diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9b5b2acc..51728e43 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,9 @@ appear at the top.
     @beatrichartz
   * `SSHKit::Backend::Printer#test` now always returns true
     [PR #312](https://github.com/capistrano/sshkit/pull/312) @mikz
+  * when using `SSHKit::CommandMap#prefix`, resolve the command through `SSHKit::CommandMap#[]`
+    [PR #311]((https://github.com/capistrano/sshkit/pull/311)
+    @mikz
 
 ### New features
 
@@ -32,6 +35,9 @@ appear at the top.
     and have a cleaner internal API. You can still completely disable the pool
     by setting `SSHKit::Backend::Netssh.pool.idle_timeout = 0`.
     @mattbrictson @byroot [PR #328](https://github.com/capistrano/sshkit/pull/328)
+  * Allow command map entries (`SSHKit::CommandMap#[]`) to be Procs
+    [PR #310]((https://github.com/capistrano/sshkit/pull/310)
+    @mikz
 
 ### Bug fixes
 
diff --git a/lib/sshkit/command_map.rb b/lib/sshkit/command_map.rb
index fde164b4..608b1be5 100644
--- a/lib/sshkit/command_map.rb
+++ b/lib/sshkit/command_map.rb
@@ -31,19 +31,17 @@ def [](command)
       end
     end
 
+    TO_VALUE = ->(obj) { obj.respond_to?(:call) ? obj.call : obj }
+
     def initialize(value = nil)
       @map = CommandHash.new(value || defaults)
     end
 
     def [](command)
-      if prefix[command].any?
-        prefixes = prefix[command].map{ |prefix| prefix.respond_to?(:call) ? prefix.call : prefix }
-        prefixes = prefixes.join(" ")
+      prefixes = prefix[command].map(&TO_VALUE)
+      cmd = TO_VALUE.(@map[command])
 
-        "#{prefixes} #{command}"
-      else
-        @map[command]
-      end
+      [*prefixes, cmd].compact.join(' ')
     end
 
     def prefix
diff --git a/test/unit/test_command_map.rb b/test/unit/test_command_map.rb
index 65e85f93..99948ebb 100644
--- a/test/unit/test_command_map.rb
+++ b/test/unit/test_command_map.rb
@@ -16,12 +16,21 @@ def test_setter
       assert_equal map[:rake], "/usr/local/rbenv/shims/rake"
     end
 
+    def test_setter_procs
+      map = CommandMap.new
+      i = 0
+      map[:rake] = -> { i += 1; "/usr/local/rbenv/shims/rake#{i}" }
+
+      assert_equal map[:rake], "/usr/local/rbenv/shims/rake1"
+      assert_equal map[:rake], "/usr/local/rbenv/shims/rake2"
+    end
+
     def test_prefix
       map = CommandMap.new
       map.prefix[:rake].push("/home/vagrant/.rbenv/bin/rbenv exec")
       map.prefix[:rake].push("bundle exec")
 
-      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec rake"
+      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec /usr/bin/env rake"
     end
 
     def test_prefix_procs
@@ -29,7 +38,7 @@ def test_prefix_procs
       map.prefix[:rake].push("/home/vagrant/.rbenv/bin/rbenv exec")
       map.prefix[:rake].push(proc{ "bundle exec" })
 
-      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec rake"
+      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec /usr/bin/env rake"
     end
 
     def test_prefix_unshift
@@ -37,7 +46,7 @@ def test_prefix_unshift
       map.prefix[:rake].push("bundle exec")
       map.prefix[:rake].unshift("/home/vagrant/.rbenv/bin/rbenv exec")
 
-      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec rake"
+      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec /usr/bin/env rake"
     end
 
     def test_indifferent_setter
@@ -53,7 +62,7 @@ def test_indifferent_prefix
       map.prefix[:rake].push("/home/vagrant/.rbenv/bin/rbenv exec")
       map.prefix["rake"].push("bundle exec")
 
-      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec rake"
+      assert_equal map[:rake], "/home/vagrant/.rbenv/bin/rbenv exec bundle exec /usr/bin/env rake"
     end
 
     def test_prefix_initialization_is_thread_safe
@@ -65,5 +74,13 @@ def test_prefix_initialization_is_thread_safe
       end
       threads.each(&:join)
     end
+
+    def test_prefix_setter
+      map = CommandMap.new({})
+      map[:rake] = 'rake2.2'
+      map.prefix[:rake].push('bundle exec')
+
+      assert_equal map[:rake], 'bundle exec rake2.2'
+    end
   end
 end