diff --git a/CHANGELOG.md b/CHANGELOG.md
index 93e893c..bdf289f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,13 @@
 # Changelog
 
+## 1.5.5
+
+Fix the PATH built by `asdf:map_bins`. SSHKit exports the environment inside
+double quotes (`PATH="..."`), where a shell never expands a tilde, so the
+default `asdf_path` of `~/.asdf` produced two dead entries and left the asdf
+shims unreachable. The PATH now carries `$HOME`; an absolute `asdf_path` is
+still used as is.
+
 ## 1.5.3
 
 Fix ASDF update when git data is not up-to-date.
diff --git a/lib/capistrano/asdf/version.rb b/lib/capistrano/asdf/version.rb
index 3f6b96e..4d71e3d 100644
--- a/lib/capistrano/asdf/version.rb
+++ b/lib/capistrano/asdf/version.rb
@@ -2,6 +2,6 @@
 
 module Capistrano
   module Asdf
-    VERSION = "1.5.4"
+    VERSION = "1.5.5"
   end
 end
diff --git a/lib/capistrano/tasks/asdf.rake b/lib/capistrano/tasks/asdf.rake
index 20355c6..2716ecc 100644
--- a/lib/capistrano/tasks/asdf.rake
+++ b/lib/capistrano/tasks/asdf.rake
@@ -88,7 +88,10 @@ namespace :asdf do
   end
 
   task :map_bins do
-    path = "#{fetch(:asdf_path)}/shims:#{fetch(:asdf_path)}/bin:" + (SSHKit.config.default_env[:path] || "$PATH")
+    # SSHKit exports the environment inside double quotes (PATH="..."), where a
+    # shell leaves a tilde alone, so the PATH has to carry $HOME instead.
+    asdf_home = fetch(:asdf_path).sub(%r{\A~(?=/|\z)}, "$HOME")
+    path = "#{asdf_home}/shims:#{asdf_home}/bin:" + (SSHKit.config.default_env[:path] || "$PATH")
     SSHKit.config.default_env[:path] = path
 
     asdf_prefix = fetch(:asdf_prefix, -> { "#{fetch(:asdf_path)}/bin/asdf exec" })
diff --git a/test/capistrano/test_map_bins.rb b/test/capistrano/test_map_bins.rb
new file mode 100644
index 0000000..3948146
--- /dev/null
+++ b/test/capistrano/test_map_bins.rb
@@ -0,0 +1,67 @@
+# frozen_string_literal: true
+
+require "test_helper"
+
+require "capistrano/all"
+require "sshkit"
+
+# A Capfile mixes the DSL into the top-level object; the rake file under test
+# reaches for `Capistrano::DSL.stages` as it loads, which relies on it.
+include Capistrano::DSL # standard:disable Style/MixinUsage
+
+module Capistrano
+  # `asdf:map_bins` prepends the asdf shims to the PATH that SSHKit exports in
+  # front of every remote command. SSHKit writes that environment inside double
+  # quotes (`PATH="..."`), and a shell does not expand a tilde there, so the
+  # PATH must be built from `$HOME` rather than from `~`.
+  class TestMapBins < Minitest::Test
+    include Capistrano::DSL
+
+    def setup
+      # `capistrano/all` turns Rake's trace on; keep it out of the test output.
+      Rake.application.options.trace = false
+      Rake::Task.clear
+      Capistrano::Configuration.reset!
+      SSHKit.config.default_env = {}
+      # The rake file hooks itself onto this task as it loads.
+      Rake::Task.define_task("deploy:updating")
+      load File.expand_path("../../lib/capistrano/tasks/asdf.rake", __dir__)
+      Rake::Task["load:defaults"].invoke
+      # Keep the task away from its jemalloc branch, which opens an SSH connection.
+      set :asdf_tools, %w[nodejs]
+    end
+
+    def teardown
+      SSHKit.config.default_env = {}
+    end
+
+    def test_the_exported_path_holds_no_tilde
+      Rake::Task["asdf:map_bins"].invoke
+
+      assert_equal "$HOME/.asdf/shims:$HOME/.asdf/bin:$PATH", exported_path
+    end
+
+    def test_it_keeps_a_path_already_set_by_the_application
+      SSHKit.config.default_env = {path: "/opt/custom/bin:$PATH"}
+
+      Rake::Task["asdf:map_bins"].invoke
+
+      assert_equal "$HOME/.asdf/shims:$HOME/.asdf/bin:/opt/custom/bin:$PATH", exported_path
+    end
+
+    def test_an_absolute_asdf_path_is_left_alone
+      set :asdf_path, "/opt/asdf"
+
+      Rake::Task["asdf:map_bins"].invoke
+
+      assert_equal "/opt/asdf/shims:/opt/asdf/bin:$PATH", exported_path
+    end
+
+    # What the shell actually receives, tilde expansion included.
+    def exported_path
+      command = SSHKit::Command.new(:node, "--version").to_command
+
+      command[/PATH="([^"]*)"/, 1]
+    end
+  end
+end