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Active Directory Federation Services (AD FS) 3.0 is a server role included in Windows Server 2012 R2.

Active Directory Federation Services (AD FS) 4.0 is a server role included in Windows Server 2016.

The Token-Signing and Token-Decrypting certificates are normally self-signed certificates good for one year, dated from the time the primary AD FS server was installed.

The Office 365 portal will warn you when these certs are about to expire and that user access to all Office 365 services will fail.

Normally the SSL certificate for the AD FS farm comes from a trusted third-party CA, like Digi Cert or Verisign.

This is a traditional SSL cert like you would use in IIS for any secure web server.

The trust policy requires an associated certificate, known as a verification certificate, which is the public key portion of the token-signing certificate.

So, 5 days after creation of the certificate, it will be promoted and the existing primary will be configured as the secondary until the next Certificate Generation Threshold window is observed.

Once the Promotion event has occurred, the Token Service will sign/encrypt all issued tokens with the new primary certificate.

If the existing primary certificate (Token Signing or Token Decryption) expiration time is within the window of the Certificate Generation Threshold value (20 days), then a new certificate is generated and configured as the secondary certificate.

Noted by event ID 335 in the event logs: It will remain as the secondary certificate until the Certificate Promotion Threshold value is observed (5 days).

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