diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 3038d541..9e3161d5 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -7,6 +7,7 @@ jobs:
     strategy:
       matrix:
         platform: [ubuntu-latest, macos-latest, windows-latest]
+      fail-fast: false
     runs-on: ${{ matrix.platform }}
     steps:
       - uses: actions/checkout@v2
diff --git a/src/config.rs b/src/config.rs
index 4acdee4a..ab844926 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -393,9 +393,9 @@ pub struct CommandLineArgs {
     #[structopt(short = "k", long = "keep")]
     keep_at_end: bool,
 
-    /// Say yes to package manager's prompt (experimental)
+    /// Say yes to package manager's prompt
     #[structopt(short = "y", long = "yes")]
-    yes: bool,
+    yes: Option<Vec<Step>>,
 
     /// Don't pull the predefined git repos
     #[structopt(long = "disable-predefined-git-repos")]
@@ -585,8 +585,20 @@ impl Config {
 
     /// Whether to say yes to package managers
     #[allow(dead_code)]
-    pub fn yes(&self) -> bool {
-        self.config_file.assume_yes.unwrap_or(self.opt.yes)
+    pub fn yes(&self, step: Step) -> bool {
+        if let Some(yes) = self.config_file.assume_yes {
+            return yes;
+        }
+
+        if let Some(yes_list) = &self.opt.yes {
+            if yes_list.is_empty() {
+                return true;
+            }
+
+            return yes_list.contains(&step);
+        }
+
+        false
     }
 
     /// Bash-it branch
diff --git a/src/steps/emacs.rs b/src/steps/emacs.rs
index 9d9a6fd6..862ff16d 100644
--- a/src/steps/emacs.rs
+++ b/src/steps/emacs.rs
@@ -1,12 +1,15 @@
-use crate::execution_context::ExecutionContext;
-use crate::terminal::print_separator;
-use crate::utils::{require, require_option, PathExt};
-use anyhow::Result;
-use directories::BaseDirs;
 #[cfg(any(windows, target_os = "macos"))]
 use std::env;
 use std::path::{Path, PathBuf};
 
+use anyhow::Result;
+use directories::BaseDirs;
+
+use crate::execution_context::ExecutionContext;
+use crate::terminal::print_separator;
+use crate::utils::{require, require_option, PathExt};
+use crate::Step;
+
 const EMACS_UPGRADE: &str = include_str!("emacs.el");
 #[cfg(windows)]
 const DOOM_PATH: &str = "bin/doom.cmd";
@@ -66,7 +69,7 @@ impl Emacs {
         let mut command = ctx.run_type().execute(doom);
         command.args(&["-y", "upgrade"]);
 
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::Emacs) {
             command.arg("--force");
         }
 
diff --git a/src/steps/os/archlinux.rs b/src/steps/os/archlinux.rs
index 76eaa9dc..cee133aa 100644
--- a/src/steps/os/archlinux.rs
+++ b/src/steps/os/archlinux.rs
@@ -1,6 +1,6 @@
-use crate::config;
 use crate::execution_context::ExecutionContext;
 use crate::utils::which;
+use crate::{config, Step};
 use anyhow::Result;
 use std::env::var_os;
 use std::ffi::OsString;
@@ -42,7 +42,7 @@ impl ArchPackageManager for YayParu {
             .args(ctx.config().yay_arguments().split_whitespace())
             .env("PATH", get_execution_path());
 
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             command.arg("--noconfirm");
         }
         command.check_run()?;
@@ -50,7 +50,7 @@ impl ArchPackageManager for YayParu {
         if ctx.config().cleanup() {
             let mut command = ctx.run_type().execute(&self.executable);
             command.arg("--pacman").arg(&self.pacman).arg("-Scc");
-            if ctx.config().yes() {
+            if ctx.config().yes(Step::System) {
                 command.arg("--noconfirm");
             }
             command.check_run()?;
@@ -82,7 +82,7 @@ impl ArchPackageManager for Trizen {
             .args(ctx.config().trizen_arguments().split_whitespace())
             .env("PATH", get_execution_path());
 
