diff --git a/src/execution_context.rs b/src/execution_context.rs
index 661e8bc8..757418c4 100644
--- a/src/execution_context.rs
+++ b/src/execution_context.rs
@@ -1,16 +1,17 @@
 #![allow(dead_code)]
 use crate::executor::RunType;
 use crate::git::Git;
+use crate::sudo::Sudo;
 use crate::utils::require_option;
 use crate::{config::Config, executor::Executor};
 use color_eyre::eyre::Result;
 use directories::BaseDirs;
-use std::path::{Path, PathBuf};
+use std::path::Path;
 use std::sync::Mutex;
 
 pub struct ExecutionContext<'a> {
     run_type: RunType,
-    sudo: &'a Option<PathBuf>,
+    sudo: Option<Sudo>,
     git: &'a Git,
     config: &'a Config,
     base_dirs: &'a BaseDirs,
@@ -23,7 +24,7 @@ pub struct ExecutionContext<'a> {
 impl<'a> ExecutionContext<'a> {
     pub fn new(
         run_type: RunType,
-        sudo: &'a Option<PathBuf>,
+        sudo: Option<Sudo>,
         git: &'a Git,
         config: &'a Config,
         base_dirs: &'a BaseDirs,
@@ -40,18 +41,7 @@ impl<'a> ExecutionContext<'a> {
 
     pub fn execute_elevated(&self, command: &Path, interactive: bool) -> Result<Executor> {
         let sudo = require_option(self.sudo.clone(), "Sudo is required for this operation".into())?;
-        let mut cmd = self.run_type.execute(&sudo);
-
-        if sudo.ends_with("sudo") {
-            cmd.arg("--preserve-env=DIFFPROG");
-        }
-
-        if interactive {
-            cmd.arg("-i");
-        }
-
-        cmd.arg(command);
-        Ok(cmd)
+        Ok(sudo.execute_elevated(self, command, interactive))
     }
 
     pub fn run_type(&self) -> RunType {
@@ -62,8 +52,8 @@ impl<'a> ExecutionContext<'a> {
         self.git
     }
 
-    pub fn sudo(&self) -> &Option<PathBuf> {
-        self.sudo
+    pub fn sudo(&self) -> &Option<Sudo> {
+        &self.sudo
     }
 
     pub fn config(&self) -> &Config {
diff --git a/src/main.rs b/src/main.rs
index 9789b701..b77a1621 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -83,10 +83,10 @@ fn run() -> Result<()> {
     let git = git::Git::new();
     let mut git_repos = git::Repositories::new(&git);
 
-    let sudo = sudo::path();
+    let sudo = sudo::Sudo::detect();
     let run_type = executor::RunType::new(config.dry_run());
 
-    let ctx = execution_context::ExecutionContext::new(run_type, &sudo, &git, &config, &base_dirs);
+    let ctx = execution_context::ExecutionContext::new(run_type, sudo, &git, &config, &base_dirs);
 
     let mut runner = runner::Runner::new(&ctx);
 
@@ -121,7 +121,9 @@ fn run() -> Result<()> {
     }
 
     if config.pre_sudo() {
-        sudo::elevate(&ctx, sudo.as_ref())?;
+        if let Some(sudo) = ctx.sudo() {
+            sudo.elevate(&ctx)?;
+        }
     }
 
     let powershell = powershell::Powershell::new();
@@ -202,17 +204,17 @@ fn run() -> Result<()> {
 
     #[cfg(target_os = "dragonfly")]
     runner.execute(Step::Pkg, "DragonFly BSD Packages", || {
-        dragonfly::upgrade_packages(sudo.as_ref(), run_type)
+        dragonfly::upgrade_packages(ctx.sudo().as_ref(), run_type)
     })?;
 
     #[cfg(target_os = "freebsd")]
     runner.execute(Step::Pkg, "FreeBSD Packages", || {
-        freebsd::upgrade_packages(&ctx, sudo.as_ref(), run_type)
+        freebsd::upgrade_packages(&ctx, ctx.sudo().as_ref(), run_type)
     })?;
 
