This bug was fixed in the package dkms - 2.6.1-4ubuntu2.1

---------------
dkms (2.6.1-4ubuntu2.1) disco; 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 Xenial)
       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:
  Fix Released
Status in dkms source package in Bionic:
  Fix Released
Status in dkms source package in Cosmic:
  Fix Released
Status in dkms source package in Disco:
  Fix Released
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.

  [Test Case]
  1. Install any out-of-tree dkms packages (like bbswitch-dkms)
  2. Un-enroll keys from MOK, ensure `mokutil --test-key 
/var/lib/shim-signed/mok/MOK.der` command returns 
"/var/lib/shim-signed/mok/MOK.der is not enrolled"
  3. Ensure SecureBoot is enabled
  4. Install any linux-headers-${version}-generic packages that is currently 
not installed, verify if it stucks at configurating state

  [Regression potential]
  Since this change will cause the output of dkms_autoinstaller to appear in 
the output of the kernel installs, this may surprise consumers of the dpkg log 
with its verbosity.

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