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             command.arg("--noconfirm");
         }
         command.check_run()?;
@@ -90,7 +90,7 @@ impl ArchPackageManager for Trizen {
         if ctx.config().cleanup() {
             let mut command = ctx.run_type().execute(&self.executable);
             command.arg("-Sc");
-            if ctx.config().yes() {
+            if ctx.config().yes(Step::System) {
                 command.arg("--noconfirm");
             }
             command.check_run()?;
@@ -120,7 +120,7 @@ impl ArchPackageManager for Pacman {
             .arg(&self.executable)
             .arg("-Syu")
             .env("PATH", get_execution_path());
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             command.arg("--noconfirm");
         }
         command.check_run()?;
@@ -128,7 +128,7 @@ impl ArchPackageManager for Pacman {
         if ctx.config().cleanup() {
             let mut command = ctx.run_type().execute(&self.sudo);
             command.arg(&self.executable).arg("-Scc");
-            if ctx.config().yes() {
+            if ctx.config().yes(Step::System) {
                 command.arg("--noconfirm");
             }
             command.check_run()?;
diff --git a/src/steps/os/linux.rs b/src/steps/os/linux.rs
index faa91243..8784ff85 100644
--- a/src/steps/os/linux.rs
+++ b/src/steps/os/linux.rs
@@ -4,6 +4,7 @@ use crate::executor::{CommandExt, RunType};
 use crate::steps::os::archlinux;
 use crate::terminal::{print_separator, print_warning};
 use crate::utils::{require, require_option, which, PathExt};
+use crate::Step;
 use anyhow::Result;
 use ini::Ini;
 use log::debug;
@@ -137,7 +138,7 @@ fn upgrade_redhat(ctx: &ExecutionContext) -> Result<()> {
         if ctx.config().rpm_ostree() {
             let mut command = ctx.run_type().execute(ostree);
             command.arg("upgrade");
-            if ctx.config().yes() {
+            if ctx.config().yes(Step::System) {
                 command.arg("-y");
             }
 
@@ -163,7 +164,7 @@ fn upgrade_redhat(ctx: &ExecutionContext) -> Result<()> {
             command.args(args.split_whitespace());
         }
 
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             command.arg("-y");
         }
 
@@ -259,7 +260,7 @@ fn upgrade_debian(ctx: &ExecutionContext) -> Result<()> {
 
         let mut command = ctx.run_type().execute(&sudo);
         command.arg(&apt).arg("dist-upgrade");
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             command.arg("-y");
         }
         if let Some(args) = ctx.config().apt_arguments() {
@@ -272,7 +273,7 @@ fn upgrade_debian(ctx: &ExecutionContext) -> Result<()> {
 
             let mut command = ctx.run_type().execute(&sudo);
             command.arg(&apt).arg("autoremove");
-            if ctx.config().yes() {
+            if ctx.config().yes(Step::System) {
                 command.arg("-y");
             }
             command.check_run()?;
@@ -391,7 +392,7 @@ fn upgrade_neon(ctx: &ExecutionContext) -> Result<()> {
         ctx.run_type().execute(&sudo).arg(&pkcon).arg("refresh").check_run()?;
         let mut exe = ctx.run_type().execute(&sudo);
         let cmd = exe.arg(&pkcon).arg("update");
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             cmd.arg("-y");
         }
         if ctx.config().cleanup() {
@@ -438,7 +439,7 @@ pub fn run_fwupdmgr(ctx: &ExecutionContext) -> Result<()> {
 
     if ctx.config().firmware_upgrade() {
         updmgr.arg("update");
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::System) {
             updmgr.arg("-y");
         }
     } else {
diff --git a/src/steps/os/macos.rs b/src/steps/os/macos.rs
index 3fb39a9f..7327eed2 100644
--- a/src/steps/os/macos.rs
+++ b/src/steps/os/macos.rs
@@ -1,7 +1,7 @@
 use crate::execution_context::ExecutionContext;
 use crate::executor::RunType;
 use crate::terminal::{print_separator, prompt_yesno};
-use crate::{error::TopgradeError, utils::require};
+use crate::{error::TopgradeError, utils::require, Step};
 use anyhow::Result;
 use log::debug;
 use std::process::Command;
@@ -42,7 +42,7 @@ pub fn run_silnite(ctx: &ExecutionContext) -> Result<()> {
 pub fn upgrade_macos(ctx: &ExecutionContext) -> Result<()> {
     print_separator("macOS system update");
 