     #[cfg(target_os = "openbsd")]
     runner.execute(Step::Pkg, "OpenBSD Packages", || {
-        openbsd::upgrade_packages(sudo.as_ref(), run_type)
+        openbsd::upgrade_packages(ctx.sudo().as_ref(), run_type)
     })?;
 
     #[cfg(target_os = "android")]
@@ -383,7 +385,7 @@ fn run() -> Result<()> {
         runner.execute(Step::DebGet, "deb-get", || linux::run_deb_get(&ctx))?;
         runner.execute(Step::Toolbx, "toolbx", || toolbx::run_toolbx(&ctx))?;
         runner.execute(Step::Flatpak, "Flatpak", || linux::flatpak_update(&ctx))?;
-        runner.execute(Step::Snap, "snap", || linux::run_snap(sudo.as_ref(), run_type))?;
+        runner.execute(Step::Snap, "snap", || linux::run_snap(ctx.sudo().as_ref(), run_type))?;
         runner.execute(Step::Pacstall, "pacstall", || linux::run_pacstall(&ctx))?;
         runner.execute(Step::Pacdef, "pacdef", || linux::run_pacdef(&ctx))?;
         runner.execute(Step::Protonup, "protonup", || linux::run_protonup_update(&ctx))?;
@@ -403,11 +405,11 @@ fn run() -> Result<()> {
     #[cfg(target_os = "linux")]
     {
         runner.execute(Step::System, "pihole", || {
-            linux::run_pihole_update(sudo.as_ref(), run_type)
+            linux::run_pihole_update(ctx.sudo().as_ref(), run_type)
         })?;
         runner.execute(Step::Firmware, "Firmware upgrades", || linux::run_fwupdmgr(&ctx))?;
         runner.execute(Step::Restarts, "Restarts", || {
-            linux::run_needrestart(sudo.as_ref(), run_type)
+            linux::run_needrestart(ctx.sudo().as_ref(), run_type)
         })?;
     }
 
@@ -420,12 +422,12 @@ fn run() -> Result<()> {
 
     #[cfg(target_os = "freebsd")]
     runner.execute(Step::System, "FreeBSD Upgrade", || {
-        freebsd::upgrade_freebsd(sudo.as_ref(), run_type)
+        freebsd::upgrade_freebsd(ctx.sudo().as_ref(), run_type)
     })?;
 
     #[cfg(target_os = "openbsd")]
     runner.execute(Step::System, "OpenBSD Upgrade", || {
-        openbsd::upgrade_openbsd(sudo.as_ref(), run_type)
+        openbsd::upgrade_openbsd(ctx.sudo().as_ref(), run_type)
     })?;
 
     #[cfg(windows)]
@@ -457,10 +459,10 @@ fn run() -> Result<()> {
         }
 
         #[cfg(target_os = "freebsd")]
-        freebsd::audit_packages(&sudo).ok();
+        freebsd::audit_packages(ctx.sudo().as_ref()).ok();
 
         #[cfg(target_os = "dragonfly")]
-        dragonfly::audit_packages(&sudo).ok();
+        dragonfly::audit_packages(ctx.sudo().as_ref()).ok();
     }
 
     let mut post_command_failed = false;
diff --git a/src/steps/generic.rs b/src/steps/generic.rs
index b6da5937..952fb8a2 100644
--- a/src/steps/generic.rs
+++ b/src/steps/generic.rs
@@ -202,7 +202,6 @@ pub fn run_juliaup(base_dirs: &BaseDirs, run_type: RunType) -> Result<()> {
     }
 
     run_type.execute(&juliaup).arg("update").status_checked()
-
 }
 
 pub fn run_choosenim(ctx: &ExecutionContext) -> Result<()> {
diff --git a/src/steps/node.rs b/src/steps/node.rs
index 5455b4c7..f1e2e89d 100644
--- a/src/steps/node.rs
+++ b/src/steps/node.rs
@@ -4,7 +4,6 @@ use std::os::unix::fs::MetadataExt;
 use std::path::PathBuf;
 use std::process::Command;
 
