APT is using dpkg's --recursive option with a temporary directory since
recently if it has to touch >5 packages to avoid producing too long
commandlines for the kernel (yes, that is a thing… although unlikely it
does happen in big upgrades). Seems like this interface in dpkg does
support only *.deb files. Debian had decided to stick with .deb for
their automatic debug packages to avoid changing all tools dealing with
deb files to also deal with ddeb (or whatever).

Anyway, as that used to work with apt and is a valid althrough uncommon
thing to have packages without .deb as extension I have just commited a
patch upstream:
https://anonscm.debian.org/cgit/apt/apt.git/commit/?id=4f242a2

As a workaround you can set the option "dpkg::install::recursive" to
false and "dpkg::install::recursive::force" to true OR set
"dpkg::install::recursive::minimum" to e.g. 100 (assuming you can accept
not installing a 100 ddebs at once for the time being). Both workarounds
effect all dpkg calls through, so please only use if needed until the
patch reaches Ubuntu – don't set it "forever" or you will eventually run
into the problems this is designed to void in the first place…

** Changed in: apt (Ubuntu)
       Status: New => Fix Committed

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https://bugs.launchpad.net/bugs/1616909

Title:
  Installing multiple dbgsym packages fails

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