diff --git a/omnibus/files/private-chef-cookbooks/private-chef/metadata.rb b/omnibus/files/private-chef-cookbooks/private-chef/metadata.rb
index cfaf32b0b2..bea21e3bb9 100644
--- a/omnibus/files/private-chef-cookbooks/private-chef/metadata.rb
+++ b/omnibus/files/private-chef-cookbooks/private-chef/metadata.rb
@@ -12,6 +12,5 @@
 end
 
 depends          'enterprise' # grabbed via Berkshelf + Git
-depends          'openssl', '>= 4.4'
 
-chef_version '>= 14'
+chef_version '>= 14.4'
diff --git a/omnibus/files/private-chef-cookbooks/private-chef/recipes/nginx.rb b/omnibus/files/private-chef-cookbooks/private-chef/recipes/nginx.rb
index 41bfdf3698..bd6e73fed4 100644
--- a/omnibus/files/private-chef-cookbooks/private-chef/recipes/nginx.rb
+++ b/omnibus/files/private-chef-cookbooks/private-chef/recipes/nginx.rb
@@ -74,7 +74,7 @@
                         "DNS"
                       end
 
-   openssl_x509 ssl_crtfile do
+   openssl_x509_certificate ssl_crtfile do
      common_name server_name
      org node['private_chef']['nginx']['ssl_company_name']
      org_unit node['private_chef']['nginx']['ssl_organizational_unit_name']
diff --git a/omnibus/files/private-chef-cookbooks/private-chef/resources/chef_run.rb b/omnibus/files/private-chef-cookbooks/private-chef/resources/chef_run.rb
index 0f07501bd6..0a52f8ef1d 100644
--- a/omnibus/files/private-chef-cookbooks/private-chef/resources/chef_run.rb
+++ b/omnibus/files/private-chef-cookbooks/private-chef/resources/chef_run.rb
@@ -45,7 +45,6 @@ def mutate_chef_config
     Chef::Config[:solo_legacy_mode] = true
   end
 
-
   def my_node
     @my_node ||= my_client.build_node
   end
diff --git a/omnibus_overrides.rb b/omnibus_overrides.rb
index 8f758be9bb..9a51771244 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: "v14.3.0"
-override :ohai, version: "v14.3.0"
+override :chef, version: "v14.4.56"
+override :ohai, version: "v14.4.2"
 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 1c63fcb3fe..ed70ddfdca 100644
--- a/src/chef-server-ctl/Gemfile
+++ b/src/chef-server-ctl/Gemfile
@@ -2,7 +2,7 @@ source "https://rubygems.org"
 