-use crate::sudo;
 use crate::utils::require_option;
 use color_eyre::eyre::Result;
 #[cfg(target_os = "linux")]
@@ -13,9 +12,7 @@ use semver::Version;
 use tracing::debug;
 
 use crate::command::CommandExt;
-use crate::executor::RunType;
 use crate::terminal::print_separator;
-use crate::utils::sudo;
 use crate::utils::{require, PathExt};
 use crate::{error::SkipStep, execution_context::ExecutionContext};
 
@@ -91,14 +88,17 @@ impl NPM {
         Version::parse(&version_str?).map_err(|err| err.into())
     }
 
-    fn upgrade(&self, run_type: RunType, use_sudo: bool) -> Result<()> {
+    fn upgrade(&self, ctx: &ExecutionContext, use_sudo: bool) -> Result<()> {
         let args = ["update", self.global_location_arg()];
         if use_sudo {
-            let sudo_option = sudo::path();
-            let sudo = require_option(sudo_option, String::from("sudo is not installed"))?;
-            run_type.execute(sudo).arg(&self.command).args(args).status_checked()?;
+            let sudo = require_option(ctx.sudo().clone(), String::from("sudo is not installed"))?;
+            ctx.run_type()
+                .execute(sudo)
+                .arg(&self.command)
+                .args(args)
+                .status_checked()?;
         } else {
-            run_type.execute(&self.command).args(args).status_checked()?;
+            ctx.run_type().execute(&self.command).args(args).status_checked()?;
         }
 
         Ok(())
@@ -151,17 +151,18 @@ impl Yarn {
             .map(|s| PathBuf::from(s.stdout.trim()))
     }
 
-    fn upgrade(&self, run_type: RunType, use_sudo: bool) -> Result<()> {
+    fn upgrade(&self, ctx: &ExecutionContext, use_sudo: bool) -> Result<()> {
         let args = ["global", "upgrade"];
 
         if use_sudo {
-            run_type
-                .execute("sudo")
+            let sudo = require_option(ctx.sudo().clone(), String::from("sudo is not installed"))?;
+            ctx.run_type()
+                .execute(sudo)
                 .arg(self.yarn.as_ref().unwrap_or(&self.command))
                 .args(args)
                 .status_checked()?;
         } else {
-            run_type.execute(&self.command).args(args).status_checked()?;
+            ctx.run_type().execute(&self.command).args(args).status_checked()?;
         }
 
         Ok(())
@@ -216,12 +217,12 @@ pub fn run_npm_upgrade(ctx: &ExecutionContext) -> Result<()> {
 
     #[cfg(target_os = "linux")]
     {
-        npm.upgrade(ctx.run_type(), should_use_sudo(&npm, ctx)?)
+        npm.upgrade(ctx, should_use_sudo(&npm, ctx)?)
     }
 
     #[cfg(not(target_os = "linux"))]
     {
-        npm.upgrade(ctx.run_type(), false)
+        npm.upgrade(ctx, false)
     }
 }
 
@@ -232,12 +233,12 @@ pub fn run_pnpm_upgrade(ctx: &ExecutionContext) -> Result<()> {
 
     #[cfg(target_os = "linux")]
     {
-        pnpm.upgrade(ctx.run_type(), should_use_sudo(&pnpm, ctx)?)
+        pnpm.upgrade(ctx, should_use_sudo(&pnpm, ctx)?)
     }
 
     #[cfg(not(target_os = "linux"))]
     {
-        pnpm.upgrade(ctx.run_type(), false)
+        pnpm.upgrade(ctx, false)
     }
 }
 
