diff --git a/src/config.rs b/src/config.rs
index 8d9043d4..ff1bcd25 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -1,5 +1,6 @@
+use super::error::{Error, ErrorKind};
 use directories::BaseDirs;
-use failure;
+use failure::ResultExt;
 use serde_derive::Deserialize;
 use shellexpand;
 use std::collections::BTreeMap;
@@ -17,13 +18,14 @@ pub struct Config {
 }
 
 impl Config {
-    pub fn read(base_dirs: &BaseDirs) -> Result<Config, failure::Error> {
+    pub fn read(base_dirs: &BaseDirs) -> Result<Config, Error> {
         let config_path = base_dirs.config_dir().join("topgrade.toml");
         if !config_path.exists() {
             return Ok(Default::default());
         }
 
-        let mut result: Self = toml::from_str(&fs::read_to_string(config_path)?)?;
+        let mut result: Self = toml::from_str(&fs::read_to_string(config_path).context(ErrorKind::Configuration)?)
+            .context(ErrorKind::Configuration)?;
 
         if let Some(ref mut paths) = &mut result.git_repos {
             for path in paths.iter_mut() {
diff --git a/src/error.rs b/src/error.rs
new file mode 100644
index 00000000..d97d0b02
--- /dev/null
+++ b/src/error.rs
@@ -0,0 +1,80 @@
+use failure::{Backtrace, Context, Fail};
+use std::fmt::{self, Display};
+use std::process::ExitStatus;
+
+#[derive(Debug)]
+pub struct Error {
+    inner: Context<ErrorKind>,
+}
+
+#[derive(Copy, Clone, Eq, PartialEq, Debug, Fail)]
+pub enum ErrorKind {
+    #[fail(display = "Error asking the user for retry")]
+    Retry,
+
+    #[fail(display = "Cannot find the user base directories")]
+    NoBaseDirectories,
+
+    #[fail(display = "A step failed")]
+    StepFailed,
+
+    #[fail(display = "Error reading the configuration")]
+    Configuration,
+
+    #[fail(display = "A custom pre-command failed")]
+    PreCommand,
+
+    #[fail(display = "{}", _0)]
+    ProcessFailed(ExitStatus),
+
+    #[fail(display = "Unknown Linux Distribution")]
+    #[cfg(target_os = "linux")]
+    UnknownLinuxDistribution,
+
+    #[fail(display = "Detected Python is not the system Python")]
+    #[cfg(target_os = "linux")]
+    NotSystemPython,
+
+    #[fail(display = "Process execution failure")]
+    ProcessExecution,
+
+    #[fail(display = "Self-update failure")]
+    #[cfg(feature = "self-update")]
+    SelfUpdate,
+}
+
+impl Fail for Error {
+    fn cause(&self) -> Option<&Fail> {
+        self.inner.cause()
+    }
+
+    fn backtrace(&self) -> Option<&Backtrace> {
+        self.inner.backtrace()
+    }
+}
+
+impl Display for Error {
+    fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
+        Display::fmt(&self.inner, f)
+    }
+}
+
+impl Error {
+    pub fn kind(&self) -> ErrorKind {
+        *self.inner.get_context()
+    }
+}
+
+impl From<ErrorKind> for Error {
+    fn from(kind: ErrorKind) -> Error {
+        Error {
+            inner: Context::new(kind),
+        }
+    }
+}
+
+impl From<Context<ErrorKind>> for Error {
+    fn from(inner: Context<ErrorKind>) -> Error {
+        Error { inner }
+    }
+}
diff --git a/src/executor.rs b/src/executor.rs
index 9f76af2b..1e0f10c7 100644
--- a/src/executor.rs
+++ b/src/executor.rs
@@ -1,7 +1,7 @@
+use super::error::{Error, ErrorKind};
 use super::utils::Check;
-use failure;
+use failure::ResultExt;
 use std::ffi::{OsStr, OsString};
-use std::io;
 use std::path::Path;
 use std::process::{Child, Command, ExitStatus};
 