 gemspec
 
-gem "chef", '~>14.3.0'
+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 cb346e9a97..af4aa9f3ef 100644
--- a/src/chef-server-ctl/Gemfile.local
+++ b/src/chef-server-ctl/Gemfile.local
@@ -1,2 +1,2 @@
-gem 'chef', '~>14.3.0'
+gem 'chef', '~>14.4.0'
 gem 'json', '~>2.0'
diff --git a/src/chef-server-ctl/Gemfile.lock b/src/chef-server-ctl/Gemfile.lock
index 695f1e250e..6a529e25e0 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 (~> 14.3.0)
+      chef (~> 14.4.0)
       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 (14.3.37)
+    chef (14.4.56)
       addressable
       bundler (>= 1.10)
-      chef-config (= 14.3.37)
+      chef-config (= 14.4.56)
       chef-zero (>= 13.0)
       diff-lcs (~> 1.2, >= 1.2.4)
       erubis (~> 2.7)
@@ -54,27 +54,27 @@ GEM
       ffi-yajl (~> 2.2)
       highline (~> 1.6, >= 1.6.9)
       iniparse (~> 1.4)
-      iso8601 (~> 0.9.1)
+      iso8601 (~> 0.11.0)
       mixlib-archive (~> 0.4)
       mixlib-authentication (~> 2.1)
       mixlib-cli (~> 1.7)
       mixlib-log (~> 2.0, >= 2.0.3)
-      mixlib-shellout (~> 2.0)
+      mixlib-shellout (~> 2.4)
       net-sftp (~> 2.1, >= 2.1.2)
       net-ssh (~> 4.2)
       net-ssh-multi (~> 1.2, >= 1.2.1)
       ohai (~> 14.0)
       plist (~> 3.2)
       proxifier (~> 1.0)
-      rspec-core (~> 3.5)
-      rspec-expectations (~> 3.5)
-      rspec-mocks (~> 3.5)
+      rspec-core (~> 3.5, < 3.8)
+      rspec-expectations (~> 3.5, < 3.8)
+      rspec-mocks (~> 3.5, < 3.8)
       rspec_junit_formatter (~> 0.2.0)
       serverspec (~> 2.7)
       specinfra (~> 2.10)
       syslog-logger (~> 1.6)
       uuidtools (~> 2.1.5)
-    chef-config (14.3.37)
+    chef-config (14.4.56)
       addressable
       fuzzyurl
       mixlib-config (>= 2.2.12, < 3.0)
@@ -97,27 +97,27 @@ GEM
     ffi-yajl (2.3.1)
       libyajl2 (~> 1.2)
     fuzzyurl (0.9.0)
-    hashie (3.5.7)
+    hashie (3.6.0)
     highline (1.7.10)
     http-cookie (1.0.3)
       domain_name (~> 0.5)
     iniparse (1.4.4)
     ipaddress (0.8.3)
-    iso8601 (0.9.1)
+    iso8601 (0.11.0)
     knife-opc (0.4.0)
     libyajl2 (1.2.0)
     method_source (0.9.0)
-    mime-types (3.1)
+    mime-types (3.2.2)
       mime-types-data (~> 3.2015)
-    mime-types-data (3.2016.0521)
-    mixlib-archive (0.4.8)
+    mime-types-data (3.2018.0812)
+    mixlib-archive (0.4.16)
       mixlib-log
     mixlib-authentication (2.1.1)
     mixlib-cli (1.7.0)
     mixlib-config (2.2.13)
       tomlrb
     mixlib-log (2.0.4)
-    mixlib-shellout (2.3.2)
+    mixlib-shellout (2.4.0)
     multi_json (1.13.1)
     net-scp (1.2.1)
       net-ssh (>= 2.6.5)
@@ -129,14 +129,14 @@ GEM
     net-ssh-multi (1.2.1)
       net-ssh (>= 2.6.5)
       net-ssh-gateway (>= 1.2.0)
-    net-telnet (0.1.1)
+    net-telnet (0.2.0)
     netrc (0.11.0)
-    ohai (14.3.0)
+    ohai (14.4.2)
       chef-config (>= 12.8, < 15)
       ffi (~> 1.9)
       ffi-yajl (~> 2.2)
       ipaddress
-      mixlib-cli
+      mixlib-cli (>= 1.7.0)
       mixlib-config (~> 2.0)
       mixlib-log (~> 2.0, >= 2.0.1)
       mixlib-shellout (~> 2.0)
@@ -155,12 +155,12 @@ GEM
     pry (0.11.3)
       coderay (~> 1.1.0)
       method_source (~> 0.9.0)
-    public_suffix (3.0.2)
+    public_suffix (3.0.3)
     rack (2.0.5)
     rainbow (3.0.0)
     rake (12.3.1)
     rb-readline (0.5.5)
-    redis (4.0.1)
+    redis (4.0.2)
     rest-client (2.0.2)
       http-cookie (>= 1.0.2, < 2.0)
       mime-types (>= 1.16, < 4.0)
@@ -192,14 +192,14 @@ GEM
       ruby-progressbar (~> 1.7)
       unicode-display_width (~> 1.0, >= 1.0.1)
     ruby-progressbar (1.9.0)
-    sequel (5.10.0)
+    sequel (5.12.0)
     serverspec (2.41.3)
       multi_json
       rspec (~> 3.0)
       rspec-its
       specinfra (~> 2.72)
     sfl (2.3)
-    specinfra (2.75.0)
+    specinfra (2.76.1)
       net-scp
       net-ssh (>= 2.7)
       net-telnet
@@ -224,7 +224,7 @@ PLATFORMS
 
 DEPENDENCIES
   bundler
-  chef
+  chef (~> 14.4.0)
   chef-server-ctl!
   chef_backup!
   chefstyle
@@ -234,4 +234,4 @@ DEPENDENCIES
   toml
 
 BUNDLED WITH
-   1.16.1
+   1.16.4
diff --git a/src/chef-server-ctl/chef-server-ctl.gemspec b/src/chef-server-ctl/chef-server-ctl.gemspec
index 85c8aaaefd..9dacabe8ef 100644
--- a/src/chef-server-ctl/chef-server-ctl.gemspec
+++ b/src/chef-server-ctl/chef-server-ctl.gemspec
@@ -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", "~> 14.3.0"
+  spec.add_runtime_dependency "chef", "~> 14.4.0"
   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 2278ac26b0..f7f24348fd 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', '~>14.3.0'
+gem 'chef', '~>14.4.0'
 gem 'knife-opc'
 EOF