opentelemetry datadog export fail on server certif...

Boris_Karnaukh · ‎2026-01-14

CheckPoint VSX R81.20, JHF Take 120

Skyline with export to Datadog as follows:

{
"enabled": true,
"export-targets": {
"add": [
{
"enabled": true,
"type": "datadog",
"name": "datadog-fu-tls-01",
"url": "datadoghq.eu",
"client-auth": {
"token": {
"custom-header": {
"key": "apikey",
"value": "########################"
}
}
},
"server-auth": {
"ca-public-key": {
"type": "PEM-X509",
"value": "-----BEGIN CERTIFICATE-----MIIG4TCCBcmgAwIBAgIQC8cT6g8vNGiyaJazoXT0fjANBgkqhkiG9w0BAQsFADBZMQswCQYDVQQGEwJVUzEVMBMGA1UEChMMRGlnaUNlcnQgSW5jMTMwMQYDVQQDEypEaWdpQ2VydCBHbG9iYWwgRzIgVExTIFJTQS
BTSEEyNTYgMjAyMCBDQTEwHhcNMjUwNjA5MDAwMDAwWhcNMjYwNzEwMjM1OTU5WjBkMQswCQYDVQQGEwJVUzERMA8GA1UECBMITmV3IFlvcmsxETAPBgNVBAcTCE5ldyBZb3JrMRYwFAYDVQQKEw1EYXRhZG9nLCBJbmMuMRcwFQYDVQQDDA4qLmRhdGFkb2docS5ldTCCASIwDQYJK
oZIhvcNAQEBBQADggEPADCCAQoCggEBAOJuZyQhXlV08CmXdMlMt/iaKLlK5Z5it9Fh8erJeL3yvcNlK6hLlXOglBU9u8OtpIRuc17k7h1EA+qQCrt75ZEXDxGxHqpbKWaYNob9Vk7L40c+ijKg2LFlElvNhTEihJ2Ru0tkUkX2kNOUsLbcWdODb79FFVmrd05LGSbiubDQeLD1aSKX
jNnsa63wlXg0lfeV4bA7n7zzG1QGl9G3beLYN0IhKF5vnwQ687E18BGiwRadYcNkPb4XmM3AsaXVrmW1dDdKbpmCJVonz0b2j115EcupEm9FEruXrOeYsgj7sBPeDReYAarsIn3XKGfHg6CawyyB9109iiMw44GIelMCAwEAAaOCA5gwggOUMB8GA1UdIwQYMBaAFHSFgMBmx9833s+
9KTeqAx2+7c0XMB0GA1UdDgQWBBSSY4n5ZnOMdNBW98Ybu8q/gnWYGTAnBgNVHREEIDAegg4qLmRhdGFkb2docS5ldYIMZGF0YWRvZ2hxLmV1MD4GA1UdIAQ3MDUwMwYGZ4EMAQICMCkwJwYIKwYBBQUHAgEWG2h0dHA6Ly93d3cuZGlnaWNlcnQuY29tL0NQUzAOBgNVHQ8BAf8EBA
MCBaAwHQYDVR0lBBYwFAYIKwYBBQUHAwEGCCsGAQUFBwMCMIGfBgNVHR8EgZcwgZQwSKBGoESGQmh0dHA6Ly9jcmwzLmRpZ2ljZXJ0LmNvbS9EaWdpQ2VydEdsb2JhbEcyVExTUlNBU0hBMjU2MjAyMENBMS0xLmNybDBIoEagRIZCaHR0cDovL2NybDQuZGlnaWNlcnQuY29tL0RpZ
2lDZXJ0R2xvYmFsRzJUTFNSU0FTSEEyNTYyMDIwQ0ExLTEuY3JsMIGHBggrBgEFBQcBAQR7MHkwJAYIKwYBBQUHMAGGGGh0dHA6Ly9vY3NwLmRpZ2ljZXJ0LmNvbTBRBggrBgEFBQcwAoZFaHR0cDovL2NhY2VydHMuZGlnaWNlcnQuY29tL0RpZ2lDZXJ0R2xvYmFsRzJUTFNSU0FT
SEEyNTYyMDIwQ0ExLTEuY3J0MAwGA1UdEwEB/wQCMAAwggF+BgorBgEEAdZ5AgQCBIIBbgSCAWoBaAB1ANgJVTuUT3r/yBYZb5RPhauw+Pxeh1UmDxXRLnK7RUsUAAABl1PrKFQAAAQDAEYwRAIgDYHDKG+sA3fLlClAa8yBZJiBSv/UksAZppq/2thq77wCIHYEiBBYuJmTflc6w6T
6k6plTdGsh0o6fds2wQImATOqAHYAwjF+V0UZo0XufzjespBB68fCIVoiv3/Vta12mtkOUs0AAAGXU+soRwAABAMARzBFAiEAoYa59cqUaHC/6+CftYRzJO6g9aQUGc4i6GtHBKZ1Mt0CIHiNlO9HutgxM47pAZhE/115E7jCKq3hYI/M9WK8gp6iAHcAlE5Dh/rswe+B8xkkJqgYZQ
HH0184AgE/cmd9VTcuGdgAAAGXU+soXAAABAMASDBGAiEA9bq6VuHODCaM2cKRQJMhUEn38smq1QgluLvm7LEw3+UCIQDpI4rguI6lJi0qCsFk9mJZpsAVqvoys85iQrqX0Jj2VDANBgkqhkiG9w0BAQsFAAOCAQEAvAeXIn3dRigdlNajFlQzyaVtRpGAK9IeLwnX6Pl16/TNaaT7t
BmhqehT2eFGspc3bd+YZA/SirDeN1e9rsNRNQpvzLdvC0gU4SCHHarlwYLdmf7G4GOYCTmqfQj0T9p5YG2iv3lwYyBc3HQ+AODwDttcDKUAqsOGYhuTwdBF3P3/lsX98dptFqzEl8UDQoH0OSp9Kab05tlH9DsvVFaJxZ+2Iwo3gZCPH+yySi698Q/VRNzmUKp4LPHgiMAmmWCDcpTk
aUdDPhgoXJBWjBNViCtaAPhSIo9mc3UDfvLbidam48MDw0CnwXdCGcODM3HzgN+zNCxbRaJbExt8aRgH1Q==-----END CERTIFICATE-----"
}
}
}
]
}
}

