diff --git a/src/main.rs b/src/main.rs
index d6c36690..826331be 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -137,6 +137,14 @@ fn run() -> Result<(), Error> {
         run_homebrew(&brew).report("Brew", &mut reports);
     }
 
+    #[cfg(windows)]
+    {
+        if let Some(choco) = utils::which("choco") {
+            terminal.print_separator("Chocolatey");
+            run_chocolatey(&choco).report("Chocolatey", &mut reports);
+        }
+    }
+
     git_repos.insert(home_path(".emacs.d"));
 
     #[cfg(unix)]
diff --git a/src/steps.rs b/src/steps.rs
index d638b5a8..9cdd10b1 100644
--- a/src/steps.rs
+++ b/src/steps.rs
@@ -141,6 +141,17 @@ pub fn upgrade_macos() -> Result<(), failure::Error> {
     Ok(())
 }
 
+#[cfg(windows)]
+pub fn run_chocolatey(choco: &PathBuf) -> Result<(), failure::Error> {
+    Command::new(&choco)
+        .args(&["upgrade", "all"])
+        .spawn()?
+        .wait()?
+        .check()?;
+
+    Ok(())
+}
+
 pub fn run_homebrew(homebrew: &PathBuf) -> Result<(), failure::Error> {
     Command::new(&homebrew)
         .arg("update")