diff --git a/Gemfile.lock b/Gemfile.lock
index c57646c198..7caad9d9a0 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -13,7 +13,8 @@ PATH
       pastel
       r18n-desktop
       toml-rb
-      train (< 3.0)
+      train (~> 3.0)
+      train-winrm
       tty-spinner
 
 GEM
@@ -92,7 +93,7 @@ GEM
       mixlib-log (>= 2.0, < 4.0)
       rack (~> 2.0, >= 2.0.6)
       uuidtools (~> 2.1)
-    chefstyle (0.13.2)
+    chefstyle (0.13.3)
       rubocop (= 0.72.0)
     citrus (3.0.2)
     coderay (1.1.2)
@@ -231,7 +232,7 @@ GEM
     os (1.0.1)
     paint (1.0.1)
     parallel (1.17.0)
-    parser (2.6.3.0)
+    parser (2.6.4.0)
       ast (~> 2.4.0)
     pastel (0.7.3)
       equatable (~> 0.6)
@@ -310,7 +311,7 @@ GEM
     toml-rb (1.1.2)
       citrus (~> 3.0, > 3.0)
     tomlrb (1.2.8)
-    train (2.1.19)
+    train (3.0.3)
       azure_graph_rbac (~> 0.16)
       azure_mgmt_key_vault (~> 0.17)
       azure_mgmt_resources (~> 0.15)
@@ -322,8 +323,6 @@ GEM
       mixlib-shellout (>= 2.0, < 4.0)
       net-scp (>= 1.2, < 3.0)
       net-ssh (>= 2.9, < 6.0)
-      winrm (~> 2.0)
-      winrm-fs (~> 1.0)
     train-core (2.1.19)
       json (>= 1.8, < 3.0)
       mixlib-shellout (>= 2.0, < 4.0)
@@ -331,6 +330,9 @@ GEM
       net-ssh (>= 2.9, < 6.0)
       winrm (~> 2.0)
       winrm-fs (~> 1.0)
+    train-winrm (0.2.3)
+      winrm (~> 2.0)
+      winrm-fs (~> 1.0)
     tty-box (0.4.1)
       pastel (~> 0.7.2)
       strings (~> 0.1.6)
diff --git a/chef-apply.gemspec b/chef-apply.gemspec
index a36fff9264..bda073bafc 100644
--- a/chef-apply.gemspec
+++ b/chef-apply.gemspec
@@ -48,9 +48,8 @@ Gem::Specification.new do |spec|
                                      # localization gem...
   spec.add_dependency "toml-rb" # This isn't ideal because mixlib-config uses 'tomlrb'
                                 # but that library does not support a dumper
-  # Train 3.x introduces changes to train-winrm that we are not ready to consume across
-  # the entire Chef Workstation ecosystem
-  spec.add_dependency "train", "< 3.0" # remote connection management over ssh, winrm
+  spec.add_dependency "train", "~> 3.0" # remote connection management over ssh, winrm
+  spec.add_dependency "train-winrm" # winrm transports were pulled out into this plugin
   spec.add_dependency "pastel" # A color library
   spec.add_dependency "tty-spinner" # Pretty output for status updates in the CLI
   spec.add_dependency "chef", ">= 15.0" # Needed to load cookbooks