to bombard you with questions. Thank you John.
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JohnBusiness Consultant (Owner)Commented:
You can go to Windows Update and start the update process so that it will come back with a (long) list of updates.

Consider doing batches of (say) the 10 oldest and see what happens. Then go to the next 10 and so on. You may get a sense you could do more after see what happens to disk space from the first 10 updates.
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JohnBusiness Consultant (Owner)Commented:
My Vista VM is 45 Gb (and is up to date). My Windows 7 VM is nearly the same size.

Run Disk Cleanup and see what it removes.
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Thomas GrassiSystems AdministratorCommented:
How many servers computers you have on the network?

We use WSUS this give you a report of all the updates and all the servers and computers on the network a status of which updates has been applied

I great tool for making sure your network is up to date.

If you have a SQL server you can use that as the database for you updates.

WSUS also has a cleanup tool that runs on your schedule that purges updates out of date. Run mine weekly

I would recommend this so this problem does not happen to you in the future.

As far as the current issue I would start by just selecting the first 10 or 15

the net frame updates take a long time to apply the security updates are rather fast.

Need help with WSUS let me know.
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Sid6_7Commented:
I would have to agree and run them in batches. There could be that one update that renders your server to no longer function.
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RantCanSr. Systems AdministratorCommented:
I would choose only critical patches. I would also start with SP1. Mind that free space, tho.
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rindiCommented:
A windows server that hasn't been patched for so long?

I'd do a clean installation.

Or first scan it for malware and remove anything it finds. It's almost impossible to not be infected.
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howardlAuthor Commented:
Thank you Everyone
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JohnBusiness Consultant (Owner)Commented:
@howardl  - You are very welcome and good luck with your Server.
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