diff --git a/src/error.rs b/src/error.rs
index d97d0b02..acc75255 100644
--- a/src/error.rs
+++ b/src/error.rs
@@ -41,6 +41,9 @@ pub enum ErrorKind {
     #[fail(display = "Self-update failure")]
     #[cfg(feature = "self-update")]
     SelfUpdate,
+
+    #[fail(display = "A step should be skipped")]
+    SkipStep,
 }
 
 impl Fail for Error {
diff --git a/src/main.rs b/src/main.rs
index 11b16fcb..998c4fbd 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -15,14 +15,16 @@ use self::report::Report;
 use self::steps::*;
 use self::terminal::*;
 use failure::{Fail, ResultExt};
+use log::debug;
 use std::borrow::Cow;
 use std::env;
+use std::fmt::Debug;
 use std::io;
 #[cfg(windows)]
 use std::path::PathBuf;
 use std::process::exit;
 
-fn execute<'a, F, M>(func: F, no_retry: bool) -> Result<Option<(M, bool)>, Error>
+fn execute_legacy<'a, F, M>(func: F, no_retry: bool) -> Result<Option<(M, bool)>, Error>
 where
     M: Into<Cow<'a, str>>,
     F: Fn() -> Option<(M, bool)>,
@@ -48,6 +50,42 @@ where
     Ok(None)
 }
 
+fn execute<'a, F, M>(report: &mut Report<'a>, key: M, func: F, no_retry: bool) -> Result<(), Error>
+where
+    F: Fn() -> Result<(), Error>,
+    M: Into<Cow<'a, str>> + Debug,
+{
+    debug!("Executing {:?}", key);
+
+    loop {
+        match func() {
+            Ok(()) => {
+                report.push_result(Some((key, true)));
+                break;
+            }
+            Err(ref e) if e.kind() == ErrorKind::SkipStep => {
+                break;
+            }
+            Err(_) => {
+                let interrupted = ctrlc::interrupted();
+                if interrupted {
+                    ctrlc::unset_interrupted();
+                }
+
+                let should_ask = interrupted || !no_retry;
+                let should_retry = should_ask && should_retry(interrupted).context(ErrorKind::Retry)?;
+
+                if !should_retry {
+                    report.push_result(Some((key, false)));
+                    break;
+                }
+            }
+        }
+    }
+
+    Ok(())
+}
+
 fn run() -> Result<(), Error> {
     ctrlc::set_handler();
 
@@ -96,7 +134,10 @@ fn run() -> Result<(), Error> {
     #[cfg(windows)]
     {
         if powershell.profile().is_some() && config.should_run(Step::Powershell) {
-            report.push_result(execute(|| powershell.update_modules(run_type), config.no_retry())?);
+            report.push_result(execute_legacy(
+                || powershell.update_modules(run_type),
+                config.no_retry(),
+            )?);
         }
     }
 
@@ -108,7 +149,7 @@ fn run() -> Result<(), Error> {
         if config.should_run(Step::System) {
             match &distribution {
                 Ok(distribution) => {
-                    report.push_result(execute(
+                    report.push_result(execute_legacy(
                         || distribution.upgrade(&sudo, config.cleanup(), run_type),
                         config.no_retry(),
                     )?);
@@ -117,28 +158,31 @@ fn run() -> Result<(), Error> {
                     println!("Error detecting current distribution: {}", e);
                 }
             }
-            report.push_result(execute(|| linux::run_etc_update(&sudo, run_type), config.no_retry())?);
+            report.push_result(execute_legacy(
+                || linux::run_etc_update(&sudo, run_type),
+                config.no_retry(),
+            )?);
         }
     }
 
     #[cfg(windows)]
-    report.push_result(execute(|| windows::run_chocolatey(run_type), config.no_retry())?);
+    report.push_result(execute_legacy(|| windows::run_chocolatey(run_type), config.no_retry())?);
 