-    let should_ask = !(ctx.config().yes()) || (ctx.config().dry_run());
+    let should_ask = !(ctx.config().yes(Step::System)) || (ctx.config().dry_run());
     if should_ask {
         println!("Finding available software");
         if system_update_available()? {
diff --git a/src/steps/os/unix.rs b/src/steps/os/unix.rs
index 124391d0..e36150fa 100644
--- a/src/steps/os/unix.rs
+++ b/src/steps/os/unix.rs
@@ -7,6 +7,7 @@ use crate::executor::CommandExt;
 use crate::executor::{Executor, ExecutorExitStatus, RunType};
 use crate::terminal::{print_separator, print_warning};
 use crate::utils::{require, require_option, PathExt};
+use crate::Step;
 use anyhow::Result;
 use directories::BaseDirs;
 use log::debug;
@@ -106,14 +107,14 @@ pub fn run_pkgin(ctx: &ExecutionContext) -> Result<()> {
 
     let mut command = ctx.run_type().execute(ctx.sudo().as_ref().unwrap());
     command.arg(&pkgin).arg("update");
-    if ctx.config().yes() {
+    if ctx.config().yes(Step::Pkgin) {
         command.arg("-y");
     }
     command.check_run()?;
 
     let mut command = ctx.run_type().execute(ctx.sudo().as_ref().unwrap());
     command.arg(&pkgin).arg("upgrade");
-    if ctx.config().yes() {
+    if ctx.config().yes(Step::Pkgin) {
         command.arg("-y");
     }
     command.check_run()
diff --git a/src/steps/os/windows.rs b/src/steps/os/windows.rs
index 850fa90e..f5bf9cae 100644
--- a/src/steps/os/windows.rs
+++ b/src/steps/os/windows.rs
@@ -1,18 +1,20 @@
-use crate::execution_context::ExecutionContext;
-use crate::executor::{CommandExt, RunType};
-use crate::powershell;
-use crate::terminal::print_separator;
-use crate::utils::require;
-use crate::{error::SkipStep, steps::git::Repositories};
-use anyhow::Result;
-use log::debug;
 use std::convert::TryFrom;
 use std::path::Path;
 use std::{ffi::OsStr, process::Command};
 
+use anyhow::Result;
+use log::debug;
+
+use crate::execution_context::ExecutionContext;
+use crate::executor::{CommandExt, RunType};
+use crate::terminal::print_separator;
+use crate::utils::require;
+use crate::{error::SkipStep, steps::git::Repositories};
+use crate::{powershell, Step};
+
 pub fn run_chocolatey(ctx: &ExecutionContext) -> Result<()> {
     let choco = require("choco")?;
-    let yes = ctx.config().yes();
+    let yes = ctx.config().yes(Step::Chocolatey);
 
     print_separator("Chocolatey");
 
@@ -70,7 +72,7 @@ pub fn run_wsl_topgrade(ctx: &ExecutionContext) -> Result<()> {
         .args(&["bash", "-c"])
         .arg(format!("TOPGRADE_PREFIX=WSL exec {}", topgrade));
 
-    if ctx.config().yes() {
+    if ctx.config().yes(Step::Wsl) {
         command.arg("-y");
     }
 
diff --git a/src/steps/powershell.rs b/src/steps/powershell.rs
index b5fa0fd2..4a0a09c3 100644
--- a/src/steps/powershell.rs
+++ b/src/steps/powershell.rs
@@ -1,13 +1,16 @@
-use crate::execution_context::ExecutionContext;
-use crate::executor::CommandExt;
-use crate::terminal::{is_dumb, print_separator};
-use crate::utils::{require_option, which, PathExt};
-use anyhow::Result;
 #[cfg(windows)]
 use std::path::Path;
 use std::path::PathBuf;
 use std::process::Command;
 