Datadog connection fails on server certificate verification:

2026-01-14T10:21:07.086+0200 error internal/queue_sender.go:103 Exporting failed. Dropping data. Try enabling retry_on_failure config option to retry on retryable errors. {"kind": "exporter", "data_
type": "metrics", "name": "datadog/datadog-fu-tls-01", "error": "max elapsed time expired Post \"https://api.datadoghq.eu/api/v2/series\": tls: failed to verify certificate: x509: certificate signed by unknown a
uthority", "dropped_items": 199}

As I can understand, Datadog cloud sends partial certificate chain: it contains server certificate and certificate authority intermediate certificate. Root certificate is omitted.

I have tried setting in JSON file root CA certificate for Datadog, it didn't work either.

Leaving server-auth on defaults does not help too.

Anyone succeeded in making Datadog export work with Skyline?

the_rock

Maybe @Duane_Toler can comment on this?

Best,
Andy

Vincent_Bacher

We don't use Datadog, but Prometheus, but I think it should look the same as ours in this case.
We also had this problem, and it was only when we integrated the server CERT of the root CA, i.e. built a cert with the complete chain, that remote write worked.

and now to something completely different - CCVS, CCAS, CCTE, CCCS, CCSM elite

Duane_Toler

The error in your output above explicitly says that your certificate chain is untrusted. I haven't used Datadog personally, yet, but I can say that your certificate issuer is:

issuer=C = US, O = DigiCert Inc, CN = DigiCert Global G2 TLS RSA SHA256 2020 CA1

This is the newer root CA from your certificate provider, so be sure you have this updated root CA installed on the host receiving this connection. Sectigo and DigiCert (in particular) rolled out new CAs recently, and many folks are getting surprised by it.

As @Vincent_Bacher said, you may also need to build the whole CA chain in one bundle and make that your "certificate". If you do, then this has to be done in the correct order:

First the base root CA
All of the intermediate CAs (in order)
Finally, your certificate for the host/service

This is a concatenated list of the PEM certificates; for example:

(cat root.pem; cat ca-bundle.crt; cat server.crt) > cert_chain.pem

Then use "cert_chain.pem" as your "certificate" in the configuration.

I hope this helps!

[edit: correct the credit ... oops! coffee hasn't fully circulated yet!]