@@ -63,9 +63,9 @@ impl Executor {
         self
     }
 
-    pub fn spawn(&mut self) -> Result<ExecutorChild, io::Error> {
-        match self {
-            Executor::Wet(c) => c.spawn().map(ExecutorChild::Wet),
+    pub fn spawn(&mut self) -> Result<ExecutorChild, Error> {
+        let result = match self {
+            Executor::Wet(c) => c.spawn().context(ErrorKind::ProcessExecution).map(ExecutorChild::Wet)?,
             Executor::Dry(c) => {
                 print!(
                     "Dry running: {} {}",
@@ -80,9 +80,11 @@ impl Executor {
                     Some(dir) => println!(" in {}", dir.to_string_lossy()),
                     None => println!(),
                 };
-                Ok(ExecutorChild::Dry)
+                ExecutorChild::Dry
             }
-        }
+        };
+
+        Ok(result)
     }
 }
 
@@ -99,11 +101,16 @@ pub enum ExecutorChild {
 }
 
 impl ExecutorChild {
-    pub fn wait(&mut self) -> Result<ExecutorExitStatus, io::Error> {
-        match self {
-            ExecutorChild::Wet(c) => c.wait().map(ExecutorExitStatus::Wet),
-            ExecutorChild::Dry => Ok(ExecutorExitStatus::Dry),
-        }
+    pub fn wait(&mut self) -> Result<ExecutorExitStatus, Error> {
+        let result = match self {
+            ExecutorChild::Wet(c) => c
+                .wait()
+                .context(ErrorKind::ProcessExecution)
+                .map(ExecutorExitStatus::Wet)?,
+            ExecutorChild::Dry => ExecutorExitStatus::Dry,
+        };
+
+        Ok(result)
     }
 }
 
@@ -113,7 +120,7 @@ pub enum ExecutorExitStatus {
 }
 
 impl Check for ExecutorExitStatus {
-    fn check(self) -> Result<(), failure::Error> {
+    fn check(self) -> Result<(), Error> {
         match self {
             ExecutorExitStatus::Wet(e) => e.check(),
             ExecutorExitStatus::Dry => Ok(()),
diff --git a/src/freebsd.rs b/src/freebsd.rs
index fa2660e1..b4817ee2 100644
--- a/src/freebsd.rs
+++ b/src/freebsd.rs
@@ -1,7 +1,8 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::{print_separator, print_warning};
 use super::utils::Check;
-use failure;
+use failure::ResultExt;
 use std::path::PathBuf;
 use std::process::Command;
 
@@ -10,7 +11,7 @@ pub fn upgrade_freebsd(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'stati
     print_separator("FreeBSD Update");
 
     if let Some(sudo) = sudo {
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(sudo, dry_run)
                 .args(&["/usr/sbin/freebsd-update", "fetch", "install"])
                 .spawn()?
@@ -32,7 +33,7 @@ pub fn upgrade_packages(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'stat
     print_separator("FreeBSD Packages");
 
     if let Some(sudo) = sudo {
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(sudo, dry_run)
                 .args(&["/usr/sbin/pkg", "upgrade"])
                 .spawn()?
@@ -49,13 +50,15 @@ pub fn upgrade_packages(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'stat
     }
 }
 
-pub fn audit_packages(sudo: &Option<PathBuf>) -> Result<(), failure::Error> {
+pub fn audit_packages(sudo: &Option<PathBuf>) -> Result<(), Error> {
     if let Some(sudo) = sudo {
         println!();
         Command::new(sudo)
             .args(&["/usr/sbin/pkg", "audit", "-Fr"])
-            .spawn()?
-            .wait()?;
+            .spawn()
+            .context(ErrorKind::ProcessExecution)?
+            .wait()
+            .context(ErrorKind::ProcessExecution)?;
     }
     Ok(())
 }
diff --git a/src/generic.rs b/src/generic.rs
index 47173e29..df6b7260 100644
--- a/src/generic.rs
+++ b/src/generic.rs
@@ -1,8 +1,9 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{self, Check, PathExt};
 use directories::BaseDirs;
-use failure::Error;
+use failure::ResultExt;
 use std::path::PathBuf;
 use std::process::Command;
 
