diff --git a/plugins/kernel_v2/config/ssh_connect.rb b/plugins/kernel_v2/config/ssh_connect.rb
index 616226154..c4c6fec0e 100644
--- a/plugins/kernel_v2/config/ssh_connect.rb
+++ b/plugins/kernel_v2/config/ssh_connect.rb
@@ -38,7 +38,7 @@ module VagrantPlugins
         @insert_key       = true if @insert_key == UNSET_VALUE
         @keys_only        = true if @keys_only == UNSET_VALUE
         @paranoid         = false if @paranoid == UNSET_VALUE
-        @verify_host_key  = false if @verify_host_key == UNSET_VALUE
+        @verify_host_key  = :never if @verify_host_key == UNSET_VALUE
         @compression      = true if @compression == UNSET_VALUE
         @dsa_authentication = true if @dsa_authentication == UNSET_VALUE
         @extra_args       = nil if @extra_args == UNSET_VALUE
@@ -51,6 +51,18 @@ module VagrantPlugins
           @verify_host_key = @paranoid
         end
 
+        # Values for verify_host_key changed in 5.0.0 of net-ssh. If old value
+        # detected, update with new value
+        case @verify_host_key
+        when true
+          @verify_host_key = :accepts_new_or_local_tunnel
+        when false
+          @verify_host_key = :never
+        when :very
+          @verify_host_key = :accept_new
+        when :secure
+          @verify_host_key = :always
+        end
       end
 
       # NOTE: This is _not_ a valid config validation method, since it
diff --git a/test/unit/plugins/kernel_v2/config/ssh_connect_test.rb b/test/unit/plugins/kernel_v2/config/ssh_connect_test.rb
new file mode 100644
index 000000000..0c2772b66
--- /dev/null
+++ b/test/unit/plugins/kernel_v2/config/ssh_connect_test.rb
@@ -0,0 +1,32 @@
+require File.expand_path("../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/kernel_v2/config/ssh_connect")
+
+describe VagrantPlugins::Kernel_V2::SSHConnectConfig do
+  subject { described_class.new }
+
+  describe "#verify_host_key" do
+    it "defaults to :never" do
+      subject.finalize!
+      expect(subject.verify_host_key).to eq(:never)
+    end
+
+    it "should modify true value to :accepts_new_or_local_tunnel" do
+      subject.verify_host_key = true
+      subject.finalize!
+      expect(subject.verify_host_key).to eq(:accepts_new_or_local_tunnel)
+    end
+
+    it "should modify :very value to :accept_new" do
+      subject.verify_host_key = :very
+      subject.finalize!
+      expect(subject.verify_host_key).to eq(:accept_new)
+    end
+
+    it "should modify :secure to :always" do
+      subject.verify_host_key = :secure
+      subject.finalize!
+      expect(subject.verify_host_key).to eq(:always)
+    end
+  end
+end
diff --git a/vagrant.gemspec b/vagrant.gemspec
index edc12f032..d67d1e83c 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -22,7 +22,7 @@ Gem::Specification.new do |s|
   s.add_dependency "listen", "~> 3.1.5"
   s.add_dependency "hashicorp-checkpoint", "~> 0.1.5"
   s.add_dependency "log4r", "~> 1.1.9", "< 1.1.11"
-  s.add_dependency "net-ssh", "~> 4.2.0"
+  s.add_dependency "net-ssh", "~> 5.0.0"
   s.add_dependency "net-sftp", "~> 2.1"
   s.add_dependency "net-scp", "~> 1.2.0"
   s.add_dependency "rb-kqueue", "~> 0.2.0"
diff --git a/website/source/docs/vagrantfile/ssh_settings.html.md b/website/source/docs/vagrantfile/ssh_settings.html.md
index 1529cebb5..810ed1b7d 100644
--- a/website/source/docs/vagrantfile/ssh_settings.html.md
+++ b/website/source/docs/vagrantfile/ssh_settings.html.md
@@ -68,7 +68,7 @@ any keys stored in ssh-agent). The default value is `true`.
 <hr>
 
 `config.ssh.verify_host_key` - Perform strict host-key verification. The default
-value is `false`.
+value is `:never`.
 
 <hr>