diff --git a/omnibus/.kitchen.yml b/omnibus/.kitchen.yml
index bf828693fe..c257256365 100644
--- a/omnibus/.kitchen.yml
+++ b/omnibus/.kitchen.yml
@@ -10,7 +10,7 @@ driver:
 provisioner:
   name: chef_zero
   product_name: chef
-  product_version: 14.2.0
+  product_version: 14.5.33
 
 platforms:
   - name: ubuntu-18.04
@@ -19,8 +19,6 @@ platforms:
     run_list: apt::default
   - name: ubuntu-14.04
     run_list: apt::default
-  - name: ubuntu-12.04
-    run_list: apt::default
   - name: centos-6
   - name: centos-7
     run_list:  yum-centos::default
diff --git a/omnibus_overrides.rb b/omnibus_overrides.rb
index 9a51771244..c5e78d7574 100644
--- a/omnibus_overrides.rb
+++ b/omnibus_overrides.rb
@@ -1,8 +1,8 @@
 override :erlang, version: "18.3"
 override :lua, version: "5.1.5"
 override :'omnibus-ctl', version: "master"
-override :chef, version: "v14.4.56"
-override :ohai, version: "v14.4.2"
+override :chef, version: "v14.5.33"
+override :ohai, version: "v14.5.4"
 override :ruby, version: "2.5.1"
 override :rubygems, version: "2.7.7"
 # This SHA is the last commit before the 6.0 release
diff --git a/src/chef-server-ctl/Gemfile b/src/chef-server-ctl/Gemfile
index ed70ddfdca..9cda301074 100644
--- a/src/chef-server-ctl/Gemfile
+++ b/src/chef-server-ctl/Gemfile
@@ -2,7 +2,6 @@ source "https://rubygems.org"
 
 gemspec
 
-gem "chef", '~>14.4.0'
 gem "chef_backup", git: "https://github.com/chef/chef_backup.git"
 gem "omnibus-ctl", git: "https://github.com/chef/omnibus-ctl.git"
 gem "toml" # for habitat-land
diff --git a/src/chef-server-ctl/Gemfile.local b/src/chef-server-ctl/Gemfile.local
index af4aa9f3ef..b6ad29f979 100644
--- a/src/chef-server-ctl/Gemfile.local
+++ b/src/chef-server-ctl/Gemfile.local
@@ -1,2 +1,2 @@
-gem 'chef', '~>14.4.0'
+gem 'chef', '~>14.5.0'
 gem 'json', '~>2.0'
diff --git a/src/chef-server-ctl/Gemfile.lock b/src/chef-server-ctl/Gemfile.lock
index 6a529e25e0..4f6bec4a7a 100644
--- a/src/chef-server-ctl/Gemfile.lock
+++ b/src/chef-server-ctl/Gemfile.lock
@@ -17,7 +17,7 @@ PATH
   specs:
     chef-server-ctl (1.0.0)
       appbundler
-      chef (~> 14.4.0)
+      chef (~> 14.5.0)
       chef_backup
       ffi-yajl (>= 1.2.0)
       highline (~> 1.6, >= 1.6.9)
@@ -43,10 +43,10 @@ GEM
     ast (2.4.0)
     bcrypt (3.1.12)
     builder (3.2.3)
-    chef (14.4.56)
+    chef (14.5.33)
       addressable
       bundler (>= 1.10)
-      chef-config (= 14.4.56)
+      chef-config (= 14.5.33)
       chef-zero (>= 13.0)
       diff-lcs (~> 1.2, >= 1.2.4)
       erubis (~> 2.7)
@@ -74,7 +74,7 @@ GEM
       specinfra (~> 2.10)
       syslog-logger (~> 1.6)
       uuidtools (~> 2.1.5)
-    chef-config (14.4.56)
+    chef-config (14.5.33)
       addressable
       fuzzyurl
       mixlib-config (>= 2.2.12, < 3.0)
@@ -110,7 +110,7 @@ GEM
     mime-types (3.2.2)
       mime-types-data (~> 3.2015)
     mime-types-data (3.2018.0812)
-    mixlib-archive (0.4.16)
+    mixlib-archive (0.4.18)
       mixlib-log
     mixlib-authentication (2.1.1)
     mixlib-cli (1.7.0)
@@ -129,9 +129,9 @@ GEM
     net-ssh-multi (1.2.1)
       net-ssh (>= 2.6.5)
       net-ssh-gateway (>= 1.2.0)
-    net-telnet (0.2.0)
+    net-telnet (0.1.1)
     netrc (0.11.0)
-    ohai (14.4.2)
+    ohai (14.6.2)
       chef-config (>= 12.8, < 15)
       ffi (~> 1.9)
       ffi-yajl (~> 2.2)
@@ -191,18 +191,18 @@ GEM
       rainbow (>= 2.2.2, < 4.0)
       ruby-progressbar (~> 1.7)
       unicode-display_width (~> 1.0, >= 1.0.1)
-    ruby-progressbar (1.9.0)
-    sequel (5.12.0)
+    ruby-progressbar (1.10.0)
+    sequel (5.13.0)
     serverspec (2.41.3)
       multi_json
       rspec (~> 3.0)
       rspec-its
       specinfra (~> 2.72)
     sfl (2.3)
-    specinfra (2.76.1)
+    specinfra (2.76.2)
       net-scp
       net-ssh (>= 2.7)
-      net-telnet
+      net-telnet (= 0.1.1)
       sfl
     syslog-logger (1.6.8)
     systemu (2.6.5)
@@ -224,7 +224,6 @@ PLATFORMS
 
