diff --git a/CHANGELOG.md b/CHANGELOG.md
index c1a64a2d..36409406 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@ appear at the top.
 
   * Your contribution here!
   * [#468](https://github.com/capistrano/sshkit/pull/468): Make `upload!` take a `:verbosity` option like `exec` does - [@grosser](https://github.com/grosser)
+  * [#469](https://github.com/capistrano/sshkit/pull/469): Fix a regression in 1.19.0 that prevented `$HOME` from being used in Capistrano paths, e.g. `:deploy_to`, etc.  - [@Madogiwa0124](https://github.com/Madogiwa0124)
 
 ## [1.19.1][] (2019-07-02)
 
diff --git a/lib/sshkit/command.rb b/lib/sshkit/command.rb
index 2dac6d1c..444633bc 100644
--- a/lib/sshkit/command.rb
+++ b/lib/sshkit/command.rb
@@ -221,7 +221,7 @@ def to_s
 
     # allow using home directory but escape everything else like spaces etc
     def self.shellescape_except_tilde(file)
-      file.shellescape.gsub("\\~", "~")
+      file.shellescape.gsub("\\~", "~").gsub("\\$HOME", "$HOME")
     end
 
     private
diff --git a/test/unit/backends/test_abstract.rb b/test/unit/backends/test_abstract.rb
index 9d8511f5..473be569 100644
--- a/test/unit/backends/test_abstract.rb
+++ b/test/unit/backends/test_abstract.rb
@@ -111,6 +111,18 @@ def test_within_home
         assert_equal 'cd ~/foo && /usr/bin/env cat file', backend.executed_command.to_command
       end
 
+      def test_within_home_by_env
+        backend = ExampleBackend.new do
+          within '$HOME/foo' do
+            execute :cat, 'file', :strip => false
+          end
+        end
+
+        backend.run
+
+        assert_equal 'cd $HOME/foo && /usr/bin/env cat file', backend.executed_command.to_command
+      end
+
       def test_background_logs_deprecation_warnings
         deprecation_out = ''
         SSHKit.config.deprecation_output = deprecation_out
diff --git a/test/unit/test_command.rb b/test/unit/test_command.rb
index 30964a16..af278686 100644
--- a/test/unit/test_command.rb
+++ b/test/unit/test_command.rb
@@ -89,6 +89,11 @@ def test_working_in_home_directory
       assert_equal "cd ~/sites && /usr/bin/env ls -l", c.to_command
     end
 
+    def test_working_in_home_directory_by_env
+      c = Command.new(:ls, '-l', in: "$HOME/sites")
+      assert_equal "cd $HOME/sites && /usr/bin/env ls -l", c.to_command
+    end
+
     def test_working_in_a_given_weird_directory
       c = Command.new(:ls, '-l', in: "/opt/sites and stuff")
       assert_equal "cd /opt/sites\\ and\\ stuff && /usr/bin/env ls -l", c.to_command