Install: Certificate verification failed: The certificate is NOT trusted.

[GeniusWiki]

Today I going to install datadog agent 7 in 4 servers. First 2 is OK, then got this error on third server and installation failed. Go back first 2 servers, got same error when running apt update.

Output of the info page (if this is a bug)
Err:7 https://apt.datadoghq.com stable Release
Certificate verification failed: The certificate is NOT trusted. The certificate chain uses expired certificate. Could not handshake: Error in the certificate verification. [IP: 99.84.191.108 443]
Reading package lists... Done
E: The repository 'https://apt.datadoghq.com stable Release' does not have a Release file.
N: Updating from such a repository can't be done securely, and is therefore disabled by default.
N: See apt-secure(8) manpage for repository creation and user configuration details.
(Paste the output of the info page here)

**Additional environment details (Operating System, Cloud provider, etc):**
ubuntu 20.04

[ramirovarandas]

We are getting the same error, but for agent version 6 on Ubuntu 18.04

[andibing]

Me too! Glad you logged a ticket. I was going to earlier this morning, but thought something was amiss. Not had any luck to resolve, including re-running the installation (same error)

The error message across several different boxes - all Ubuntu 20.04 but x64 and Arm - is:

Err:23 https://apt.datadoghq.com stable Release
Certificate verification failed: The certificate is NOT trusted. The certificate chain uses expired certificate. Could not handshake: Error in the certificate verification. [IP: 13.224.226.40 443]

Contents of /etc/apt/sources.list.d/datadog.list

deb https://apt.datadoghq.com/ stable 7

[gusy]

Same thing over here, plus my machine is not being monitorized for last 5 hours

these are the outputs of sudo service datadog-agent status

May 30 15:07:14 labs dd.forwarder[2044]: WARNING (transaction.py:268): Transaction 105 in error (1 error), it will be replayed after 2020-05-30 15:07:34
May 30 15:07:15 labs dd.forwarder[2044]: WARNING (iostream.py:845): SSL Error on 10 ('52.0.188.242', 443): [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)
May 30 15:07:15 labs dd.forwarder[2044]: ERROR (ddagent.py:282): Response: HTTPResponse(_body=None,buffer=None,code=599,effective_url='https://5-32-6-app.agent.datadoghq.com/api/v1/check_run/?api_key=*************************51ca7',error=HTTPError('HTTP 599: [SSL: CERTI
May 30 15:07:15 labs dd.forwarder[2044]: WARNING (transaction.py:268): Transaction 101 in error (2 errors), it will be replayed after 2020-05-30 15:07:55
May 30 15:07:15 labs dd.forwarder[2044]: WARNING (iostream.py:845): SSL Error on 10 ('52.0.188.242', 443): [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)
May 30 15:07:15 labs dd.forwarder[2044]: ERROR (ddagent.py:282): Response: HTTPResponse(_body=None,buffer=None,code=599,effective_url='https://5-32-6-app.agent.datadoghq.com/api/v1/series/?api_key=*************************51ca7',error=HTTPError('HTTP 599: [SSL: CERTIFIC
May 30 15:07:15 labs dd.forwarder[2044]: WARNING (transaction.py:268): Transaction 100 in error (2 errors), it will be replayed after 2020-05-30 15:07:55
May 30 15:07:19 labs dd.forwarder[2044]: WARNING (iostream.py:845): SSL Error on 10 ('3.223.166.206', 443): [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)

this is the agent info

» sudo apt show datadog-agent                                                                                                                                                                                           127 ↵
Package: datadog-agent
Version: 1:5.32.6-1
Priority: extra
Section: utils
Maintainer: Datadog Packages <package@datadoghq.com>
Installed-Size: 343 MB
Conflicts: datadog-agent-base (<< 5.0.0)
Replaces: datadog-agent-base (<< 5.0.0), datadog-agent-lib (<< 5.0.0)
Homepage: http://www.datadoghq.com
License: Simplified BSD License
Vendor: Datadog <info@datadoghq.com>
Download-Size: 105 MB
APT-Manual-Installed: yes
APT-Sources: https://apt.datadoghq.com stable/main amd64 Packages
Description: Datadog Monitoring Agent
 The Datadog Monitoring Agent is a lightweight process that monitors system
 processes and services, and sends information back to your Datadog account.
 .
 This package installs and runs the advanced Agent daemon, which queues and
 forwards metrics from your applications as well as system services.
 .
 See http://www.datadoghq.com/ for more information

N: There are 107 additional records. Please use the '-a' switch to see them.

[truthbk]

Fixed here: DataDog/dd-agent#3882

We're trying to get this shipped ASAP.

Some workarounds provided in that link for those who cannot wait for 5.32.7.

[clamoriniere]

Hi @GeniusWiki @ramirovarandas @andibing

The certificat issue has been solved for Agent v6-7. You should be able to run apt [install|update] command.

We are still working on fixing it for Agent v5: #5656 (comment)