@@ -253,12 +254,12 @@ pub fn run_yarn_upgrade(ctx: &ExecutionContext) -> Result<()> {
 
     #[cfg(target_os = "linux")]
     {
-        yarn.upgrade(ctx.run_type(), should_use_sudo_yarn(&yarn, ctx)?)
+        yarn.upgrade(ctx, should_use_sudo_yarn(&yarn, ctx)?)
     }
 
     #[cfg(not(target_os = "linux"))]
     {
-        yarn.upgrade(ctx.run_type(), false)
+        yarn.upgrade(ctx, false)
     }
 }
 
diff --git a/src/steps/os/archlinux.rs b/src/steps/os/archlinux.rs
index 7c4e938c..e75fb855 100644
--- a/src/steps/os/archlinux.rs
+++ b/src/steps/os/archlinux.rs
@@ -10,6 +10,7 @@ use walkdir::WalkDir;
 use crate::command::CommandExt;
 use crate::error::TopgradeError;
 use crate::execution_context::ExecutionContext;
+use crate::sudo::Sudo;
 use crate::utils::which;
 use crate::{config, Step};
 
@@ -110,7 +111,7 @@ impl Trizen {
 }
 
 pub struct Pacman {
-    sudo: PathBuf,
+    sudo: Sudo,
     executable: PathBuf,
 }
 
@@ -229,7 +230,7 @@ impl ArchPackageManager for Pamac {
 
 pub struct Aura {
     executable: PathBuf,
-    sudo: PathBuf,
+    sudo: Sudo,
 }
 
 impl Aura {
diff --git a/src/steps/os/dragonfly.rs b/src/steps/os/dragonfly.rs
index b314a47f..63452a82 100644
--- a/src/steps/os/dragonfly.rs
+++ b/src/steps/os/dragonfly.rs
@@ -1,12 +1,13 @@
 use crate::command::CommandExt;
 use crate::executor::RunType;
+use crate::sudo::Sudo;
 use crate::terminal::print_separator;
 use crate::utils::require_option;
 use color_eyre::eyre::Result;
 use std::path::PathBuf;
 use std::process::Command;
 
-pub fn upgrade_packages(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn upgrade_packages(sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("No sudo detected"))?;
     print_separator("DragonFly BSD Packages");
     run_type
@@ -15,7 +16,7 @@ pub fn upgrade_packages(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()>
         .status_checked()
 }
 
-pub fn audit_packages(sudo: &Option<PathBuf>) -> Result<()> {
+pub fn audit_packages(sudo: Option<&Sudo>) -> Result<()> {
     if let Some(sudo) = sudo {
         println!();
         Command::new(sudo)
diff --git a/src/steps/os/freebsd.rs b/src/steps/os/freebsd.rs
index 8109057a..3cb06848 100644
--- a/src/steps/os/freebsd.rs
+++ b/src/steps/os/freebsd.rs
@@ -1,14 +1,14 @@
 use crate::command::CommandExt;
 use crate::execution_context::ExecutionContext;
 use crate::executor::RunType;
+use crate::sudo::Sudo;
 use crate::terminal::print_separator;
 use crate::utils::require_option;
 use crate::Step;
 use color_eyre::eyre::Result;
-use std::path::PathBuf;
 use std::process::Command;
 
-pub fn upgrade_freebsd(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn upgrade_freebsd(sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("No sudo detected"))?;
     print_separator("FreeBSD Update");
     run_type
@@ -17,7 +17,7 @@ pub fn upgrade_freebsd(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()>
         .status_checked()
 }
 
-pub fn upgrade_packages(ctx: &ExecutionContext, sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn upgrade_packages(ctx: &ExecutionContext, sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("No sudo detected"))?;
     print_separator("FreeBSD Packages");
 
@@ -30,7 +30,7 @@ pub fn upgrade_packages(ctx: &ExecutionContext, sudo: Option<&PathBuf>, run_type
     command.status_checked()
 }
 