     #[cfg(windows)]
-    report.push_result(execute(|| windows::run_scoop(run_type), config.no_retry())?);
+    report.push_result(execute_legacy(|| windows::run_scoop(run_type), config.no_retry())?);
 
     #[cfg(unix)]
-    report.push_result(execute(
+    report.push_result(execute_legacy(
         || unix::run_homebrew(config.cleanup(), run_type),
         config.no_retry(),
     )?);
     #[cfg(target_os = "freebsd")]
-    report.push_result(execute(
+    report.push_result(execute_legacy(
         || freebsd::upgrade_packages(&sudo, run_type),
         config.no_retry(),
     )?);
     #[cfg(unix)]
-    report.push_result(execute(|| unix::run_nix(run_type), config.no_retry())?);
+    report.push_result(execute_legacy(|| unix::run_nix(run_type), config.no_retry())?);
 
     if config.should_run(Step::Emacs) {
         #[cfg(unix)]
@@ -182,48 +226,97 @@ fn run() -> Result<(), Error> {
         }
     }
     for repo in git_repos.repositories() {
-        report.push_result(execute(|| git.pull(&repo, run_type), config.no_retry())?);
+        report.push_result(execute_legacy(|| git.pull(&repo, run_type), config.no_retry())?);
     }
 
     #[cfg(unix)]
     {
-        report.push_result(execute(|| unix::run_zplug(&base_dirs, run_type), config.no_retry())?);
-        report.push_result(execute(|| unix::run_fisher(&base_dirs, run_type), config.no_retry())?);
-        report.push_result(execute(|| tmux::run_tpm(&base_dirs, run_type), config.no_retry())?);
+        report.push_result(execute_legacy(
+            || unix::run_zplug(&base_dirs, run_type),
+            config.no_retry(),
+        )?);
+        report.push_result(execute_legacy(
+            || unix::run_fisher(&base_dirs, run_type),
+            config.no_retry(),
+        )?);
+        report.push_result(execute_legacy(
+            || tmux::run_tpm(&base_dirs, run_type),
+            config.no_retry(),
+        )?);
     }
 
-    report.push_result(execute(
+    execute(
+        &mut report,
+        "rustup",
         || generic::run_rustup(&base_dirs, run_type),
         config.no_retry(),
-    )?);
-    report.push_result(execute(|| generic::run_cargo_update(run_type), config.no_retry())?);
+    )?;
+    execute(
+        &mut report,
+        "cargo",
+        || generic::run_cargo_update(run_type),
+        config.no_retry(),
+    )?;
 
     if config.should_run(Step::Emacs) {
-        report.push_result(execute(|| generic::run_emacs(&base_dirs, run_type), config.no_retry())?);
+        execute(
+            &mut report,
+            "Emacs",
+            || generic::run_emacs(&base_dirs, run_type),
+            config.no_retry(),
+        )?;
     }
 
-    report.push_result(execute(|| generic::run_opam_update(run_type), config.no_retry())?);
-    report.push_result(execute(|| generic::run_vcpkg_update(run_type), config.no_retry())?);
-    report.push_result(execute(|| generic::run_pipx_update(run_type), config.no_retry())?);
-    report.push_result(execute(|| generic::run_jetpack(run_type), config.no_retry())?);
+    execute(
+        &mut report,
+        "opam",
+        || generic::run_opam_update(run_type),
+        config.no_retry(),
+    )?;
+    execute(
+        &mut report,
+        "vcpkg",
+        || generic::run_vcpkg_update(run_type),
+        config.no_retry(),
+    )?;
+    execute(
+        &mut report,
+        "pipx",
+        || generic::run_pipx_update(run_type),
+        config.no_retry(),
+    )?;
+    execute(
+        &mut report,
+        "jetpak",
+        || generic::run_jetpack(run_type),
+        config.no_retry(),
+    )?;
 
     if config.should_run(Step::Vim) {
-        report.push_result(execute(|| vim::upgrade_vim(&base_dirs, run_type), config.no_retry())?);
-        report.push_result(execute(
+        report.push_result(execute_legacy(
+            || vim::upgrade_vim(&base_dirs, run_type),
+            config.no_retry(),
+        )?);
+        report.push_result(execute_legacy(
             || vim::upgrade_neovim(&base_dirs, run_type),
             config.no_retry(),
         )?);
     }
 
