I have 98 Windows updates to apply.. need advice on the safest way to do so.

I've taken over an account that has a SBS2011 (2008 R2) OS and when I checked on the Windows update status, I learned that the Windows Update feature was corrupt.  When I resolved this issue, I learned that 98 updates need to be applied.  The server is a production server and has been installed since 2013.

I've not experienced this number of updates on a peroduction server and am concerned if I just throw the update switch and let it run... I could experience bigger problems.

If anyone has experienced this before and, what is the best/safest way to approach this challenge?

Thanks, in advance, for your consideration.

Davis AllenIT ManagerAsked:
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JohnBusiness Consultant (Owner)Commented:
Look at the dates of the updates and install the oldest (earliest date) updates first so as to accommodate dependencies.

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Davis AllenIT ManagerAuthor Commented:
Thanks John.  I was thinking this but needed confirmation.  Thank you!
JohnBusiness Consultant (Owner)Commented:
You are very welcome and I was happy to help. Good luck with all the updates.
Davis AllenIT ManagerAuthor Commented:
Apologies, John.  I just realized that I missed the step where I issue rewards.  If there is a way to provide this after the fact, please let me know and I'll be happy to do so.
JohnBusiness Consultant (Owner)Commented:
You have closed the question properly, so no issue.
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