diff --git a/.vscode/launch.json b/.vscode/launch.json
new file mode 100644
index 00000000..35d619fe
--- /dev/null
+++ b/.vscode/launch.json
@@ -0,0 +1,46 @@
+{
+    // Use IntelliSense to learn about possible attributes.
+    // Hover to view descriptions of existing attributes.
+    // For more information, visit: https://go.microsoft.com/fwlink/?linkid=830387
+    "version": "0.2.0",
+    "configurations": [
+        {
+            "type": "lldb",
+            "request": "launch",
+            "name": "Debug executable 'topgrade'",
+            "console": "integratedTerminal",
+            "cargo": {
+                "args": [
+                    "build",
+                    "--bin=topgrade",
+                    "--package=topgrade"
+                ],
+                "filter": {
+                    "name": "topgrade",
+                    "kind": "bin"
+                }
+            },
+            "args": [],
+            "cwd": "${workspaceFolder}"
+        },
+        {
+            "type": "lldb",
+            "request": "launch",
+            "name": "Debug unit tests in executable 'topgrade'",
+            "cargo": {
+                "args": [
+                    "test",
+                    "--no-run",
+                    "--bin=topgrade",
+                    "--package=topgrade"
+                ],
+                "filter": {
+                    "name": "topgrade",
+                    "kind": "bin"
+                }
+            },
+            "args": [],
+            "cwd": "${workspaceFolder}"
+        }
+    ]
+}
diff --git a/.vscode/topgrade.code-snippets b/.vscode/topgrade.code-snippets
index b0722d18..002d26f2 100644
--- a/.vscode/topgrade.code-snippets
+++ b/.vscode/topgrade.code-snippets
@@ -21,5 +21,15 @@
 		"body": [
 			"return Err(SkipStep(format!(\"$1\").into()));"
 		]
+	},
+	"Step": {
+		"scope": "rust",
+		"prefix": "step",
+		"body": [
+			"pub fn $1(ctx: &ExecutionContext) -> Result<()> {",
+			"    $0",
+			"    Ok(())",
+			"}"
+		]
 	}
-}
\ No newline at end of file
+}
diff --git a/src/main.rs b/src/main.rs
index a61cd2be..24f95d82 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -392,6 +392,7 @@ fn run() -> Result<()> {
             }
         }
     }
+    runner.execute(Step::Vagrant, "Vagrant boxes", || vagrant::upgrade_vagrant_boxes(&ctx))?;
 
     if !runner.report().data().is_empty() {
         print_separator("Summary");
diff --git a/src/steps/remote/vagrant.rs b/src/steps/remote/vagrant.rs
index ed3dfad3..1a248b26 100644
--- a/src/steps/remote/vagrant.rs
+++ b/src/steps/remote/vagrant.rs
@@ -4,6 +4,7 @@ use std::{fmt::Display, rc::Rc, str::FromStr};
 
 use anyhow::Result;
 use log::{debug, error};
+use regex::Regex;
 use strum::EnumString;
 
 use crate::execution_context::ExecutionContext;
@@ -200,3 +201,35 @@ pub fn topgrade_vagrant_box(ctx: &ExecutionContext, vagrant_box: &VagrantBox) ->
         .args(&["ssh", "-c", &command])
         .check_run()
 }
+
+pub fn upgrade_vagrant_boxes(ctx: &ExecutionContext) -> Result<()> {
+    let vagrant = utils::require("vagrant")?;
+    print_separator("Vagrant boxes");
+
+    let outdated = Command::new(&vagrant)
+        .args(&["box", "outdated", "--global"])
+        .check_output()?;
+
+    let re = Regex::new(r"\* '(.*?)' for '(.*?)' is outdated").unwrap();
+
+    let mut found = false;
+    for ele in re.captures_iter(&outdated) {
+        found = true;
+        let _ = ctx
+            .run_type()
+            .execute(&vagrant)
+            .args(&["box", "update", "--box"])
+            .arg(&ele.get(1).unwrap().as_str())
+            .arg("--provider")
+            .arg(ele.get(2).unwrap().as_str())
+            .check_run();
+    }
+
+    if !found {
+        println!("No outdated boxes")
+    } else {
+        ctx.run_type().execute(&vagrant).args(&["box", "prune"]).check_run()?;
+    }
+
+    Ok(())
+}