--
Ansible for Check Point APIs series: https://www.youtube.com/@EdgeCaseScenario and Substack

Vincent_Bacher

Hey, that was me who said you have to put all the certificates in the chain into one certificate 😄

and now to something completely different - CCVS, CCAS, CCTE, CCCS, CCSM elite

Duane_Toler

Argh!! Apologies! I corrected it. Thank you! (now back to my morning coffee...)

--
Ansible for Check Point APIs series: https://www.youtube.com/@EdgeCaseScenario and Substack

the_rock

Kudos to both of you!

Best,
Andy

Boris_Karnaukh

Hi Duane,

I have found the root cert you are referring to under /opt/CPshrd-R81.20/conf/ca-bundle.crt, simple test with 'curl_cli -I --cacert $CPDIR/conf/ca-bundle.crt ...' confirms that CheckPoint certificate repository indeed contains proper DigiCert certificate.

It just seems to me that by default log exporter looks for trusted CA bundle somewhere else.

I have tried approach with cat root.pem subca.pem server.pem > chain.pem, but it didn't work properly in my case.

Vincent_Bacher

I'm not 100% sure, but looking at your openssl output, I think I see what might be going wrong:

Just tried to download the cert chaiin. It looks like Datadog is only sending 2 certificates in the chain:

Server Cert: *.datadoghq.eu
Intermediate CA: DigiCert Global G2 TLS RSA SHA256 2020 CA1
Missing: DigiCert Global Root G2 (Root CA)

That's probably why you're getting "unable to get local issuer certificate".

Maybe you could try extracting the missing Root CA and adding it to your chain? Something like:

Option 1 - Extract Root CA from Check Point's bundle:

grep -A 30 "DigiCert Global Root G2" $CPDIR/conf/ca-bundle.crt | \  sed -n '/-----BEGIN CERTIFICATE-----/,/-----END CERTIFICATE-----/p' > digicert-root-g2.pem

Option 2 - Download it from DigiCert:

curl_cli -o digicert-root-g2.pem https://cacerts.digicert.com/DigiCertGlobalRootG2.crt.pem

Then try creating a complete chain:

cpopenssl s_client -connect api.datadoghq.eu:443 -showcerts 2>/dev/null < /dev/null | \  sed -n '/-----BEGIN CERTIFICATE-----/,/-----END CERTIFICATE-----/p' > datadog-chain.pemcat digicert-root-g2.pem >> datadog-chain.pem

Now datadog-chain.pem should have all 3 certificates. Put that into your Skyline server-auth config and see if it works?

Not entirely sure if this will solve it, but it might be worth a try.

and now to something completely different - CCVS, CCAS, CCTE, CCCS, CCSM elite

Boris_Karnaukh

Hi Vincent,

Unfortunately, importing full certificate chain like this still doesn't solve the problem:

