diff --git a/README.md b/README.md
index 2482b03f..69e4e78f 100644
--- a/README.md
+++ b/README.md
@@ -95,6 +95,7 @@ Just run `topgrade`. It will run the following steps:
 * `--no-system` - Skip the system upgrade phase.
 * `--no-git-repos` - Don't pull custom git repositories.
 * `--no-emacs` - Don't upgrade Emacs packages or configuration files.
+* `--no-retry` - Don't ask to retry failed steps.
 
 ## Customization
 You can place a configuration file at `~/.config/topgrade.toml` (on macOS `~/Library/Preferences/topgrade.toml`).. Here's an example:
diff --git a/src/config.rs b/src/config.rs
index aaab2663..4f81036c 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -73,4 +73,8 @@ pub struct Opt {
     /// Print what would be done
     #[structopt(short = "n", long = "dry-run")]
     pub dry_run: bool,
+
+    /// Do not ask to retry failed steps
+    #[structopt(long = "no-retry")]
+    pub no_retry: bool,
 }
diff --git a/src/main.rs b/src/main.rs
index 1c319878..924fc4e0 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -67,7 +67,7 @@ struct NoBaseDirectories;
 #[fail(display = "Process Interrupted")]
 pub struct Interrupted;
 
-fn execute<'a, F, M>(func: F) -> Result<Option<(M, bool)>, Error>
+fn execute<'a, F, M>(func: F, no_retry: bool) -> Result<Option<(M, bool)>, Error>
 where
     M: Into<Cow<'a, str>>,
     F: Fn() -> Option<(M, bool)>,
@@ -82,7 +82,8 @@ where
             ctrlc::set_running(true);
         }
 
-        let should_retry = should_retry(running).map_err(|e| {
+        let should_ask = !running || !no_retry;
+        let should_retry = should_ask && should_retry(running).map_err(|e| {
             if e.kind() == ErrorKind::Interrupted {
                 Error::from(Interrupted)
             } else {
@@ -141,7 +142,7 @@ fn run() -> Result<(), Error> {
     let powershell = windows::Powershell::new();
 
     #[cfg(windows)]
-    report.push_result(execute(|| powershell.update_modules(opt.dry_run))?);
+    report.push_result(execute(|| powershell.update_modules(opt.dry_run), opt.no_retry)?);
 
     #[cfg(target_os = "linux")]
     let distribution = linux::Distribution::detect();
@@ -151,28 +152,28 @@ fn run() -> Result<(), Error> {
         if !opt.no_system {
             match &distribution {
                 Ok(distribution) => {
-                    report.push_result(execute(|| distribution.upgrade(&sudo, opt.dry_run))?);
+                    report.push_result(execute(|| distribution.upgrade(&sudo, opt.dry_run), opt.no_retry)?);
                 }
                 Err(e) => {
                     println!("Error detecting current distribution: {}", e);
                 }
             }
-            report.push_result(execute(|| linux::run_etc_update(&sudo, opt.dry_run))?);
+            report.push_result(execute(|| linux::run_etc_update(&sudo, opt.dry_run), opt.no_retry)?);
         }
     }
 
     #[cfg(windows)]
-    report.push_result(execute(|| windows::run_chocolatey(opt.dry_run))?);
+    report.push_result(execute(|| windows::run_chocolatey(opt.dry_run), opt.no_retry)?);
 
     #[cfg(windows)]
-    report.push_result(execute(|| windows::run_scoop(opt.dry_run))?);
+    report.push_result(execute(|| windows::run_scoop(opt.dry_run), opt.no_retry)?);
 
     #[cfg(unix)]
-    report.push_result(execute(|| unix::run_homebrew(opt.cleanup, opt.dry_run))?);
+    report.push_result(execute(|| unix::run_homebrew(opt.cleanup, opt.dry_run), opt.no_retry)?);
     #[cfg(target_os = "freebsd")]
-    report.push_result(execute(|| freebsd::upgrade_packages(&sudo, opt.dry_run))?);
+    report.push_result(execute(|| freebsd::upgrade_packages(&sudo, opt.dry_run), opt.no_retry)?);
     #[cfg(unix)]
-    report.push_result(execute(|| unix::run_nix(opt.dry_run))?);
+    report.push_result(execute(|| unix::run_nix(opt.dry_run), opt.no_retry)?);
 
     if !opt.no_emacs {
         git_repos.insert(base_dirs.home_dir().join(".emacs.d"));
@@ -205,32 +206,38 @@ fn run() -> Result<(), Error> {
         }
     }
     for repo in git_repos.repositories() {
-        report.push_result(execute(|| git.pull(&repo, opt.dry_run))?);
+        report.push_result(execute(|| git.pull(&repo, opt.dry_run), opt.no_retry)?);
     }
 
     #[cfg(unix)]
     {
-        report.push_result(execute(|| unix::run_zplug(&base_dirs, opt.dry_run))?);
-        report.push_result(execute(|| unix::run_fisher(&base_dirs, opt.dry_run))?);
-        report.push_result(execute(|| tmux::run_tpm(&base_dirs, opt.dry_run))?);
+        report.push_result(execute(|| unix::run_zplug(&base_dirs, opt.dry_run), opt.no_retry)?);
+        report.push_result(execute(|| unix::run_fisher(&base_dirs, opt.dry_run), opt.no_retry)?);
+        report.push_result(execute(|| tmux::run_tpm(&base_dirs, opt.dry_run), opt.no_retry)?);
     }
 
