Import of newer certificate version into Key Vault terminates with "Unable to parse X5c certificate chain and locate leaf certificate"

Rene Wagner 20 Reputation points


I've found a few entries to this type of error, but was not able to get it to work.
There is a certificate in the Vault that's expiring soon. As before, I wanted to upload a newer version but it failed in every attempt (via Portal as well as AZ CLI). I've stuck to the format of:


as listed here:
but I am getting the "Unable to parse X5c certificate chain and locate leaf certificate" error.

I've tried to assemble the certificate another way (server certificate->public key-> root certificate) but that got me the error: "Private key is not specified in the specified X.509 PEM certificate content. Please specify private key in the X.509 PEM certificate content."

The certificate data originates from DigiCert which is not set-up as a certificate authority in the Vault. So far this was never an issue.

Thanks in advance!

Azure Key Vault
Azure Key Vault
An Azure service that is used to manage and protect cryptographic keys and other secrets used by cloud apps and services.
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Accepted answer
  1. Carlos Solís Salazar 14,866 Reputation points

    The issues you're encountering while trying to upload a certificate to Azure Key Vault seem to be related to the format and composition of the certificate and private key you're using. Here are some steps and checks to resolve these errors:

    Error 1: "Unable to parse X5c certificate chain and locate leaf certificate"

    This error typically occurs when Azure Key Vault cannot correctly interpret the certificate chain. To resolve it:

    1. Certificate Chain Order: Ensure the certificate chain is correctly ordered. The typical order is:
      • Leaf certificate (your domain certificate)
      • Intermediate certificates (if any)
      • Root certificate (last in the chain)
    2. Correct Format: Confirm that each certificate in the chain is in PEM format and properly enclosed with -----BEGIN CERTIFICATE----- and -----END CERTIFICATE-----.
    3. No Extra Characters or Spaces: Check for any extra characters or spaces, especially at the beginning and end of each certificate block.

    Error 2: "Private key is not specified in the specified X.509 PEM certificate content."

    This error indicates that the private key is either missing or not correctly formatted. To address this:

    1. Include Private Key: Ensure that the private key is included in your PEM file and is correctly formatted with -----BEGIN PRIVATE KEY----- and -----END PRIVATE KEY-----.
    2. Match Certificate and Private Key: The private key must correspond to the leaf certificate. If they don't match, Azure Key Vault will not be able to use them.
    3. PEM Format for Private Key: Verify that the private key is in PEM format.
    4. No Extra Content: Similar to certificates, ensure there are no extra characters or spaces in the private key block.

    Additional Steps

    1. DigiCert Certificate Format: Double-check that the certificate format provided by DigiCert is compatible with Azure Key Vault. Sometimes, the format might need conversion or re-structuring.
    2. Re-download or Re-export: If you suspect the certificate files might be corrupted or modified incorrectly, consider re-downloading or re-exporting them from DigiCert.
    3. Test with a Different Tool: You can use OpenSSL to verify the format and content of your PEM file. This can help identify any discrepancies in the certificate or private key.
    4. Azure CLI vs Portal: If one method (Portal or Azure CLI) fails, try the other. Sometimes, the issue might be specific to the method of upload.
    5. Consult Azure Documentation: Review the Azure Key Vault documentation, especially the tutorial on importing a certificate, to ensure all steps are correctly followed.

    If you continue to face issues, consider reaching out to Azure support with the specific details of your problem for more targeted assistance.

    Accept the answer if the information helped you. This will help us and others in the community as well.

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