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diff --git a/knife/spec/unit/ssl_check_spec.rb b/knife/spec/unit/ssl_check_spec.rb
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+++ b/knife/spec/unit/ssl_check_spec.rb
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+#
+# Author:: Daniel DeLeo (<dan@chef.io>)
+# Copyright:: Copyright (c) Chef Software Inc.
+# License:: Apache License, Version 2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+require "spec_helper"
+require "stringio"
+
+describe Chef::Knife::SslCheck do
+
+  let(:name_args) { [] }
+  let(:stdout_io) { StringIO.new }
+  let(:stderr_io) { StringIO.new }
+
+  def stderr
+    stderr_io.string
+  end
+
+  def stdout
+    stdout_io.string
+  end
+
+  subject(:ssl_check) do
+    s = Chef::Knife::SslCheck.new
+    allow(s.ui).to receive(:stdout).and_return(stdout_io)
+    allow(s.ui).to receive(:stderr).and_return(stderr_io)
+    s.name_args = name_args
+    s
+  end
+
+  before do
+    Chef::Config.chef_server_url = "https://example.com:8443/chef-server"
+  end
+
+  context "when no arguments are given" do
+    it "uses the chef_server_url as the host to check" do
+      expect(ssl_check.host).to eq("example.com")
+      expect(ssl_check.port).to eq(8443)
+    end
+  end
+
+  context "when a specific URI is given" do
+    let(:name_args) { %w{https://example.test:10443/foo} }
+
+    it "checks the SSL configuration against the given host" do
+      expect(ssl_check.host).to eq("example.test")
+      expect(ssl_check.port).to eq(10443)
+    end
+  end
+
+  context "when an invalid URI is given" do
+
+    let(:name_args) { %w{foo.test} }
+
+    it "prints an error and exits" do
+      expect { ssl_check.run }.to raise_error(SystemExit)
+      expected_stdout = <<~E
+        USAGE: knife ssl check [URL] (options)
+      E
+      expected_stderr = <<~E
+        ERROR: Given URI: `foo.test' is invalid
+      E
+      expect(stdout_io.string).to eq(expected_stdout)
+      expect(stderr_io.string).to eq(expected_stderr)
+    end
+
+    context "and its malformed enough to make URI.parse barf" do
+
+      let(:name_args) { %w{ftp://lkj\\blah:example.com/blah} }
+
+      it "prints an error and exits" do
+        expect { ssl_check.run }.to raise_error(SystemExit)
+        expected_stdout = <<~E
+          USAGE: knife ssl check [URL] (options)
+        E
+        expected_stderr = <<~E
+          ERROR: Given URI: `#{name_args[0]}' is invalid
+        E
+        expect(stdout_io.string).to eq(expected_stdout)
+        expect(stderr_io.string).to eq(expected_stderr)
+      end
+    end
+  end
+
+  describe "verifying trusted certificate X509 properties" do
+    let(:name_args) { %w{https://foo.example.com:8443} }
+
+    let(:trusted_certs_dir) { File.join(CHEF_SPEC_DATA, "trusted_certs") }
+    let(:trusted_cert_file) { File.join(trusted_certs_dir, "example.crt") }
+
+    let(:store) { OpenSSL::X509::Store.new }
+    let(:certificate) { OpenSSL::X509::Certificate.new(IO.read(trusted_cert_file)) }
+
+    before do
+      Chef::Config[:trusted_certs_dir] = trusted_certs_dir
+      allow(ssl_check).to receive(:trusted_certificates).and_return([trusted_cert_file])
+      allow(store).to receive(:add_cert).with(certificate)
+      allow(OpenSSL::X509::Store).to receive(:new).and_return(store)
+      allow(OpenSSL::X509::Certificate).to receive(:new).with(IO.read(trusted_cert_file)).and_return(certificate)
+      allow(ssl_check).to receive(:verify_cert).and_return(true)
+      allow(ssl_check).to receive(:verify_cert_host).and_return(true)
+    end
+
+    context "when the trusted certificates directory is not glob escaped", :windows_only do
+      let(:trusted_certs_dir) { File.join(CHEF_SPEC_DATA.tr("/", "\\"), "trusted_certs") }
+
+      before do
+        allow(ssl_check).to receive(:trusted_certificates).and_call_original
+        allow(store).to receive(:verify).with(certificate).and_return(true)
+      end
+
+      it "escpaes the trusted certificates directory" do
+        expect(Dir).to receive(:glob)
+          .with("#{ChefConfig::PathHelper.escape_glob_dir(trusted_certs_dir)}/*.{crt,pem}")
+          .and_return([trusted_cert_file])
+        ssl_check.run
+      end
+    end
+
+    context "when the trusted certificates have valid X509 properties" do
+      before do
+        allow(store).to receive(:verify).with(certificate).and_return(true)
+      end
+
+      it "does not generate any X509 warnings" do
+        expect(ssl_check.ui).not_to receive(:warn).with(/There are invalid certificates in your trusted_certs_dir/)
+        ssl_check.run