-    report.push_result(execute(
+    report.push_result(execute_legacy(
         || node::run_npm_upgrade(&base_dirs, run_type),
         config.no_retry(),
     )?);
-    report.push_result(execute(
+    execute(
+        &mut report,
+        "composer",
         || generic::run_composer_update(&base_dirs, run_type),
         config.no_retry(),
+    )?;
+    report.push_result(execute_legacy(
+        || node::yarn_global_update(run_type),
+        config.no_retry(),
     )?);
-    report.push_result(execute(|| node::yarn_global_update(run_type), config.no_retry())?);
 
     #[cfg(not(any(
         target_os = "freebsd",
@@ -231,21 +324,26 @@ fn run() -> Result<(), Error> {
         target_os = "netbsd",
         target_os = "dragonfly"
     )))]
-    report.push_result(execute(|| generic::run_apm(run_type), config.no_retry())?);
+    execute(&mut report, "apm", || generic::run_apm(run_type), config.no_retry())?;
 
     if config.should_run(Step::Gem) {
-        report.push_result(execute(|| generic::run_gem(&base_dirs, run_type), config.no_retry())?);
+        execute(
+            &mut report,
+            "gem",
+            || generic::run_gem(&base_dirs, run_type),
+            config.no_retry(),
+        )?;
     }
 
     #[cfg(target_os = "linux")]
     {
-        report.push_result(execute(|| linux::flatpak_update(run_type), config.no_retry())?);
-        report.push_result(execute(|| linux::run_snap(&sudo, run_type), config.no_retry())?);
+        report.push_result(execute_legacy(|| linux::flatpak_update(run_type), config.no_retry())?);
+        report.push_result(execute_legacy(|| linux::run_snap(&sudo, run_type), config.no_retry())?);
     }
 
     if let Some(commands) = config.commands() {
         for (name, command) in commands {
-            report.push_result(execute(
+            report.push_result(execute_legacy(
                 || Some((name, generic::run_custom_command(&name, &command, run_type).is_ok())),
                 config.no_retry(),
             )?);
@@ -254,21 +352,24 @@ fn run() -> Result<(), Error> {
 
     #[cfg(target_os = "linux")]
     {
-        report.push_result(execute(|| linux::run_fwupdmgr(run_type), config.no_retry())?);
-        report.push_result(execute(|| linux::run_needrestart(&sudo, run_type), config.no_retry())?);
+        report.push_result(execute_legacy(|| linux::run_fwupdmgr(run_type), config.no_retry())?);
+        report.push_result(execute_legacy(
+            || linux::run_needrestart(&sudo, run_type),
+            config.no_retry(),
+        )?);
     }
 
     #[cfg(target_os = "macos")]
     {
         if config.should_run(Step::System) {
-            report.push_result(execute(|| macos::upgrade_macos(run_type), config.no_retry())?);
+            report.push_result(execute_legacy(|| macos::upgrade_macos(run_type), config.no_retry())?);
         }
     }
 
