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Microsoft failed to rotate certificates for winget CDN on time

cdn.winget.microsoft.com

1–10 of 69 posts

Re: Microsoft failed to rotate certificates for winget CDN on time

#2
reminds me of that time the regular guy, might've been a student, re-registered hotmail.com just to get his email working again after Microsoft let it expire.

oh, looks like it was either hotmail.co.uk or passport.com

https://slashdot.org/story/99/12/25/114201/microsoft-hotmail...

from

https://whoapi.com/blog/5-all-time-domain-expirations-in-int...

Re: Microsoft failed to rotate certificates for winget CDN on time

#3
While I appreciate TLS, this thing with certificate expiration is one of the biggest sources of downtime IMO. Something should be done about it. May be throw error not permanently but in a some probabilistic way. Like if 1 year certificate expired, after 3 months 25% of connections would fail. It'll allow eventually to find out about problem but it'll allow for connections to somewhat work, with few retries here an there. Expired certificate is not compromised certificate and should not be treated like one. Often next certificate is issued with the same private key.

Especially with short-lived letsencrypt certificates. Despite all the evangelists assurances, certbot is not always easy to set up. After letsencrypt gained popularity, the percentage of small websites with expired certificates significantly increased IMO.

Re: Microsoft failed to rotate certificates for winget CDN on time

#4
I think the default certificate expiration time (2 years) is a terrible idea. Its long enough that there's a good chance whoever registered the cert last time has left the team or the company. Its long enough that I've forgotten how to generate a certificate with openssl on the command line. And its long enough that each time, I (and everyone else) can justify not bothering to automate the process.

But 2 years is still short enough that if you have a couple domains, remembering to renew them is an ongoing hassle!

Letsencrypt certificates last 90 days, and they recommend renewing them every 60 days. This is a much better duration, because it encourages the entire ecosystem - developers and admins - to set up processes which automate renewal. And if the automated renewal process fails, letsencrypt starts emailing you about it to let you know your certificate is about to expire. (And you have enough time to fix it).

https://letsencrypt.org/2015/11/09/why-90-days.html

Re: Microsoft failed to rotate certificates for winget CDN on time

#5
post #4

I think the default certificate expiration time (2 years) is a terrible idea. Its long enough that there's a good chance whoever registered the cert last time has left the team or the company. Its long enough that I've forgotten how to generate a certificate with openssl on the command line. And its long enough that each time, I (and everyone else) can justify not bothering to automate the process. But 2 years is sti…

The maximum expiration time is now down to 13 months, for certs that need to be valid in a browser. And if you want to cycle yours more frequently, you can. But there's enough places that can't set up automated processes that trying to make it 90 days for everyone would be a lot of pain and a lot of broken sites.

Re: Microsoft failed to rotate certificates for winget CDN on time

#6
post #4

I think the default certificate expiration time (2 years) is a terrible idea. Its long enough that there's a good chance whoever registered the cert last time has left the team or the company. Its long enough that I've forgotten how to generate a certificate with openssl on the command line. And its long enough that each time, I (and everyone else) can justify not bothering to automate the process. But 2 years is sti…

>>to set up processes which automate renewal.

that is all fine and good for things that have the ability to automate that process, plenty of hardware and device do not. Some are not even legacy are still actively being sold and developed

It is also not good for internal networks where you can not valid out to something like lets encrypt to automate that validation process, sure you could do your own internal PKI and run your own CA for that but......

In my current org 60 days would be a NIGHTMARE to manage.

Re: Microsoft failed to rotate certificates for winget CDN on time

#7

While I appreciate TLS, this thing with certificate expiration is one of the biggest sources of downtime IMO. Something should be done about it. May be throw error not permanently but in a some probabilistic way. Like if 1 year certificate expired, after 3 months 25% of connections would fail. It'll allow eventually to find out about problem but it'll allow for connections to somewhat work, with few retries here an t…

I don't like intermittent bugs.

Re: Microsoft failed to rotate certificates for winget CDN on time

#8

While I appreciate TLS, this thing with certificate expiration is one of the biggest sources of downtime IMO. Something should be done about it. May be throw error not permanently but in a some probabilistic way. Like if 1 year certificate expired, after 3 months 25% of connections would fail. It'll allow eventually to find out about problem but it'll allow for connections to somewhat work, with few retries here an t…

We already have CRL lists. So Why do we need certificate expiration?

Re: Microsoft failed to rotate certificates for winget CDN on time

#9
post #4

I think the default certificate expiration time (2 years) is a terrible idea. Its long enough that there's a good chance whoever registered the cert last time has left the team or the company. Its long enough that I've forgotten how to generate a certificate with openssl on the command line. And its long enough that each time, I (and everyone else) can justify not bothering to automate the process. But 2 years is sti…

> And its long enough that each time, I (and everyone else) can justify not bothering to automate the process

And even worse, if you do automate it there is a pretty good chance something changes and breaks your automation by the time it is needed. And that is assuming you actually tested the automation before your new cert is close to expiring.

Re: Microsoft failed to rotate certificates for winget CDN on time

#10
post #4

I think the default certificate expiration time (2 years) is a terrible idea. Its long enough that there's a good chance whoever registered the cert last time has left the team or the company. Its long enough that I've forgotten how to generate a certificate with openssl on the command line. And its long enough that each time, I (and everyone else) can justify not bothering to automate the process. But 2 years is sti…

I like to renew certificates long before expiry. At my job certs last a year but I automate renewal after 5 months. If you find a certificate that is older than 6 months you know something is wrong (long before expiry).
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