-pub fn audit_packages(sudo: &Option<PathBuf>) -> Result<()> {
+pub fn audit_packages(sudo: Option<&Sudo>) -> Result<()> {
     if let Some(sudo) = sudo {
         println!();
         Command::new(sudo)
diff --git a/src/steps/os/linux.rs b/src/steps/os/linux.rs
index 25a40c0a..20d3653f 100644
--- a/src/steps/os/linux.rs
+++ b/src/steps/os/linux.rs
@@ -10,6 +10,7 @@ use crate::error::{SkipStep, TopgradeError};
 use crate::execution_context::ExecutionContext;
 use crate::executor::RunType;
 use crate::steps::os::archlinux;
+use crate::sudo::Sudo;
 use crate::terminal::{print_separator, print_warning};
 use crate::utils::{require, require_option, which, PathExt};
 use crate::Step;
@@ -498,7 +499,7 @@ fn upgrade_neon(ctx: &ExecutionContext) -> Result<()> {
     Ok(())
 }
 
-pub fn run_needrestart(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn run_needrestart(sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("sudo is not installed"))?;
     let needrestart = require("needrestart")?;
     let distribution = Distribution::detect()?;
@@ -603,7 +604,7 @@ pub fn flatpak_update(ctx: &ExecutionContext) -> Result<()> {
     Ok(())
 }
 
-pub fn run_snap(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn run_snap(sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("sudo is not installed"))?;
     let snap = require("snap")?;
 
@@ -615,7 +616,7 @@ pub fn run_snap(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
     run_type.execute(sudo).arg(snap).arg("refresh").status_checked()
 }
 
-pub fn run_pihole_update(sudo: Option<&PathBuf>, run_type: RunType) -> Result<()> {
+pub fn run_pihole_update(sudo: Option<&Sudo>, run_type: RunType) -> Result<()> {
     let sudo = require_option(sudo, String::from("sudo is not installed"))?;
     let pihole = require("pihole")?;
     Path::new("/opt/pihole/update.sh").require()?;
diff --git a/src/steps/os/windows.rs b/src/steps/os/windows.rs
index 909847c9..987704aa 100644
--- a/src/steps/os/windows.rs
+++ b/src/steps/os/windows.rs
@@ -19,17 +19,16 @@ pub fn run_chocolatey(ctx: &ExecutionContext) -> Result<()> {
 
     print_separator("Chocolatey");
 
-    let mut cmd = &choco;
-    let mut args = vec!["upgrade", "all"];
+    let mut command = match ctx.sudo() {
+        Some(sudo) => {
+            let mut command = ctx.run_type().execute(sudo);
+            command.arg(choco);
+            command
+        }
+        None => ctx.run_type().execute(choco),
+    };
 
-    if let Some(sudo) = ctx.sudo() {
-        cmd = sudo;
-        args.insert(0, "choco");
-    }
-
-    let mut command = ctx.run_type().execute(cmd);
-
-    command.args(&args);
+    command.args(["upgrade", "all"]);
 
     if yes {
         command.arg("--yes");
diff --git a/src/sudo.rs b/src/sudo.rs
index 0a66cf37..28c6fee9 100644
--- a/src/sudo.rs
+++ b/src/sudo.rs
@@ -1,3 +1,5 @@
+use std::ffi::OsStr;
+use std::path::Path;
 use std::path::PathBuf;
 
 use color_eyre::eyre::Context;
@@ -5,30 +7,102 @@ use color_eyre::eyre::Result;
 
 use crate::command::CommandExt;
 use crate::execution_context::ExecutionContext;
+use crate::executor::Executor;
 use crate::terminal::print_separator;
 use crate::utils::which;
 