@@ -229,9 +230,12 @@ pub fn run_composer_update(base_dirs: &BaseDirs, dry_run: bool) -> Option<(&'sta
         let composer_home = || -> Result<PathBuf, Error> {
             let output = Command::new(&composer)
                 .args(&["global", "config", "--absolute", "home"])
-                .output()?;
+                .output()
+                .context(ErrorKind::ProcessExecution)?;
             output.status.check()?;
-            Ok(PathBuf::from(&String::from_utf8(output.stdout)?))
+            Ok(PathBuf::from(
+                &String::from_utf8(output.stdout).context(ErrorKind::ProcessExecution)?,
+            ))
         }();
 
         if let Ok(composer_home) = composer_home {
diff --git a/src/git.rs b/src/git.rs
index 40d8132d..1d3485b8 100644
--- a/src/git.rs
+++ b/src/git.rs
@@ -1,7 +1,7 @@
+use super::error::Error;
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{which, Check};
-use failure::Error;
 use log::{debug, error};
 use std::collections::HashSet;
 use std::io;
diff --git a/src/linux.rs b/src/linux.rs
index bd2a265c..6fccefd1 100644
--- a/src/linux.rs
+++ b/src/linux.rs
@@ -1,8 +1,8 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::{print_separator, print_warning};
 use super::utils::{which, Check};
-use failure;
-use failure_derive::Fail;
+use failure::ResultExt;
 use std::fs;
 use std::path::PathBuf;
 use walkdir::WalkDir;
@@ -19,17 +19,9 @@ pub enum Distribution {
     Void,
 }
 
-#[derive(Debug, Fail)]
-#[fail(display = "Unknown Linux Distribution")]
-struct UnknownLinuxDistribution;
-
-#[derive(Debug, Fail)]
-#[fail(display = "Detected Python is not the system Python")]
-struct NotSystemPython;
-
 impl Distribution {
-    pub fn detect() -> Result<Self, failure::Error> {
-        let content = fs::read_to_string("/etc/os-release")?;
+    pub fn detect() -> Result<Self, Error> {
+        let content = fs::read_to_string("/etc/os-release").context(ErrorKind::UnknownLinuxDistribution)?;
 
         if content.contains("Arch") | content.contains("Manjaro") | content.contains("Antergos") {
             return Ok(Distribution::Arch);
@@ -63,7 +55,7 @@ impl Distribution {
             return Ok(Distribution::Gentoo);
         }
 
-        Err(UnknownLinuxDistribution.into())
+        Err(ErrorKind::UnknownLinuxDistribution)?
     }
 
     #[must_use]
@@ -111,7 +103,7 @@ pub fn show_pacnew() {
     }
 }
 
-fn upgrade_arch_linux(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_arch_linux(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(yay) = which("yay") {
         if let Some(python) = which("python") {
             if python != PathBuf::from("/usr/bin/python") {
@@ -120,7 +112,7 @@ fn upgrade_arch_linux(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failu
 It's dangerous to run yay since Python based AUR packages will be installed in the wrong location",
                     python
                 ));
-                return Err(NotSystemPython.into());
+                return Err(ErrorKind::NotSystemPython)?;
             }
         }
 
@@ -138,7 +130,7 @@ It's dangerous to run yay since Python based AUR packages will be installed in t
     Ok(())
 }
 
-fn upgrade_redhat(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_redhat(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         Executor::new(&sudo, dry_run)
             .args(&["/usr/bin/yum", "upgrade"])
@@ -152,7 +144,7 @@ fn upgrade_redhat(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::
     Ok(())
 }
 
