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Managing SSL Certificates


This article is about a SSL/TLS certificate expiry issue we faced with one of the web properties I was managing. I wanted to share the lessons I had learnt and a few hacks around how certificates can be managed better using the current tools. Keep reading till the end to also know how we can automate most of the parts.


Every website today uses SSL/TLS a certificate to secure the content that is delivered to end users. And these certificates have a certain fixed expiry, generally 3 months - 1 year max. And Shorter validity periods limit damage from key compromises and mis-issuance. Which means we need to renew or create new certificates post expiry, so that your users will continue to have a secured experience. Since there is a periodic renewal and upgrading/updating of certificates needed for the web properties, we need to monitor them for expiry, update/renew/create certificates and finally apply them to our web properties. We will see what we can do for managing/maintaining the certificates.

The below steps will apply even for folks who are creating new TLS certificates, since they will need to keep their certificates up to date.

If you need more details around securing the certificates and details of SSL, this is beyond the scope of this article.

Let's start looking at various steps involved in monitoring, updating/creating and applying them to your web properties.

Monitoring Certificates

In 2020, if you had thought that there was no need to monitor certificates for expiry and other stuff, it’s time to revisit your thoughts! Even when your infrastructure is hosted on cloud providers like AWS, which also offers TLS certificates via ACM - monitoring certificates is still essential and mandatory.

However, if you are hosted on GitHub pages or Netlify for personal websites (then they might take care of the certification part for you). They both use LetsEncrypt for TLS infrastructure. Similarly, it could be the case if you are running your commerce on shopify with a custom domain (I haven’t tried it yet)

Now, let’s look at various options for monitoring our website TLS certificates. We will look at online tools and cli tools as well which can be easily automated in your workflow.

Online Tools

You may use online tools like site24x7, letsencrypt monitor, or even do this in nagios or solarwinds or ssllabs tools

CLI tools - validity


Applicable only if you are hosted on AWS and you have certificates created with ACM.

You can use aws acm to find the certificate you need. If you don't have aws cli installed, head here and get started

aws acm list-certificates --certificate-statuses "ISSUED" "PENDING_VALIDATION" | jq '.CertificateSummaryList[] | select(.DomainName == "") | .CertificateArn'

The above command looks for certificates that are issued or are pending_validation and we will run it through jq and filter the ones with my domain and project only CertificateArn. jq is a command line tool that lets you process json as you would do with any programming languages. You may learn more here

We can use the above CertificateArn and use it to check the validity of our certificate with the following command

aws acm describe-certificate --certificate-arn "certificatearn" | jq '.Certificate.NotAfter'


There are ready made tools cli on Linux to find validity of certificates

ssl-cert-check -s -p 443

If you don't want to install ssl-cert-check, you may choose more primitive tools like the ones listed below to find the same with some work

 curl --insecure -v 2>&1 | awk 'BEGIN { cert=0 } /^\* SSL connection/ { cert=1 } /^\*/ { if (cert) print }'

You may compute/use the no of days from the above script and then generate alerts basis checks.

CLI Tools - Vulnerability

This tool checks a server's service on any port for the support of TLS/SSL ciphers, protocols as well as cryptographic flaws and much more. Give it a spin and you will be overwhelmed with the output, also its good to be able to see so many details.

AWS Config

AWS config is a tool that can be used to set rules like acm-certificate-expiration-check to check for certificate expiration. Here is the complete **** list of what you can do with those rules. There are some interesting things you can do to improve visibility and monitoring of storage, vpc, networking, and ec2 - will keep the details for other posts and not digress from that.

Upgrade/Renewal of Certificates

Like I had mentioned in the introduction, certificates only have a certain validity and after they are invalid, you will need to renew/upgrade them.

AWS does not have any options to renew public certificates using aws cli, you can renew only private certificates.

Create Certificate on AWS

Method 1


You can use aws sdk to create a certificate for then you could use the below command

aws acm request-certificate --domain-name --validation-method DNS --idempotency-token 91224

In the above command we are requesting a new certificate for (remember we cannot renew public certificates on AWS ACM), our validation method is DNS (dns entries can be automated and hence the choice) and also idempotency to make sure even accidental repeat requests are considered as one. For more options, please check this link.