-/// Get the path of the `sudo` utility.
-///
-/// Detects `doas`, `sudo`, `gsudo`, or `pkexec`.
-pub fn path() -> Option<PathBuf> {
-    which("doas")
-        .or_else(|| which("sudo"))
-        .or_else(|| which("gsudo"))
-        .or_else(|| which("pkexec"))
+#[derive(Clone, Debug)]
+pub struct Sudo {
+    /// The path to the `sudo` binary.
+    path: PathBuf,
+    /// The type of program being used as `sudo`.
+    kind: SudoKind,
 }
 
-/// Elevate permissions with `sudo`.
-pub fn elevate(ctx: &ExecutionContext, sudo: Option<&PathBuf>) -> Result<()> {
-    if let Some(sudo) = sudo {
-        print_separator("Sudo");
-        ctx.run_type()
-            .execute(sudo)
-            // TODO: Does this work with `doas`, `pkexec`, `gsudo`, GNU `sudo`...?
-            .arg("-v")
-            .status_checked()
-            .wrap_err("Failed to elevate permissions")?;
+impl Sudo {
+    /// Get the `sudo` binary for this platform.
+    pub fn detect() -> Option<Self> {
+        which("doas")
+            .map(|p| (p, SudoKind::Doas))
+            .or_else(|| which("sudo").map(|p| (p, SudoKind::Sudo)))
+            .or_else(|| which("gsudo").map(|p| (p, SudoKind::Gsudo)))
+            .or_else(|| which("pkexec").map(|p| (p, SudoKind::Pkexec)))
+            .map(|(path, kind)| Self { path, kind })
     }
 
-    Ok(())
+    /// Elevate permissions with `sudo`.
+    ///
+    /// This helps prevent blocking `sudo` prompts from stopping the run in the middle of a
+    /// step.
+    ///
+    /// See: https://github.com/topgrade-rs/topgrade/issues/205
+    pub fn elevate(&self, ctx: &ExecutionContext) -> Result<()> {
+        print_separator("Sudo");
+        let mut cmd = ctx.run_type().execute(self);
+        match self.kind {
+            SudoKind::Doas => {
+                // `doas` doesn't have anything like `sudo -v` to cache credentials,
+                // so we just execute a dummy `echo` command so we have something
+                // unobtrusive to run.
+                // See: https://man.openbsd.org/doas
+                cmd.arg("echo");
+            }
+            SudoKind::Sudo => {
+                // From `man sudo` on macOS:
+                //   -v, --validate
+                //   Update the user's cached credentials, authenticating the user
+                //   if necessary.  For the sudoers plugin, this extends the sudo
+                //   timeout for another 5 minutes by default, but does not run a
+                //   command.  Not all security policies support cached credentials.
+                cmd.arg("-v");
+            }
+            SudoKind::Gsudo => {
+                // Shows current user, cache and console status.
+                // See: https://gerardog.github.io/gsudo/docs/usage
+                cmd.arg("status");
+            }
+            SudoKind::Pkexec => {
+                // I don't think this does anything; `pkexec` usually asks for
+                // authentication every time, although it can be configured
+                // differently.
+                //
+                // See the note for `doas` above.
+                //
+                // See: https://linux.die.net/man/1/pkexec
+                cmd.arg("echo");
+            }
+        }
+        cmd.status_checked().wrap_err("Failed to elevate permissions")
+    }
+
+    /// Execute a command with `sudo`.
+    pub fn execute_elevated(&self, ctx: &ExecutionContext, command: &Path, interactive: bool) -> Executor {
+        let mut cmd = ctx.run_type().execute(self);
+
+        if let SudoKind::Sudo = self.kind {
+            cmd.arg("--preserve-env=DIFFPROG");
+        }
+
+        if interactive {
+            cmd.arg("-i");
+        }
+
+        cmd.arg(command);
+
+        cmd
+    }
+}
+
+#[derive(Clone, Copy, Debug)]
+enum SudoKind {
+    Doas,
+    Sudo,
+    Gsudo,
+    Pkexec,
+}
+
+impl AsRef<OsStr> for Sudo {
+    fn as_ref(&self) -> &OsStr {
+        self.path.as_ref()
+    }
 }