"server-auth": {
"ca-public-key": {
"type": "PEM-X509",
"value": "-----BEGIN CERTIFICATE-----MIIG4TCCBcmgAwIBAgIQC8cT6g8vNGiyaJazoXT0fjANBgkqhkiG9w0BAQsFADBZMQswCQYDVQQGEwJVUzEVMBMGA1UEChMMRGlnaUNlcnQgSW5jMTMwMQYDVQQDEypEaWdpQ2VydCBHbG9iYWwgRzIgVExTIF
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AK9IeLwnX6Pl16/TNaaT7tBmhqehT2eFGspc3bd+YZA/SirDeN1e9rsNRNQpvzLdvC0gU4SCHHarlwYLdmf7G4GOYCTmqfQj0T9p5YG2iv3lwYyBc3HQ+AODwDttcDKUAqsOGYhuTwdBF3P3/lsX98dptFqzEl8UDQoH0OSp9Kab05tlH9DsvVFaJxZ+2Iwo3gZCPH+yySi698Q/V
RNzmUKp4LPHgiMAmmWCDcpTkaUdDPhgoXJBWjBNViCtaAPhSIo9mc3UDfvLbidam48MDw0CnwXdCGcODM3HzgN+zNCxbRaJbExt8aRgH1Q==-----END CERTIFICATE----------BEGIN CERTIFICATE-----MIIEyDCCA7CgAwIBAgIQDPW9BitWAvR6uFAsI8zwZjANBgkqh
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XaZd8dP3A+iZ7U6utzWX9upwGnIrXWkOH7U1MVl+twcW1BSAuWdH/SvWgKtiwla3JLko716f2b4gp/DA/JIS7w7d7kwcsr4drdjPtAFVSslme5LnQ89/nD/7d+MS5EHKBCQRfz5eeLjJ1js+aWNJXMX43AYGyZm0pGrFmCW3RbpD0ufovARTFXFZkAdl9h6g4U5+LXUZtXMYnhIHU
foyMo5tS58aI7Dd8KvvwVVo4chDYABPPTHPbqjc1qCmBaZx2vN4Ye5DUys/vZwP9BFohFrH/6j/f3IL16/RZkiMNJCqVJUzKoZHm1Lesh3Sz8W2jmdv51b2EQJ8HmA==-----END CERTIFICATE----------BEGIN CERTIFICATE-----MIIDjjCCAnagAwIBAgIQAzrx5qcRq
aC7KGSxHQn65TANBgkqhkiG9w0BAQsFADBhMQswCQYDVQQGEwJVUzEVMBMGA1UEChMMRGlnaUNlcnQgSW5jMRkwFwYDVQQLExB3d3cuZGlnaWNlcnQuY29tMSAwHgYDVQQDExdEaWdpQ2VydCBHbG9iYWwgUm9vdCBHMjAeFw0xMzA4MDExMjAwMDBaFw0zODAxMTUxMjAwMDBaMG
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4GxJUTFy8bJZ918rGOmaFvE7FBcf6IKshPECBV1/MUReXgRPTqh5Uykw7+U0b6LJ3/iyK5S9kJRaTepLiaWN0bfVKfjllDiIGknibVb63dDcY3fe0Dkhvld1927jyNxF1WW6LZZm6zNTflMrY=-----END CERTIFICATE-----"
}
}

That's exactly what I have started with.

Vincent_Bacher

Oh, i am sorry, i mixed up the use-cases. In this case i checked my Skyline config and viewed the certificate and i saw that i just used the intermediate CA cert of our organization.
Sorry for confusing.

I had a look at your chain.
First cert:

Certificate Information:

Common Name: *.datadoghq.eu

Subject Alternative Names: *.datadoghq.eu, datadoghq.eu

Organization: Datadog, Inc.

Organization Unit:

Locality: New York

State: New York

Country: US

Valid From: June 8, 2025

Valid To: July 10, 2026

Issuer: DigiCert Global G2 TLS RSA SHA256 2020 CA1, DigiCert Inc Write review of DigiCert

Serial Number: 0bc713ea0f2f3468b26896b3a174f47e

Second Cert

Certificate Information:

Common Name: DigiCert Global G2 TLS RSA SHA256 2020 CA1

Subject Alternative Names:

Organization: DigiCert Inc

Organization Unit:

Locality:

State:

Country: US

Valid From: March 29, 2021

Valid To: March 29, 2031

Issuer: DigiCert Global Root G2, DigiCert Inc Write review of DigiCert

Serial Number: 0cf5bd062b5602f47ab8502c23ccf066

Would try just to use second one as you see that this is the issuer of the datahog server cert.

and now to something completely different - CCVS, CCAS, CCTE, CCCS, CCSM elite

Boris_Karnaukh

Thank you for replying. I have found that datadog configuration translates into something like this:

sklnctl otelcol config | jq .exporters
{
"datadog/datadog-tls-01": {
"api": {
"key": "#####################",
"site": "datadoghq.eu"
},
"tls": {
"ca_file": "/var/log/otlp_certs/ca-bundle.crt"
}
},
"s1cdtexporter": {
"access_keys_file": "$FWDIR/conf/s1c-metrics-keys.conf",
"debug": false,
"dry_run": false
},
"unix": {
"format": "json",
"path": "/home/admin/mytest.sock",
"transport": "unixgram"
}
}

I have tried populating file /var/log/otlp_certs/ca-bundle.crt with all certificates in the chain, but it seems to me that it doesn't get fully used by Open Telemetry collector.

Vincent_Bacher

Interesting Json output.

On our side using Prometheus remote write it was easy going so I would now prefer creating a sr for tac support.

Better than to wait if anyone here has an idea of a solution.

and now to something completely different - CCVS, CCAS, CCTE, CCCS, CCSM elite

Are you a member of CheckMates?