We can also automate addition of dns entries to Route 53, if the domain is hosted there. If your domain is hosted on non-AWS infrastructure, it's gonna be manual.

certificatearn=$(aws acm list-certificates --certificate-statuses "ISSUED" "PENDING_VALIDATION" | jq '.CertificateSummaryList[] | select(.DomainName == "") | .CertificateArn')

We get the certificate arn from the above command which we use to find the dns validation records with the help of below command

aws acm describe-certificate --certificate-arn $certificatearn | jq '.Certificate.DomainValidationOptions[] | select(.DomainName == "") | .ResourceRecord | {Name: .Name, Type: .Type, Value: .Value} '

Now we take the Name, Type and Value and use them to create the dns records

(hosted_zone_id)=$(aws route53 list-hosted-zones | jq '.HostedZones[] | select(.Name == "") | .Id')

aws route53 change-resource-record-sets --hosted-zone-id $(hosted_zone_id) --change-batch $(change_batch) | jq -r '.ChangeInfo.Id' | cut -d'/' -f3
function change_batch()
  jq -c -n "{\"Changes\": [{\"Action\": \"INSERT\", \"ResourceRecordSet\": {\"Name\": \"$record_name\", \"Type\": \"CNAME\", \"TTL\": 300, \"ResourceRecords\": [{\"Value\": \"$record_value\"} ] } } ] }"

In the above script you need to set recordnameandrecord_name and record_value from the describe-certificate cmd. Reference script is attached in the references.

Method 2

You may also use cloud formation template to link the aws hosted zone and add the dns records readily. The script is here


LetsEncrypt has become the default TLS provider for most orgs as it costs nothing for the organizations and LetsEncrypt lets you automate all aspects of Certificate management - this was built right from the beginning . When I had checked last, they would let you choose a webserver and it was necessary to run your web server on the machine where you run certbot.

It has come a long long way and lets you create certificates in a standalone way (no web server needed). In the standalone mode it lets you identify the website owner in below ways

  • HTTP-01 - needs you to be able to return 404 in a certain format, details here
  • DNS-01 - needs you to have api access to the DNS provider, AWS is not here
  • TLS-SNI-01 - deprecated now

I wanted to use HTTP-01 but it did not work with my github-pages (my site is on GH, not very easy to customize 404). Then I tried DNS-01, provider dnsmadeeasy was one of the listed providers so went ahead and got the api key and secret key to create the certificate.

certbot certonly \
  --dns-dnsmadeeasy \
  --dns-dnsmadeeasy-credentials ~/.secrets/certbot/dnsmadeeasy.ini \
  --dns-dnsmadeeasy-propagation-seconds 120 \

This generated the below files

  |-- cert.pem
  |-- chain.pem
  |-- fullchain.pem
  |-- privkey.pem

You can take and apply these files to any web server or Load balancer that you have. We have the private key, certificate and full chain, so it's complete in all sense. If you would like to apply it to any web server you will have to change the format and use it. Follow this link if you want to transform to other formats.

If you would like certificate file formats, kindly read these and these links.

The next task was to import this to ACM (you may end up using certificates offered by AWS ACM), assuming you want to use LetsEncrypt certificates in AWS, we may use the below command to import the certificates to ACM.

sudo aws acm import-certificate --certificate fileb:///etc/letsencrypt/live/ --private-key fileb:///etc/letsencrypt/live/ --certificate-chain fileb:///etc/letsencrypt/live/

And you are set, your certificate is imported into AWS ACM. Run the below command to query the certificate

aws acm list-certificates  | jq '.CertificateSummaryList[] | select(.DomainName == "") | .CertificateArn'

In order to apply to the listener on your Load Balancer, you need the listenerarn. You may find that using the steps I mentioned in one of my previous article

Finally, run this command to apply the certificate to the listener

aws elbv2 add-listener-certificates --listener-arn [ListenerArn] --certificates [CertificateArn]

This completes all the approaches I had in mind.


  • Starting anything new is easy, maintainability is tough
  • You need to manage your certificates even in the managed cloud world
  • TLS certificates renew/updation are the most ignored ones, they are issues due to this from time to time
  • Set actionable alerts that monitor TLS certificates validity and have a DRI who handles this, could be multiple DRI’s in this case
  • Make sure you monitor your certificate for vulnerable, especially for ones you created the CSR
  • Certificate updates/renewals need to be treated with utmost priority and done in time - don't set a 1 month limit and fail to renew thinking you have a 1 month window
  • AWS Config was a pleasant surprise, did not know it existed - has great features for security and monitoring across many AWS offerings