When looking to install newer versions of Casks, running brew upgrade then brew cask info [cask] shows an older version of the cask until brew cask update is run.

Please follow the general troubleshooting steps first:

• Ran brew update and retried your prior step?
• Ran brew doctor, fixed as many issues as possible and retried your prior step?
• Confirmed this is problem with Homebrew/brew and not specific formulae? If it’s a formulae-specific problem please file this issue at https://github.com/Homebrew/homebrew-core/issues/new

Bug reports:

Having immediately run a brew upgrade just prior, an attempt to identify and install a newer cask shows the older version until brew cask update is run. While I don’t have the option to provide output to this effect, a brew update fails to update casks in the same way.

$ brew upgrade
Updating Homebrew...
==> Auto-updated Homebrew!
Updated 1 tap (homebrew/core).
==> Updated Formulae
artifactory                ldc                        rakudo-star
bazel                      libressl                   riak
bit                        logstash                   ruby-build
certbot                    mediaconch                 saldl
conan                      mercurial ✔                skinny
docker-compose             minimesos                  tika
docker-compose-completion  mpd                        vim ✔
filebeat                   nginx                      vnu
grails                     node                       wallpaper
ipmitool                   node-build                 wpcli-completion ✔
jenkins                    nodeenv                    yarn
jsonnet                    oath-toolkit               you-get
knot                       portaudio                  youtube-dl
kobalt                     qt5

==> Upgrading 16 outdated packages, with result:
awscli 1.11.44, vitorgalvao/tiny-scripts/cask-repair 0.30.1, homebrew/php/composer 1.3.2, gd 2.2.4_1, go 1.7.5, imagemagick 7.0.4-6, libevent 2.1.8, libtiff 4.0.7_2, mercurial 4.1, openssl 1.0.2k, openssl@1.1 1.1.0d, redis 3.2.7, tmux 2.3_3, vim 8.0.0295, webp 0.6.0, wpcli-completion 1.1.0

... upgrades of above packages removed for some level of brevity ...

$ brew cask info chefdk
chefdk: 1.1.16-1
https://downloads.chef.io/chefdk/
/usr/local/Caskroom/chefdk/1.1.16-1 (2 files, 65.2M)
From: https://github.com/caskroom/homebrew-cask/blob/master/Casks/chefdk.rb
==> Names
Chef Development Kit
ChefDK
==> Artifacts
chefdk-1.1.16-1.pkg (pkg)

$ brew cask update
Warning: Calling `brew cask update` is deprecated and will be disabled on 2017-07-01!
Use `brew update` instead.
/usr/local/Homebrew/Library/Homebrew/cask/lib/hbc/cli.rb:111:in `run_command'

==> Updated 3 taps (caskroom/cask, caskroom/drivers, caskroom/versions).

$ brew cask info chefdk
chefdk: 1.2.20-1
https://downloads.chef.io/chefdk/
/usr/local/Caskroom/chefdk/1.1.16-1 (2 files, 65.2M)
From: https://github.com/caskroom/homebrew-cask/blob/master/Casks/chefdk.rb
==> Names
Chef Development Kit
ChefDK
==> Artifacts
chefdk-1.2.20-1.pkg (pkg)

brew doctor:

$ brew doctor
Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry and just ignore them. Thanks!

Warning: "config" scripts exist outside your system or Homebrew directories.
`./configure` scripts often look for *-config scripts to determine if
software packages are installed, and what additional flags to use when
compiling and linking.

Having additional scripts in your path can confuse software installed via
Homebrew if the config script overrides a system or Homebrew provided
script of the same name. We found the following "config" scripts:
  /Users/ssmith/.pyenv/shims/python-config
  /Users/ssmith/.pyenv/shims/python2-config
  /Users/ssmith/.pyenv/shims/python2.7-config
  /Users/ssmith/.pyenv/shims/python3-config
  /Users/ssmith/.pyenv/shims/python3.5-config
  /Users/ssmith/.pyenv/shims/python3.5m-config

brew config:

$ brew config
HOMEBREW_VERSION: 1.1.9
ORIGIN: https://github.com/Homebrew/brew.git
HEAD: 664d0c67d5947605c914c4c56ebcfaa80cb6eca0
Last commit: 3 days ago
Core tap ORIGIN: https://github.com/Homebrew/homebrew-core
Core tap HEAD: 9f9a3222a276e27ad229bcd6be9a5d69b8862037
Core tap last commit: 11 minutes ago
HOMEBREW_PREFIX: /usr/local
HOMEBREW_REPOSITORY: /usr/local/Homebrew
HOMEBREW_CELLAR: /usr/local/Cellar
HOMEBREW_BOTTLE_DOMAIN: https://homebrew.bintray.com
CPU: octa-core 64-bit haswell
Homebrew Ruby: 2.0.0-p648
GCC-4.2: build 5666
Clang: 8.0 build 800
Git: 2.11.0 => /usr/local/bin/git
Perl: /usr/bin/perl
Python: /Users/ssmith/.pyenv/shims/python => /usr/local/Cellar/python/2.7.13/Frameworks/Python.framework/Versions/2.7/bin/python2.7
Ruby: /Users/ssmith/.rbenv/shims/ruby => /Users/ssmith/.rbenv/versions/2.4.0/bin/ruby
Java: 1.8.0_112, 1.8.0_92, 1.8.0_77, 1.8.0_74, 1.8.0_72, 1.8.0_66, 1.8.0_60, 1.8.0_51, 1.8.0_45, 1.8.0_40, 1.8.0_31, 1.8.0_25, 1.8.0_20
macOS: 10.12.3-x86_64
Xcode: 8.2.1
CLT: 8.2.0.0.1.1480973914
X11: 2.7.11 => /opt/X11