CERTIFICATE_VERIFY_FAILED error

What happened?

On Saturday May 30th, 2020, at 10:48 UTC, an SSL root certificate used to cross-sign some of the Datadog certificates expired, and caused some of your Agents to lose connectivity with Datadog endpoints. Because this root certificate is embedded in certain Agent versions, you need to take action to restore connectivity.

What versions of the Agent are affected?

Agent versions spanning 3.6.x to 5.32.6 embed the expired certificate and are affected.

Agent versions 6.x and 7.x are fine and don’t need to be updated.

Fixing by upgrading to Agent 5.32.7

If you are running Agent v5.x on a 64-bit host, Datadog recommends upgrading to Agent 5.32.7+. This ensures that the Agent continues to function in a variety of different scenarios, with the minimum amount of changes.

Centos/Red Hat: sudo yum check-update && sudo yum install datadog-agent Debian/Ubuntu: sudo apt-get update && sudo apt-get install datadog-agent Windows (from versions > 5.12.0): Download the Datadog Agent installer. start /wait msiexec /qn /i ddagent-cli-latest.msi More platforms and configuration management options detailed on the Agent install page.

The last compatible Agent released for 32-bit systems was 5.10.1. Follow the Fixing without upgrading the Agent instructions for 32-bit hosts.

Fixing without upgrading the Agent

Linux

sudo rm -f /opt/datadog-agent/agent/datadog-cert.pem && sudo /etc/init.d/datadog-agent restart

Windows

If your Agent is configured to use a proxy, follow the dedicated section below instead.

Using the CLI

Using PowerShell, take the following actions for Agent >= 5.12.0:

rm "C:\Program Files\Datadog\Datadog Agent\agent\datadog-cert.pem"
restart-service -Force datadogagent

Note: For Agent versions <= 5.11, the location is different. For users on the 32-bit Agent <= 5.11 on 64-bit Windows the steps are:

rm "C:\Program Files (x86)\Datadog\Datadog Agent\files\datadog-cert.pem"
restart-service -Force datadogagent

For all other users on Agent <= 5.11 the steps are:

rm "C:\Program Files\Datadog\Datadog Agent\files\datadog-cert.pem"
restart-service -Force datadogagent

Using the Windows GUI

Delete datadog-cert.pem. You can locate this file in:

  • Agent >=5.12.0:
    • 64-bit Windows: C:\Program Files\Datadog\Datadog Agent\agent\
    • 32-bit Windows: The Datadog Agent was not available for 32-bit Windows systems starting in Agent 5.12
  • Agent <= 5.11.x:
    • 64-bit Windows: C:\Program Files (x86)\Datadog\Datadog Agent\files\
    • 32-bit Windows: C:\Program Files\Datadog\Datadog Agent\files\

After the file is removed, restart the Datadog Service from the Windows Service Manager.

Fixing by upgrading to Agent 6 or 7

You can upgrade to Agent 7 or Agent 6 to resolve this issue, but see the Agent CHANGELOG for backward incompatible changes for Agent 6 and 7.

Upgrade the Agent after deleting the certificate

Datadog recommends keeping up to date and updating to the latest version of the Agent. Deployments set to auto-update are enabled with v5.32.7.

Encrypting traffic with SSL

Encrypt the traffic with SSL even if you delete the certificate. The certificate is a preset for the client to use and is not necessary to connect with SSL. Datadog Agent endpoints only accept SSL traffic.

Windows Agent 5.x configured to use a proxy or the curl http client

This section applies to the Windows Agent 5.x (<= 5.32.6), if the Agent is configured to either:

  • use a proxy with the proxy_host configuration option in datadog.conf or the HTTPS_PROXY environment variable, or
  • use the curl HTTP client with the use_curl_http_client: yes configuration option in datadog.conf

Note: datadog.conf is located in C:\ProgramData\Datadog\datadog.conf.

In this case, removing datadog-cert.pem does not allow the Agent to regain connectivity to Datadog. Instead, take this action:

  • Windows Agent v5, >= 5.12.0: replace the datadog-cert.pem file with the version that is shipped in 5.32.7. Using the Powershell CLI:
Invoke-WebRequest -Uri "https://raw.githubusercontent.com/DataDog/dd-agent/5.32.7/datadog-cert.pem" -OutFile "C:\Program Files\Datadog\Datadog Agent\agent\datadog-cert.pem"
restart-service -Force datadogagent

  • Windows Agent v5, <= 5.11.x: set the following option in datadog.conf using the Datadog Agent Manager program provided by the Agent or by directly editing the datadog.conf file:

    • 64-bit Windows: ca_certs: C:\Program Files (x86)\Datadog\Datadog Agent\files\ca-certificates.crt
    • 32-bit Windows: ca_certs: C:\Program Files\Datadog\Datadog Agent\files\ca-certificates.crt

    After datadog.conf has been updated, restart the Datadog Service from the Windows Service Manager.