> Let's Encrypt's Root Certificate is expiring!
> By SCOTT HELME  20 SEP 2021 
> https://scotthelme.co.uk/lets-encrypt-old-root-expiration/
>
> On 30th September 2021, the root certificate that Let's Encrypt are currently 
> using, the IdentTrust
> DST Root CA X3 certificate, will expire.. You may or may not need to do 
> anything about this Root CA
> expiring, but I'm betting a few things will probably break on that day so 
> here's what you need to know!


“Fortinet, Shopify and more report issues after root CA certificate from Lets 
Encrypt expires”

By Jonathan Greig | October 1, 2021 | Topic: Security


A number of websites and services reported issues on Thursday thanks to the 
expiration of a root certificate provided by Let's Encrypt, one of the largest 
providers of HTTPS certificates.

At around 10 am ET, IdentTrust DST Root CA X3 expired, according to Scott 
Helme, founder of Security Headers. He has been tracking the issue and 
explained millions of websites rely on Let's Encrypt services. Without them, 
some older devices will no longer be able to verify certain certificates.

Let's Encrypt operates as a free non-profit that makes sure the connections 
between your device and the internet are secure and encrypted.

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Despite advance warning that the expiration date would be on September 30, when 
the deadline hit, dozens of users reported issues with a variety of services 
and websites.

Helme told ZDNet that he confirmed issues with Palo Alto, Bluecoat, Cisco 
Umbrella, Catchpoint, Guardian Firewall, Monday.com, PFsense, Google Cloud 
Monitoring, Azure Application Gateway, OVH, Auth0, Shopify, Xero, QuickBooks, 
Fortinet, Heroku, Rocket League, InstaPage, Ledger, Netlify and Cloudflare 
Pages, but noted that there may be more.

"There are a couple of ways to solve this depending on what the exact problem 
is, but it boils down to: The service/website needs to update the certificate 
chain they are serving to clients or, the client talking to the website/service 
needs an update," Helme explained.

"For the affected companies, it's not like everything is down, but they're 
certainly having service issues and have incidents open with staff working to 
resolve. In many ways, I've been talking about this for over a year since it 
last happened, but it's a difficult problem to identify. it's like looking for 
something that could cause a fire: it's really obvious when you can see the 
smoke!"

Some sites posted notices on their website about potential issues, and many 
have resolved the issues. Shopify posted a note on its incident page that by 
about 3:30 pm, merchant and company partners who were struggling to login had 
their services restored. Merchant authentication for Support interactions have 
also been restored, the company said.

Fortinet told ZDNet they were aware of and have investigated the issue relating 
to the expired root CA certificate provided by Lets Encrypt.

"We are communicating directly with customers and have provided a temporary 
workaround. Additionally, we are working on a longer-term solution to address 
this edge case issue directly within our product," the company said in a 
statement.

Digital certificates expert Tim Callan said all modern digital systems depend 
on certificates for their continued operation, including those that secure our 
cyber and physical environments.

"If software depends on an expired root to validate the trust chain for a 
certificate, then the certificate's trust will fail, and in most cases, the 
software will cease to function correctly. The consequences of that are as 
broad and varied as our individual systems are, and many times cascading 
failures or 'downstream' failures will lead to problems with entirely different 
systems than the one with the original certificate trust problem," Callan said.

"IT systems that enforce or monitor security policies can stop working. 
Alerting and reporting systems can fail. Or, if the processes that humans 
depend on to do our work stop functioning, often those people will find 
"workarounds" that are fundamentally insecure."

Callan added that outages can occur when developers embedded in lines of 
business operations or other skunkworks projects "obtain certificates" without 
the knowledge of central IT and then move on to new tasks or otherwise fail to 
monitor the lifecycle of these certificates.

He noted that most systems would be able to weather a root expiration because 
of modern root chaining capabilities that allow another root to establish trust.

"However, legacy systems or those with previously unaddressed (or unknown) 
certificate handling bugs are at risk for failures like these to occur. In the 
event of a commonly used root from a popular CA, the risk of these failures 
goes up considerably," Callan explained.

TechCrunch reported that devices that may face issues include older macOS 2016 
and Windows XP (with Service Pack 3) as well as older versions of Playstations 
and any tools relying on OpenSSL 1.0.2 or earlier.

Other experts said PlayStations 4s or earlier devices that have not had their 
firmware upgraded would not be able to access the Internet. Devices like 
Android 7.1.1 or earlier will also be affected.

According to Callan, who serves as chief compliance officer at Sectigo, most 
modern software allows the use of sophisticated trust chains that will enable 
root transitions without requiring the replacement of production certificates. 
But those that are old or poorly designed or containing trust chain handling 
bugs may not handle this transition correctly, leading to various potential 
failures.

As many of the affected companies have since done, Callan suggested enterprises 
take an inventory of the systems using certificates and the actual certificates 
in use before ensuring that software has the latest root certificates in its 
root store.

"By identifying where potential failure points occur, IT departments can 
investigate these systems ahead of time to identify problem areas and implement 
fixes. If you can set up a version of the system in a sandbox environment, then 
it's easy to test expected behaviour once the root expiration occurs," Callan 
said.

"Just set the client system clock forward to a date after the expiration date 
to ensure certificate chaining will work correctly. Alternately, you can 
manually uninstall or distrust the root that is set to expire (in the sandbox 
environment, of course) to assure yourself that systems are only using the 
newer roots."

He added that the popularity of DevOps-friendly architectures like 
containerization, virtualization and cloud has greatly increased the number of 
certificates the enterprise needs while radically decreasing their average 
lifespan.

"That means many more expiration events, much more administration time 
required, and greatly increased risk of a failed renewal," he said.

Digital Shadows senior cyber threat analyst Sean Nikkel told ZDNet that Let's 
Encrypt put everyone on notice back in May about the expiration of the Root CA 
today and offered alternatives and workarounds to ensure that devices would not 
be affected during the changeover.

They have also kept a running forum thread open on this issue with fairly quick 
responses, Nikkel added.

"A not-great practice that's been floated already as a workaround to the 
problem is allowing untrusted or invalid certificates. Users should be cautious 
about making a move that potentially opens the door to attackers using 
compromised certificates," Nikkel said.

"Some users have recommended settings allowing for expired certificates from 
trusted issuers; however, these can also have malicious uses. In any case, 
administrators should examine the best solution for them but also understand 
the risks to any workarounds. Alternatively, administrators can look at 
alternate trust paths by using the intermediate certificate that Let's Encrypt 
has set up or following suggested configurations from their May bulletin."

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