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I've been using this product for about a year and would like to share my experience re certificates - I hope this is the right place !
Feel free to change/delete anything that is wrong

1) Self signed certificates are only valid for 365 days.
2) When you generate your new certificate leave the old one in place (ie don't remove it from Group Policy)
3) create your certificate 60 days before the old one expires (you need to get all NON MS updates installed using a valid certificate - updates approved NOW with the old certificate will only be valid until the certificate expires)
4) When you add your new certificate to WPP remember that all updates created from this point on will have the new certificate - any updates sent to WSUS prior to this will have the old certificate - hence point 2 - leave your old certificate in place.
5) Once the old certificate has expired 're-publish' all non MS updates. ie remove them and then put them back with the new certificate.

I hope the above helps

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