+use anyhow::Result;
+
+use crate::execution_context::ExecutionContext;
+use crate::executor::CommandExt;
+use crate::terminal::{is_dumb, print_separator};
+use crate::utils::{require_option, which, PathExt};
+use crate::Step;
+
 pub struct Powershell {
     path: Option<PathBuf>,
     profile: Option<PathBuf>,
@@ -69,7 +72,7 @@ impl Powershell {
             cmd.push("-Verbose")
         }
 
-        if ctx.config().yes() {
+        if ctx.config().yes(Step::Powershell) {
             cmd.push("-Confirm")
         }
 
diff --git a/src/steps/remote/ssh.rs b/src/steps/remote/ssh.rs
index e8345f53..c759259a 100644
--- a/src/steps/remote/ssh.rs
+++ b/src/steps/remote/ssh.rs
@@ -1,6 +1,7 @@
-use crate::{error::SkipStep, execution_context::ExecutionContext, terminal::print_separator, utils};
 use anyhow::Result;
 
+use crate::{error::SkipStep, execution_context::ExecutionContext, terminal::print_separator, utils};
+
 fn prepare_async_ssh_command(args: &mut Vec<&str>) {
     args.insert(0, "ssh");
     args.push("--keep");
@@ -19,10 +20,6 @@ pub fn ssh_step(ctx: &ExecutionContext, hostname: &str) -> Result<()> {
     let env = format!("TOPGRADE_PREFIX={}", hostname);
     args.extend(&["env", &env, "$SHELL", "-lc", topgrade]);
 
-    if ctx.config().yes() {
-        args.push("-y");
-    }
-
     if ctx.config().run_in_tmux() && !ctx.run_type().dry() {
         #[cfg(unix)]
         {
@@ -47,10 +44,6 @@ pub fn ssh_step(ctx: &ExecutionContext, hostname: &str) -> Result<()> {
         let env = format!("TOPGRADE_PREFIX={}", hostname);
         args.extend(&["env", &env, "$SHELL", "-lc", topgrade]);
 
-        if ctx.config().yes() {
-            args.push("-y");
-        }
-
         print_separator(format!("Remote ({})", hostname));
         println!("Connecting to {}...", hostname);
 
diff --git a/src/steps/remote/vagrant.rs b/src/steps/remote/vagrant.rs
index 3c4af976..ed3dfad3 100644
--- a/src/steps/remote/vagrant.rs
+++ b/src/steps/remote/vagrant.rs
@@ -1,14 +1,16 @@
-use crate::execution_context::ExecutionContext;
-use crate::executor::CommandExt;
-use crate::terminal::print_separator;
-use crate::{error::SkipStep, utils};
-use anyhow::Result;
-use log::{debug, error};
 use std::path::{Path, PathBuf};
 use std::process::Command;
 use std::{fmt::Display, rc::Rc, str::FromStr};
+
+use anyhow::Result;
+use log::{debug, error};
 use strum::EnumString;
 
+use crate::execution_context::ExecutionContext;
+use crate::executor::CommandExt;
+use crate::terminal::print_separator;
+use crate::{error::SkipStep, utils, Step};
+
 #[derive(Debug, Copy, Clone, EnumString)]
 #[strum(serialize_all = "lowercase")]
 enum BoxStatus {
@@ -188,7 +190,7 @@ pub fn topgrade_vagrant_box(ctx: &ExecutionContext, vagrant_box: &VagrantBox) ->
         print_separator(seperator);
     }
     let mut command = format!("env TOPGRADE_PREFIX={} topgrade", vagrant_box.smart_name());
-    if ctx.config().yes() {
+    if ctx.config().yes(Step::Vagrant) {
         command.push_str(" -y");
     }