diff --git a/src/main.rs b/src/main.rs
index 33971643..a6183008 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -134,10 +134,12 @@ fn run() -> Result<(), Error> {
     #[cfg(windows)]
     {
         if powershell.profile().is_some() && config.should_run(Step::Powershell) {
-            report.push_result(execute_legacy(
+            execute(
+                &mut report,
+                "Powershell Modules Update",
                 || powershell.update_modules(run_type),
                 config.no_retry(),
-            )?);
+            )?;
         }
     }
 
@@ -168,10 +170,15 @@ fn run() -> Result<(), Error> {
     }
 
     #[cfg(windows)]
-    report.push_result(execute_legacy(|| windows::run_chocolatey(run_type), config.no_retry())?);
+    execute(
+        &mut report,
+        "Chocolatey",
+        || windows::run_chocolatey(run_type),
+        config.no_retry(),
+    )?;
 
     #[cfg(windows)]
-    report.push_result(execute_legacy(|| windows::run_scoop(run_type), config.no_retry())?);
+    execute(&mut report, "Scoop", || windows::run_scoop(run_type), config.no_retry())?;
 
     #[cfg(unix)]
     report.push_result(execute_legacy(
@@ -383,10 +390,12 @@ fn run() -> Result<(), Error> {
     #[cfg(windows)]
     {
         if config.should_run(Step::System) {
-            report.push_result(execute_legacy(
+            execute(
+                &mut report,
+                "Windows update",
                 || powershell.windows_update(run_type),
                 config.no_retry(),
-            )?);
+            )?;
         }
     }
 
diff --git a/src/steps/os/windows.rs b/src/steps/os/windows.rs
index 5157f1b0..c9115ee3 100644
--- a/src/steps/os/windows.rs
+++ b/src/steps/os/windows.rs
@@ -1,43 +1,24 @@
-use crate::error::Error;
+use crate::error::{Error, ErrorKind};
 use crate::executor::{CommandExt, RunType};
 use crate::terminal::{is_dumb, print_separator};
-use crate::utils::{self, which};
+use crate::utils::{require, require_option, which};
 use std::path::PathBuf;
 use std::process::Command;
 
-#[must_use]
-pub fn run_chocolatey(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(choco) = utils::which("choco") {
-        print_separator("Chocolatey");
+pub fn run_chocolatey(run_type: RunType) -> Result<(), Error> {
+    let choco = require("choco")?;
 
-        let success = || -> Result<(), Error> {
-            run_type.execute(&choco).args(&["upgrade", "all"]).check_run()?;
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("Chocolatey", success));
-    }
-
-    None
+    print_separator("Chocolatey");
+    run_type.execute(&choco).args(&["upgrade", "all"]).check_run()
 }
 
-#[must_use]
-pub fn run_scoop(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(scoop) = utils::which("scoop") {
-        print_separator("Scoop");
+pub fn run_scoop(run_type: RunType) -> Result<(), Error> {
+    let scoop = require("scoop")?;
 
-        let success = || -> Result<(), Error> {
-            run_type.execute(&scoop).args(&["update"]).check_run()?;
-            run_type.execute(&scoop).args(&["update", "*"]).check_run()?;
-            Ok(())
-        }()
-        .is_ok();
+    print_separator("Scoop");
 
-        return Some(("Scoop", success));
-    }
-
-    None
+    run_type.execute(&scoop).args(&["update"]).check_run()?;
+    run_type.execute(&scoop).args(&["update", "*"]).check_run()
 }
 
 pub struct Powershell {
@@ -78,45 +59,24 @@ impl Powershell {
         self.profile.as_ref()
     }
 
-    #[must_use]
-    pub fn update_modules(&self, run_type: RunType) -> Option<(&'static str, bool)> {
-        if let Some(powershell) = &self.path {
-            print_separator("Powershell Modules Update");
+    pub fn update_modules(&self, run_type: RunType) -> Result<(), Error> {
+        let powershell = require_option(self.path.as_ref())?;
 
-            let success = || -> Result<(), Error> {
-                run_type
-                    .execute(&powershell)
-                    .args(&["Update-Module", "-v"])
-                    .check_run()?;
-                Ok(())
-            }()
-            .is_ok();
-
-            return Some(("Powershell Modules Update", success));
-        }
-
-        None
+        print_separator("Powershell Modules Update");
+        run_type.execute(&powershell).args(&["Update-Module", "-v"]).check_run()
     }
 
-    #[must_use]
-    pub fn windows_update(&self, run_type: RunType) -> Option<(&'static str, bool)> {
-        if let Some(powershell) = &self.path {
-            if Self::has_command(&powershell, "Install-WindowsUpdate") {
-                print_separator("Windows Update");
+    pub fn windows_update(&self, run_type: RunType) -> Result<(), Error> {
+        let powershell = require_option(self.path.as_ref())?;
 
-                let success = || -> Result<(), Error> {
-                    run_type
-                        .execute(&powershell)
-                        .args(&["-Command", "Install-WindowsUpdate -MicrosoftUpdate -AcceptAll -Verbose"])
-                        .check_run()?;
-                    Ok(())
-                }()
-                .is_ok();
-
-                return Some(("Windows Update", success));
-            }
+        if !Self::has_command(&powershell, "Install-WindowsUpdate") {
+            Err(ErrorKind::SkipStep)?;
         }
+        print_separator("Windows Update");
 
-        None
+        run_type
+            .execute(&powershell)
+            .args(&["-Command", "Install-WindowsUpdate -MicrosoftUpdate -AcceptAll -Verbose"])
+            .check_run()
     }
 }
diff --git a/src/utils.rs b/src/utils.rs
index e7e88030..ceaf3842 100644
--- a/src/utils.rs
+++ b/src/utils.rs
@@ -181,7 +181,7 @@ pub fn require<T: AsRef<OsStr> + Debug>(binary_name: T) -> Result<PathBuf, Error
     }
 }
 
-#[cfg(target_os = "linux")]
+#[allow(dead_code)]
 pub fn require_option<T>(option: Option<T>) -> Result<T, Error> {
     if let Some(value) = option {
         Ok(value)