-fn upgrade_opensuse(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_opensuse(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         Executor::new(&sudo, dry_run)
             .args(&["/usr/bin/zypper", "refresh"])
@@ -172,7 +164,7 @@ fn upgrade_opensuse(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure
     Ok(())
 }
 
-fn upgrade_void(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_void(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         Executor::new(&sudo, dry_run)
             .args(&["/usr/bin/xbps-install", "-Su"])
@@ -186,7 +178,7 @@ fn upgrade_void(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Er
     Ok(())
 }
 
-fn upgrade_fedora(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_fedora(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         Executor::new(&sudo, dry_run)
             .args(&["/usr/bin/dnf", "upgrade"])
@@ -200,7 +192,7 @@ fn upgrade_fedora(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::
     Ok(())
 }
 
-fn upgrade_gentoo(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_gentoo(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         if let Some(layman) = which("layman") {
             Executor::new(&sudo, dry_run)
@@ -236,7 +228,7 @@ fn upgrade_gentoo(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::
     Ok(())
 }
 
-fn upgrade_debian(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), failure::Error> {
+fn upgrade_debian(sudo: &Option<PathBuf>, dry_run: bool) -> Result<(), Error> {
     if let Some(sudo) = &sudo {
         Executor::new(&sudo, dry_run)
             .args(&["/usr/bin/apt", "update"])
@@ -262,7 +254,7 @@ pub fn run_needrestart(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'stati
         if let Some(needrestart) = which("needrestart") {
             print_separator("Check for needed restarts");
 
-            let success = || -> Result<(), failure::Error> {
+            let success = || -> Result<(), Error> {
                 Executor::new(&sudo, dry_run)
                     .arg(needrestart)
                     .spawn()?
@@ -285,7 +277,7 @@ pub fn run_fwupdmgr(dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(fwupdmgr) = which("fwupdmgr") {
         print_separator("Firmware upgrades");
 
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(&fwupdmgr, dry_run)
                 .arg("refresh")
                 .spawn()?
@@ -311,7 +303,7 @@ pub fn flatpak_user_update(dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(flatpak) = which("flatpak") {
         print_separator("Flatpak User Packages");
 
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(&flatpak, dry_run)
                 .args(&["update", "--user", "-y"])
                 .spawn()?
@@ -333,7 +325,7 @@ pub fn flatpak_global_update(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&
         if let Some(flatpak) = which("flatpak") {
             print_separator("Flatpak Global Packages");
 
-            let success = || -> Result<(), failure::Error> {
+            let success = || -> Result<(), Error> {
                 Executor::new(&sudo, dry_run)
                     .args(&[flatpak.to_str().unwrap(), "update", "-y"])
                     .spawn()?
@@ -357,7 +349,7 @@ pub fn run_snap(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'static str,
             if PathBuf::from("/var/snapd.socket").exists() {
                 print_separator("snap");
 
-                let success = || -> Result<(), failure::Error> {
+                let success = || -> Result<(), Error> {
                     Executor::new(&sudo, dry_run)
                         .args(&[snap.to_str().unwrap(), "refresh"])
                         .spawn()?
@@ -382,7 +374,7 @@ pub fn run_etc_update(sudo: &Option<PathBuf>, dry_run: bool) -> Option<(&'static
         if let Some(etc_update) = which("etc-update") {
             print_separator("etc-update");
 
-            let success = || -> Result<(), failure::Error> {
+            let success = || -> Result<(), Error> {
                 Executor::new(&sudo, dry_run)
                     .arg(&etc_update.to_str().unwrap())
                     .spawn()?
diff --git a/src/macos.rs b/src/macos.rs
index ef782771..b4f8a912 100644
--- a/src/macos.rs
+++ b/src/macos.rs
@@ -1,13 +1,13 @@
+use super::error::Error;
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::Check;
-use failure;
 
