Azure App Service unable to validate .pfx file: Certificate failed validation because it could not be loaded

Question

For years I was able to upload new pfx files for SSL binding on Azure App Services using the OpenSSL creation method in this Stack Overflow answer:

openssl pkcs12 -export -out domain.name.pfx -inkey domain.name.key -in domain.name.crt

However, doing the same now provides this error:

At least one certificate is not valid (Certificate failed validation because it could not be loaded.)

What ways can this issue be resolved?

Answer 1

App Service private certificate requirements

App Service private certificates must meet the following requirements:

• Exported as a password-protected PFX file, encrypted using triple DES.
• Contains private key at least 2048 bits long
• Contains all intermediate certificates and the root certificate in the certificate chain.

Option 1: Use legacy provider in OpenSSL 3+

OpenSSL 3+ no longer uses DES encryption as a default. The original command needs the -legacy and -provider-path (path to legacy.dll) arguments appended:

openssl pkcs12 -export -out domain.name.pfx -inkey domain.name.key -in domain.name.crt -legacy -provider-path 'C:\Program Files\OpenSSL-Win64\bin'

Option 2: Let Windows re-encrypt the file

If for some reason your OpenSSL installation does not contain the legacy provider:

Open PowerShell and run this command, replacing -FilePath with the path to your non-working pfx file, and the password -String argument with its respective password:

Import-PfxCertificate -FilePath "pfx file path" -CertStoreLocation Cert:\LocalMachine\My -Password (ConvertTo-SecureString -String 'MyPassword' -AsPlainText -Force) -Exportable

A successful output will look like:

Use this thumbprint to export the cert to a new pfx file, replacing the -Cert, -FilePath, and password -String arguments:

Export-PfxCertificate -Cert Microsoft.PowerShell.Security\Certificate::LocalMachine\My\B56CE9B122FB04E29A974A4D0DB3F6EAC2D150C0 -FilePath 'newPfxName.pfx' -Password (ConvertTo-SecureString -String 'MyPassword' -AsPlainText -Force)

Azure should now be able to validate the new pfx file output.

Answer 2

For me, the issue was simply solved by changing the password. My previous password had special characters, which then i changed to only alphabetic letters.