     #[cfg(target_os = "freebsd")]
     {
         if config.should_run(Step::System) {
-            report.push_result(execute(
+            report.push_result(execute_legacy(
                 || freebsd::upgrade_freebsd(&sudo, run_type),
                 config.no_retry(),
             )?);
@@ -278,7 +379,10 @@ fn run() -> Result<(), Error> {
     #[cfg(windows)]
     {
         if config.should_run(Step::System) {
-            report.push_result(execute(|| powershell.windows_update(run_type), config.no_retry())?);
+            report.push_result(execute_legacy(
+                || powershell.windows_update(run_type),
+                config.no_retry(),
+            )?);
         }
     }
 
diff --git a/src/steps/generic.rs b/src/steps/generic.rs
index eaf19882..15640153 100644
--- a/src/steps/generic.rs
+++ b/src/steps/generic.rs
@@ -1,4 +1,4 @@
-use crate::error::Error;
+use crate::error::{Error, ErrorKind};
 use crate::executor::{CommandExt, RunType};
 use crate::terminal::print_separator;
 use crate::utils::{self, PathExt};
@@ -8,223 +8,120 @@ use std::process::Command;
 
 const EMACS_UPGRADE: &str = include_str!("emacs.el");
 
-#[must_use]
-pub fn run_cargo_update(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(cargo_update) = utils::which("cargo-install-update") {
-        print_separator("Cargo");
+pub fn run_cargo_update(run_type: RunType) -> Result<(), Error> {
+    let cargo_update = utils::require("cargo-install-update")?;
 
-        let success = || -> Result<(), Error> {
-            run_type
-                .execute(cargo_update)
-                .args(&["install-update", "--git", "--all"])
-                .check_run()?;
+    print_separator("Cargo");
 
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("Cargo", success));
-    }
-
-    None
+    run_type
+        .execute(cargo_update)
+        .args(&["install-update", "--git", "--all"])
+        .check_run()
 }
 
-#[must_use]
-pub fn run_gem(base_dirs: &BaseDirs, run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(gem) = utils::which("gem") {
-        if base_dirs.home_dir().join(".gem").exists() {
-            print_separator("RubyGems");
+pub fn run_gem(base_dirs: &BaseDirs, run_type: RunType) -> Result<(), Error> {
+    let gem = utils::require("gem")?;
+    base_dirs.home_dir().join(".gem").require()?;
 
-            let success = || -> Result<(), Error> {
-                run_type.execute(&gem).args(&["update", "--user-install"]).check_run()?;
+    print_separator("RubyGems");
 
-                Ok(())
-            }()
-            .is_ok();
-
-            return Some(("RubyGems", success));
-        }
-    }
-    None
+    run_type.execute(&gem).args(&["update", "--user-install"]).check_run()
 }
 
-#[must_use]
-pub fn run_emacs(base_dirs: &BaseDirs, run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(emacs) = utils::which("emacs") {
-        if let Some(init_file) = base_dirs.home_dir().join(".emacs.d/init.el").if_exists() {
-            print_separator("Emacs");
+pub fn run_emacs(base_dirs: &BaseDirs, run_type: RunType) -> Result<(), Error> {
+    let emacs = utils::require("emacs")?;
+    let init_file = base_dirs.home_dir().join(".emacs.d/init.el").require()?;
 
-            let success = || -> Result<(), Error> {
-                run_type
-                    .execute(&emacs)
-                    .args(&["--batch", "-l", init_file.to_str().unwrap(), "--eval", EMACS_UPGRADE])
-                    .check_run()?;
+    print_separator("Emacs");
 
-                Ok(())
-            }()
-            .is_ok();
-
-            return Some(("Emacs", success));
-        }
-    }
-    None
+    run_type
+        .execute(&emacs)
+        .args(&["--batch", "-l", init_file.to_str().unwrap(), "--eval", EMACS_UPGRADE])
+        .check_run()
 }
 
-#[must_use]
 #[cfg(not(any(
     target_os = "freebsd",
     target_os = "openbsd",
     target_os = "netbsd",
     target_os = "dragonfly"
 )))]
-pub fn run_apm(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(apm) = utils::which("apm") {
-        print_separator("Atom Package Manager");
+pub fn run_apm(run_type: RunType) -> Result<(), Error> {
+    let apm = utils::require("apm")?;
 
-        let success = || -> Result<(), Error> {
-            run_type
-                .execute(&apm)
-                .args(&["upgrade", "--confirm=false"])
-                .check_run()?;
+    print_separator("Atom Package Manager");
 
