diff --git a/src/config.rs b/src/config.rs
index 599783fe..282662ea 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -129,6 +129,7 @@ pub struct Vagrant {
 pub struct Windows {
     accept_all_updates: Option<bool>,
     self_rename: Option<bool>,
+    use_gsudo_with_choco: Option<bool>,
 }
 
 #[derive(Deserialize, Default, Debug)]
@@ -519,6 +520,16 @@ impl Config {
             .unwrap_or(false)
     }
 
+    /// Whether to use gsudo command with choco if available
+    #[allow(dead_code)]
+    pub fn use_gsudo_with_choco(&self) -> bool {
+        self.config_file
+            .windows
+            .as_ref()
+            .and_then(|w| w.use_gsudo_with_choco)
+            .unwrap_or(false)
+    }
+
     /// Whether Brew cask should be greedy
     #[allow(dead_code)]
     pub fn brew_cask_greedy(&self) -> bool {
diff --git a/src/steps/os/windows.rs b/src/steps/os/windows.rs
index 68370489..04315010 100644
--- a/src/steps/os/windows.rs
+++ b/src/steps/os/windows.rs
@@ -3,19 +3,31 @@ use crate::execution_context::ExecutionContext;
 use crate::executor::{CommandExt, RunType};
 use crate::powershell;
 use crate::terminal::print_separator;
-use crate::utils::require;
+use crate::utils::{require, which};
 use anyhow::Result;
 use std::process::Command;
 
 pub fn run_chocolatey(ctx: &ExecutionContext) -> Result<()> {
     let choco = require("choco")?;
     let yes = ctx.config().yes();
+    let use_gsudo = ctx.config().use_gsudo_with_choco();
 
     print_separator("Chocolatey");
 
-    let mut command = ctx.run_type().execute(&choco);
+    let mut cmd = choco;
+    let mut args = vec!["upgrade", "all"];
 
-    command.args(&["upgrade", "all"]);
+    if use_gsudo {
+        let gsudo = which("gsudo");
+        if let Some(gsudo) = gsudo {
+            cmd = gsudo;
+            args = vec!["choco", "upgrade", "all"];
+        }
+    }
+
+    let mut command = ctx.run_type().execute(&cmd);
+
+    command.args(&args);
 
     if yes {
         command.arg("--yes");