In trusty, this works as expected.

ii  apt                              1.0.1ubuntu2.1                             
              amd64        commandline package manager
ii  apt-transport-https              1.0.1ubuntu2.1                             
              amd64        https download transport for APT
ii  apt-utils                        1.0.1ubuntu2.1                             
              amd64        package management related utility programs
ii  libapt-inst1.5:amd64             1.0.1ubuntu2.1                             
              amd64        deb package format runtime library
ii  libapt-pkg4.12:amd64             1.0.1ubuntu2.1                             
              amd64        package management runtime library

Running "apt-get update" the first time, apache returns 200:

> 10.0.4.72 - - [20/Feb/2018:13:49:27 -0500] "GET
/instafreight/dists/trusty/php/binary-amd64/Packages.gz HTTP/1.1" 200
951 "-" "Debian APT-HTTP/1.3 (1.0.1ubuntu2)"

Running "apt-get update" the second time:

> 10.0.4.72 - - [20/Feb/2018:13:49:53 -0500] "GET
/instafreight/dists/trusty/php/binary-amd64/Packages.gz HTTP/1.1" 304
124 "-" "Debian APT-HTTP/1.3 (1.0.1ubuntu2)"

> Hit http://ubuntu.pp trusty/php amd64 Packages

... and third time:

> 10.0.4.72 - - [20/Feb/2018:13:49:59 -0500] "GET
/instafreight/dists/trusty/php/binary-amd64/Packages.gz HTTP/1.1" 304
124 "-" "Debian APT-HTTP/1.3 (1.0.1ubuntu2)"

> Hit http://ubuntu.pp trusty/main amd64 Packages

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https://bugs.launchpad.net/bugs/1750625

Title:
  update misinterprets 304 response on Packages.gz

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