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("apm", success));
-    }
-
-    None
+    run_type.execute(&apm).args(&["upgrade", "--confirm=false"]).check_run()
 }
 
-#[must_use]
-pub fn run_rustup(base_dirs: &BaseDirs, run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(rustup) = utils::which("rustup") {
-        print_separator("rustup");
+pub fn run_rustup(base_dirs: &BaseDirs, run_type: RunType) -> Result<(), Error> {
+    let rustup = utils::require("rustup")?;
 
-        let success = || -> Result<(), Error> {
-            if rustup.is_descendant_of(base_dirs.home_dir()) {
-                run_type.execute(&rustup).args(&["self", "update"]).check_run()?;
-            }
+    print_separator("rustup");
 
-            run_type.execute(&rustup).arg("update").check_run()?;
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("rustup", success));
+    if rustup.is_descendant_of(base_dirs.home_dir()) {
+        run_type.execute(&rustup).args(&["self", "update"]).check_run()?;
     }
 
-    None
+    run_type.execute(&rustup).arg("update").check_run()
 }
 
-#[must_use]
-pub fn run_jetpack(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(jetpack) = utils::which("jetpack") {
-        print_separator("Jetpack");
+pub fn run_jetpack(run_type: RunType) -> Result<(), Error> {
+    let jetpack = utils::require("jetpack")?;
 
-        let success = || -> Result<(), Error> {
-            run_type.execute(&jetpack).args(&["global", "update"]).check_run()?;
-            Ok(())
-        }()
-        .is_ok();
+    print_separator("Jetpack");
 
-        return Some(("Jetpack", success));
-    }
-
-    None
+    run_type.execute(&jetpack).args(&["global", "update"]).check_run()
 }
 
-#[must_use]
-pub fn run_opam_update(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(opam) = utils::which("opam") {
-        print_separator("OCaml Package Manager");
+pub fn run_opam_update(run_type: RunType) -> Result<(), Error> {
+    let opam = utils::require("opam")?;
 
-        let success = || -> Result<(), Error> {
-            run_type.execute(&opam).arg("update").check_run()?;
-            run_type.execute(&opam).arg("upgrade").check_run()?;
-            Ok(())
-        }()
-        .is_ok();
+    print_separator("OCaml Package Manager");
 
-        return Some(("OPAM", success));
-    }
-
-    None
+    run_type.execute(&opam).arg("update").check_run()?;
+    run_type.execute(&opam).arg("upgrade").check_run()
 }
 
-#[must_use]
-pub fn run_vcpkg_update(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(vcpkg) = utils::which("vcpkg") {
-        print_separator("vcpkg");
+pub fn run_vcpkg_update(run_type: RunType) -> Result<(), Error> {
+    let vcpkg = utils::require("vcpkg")?;
+    print_separator("vcpkg");
 
-        let success = || -> Result<(), Error> {
-            run_type
-                .execute(&vcpkg)
-                .args(&["upgrade", "--no-dry-run"])
-                .check_run()?;
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("vcpkg", success));
-    }
-
-    None
+    run_type.execute(&vcpkg).args(&["upgrade", "--no-dry-run"]).check_run()
 }
 
-#[must_use]
-pub fn run_pipx_update(run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(pipx) = utils::which("pipx") {
-        print_separator("pipx");
+pub fn run_pipx_update(run_type: RunType) -> Result<(), Error> {
+    let pipx = utils::require("pipx")?;
+    print_separator("pipx");
 
-        let success = || -> Result<(), Error> {
-            run_type.execute(&pipx).arg("upgrade-all").check_run()?;
-            Ok(())
-        }()
-        .is_ok();
-
-        return Some(("pipx", success));
-    }
-
-    None
+    run_type.execute(&pipx).arg("upgrade-all").check_run()
 }
 
