This bug was fixed in the package dkms - 2.6.1-4ubuntu4

---------------
dkms (2.6.1-4ubuntu4) eoan; urgency=medium

  * Do not invoke dkms_autoinstaller from /etc/kernel/header_postinst.d/dkms
    with redirection to /dev/null (LP: #1827697), this caused debconf dialog
    to not be shown.

 -- Julian Andres Klode <juli...@ubuntu.com>  Fri, 17 May 2019 12:56:47
+0200

** Changed in: dkms (Ubuntu Eoan)
       Status: Fix Committed => Fix Released

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https://bugs.launchpad.net/bugs/1827697

Title:
  Enroll key whiptail prompt blocks kernel header package upgrades

Status in dkms package in Ubuntu:
  Fix Released
Status in dkms source package in Xenial:
  In Progress
Status in dkms source package in Bionic:
  In Progress
Status in dkms source package in Cosmic:
  In Progress
Status in dkms source package in Disco:
  In Progress
Status in dkms source package in Eoan:
  Fix Released

Bug description:
  I noticed that sometimes the system upgrade is blocked in the kernel
  header package's configure phase, in the process manager I found that
  it is blocked by the "Configuring Secure Boot" whiptail prompt started
  by `update-secureboot-policy --enroll-key` which doesn't surface to
  the terminal and hence not interactable.

  Refer the attached screenshot for the process status at the time.

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