diff --git a/config.example.toml b/config.example.toml
index e171263a..7ee2c947 100644
--- a/config.example.toml
+++ b/config.example.toml
@@ -213,6 +213,10 @@
 # Manually select Windows updates
 # accept_all_updates = false
 
+# Controls whether to automatically reboot the computer when updates are
+# installed that request it. (default: "no", allowed values: "yes", "no", "ask")
+# updates_auto_reboot = "yes"
+
 # open_remotes_in_new_terminal = true
 
 # wsl_update_pre_release = true
diff --git a/src/config.rs b/src/config.rs
index a6174bb2..76d38eec 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -235,10 +235,20 @@ pub struct Vagrant {
     always_suspend: Option<bool>,
 }
 
+#[derive(Deserialize, Default, Debug, Copy, Clone)]
+#[serde(rename_all = "snake_case")]
+pub enum UpdatesAutoReboot {
+    Yes,
+    #[default]
+    No,
+    Ask,
+}
+
 #[derive(Deserialize, Default, Debug, Merge)]
 #[serde(deny_unknown_fields)]
 pub struct Windows {
     accept_all_updates: Option<bool>,
+    updates_auto_reboot: Option<UpdatesAutoReboot>,
     self_rename: Option<bool>,
     open_remotes_in_new_terminal: Option<bool>,
     wsl_update_pre_release: Option<bool>,
@@ -1219,6 +1229,15 @@ impl Config {
             .unwrap_or(true)
     }
 
+    /// Whether to auto reboot for Windows updates that require it
+    pub fn windows_updates_auto_reboot(&self) -> UpdatesAutoReboot {
+        self.config_file
+            .windows
+            .as_ref()
+            .and_then(|windows| windows.updates_auto_reboot)
+            .unwrap_or_default()
+    }
+
     /// Whether to self rename the Topgrade executable during the run
     pub fn self_rename(&self) -> bool {
         self.config_file
diff --git a/src/steps/powershell.rs b/src/steps/powershell.rs
index 75a11708..cf5d930f 100644
--- a/src/steps/powershell.rs
+++ b/src/steps/powershell.rs
@@ -156,6 +156,7 @@ impl Powershell {
 #[cfg(windows)]
 mod windows {
     use super::*;
+    use crate::config::UpdatesAutoReboot;
 
     pub fn supports_windows_update(powershell: &Powershell) -> bool {
         powershell
@@ -174,6 +175,11 @@ mod windows {
         if ctx.config().accept_all_windows_updates() {
             command_str.push_str(" -AcceptAll");
         }
+        match ctx.config().windows_updates_auto_reboot() {
+            UpdatesAutoReboot::Yes => command_str.push_str(" -AutoReboot"),
+            UpdatesAutoReboot::No => command_str.push_str(" -IgnoreReboot"),
+            UpdatesAutoReboot::Ask => (), // Prompting is the default for Install-WindowsUpdate
+        }
 
         // Pass the command string using the -Command flag
         powershell