+      end
+    end
+
+    context "when the trusted certificates have invalid X509 properties" do
+      before do
+        allow(store).to receive(:verify).with(certificate).and_return(false)
+        allow(store).to receive(:error_string).and_return("unable to get local issuer certificate")
+      end
+
+      it "generates a warning message with invalid certificate file names" do
+        expect(ssl_check.ui).to receive(:warn).with(/#{trusted_cert_file}: unable to get local issuer certificate/)
+        ssl_check.run
+      end
+    end
+  end
+
+  describe "verifying the remote certificate" do
+    let(:name_args) { %w{https://foo.example.com:8443} }
+
+    let(:tcp_socket) { double(TCPSocket) }
+    let(:ssl_socket) { double(OpenSSL::SSL::SSLSocket) }
+
+    before do
+      expect(ssl_check).to receive(:proxified_socket).with("foo.example.com", 8443).and_return(tcp_socket)
+      expect(OpenSSL::SSL::SSLSocket).to receive(:new).with(tcp_socket, ssl_check.verify_peer_ssl_context).and_return(ssl_socket)
+    end
+
+    def run
+      ssl_check.run
+    rescue Exception
+      # puts "OUT: #{stdout_io.string}"
+      # puts "ERR: #{stderr_io.string}"
+      raise
+    end
+
+    context "when the remote host's certificate is valid" do
+
+      before do
+        expect(ssl_check).to receive(:verify_X509).and_return(true) # X509 valid certs (no warn)
+        expect(ssl_socket).to receive(:connect) # no error
+        expect(ssl_socket).to receive(:post_connection_check).with("foo.example.com") # no error
+        expect(ssl_socket).to receive(:hostname=).with("foo.example.com") # no error
+      end
+
+      it "prints a success message" do
+        ssl_check.run
+        expect(stdout_io.string).to include("Successfully verified certificates from `foo.example.com'")
+      end
+    end
+
+    describe "and the certificate is not valid" do
+
+      let(:tcp_socket_for_debug) { double(TCPSocket) }
+      let(:ssl_socket_for_debug) { double(OpenSSL::SSL::SSLSocket) }
+
+      let(:self_signed_crt_path) { File.join(CHEF_SPEC_DATA, "trusted_certs", "example.crt") }
+      let(:self_signed_crt) { OpenSSL::X509::Certificate.new(File.read(self_signed_crt_path)) }
+
+      before do
+        @old_signal = trap(:INT, "DEFAULT")
+
+        expect(ssl_check).to receive(:proxified_socket)
+          .with("foo.example.com", 8443)
+          .and_return(tcp_socket_for_debug)
+        expect(OpenSSL::SSL::SSLSocket).to receive(:new)
+          .with(tcp_socket_for_debug, ssl_check.noverify_peer_ssl_context)
+          .and_return(ssl_socket_for_debug)
+      end
+
+      after do
+        trap(:INT, @old_signal)
+      end
+
+      context "when the certificate's CN does not match the hostname" do
+        before do
+          expect(ssl_check).to receive(:verify_X509).and_return(true) # X509 valid certs
+          expect(ssl_socket).to receive(:connect) # no error
+          expect(ssl_socket).to receive(:post_connection_check)
+            .with("foo.example.com")
+            .and_raise(OpenSSL::SSL::SSLError)
+          expect(ssl_socket).to receive(:hostname=).with("foo.example.com") # no error
+          expect(ssl_socket_for_debug).to receive(:connect)
+          expect(ssl_socket_for_debug).to receive(:peer_cert).and_return(self_signed_crt)
+        end
+
+        it "shows the CN used by the certificate and prints an error" do
+          expect { run }.to raise_error(SystemExit)
+          expect(stderr).to include("The SSL cert is signed by a trusted authority but is not valid for the given hostname")
+          expect(stderr).to include("You are attempting to connect to:   'foo.example.com'")
+          expect(stderr).to include("The server's certificate belongs to 'example.local'")
+        end
+
+      end
+
+      context "when the cert is not signed by any trusted authority" do
+        before do
+          expect(ssl_check).to receive(:verify_X509).and_return(true) # X509 valid certs
+          expect(ssl_socket).to receive(:connect)
+            .and_raise(OpenSSL::SSL::SSLError)
+          expect(ssl_socket).to receive(:hostname=)
+            .with("foo.example.com") # no error
+          expect(ssl_socket_for_debug).to receive(:connect)
+          expect(ssl_socket_for_debug).to receive(:peer_cert).and_return(self_signed_crt)
+        end
+
+        it "shows the CN used by the certificate and prints an error" do
+          expect { run }.to raise_error(SystemExit)
+          expect(stderr).to include("The SSL certificate of foo.example.com could not be verified")
+        end
+
+      end
+    end
+
+  end
+
+end