We tracked this down to the Pulp repository not having Size fields.
While this is a broken repository, APT should also more gracefully
handle that situation, either by warning about missing Size values,
erroring out, disabling pipelining; or by fixing pipelining to behave if
we don't know the size in advance.

** Changed in: apt (Ubuntu)
       Status: Incomplete => Triaged

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https://bugs.launchpad.net/bugs/1921626

Title:
  apt install - File has unexpected size - http pipeline

Status in apt package in Ubuntu:
  Triaged

Bug description:
  1) Ubuntu 18.04.5 LTS

  2) apt 1.6.12ubuntu0.2

  3) What you expected to happen

  I set a custom set of repositories in /etc/apt/sources.list and then I
  run "apt install <list of packages>". I expect the command to download
  and install the packages.

  4) What happened instead

  "apt install ..." fails during the download phase with "File has
  unexpected size ...."

  
  5) What I've established trying to debug the issue:

  - Disabling http pipelining resolves the issue: "apt 
-oAcquire::http::Pipeline-Depth=0 install ..."
  - All the packages, and repo metadata in the referenced repositories is 
correct
  - The issue is easily reproducible in my setup with different repositories
  - tcpdump shows that requests and responses are in the correct order, and 
contain the correct data

  More details about the issue:
  https://projects.theforeman.org/issues/32178

  With all the above in mind, it appears that this must be a bug in apt's http 
pipeline handling.
  It seem that apt is trying to match a request to do wrong response, and size 
doesn't match. 

  I've attached an example log, where the error pops up for multiple
  packages, and they all appear to be compared to one size (86464
  bytes). That size is correct for one of the package being downloaded,
  but somehow apt is trying to match to multiple other packages.

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