-    report.push_result(execute(|| generic::run_rustup(&base_dirs, opt.dry_run))?);
-    report.push_result(execute(|| generic::run_cargo_update(opt.dry_run))?);
+    report.push_result(execute(|| generic::run_rustup(&base_dirs, opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| generic::run_cargo_update(opt.dry_run), opt.no_retry)?);
 
     if !opt.no_emacs {
-        report.push_result(execute(|| generic::run_emacs(&base_dirs, opt.dry_run))?);
+        report.push_result(execute(|| generic::run_emacs(&base_dirs, opt.dry_run), opt.no_retry)?);
     }
 
-    report.push_result(execute(|| generic::run_opam_update(opt.dry_run))?);
-    report.push_result(execute(|| generic::run_vcpkg_update(opt.dry_run))?);
-    report.push_result(execute(|| generic::run_pipx_update(opt.dry_run))?);
-    report.push_result(execute(|| generic::run_jetpack(opt.dry_run))?);
-    report.push_result(execute(|| vim::upgrade_vim(&base_dirs, opt.dry_run))?);
-    report.push_result(execute(|| vim::upgrade_neovim(&base_dirs, opt.dry_run))?);
-    report.push_result(execute(|| node::run_npm_upgrade(&base_dirs, opt.dry_run))?);
-    report.push_result(execute(|| generic::run_composer_update(&base_dirs, opt.dry_run))?);
-    report.push_result(execute(|| node::yarn_global_update(opt.dry_run))?);
+    report.push_result(execute(|| generic::run_opam_update(opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| generic::run_vcpkg_update(opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| generic::run_pipx_update(opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| generic::run_jetpack(opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| vim::upgrade_vim(&base_dirs, opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| vim::upgrade_neovim(&base_dirs, opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(
+        || node::run_npm_upgrade(&base_dirs, opt.dry_run),
+        opt.no_retry,
+    )?);
+    report.push_result(execute(
+        || generic::run_composer_update(&base_dirs, opt.dry_run),
+        opt.no_retry,
+    )?);
+    report.push_result(execute(|| node::yarn_global_update(opt.dry_run), opt.no_retry)?);
 
     #[cfg(not(any(
         target_os = "freebsd",
@@ -238,48 +245,52 @@ fn run() -> Result<(), Error> {
         target_os = "netbsd",
         target_os = "dragonfly"
     )))]
-    report.push_result(execute(|| generic::run_apm(opt.dry_run))?);
-    report.push_result(execute(|| generic::run_gem(&base_dirs, opt.dry_run))?);
+    report.push_result(execute(|| generic::run_apm(opt.dry_run), opt.no_retry)?);
+    report.push_result(execute(|| generic::run_gem(&base_dirs, opt.dry_run), opt.no_retry)?);
 
     #[cfg(target_os = "linux")]
     {
-        report.push_result(execute(|| linux::flatpak_user_update(opt.dry_run))?);
-        report.push_result(execute(|| linux::flatpak_global_update(&sudo, opt.dry_run))?);
-        report.push_result(execute(|| linux::run_snap(&sudo, opt.dry_run))?);
+        report.push_result(execute(|| linux::flatpak_user_update(opt.dry_run), opt.no_retry)?);
+        report.push_result(execute(
+            || linux::flatpak_global_update(&sudo, opt.dry_run),
+            opt.no_retry,
+        )?);
+        report.push_result(execute(|| linux::run_snap(&sudo, opt.dry_run), opt.no_retry)?);
     }
 
     if let Some(commands) = config.commands() {
         for (name, command) in commands {
-            report.push_result(execute(|| {
-                Some((name, generic::run_custom_command(&name, &command, opt.dry_run).is_ok()))
-            })?);
+            report.push_result(execute(
+                || Some((name, generic::run_custom_command(&name, &command, opt.dry_run).is_ok())),
+                opt.no_retry,
+            )?);
         }
     }
 
     #[cfg(target_os = "linux")]
     {
-        report.push_result(execute(|| linux::run_fwupdmgr(opt.dry_run))?);
-        report.push_result(execute(|| linux::run_needrestart(&sudo, opt.dry_run))?);
+        report.push_result(execute(|| linux::run_fwupdmgr(opt.dry_run), opt.no_retry)?);
+        report.push_result(execute(|| linux::run_needrestart(&sudo, opt.dry_run), opt.no_retry)?);
     }
 
     #[cfg(target_os = "macos")]
     {
         if !opt.no_system {
-            report.push_result(execute(|| macos::upgrade_macos(opt.dry_run))?);
+            report.push_result(execute(|| macos::upgrade_macos(opt.dry_run), opt.no_retry)?);
         }
     }
 
     #[cfg(target_os = "freebsd")]
     {
         if !opt.no_system {
-            report.push_result(execute(|| freebsd::upgrade_freebsd(&sudo, opt.dry_run))?);
+            report.push_result(execute(|| freebsd::upgrade_freebsd(&sudo, opt.dry_run), opt.no_retry)?);
         }
     }
 
     #[cfg(windows)]
     {
         if !opt.no_system {
-            report.push_result(execute(|| powershell.windows_update(opt.dry_run))?);
+            report.push_result(execute(|| powershell.windows_update(opt.dry_run), opt.no_retry)?);
         }
     }