The proxy shows no attempts to download Release.gpg, just InRelease:

18/Jan/2017:12:29:02 +0000     69 y.y.y.y TCP_MISS/404 631 GET 
http://ubuntu-cloud.archive.canonical.com/ubuntu/dists/xenial-updates/newton/InRelease
 - FIRSTUP_PARENT/x.x.x.x text/html
18/Jan/2017:12:29:02 +0000     67 y.y.y.y TCP_REFRESH_UNMODIFIED/304 335 GET 
http://ubuntu-cloud.archive.canonical.com/ubuntu/dists/xenial-updates/newton/Release
 - FIRSTUP_PARENT/x.x.x.x -
18/Jan/2017:12:29:02 +0000    133 y.y.y.y TCP_REFRESH_UNMODIFIED/304 420 GET 
http://archive.ubuntu.com/ubuntu/dists/xenial/InRelease - 
FIRSTUP_PARENT/x.x.x.x -
18/Jan/2017:12:29:02 +0000    134 y.y.y.y TCP_REFRESH_UNMODIFIED/304 438 GET 
http://security.ubuntu.com/ubuntu/dists/xenial-security/InRelease - 
FIRSTUP_PARENT/x.x.x.x -
18/Jan/2017:12:29:02 +0000     67 y.y.y.y TCP_REFRESH_UNMODIFIED/304 423 GET 
http://archive.ubuntu.com/ubuntu/dists/xenial-updates/InRelease - 
FIRSTUP_PARENT/x.x.x.x -
18/Jan/2017:12:29:02 +0000     66 y.y.y.y TCP_REFRESH_UNMODIFIED/304 420 GET 
http://archive.ubuntu.com/ubuntu/dists/xenial-backports/InRelease - 
FIRSTUP_PARENT/x.x.x.x -

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https://bugs.launchpad.net/bugs/1657440

Title:
  apt won't redownload Release.gpg

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