diff --git a/src/chef-server-ctl/Gemfile.lock b/src/chef-server-ctl/Gemfile.lock
index c1b0ae450e..4a061e6385 100644
--- a/src/chef-server-ctl/Gemfile.lock
+++ b/src/chef-server-ctl/Gemfile.lock
@@ -7,7 +7,7 @@ PATH
       chef_backup
       chef_fixie
       ffi-yajl (>= 1.2.0)
-      highline (~> 1.6, >= 1.6.9)
+      highline (>= 1.6.9, < 3.0)
       knife-ec-backup
       knife-opc
       license-acceptance
@@ -103,9 +103,10 @@ GEM
       rack (~> 2.0, >= 2.0.6)
       uuidtools (~> 2.1)
       webrick
-    chef_backup (0.1.1)
-      highline (~> 1.6, >= 1.6.9)
+    chef_backup (0.2.0)
       mixlib-shellout (>= 2.0, < 4.0)
+      pastel
+      tty-prompt (~> 0.21)
     chef_fixie (1.0.2)
       chef (>= 16)
       ffi-yajl (>= 1.2.0)
@@ -151,7 +152,7 @@ GEM
     gyoku (1.3.1)
       builder (>= 2.1.2)
     hashie (4.1.0)
-    highline (1.7.10)
+    highline (2.0.3)
     http-accept (1.7.0)
     http-cookie (1.0.4)
       domain_name (~> 0.5)
diff --git a/src/chef-server-ctl/chef-server-ctl.gemspec b/src/chef-server-ctl/chef-server-ctl.gemspec
index adf04dfb97..d436b888d7 100644
--- a/src/chef-server-ctl/chef-server-ctl.gemspec
+++ b/src/chef-server-ctl/chef-server-ctl.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |spec|
 
   spec.required_ruby_version = ">= 2.7.0"
 
-  spec.add_runtime_dependency "highline", "~> 1.6", ">= 1.6.9"
+  spec.add_runtime_dependency "highline", ">= 1.6.9", "< 3.0"
 
   spec.add_runtime_dependency "ffi-yajl", ">= 1.2.0"