 DEPENDENCIES
   bundler
-  chef (~> 14.4.0)
   chef-server-ctl!
   chef_backup!
   chefstyle
@@ -234,4 +233,4 @@ DEPENDENCIES
   toml
 
 BUNDLED WITH
-   1.16.4
+   1.16.5
diff --git a/src/chef-server-ctl/chef-server-ctl.gemspec b/src/chef-server-ctl/chef-server-ctl.gemspec
index 9dacabe8ef..46f5a3a575 100644
--- a/src/chef-server-ctl/chef-server-ctl.gemspec
+++ b/src/chef-server-ctl/chef-server-ctl.gemspec
@@ -11,7 +11,7 @@ Gem::Specification.new do |spec|
   spec.email         = ["mark@chef.io"]
   spec.description   = %q{Commands to control Chef Server}
   spec.summary       = spec.description
-  spec.licenses      = "Apache2"
+  spec.licenses      = "Apache-2.0"
 
   spec.files         = %w{LICENSE README.md} + Dir.glob("{bin,doc,helpers,lib,plugins,spec}/**/*")
   spec.bindir        = "bin"
@@ -45,7 +45,7 @@ Gem::Specification.new do |spec|
   spec.add_runtime_dependency "chef_backup" # Gemfile has us getting latest from git
   spec.add_runtime_dependency "omnibus-ctl" # Gemfile has us getting latest from git
 
-  spec.add_runtime_dependency "chef", "~> 14.4.0"
+  spec.add_runtime_dependency "chef", "~> 14.5.0"
   spec.add_runtime_dependency "appbundler"
 
   spec.add_development_dependency "chefstyle"
diff --git a/src/chef-server-ctl/habitat/plan.sh b/src/chef-server-ctl/habitat/plan.sh
index f7f24348fd..70531b7e02 100644
--- a/src/chef-server-ctl/habitat/plan.sh
+++ b/src/chef-server-ctl/habitat/plan.sh
@@ -82,7 +82,7 @@ do_install() {
 
   cat > Gemfile << EOF
 source 'https://rubygems.org'
-gem 'chef', '~>14.4.0'
+gem 'chef', '~>14.5.0'
 gem 'knife-opc'
 EOF