-#[must_use]
 pub fn run_custom_command(name: &str, command: &str, run_type: RunType) -> Result<(), Error> {
     print_separator(name);
-    run_type.execute("sh").arg("-c").arg(command).check_run()?;
+    run_type.execute("sh").arg("-c").arg(command).check_run()
+}
+
+pub fn run_composer_update(base_dirs: &BaseDirs, run_type: RunType) -> Result<(), Error> {
+    let composer = utils::require("composer")?;
+    let composer_home = Command::new(&composer)
+        .args(&["global", "config", "--absolute", "home"])
+        .check_output()
+        .map_err(|_| Error::from(ErrorKind::SkipStep))
+        .map(PathBuf::from)
+        .and_then(|p| p.require())?;
+
+    if !composer_home.is_descendant_of(base_dirs.home_dir()) {
+        Err(ErrorKind::SkipStep)?;
+    }
+
+    print_separator("Composer");
+
+    run_type.execute(&composer).args(&["global", "update"]).check_run()?;
+
+    if let Some(valet) = utils::which("valet") {
+        run_type.execute(&valet).arg("install").check_run()?;
+    }
 
     Ok(())
 }
-
-#[must_use]
-pub fn run_composer_update(base_dirs: &BaseDirs, run_type: RunType) -> Option<(&'static str, bool)> {
-    if let Some(composer) = utils::which("composer") {
-        let composer_home = Command::new(&composer)
-            .args(&["global", "config", "--absolute", "home"])
-            .check_output()
-            .map(PathBuf::from);
-
-        if let Ok(composer_home) = composer_home {
-            if composer_home.is_descendant_of(base_dirs.home_dir()) {
-                print_separator("Composer");
-
-                let success = || -> Result<(), Error> {
-                    run_type.execute(&composer).args(&["global", "update"]).check_run()?;
-
-                    if let Some(valet) = utils::which("valet") {
-                        run_type.execute(&valet).arg("install").check_run()?;
-                    }
-
-                    Ok(())
-                }()
-                .is_ok();
-
-                return Some(("Composer", success));
-            }
-        }
-    }
-
-    None
-}
diff --git a/src/utils.rs b/src/utils.rs
index 83b77a59..723d54d2 100644
--- a/src/utils.rs
+++ b/src/utils.rs
@@ -32,6 +32,9 @@ where
 {
     fn if_exists(self) -> Option<Self>;
     fn is_descendant_of(&self, ancestor: &Path) -> bool;
+
+    /// Returns the path if it exists or ErrorKind::SkipStep otherwise
+    fn require(self) -> Result<Self, Error>;
 }
 
 impl PathExt for PathBuf {
@@ -46,6 +49,14 @@ impl PathExt for PathBuf {
     fn is_descendant_of(&self, ancestor: &Path) -> bool {
         self.iter().zip(ancestor.iter()).all(|(a, b)| a == b)
     }
+
+    fn require(self) -> Result<Self, Error> {
+        if self.exists() {
+            Ok(self)
+        } else {
+            Err(ErrorKind::SkipStep)?
+        }
+    }
 }
 
 pub fn which<T: AsRef<OsStr> + Debug>(binary_name: T) -> Option<PathBuf> {
@@ -151,3 +162,21 @@ mod tests {
         assert_eq!("C:\\hi", humanize("//?/C:/hi"));
     }
 }
+
+pub fn require<T: AsRef<OsStr> + Debug>(binary_name: T) -> Result<PathBuf, Error> {
+    match which_crate::which(&binary_name) {
+        Ok(path) => {
+            debug!("Detected {:?} as {:?}", &path, &binary_name);
+            Ok(path)
+        }
+        Err(e) => match e.kind() {
+            which_crate::ErrorKind::CannotFindBinaryPath => {
+                debug!("Cannot find {:?}", &binary_name);
+                Err(ErrorKind::SkipStep)?
+            }
+            _ => {
+                panic!("Detecting {:?} failed: {}", &binary_name, e);
+            }
+        },
+    }
+}