diff --git a/src/config.rs b/src/config.rs
index 49cf250b..19bd36d1 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -76,6 +76,7 @@ pub enum Step {
     Tldr,
     Wsl,
     Tmux,
+    Vagrant,
 }
 
 #[derive(Deserialize, Default, Debug)]
@@ -86,6 +87,12 @@ pub struct Git {
     pull_predefined: Option<bool>,
 }
 
+#[derive(Deserialize, Default, Debug)]
+pub struct Vagrant {
+    directories: Option<Vec<String>>,
+    power_on: Option<bool>,
+}
+
 #[derive(Deserialize, Default, Debug)]
 pub struct Windows {
     accept_all_updates: Option<bool>,
@@ -136,6 +143,7 @@ pub struct ConfigFile {
     linux: Option<Linux>,
     git: Option<Git>,
     windows: Option<Windows>,
+    vagrant: Option<Vagrant>,
 }
 
 impl ConfigFile {
@@ -487,6 +495,19 @@ impl Config {
         self.config_file.git.as_ref().and_then(|git| git.max_concurrency)
     }
 
+    /// Should we power on vagrant boxes if needed
+    pub fn vagrant_power_on(&self) -> Option<bool> {
+        self.config_file.vagrant.as_ref().and_then(|vagrant| vagrant.power_on)
+    }
+
+    /// Vagrant directories
+    pub fn vagrant_directories(&self) -> Option<&Vec<String>> {
+        self.config_file
+            .vagrant
+            .as_ref()
+            .and_then(|vagrant| vagrant.directories.as_ref())
+    }
+
     /// Extra yay arguments
     #[allow(dead_code)]
     pub fn enable_tlmgr_linux(&self) -> bool {
diff --git a/src/main.rs b/src/main.rs
index dff68d91..31810136 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -388,6 +388,10 @@ fn run() -> Result<()> {
         }
     }
 
+    if config.should_run(Step::Vagrant) {
+        runner.execute("Vagrant", || vagrant::topgrade_vagrant_boxes(&ctx))?;
+    }
+
     if !runner.report().data().is_empty() {
         print_separator("Summary");
 
diff --git a/src/steps/mod.rs b/src/steps/mod.rs
index 09410d66..7757c070 100644
--- a/src/steps/mod.rs
+++ b/src/steps/mod.rs
@@ -6,6 +6,7 @@ pub mod os;
 pub mod powershell;
 #[cfg(unix)]
 pub mod tmux;
+pub mod vagrant;
 pub mod vim;
 #[cfg(unix)]
 pub mod zsh;
diff --git a/src/steps/vagrant.rs b/src/steps/vagrant.rs
new file mode 100644
index 00000000..dcd2e534
--- /dev/null
+++ b/src/steps/vagrant.rs
@@ -0,0 +1,151 @@
+use crate::execution_context::ExecutionContext;
+use crate::executor::CommandExt;
+use crate::terminal::print_separator;
+use crate::utils;
+use anyhow::Result;
+use log::debug;
+use std::path::{Path, PathBuf};
+use std::process::Command;
+use std::{fmt::Display, str::FromStr};
+use strum::EnumString;
+
+#[derive(Debug, Copy, Clone, EnumString)]
+#[strum(serialize_all = "lowercase")]
+enum BoxStatus {
+    PowerOff,
+    Running,
+}
+
+impl BoxStatus {
+    fn powered_on(self) -> bool {
+        match self {
+            BoxStatus::PowerOff => false,
+            BoxStatus::Running => true,
+        }
+    }
+}
+
+#[derive(Debug)]
+struct VagrantBox<'a> {
+    path: &'a str,
+    name: String,
+}
+
+impl<'a> Display for VagrantBox<'a> {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        write!(f, "{} @ {}", self.name, self.path)
+    }
+}
+
+struct Vagrant {
+    path: PathBuf,
+}
+
+impl Vagrant {
+    fn get_boxes<'a>(&self, directory: &'a str) -> Result<Vec<(VagrantBox<'a>, BoxStatus)>> {
+        let output = Command::new(&self.path)
+            .arg("status")
+            .current_dir(directory)
+            .check_output()?;
+        debug!("Vagrant output in {}: {}", directory, output);
+
+        let boxes = output
+            .split('\n')
+            .skip(2)
+            .take_while(|line| !(line.is_empty() || line.starts_with('\r')))
+            .map(|line| {
+                debug!("Vagrant line: {:?}", line);
+                let mut elements = line.split_whitespace();
+                let vagrant_box = VagrantBox {
+                    name: elements.next().unwrap().to_string(),
+                    path: directory,
+                };
+                let box_status = BoxStatus::from_str(elements.next().unwrap()).unwrap();
+                debug!("{:?}: {:?}", vagrant_box, box_status);
+                (vagrant_box, box_status)
+            })
+            .collect();
+
+        Ok(boxes)
+    }
+
+    fn temporary_power_on<'a>(
+        &'a self,
+        vagrant_box: &'a VagrantBox,
+        ctx: &'a ExecutionContext,
+    ) -> Result<TemporaryPowerOn<'a>> {
+        TemporaryPowerOn::create(&self.path, vagrant_box, ctx)
+    }
+}
+
+struct TemporaryPowerOn<'a> {
+    vagrant: &'a Path,
+    vagrant_box: &'a VagrantBox<'a>,
+    ctx: &'a ExecutionContext<'a>,
+}
+
+impl<'a> TemporaryPowerOn<'a> {
+    fn create(vagrant: &'a Path, vagrant_box: &'a VagrantBox<'a>, ctx: &'a ExecutionContext<'a>) -> Result<Self> {
+        println!("Powering on {}", vagrant_box);
+        ctx.run_type()
+            .execute(vagrant)
+            .args(&["up", &vagrant_box.name])
+            .current_dir(vagrant_box.path)
+            .check_run()?;
+        Ok(TemporaryPowerOn {
+            vagrant,
+            vagrant_box,
+            ctx,
+        })
+    }
+}
+
+impl<'a> Drop for TemporaryPowerOn<'a> {
+    fn drop(&mut self) {
+        println!("Powering off {}", self.vagrant_box);
+        self.ctx
+            .run_type()
+            .execute(self.vagrant)
+            .args(&["halt", &self.vagrant_box.name])
+            .current_dir(self.vagrant_box.path)
+            .check_run()
+            .ok();
+    }
+}
+
+pub fn topgrade_vagrant_boxes(ctx: &ExecutionContext) -> Result<()> {
+    let directories = utils::require_option(ctx.config().vagrant_directories())?;
+    let vagrant = Vagrant {
+        path: utils::require("vagrant")?,
+    };
+
+    print_separator("Vagrant");
+
+    for directory in directories {
+        let boxes = vagrant.get_boxes(directory)?;
+        debug!("{:?}", boxes);
+        for (vagrant_box, status) in boxes {
+            let mut _poweron = None;
+            if !status.powered_on() {
+                if !(ctx.config().vagrant_power_on().unwrap_or(true)) {
+                    debug!("Skipping powered off box {}", vagrant_box);
+                    continue;
+                } else {
+                    _poweron = Some(vagrant.temporary_power_on(&vagrant_box, ctx)?);
+                }
+            }
+
+            println!("Running Topgrade in {} @ {}", vagrant_box, directory);
+            let mut command = format!("env TOPGRADE_PREFIX={} topgrade", vagrant_box.name);
+            if ctx.config().yes() {
+                command.push_str(" -y");
+            }
+
+            ctx.run_type()
+                .execute(&vagrant.path)
+                .args(&["ssh", "-c", &command])
+                .check_run()?;
+        }
+    }
+    Ok(())
+}