In addition to what Steve has said, I'm wondering if you can work around
this by using faketime when signing.

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https://bugs.launchpad.net/bugs/2003701

Title:
  PKCS7: Message signed outside of X.509 validity window

Status in openssl package in Ubuntu:
  New
Status in sbsigntool package in Ubuntu:
  New

Bug description:
  When signing UEFI applications, the signature includes signing
  timestamp.

  Kernels, upon kexec, check that message signature is within the
  validity of the X.509 signing certificate.

  When using original canonical kernel team test key, I no longer can
  kexec kernels, as the test key has expired.

  UEFI specifications in general ignore signing time.

  IMHO we should remove / not include signing timestamp in the UEFI
  signatures to avoid this.

  ---

  i guess openssl needs to provide ability to create signatures without
  signingtime attribute.

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