 #[must_use]
 pub fn upgrade_macos(dry_run: bool) -> Option<(&'static str, bool)> {
     print_separator("App Store");
 
-    let success = || -> Result<(), failure::Error> {
+    let success = || -> Result<(), Error> {
         Executor::new("softwareupdate", dry_run)
             .args(&["--install", "--all"])
             .spawn()?
diff --git a/src/main.rs b/src/main.rs
index f8ff3508..e28ecb93 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -32,6 +32,7 @@ mod windows;
 
 mod config;
 mod ctrlc;
+mod error;
 mod executor;
 mod generic;
 mod git;
@@ -44,29 +45,17 @@ mod utils;
 mod vim;
 
 use self::config::Config;
+use self::error::{Error, ErrorKind};
 use self::git::{Git, Repositories};
 use self::report::Report;
-use failure::Error;
-use failure_derive::Fail;
+use failure::{Fail, ResultExt};
 use std::borrow::Cow;
 use std::env;
-use std::io::ErrorKind;
+use std::io;
 use std::process::exit;
 use structopt::StructOpt;
 use terminal::*;
 
-#[derive(Fail, Debug)]
-#[fail(display = "A step failed")]
-struct StepFailed;
-
-#[derive(Fail, Debug)]
-#[fail(display = "Cannot find the user base directories")]
-struct NoBaseDirectories;
-
-#[derive(Fail, Debug)]
-#[fail(display = "Process Interrupted")]
-pub struct Interrupted;
-
 fn execute<'a, F, M>(func: F, no_retry: bool) -> Result<Option<(M, bool)>, Error>
 where
     M: Into<Cow<'a, str>>,
@@ -83,14 +72,7 @@ where
         }
 
         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 {
-                    Error::from(e)
-                }
-            })?;
+        let should_retry = should_ask && should_retry(running).context(ErrorKind::Retry)?;
 
         if !should_retry {
             return Ok(Some((key, success)));
@@ -114,7 +96,7 @@ fn run() -> Result<(), Error> {
 
     env_logger::init();
 
-    let base_dirs = directories::BaseDirs::new().ok_or(NoBaseDirectories)?;
+    let base_dirs = directories::BaseDirs::new().ok_or(ErrorKind::NoBaseDirectories)?;
     let git = Git::new();
     let mut git_repos = Repositories::new(&git);
 
@@ -135,7 +117,7 @@ fn run() -> Result<(), Error> {
 
     if let Some(commands) = config.pre_commands() {
         for (name, command) in commands {
-            generic::run_custom_command(&name, &command, opt.dry_run)?;
+            generic::run_custom_command(&name, &command, opt.dry_run).context(ErrorKind::PreCommand)?;
         }
     }
 
@@ -322,7 +304,7 @@ fn run() -> Result<(), Error> {
     if report.data().iter().all(|(_, succeeded)| *succeeded) {
         Ok(())
     } else {
-        Err(StepFailed.into())
+        Err(ErrorKind::StepFailed)?
     }
 }
 
@@ -332,9 +314,21 @@ fn main() {
             exit(0);
         }
         Err(error) => {
-            if (error.downcast_ref::<StepFailed>().is_some()) || (error.downcast_ref::<Interrupted>().is_some()) {
-            } else {
-                println!("ERROR: {}", error)
+            let should_print = match error.kind() {
+                ErrorKind::StepFailed => false,
+                ErrorKind::Retry => error
+                    .cause()
+                    .and_then(|cause| cause.downcast_ref::<io::Error>())
+                    .filter(|io_error| io_error.kind() == io::ErrorKind::Interrupted)
+                    .is_none(),
+                _ => true,
+            };
+
+            if should_print {
+                println!("Error: {}", error);
+                if let Some(cause) = error.cause() {
+                    println!("Caused by: {}", cause);
+                }
             }
             exit(1);
         }
diff --git a/src/node.rs b/src/node.rs
index e2ed2ee9..4e1e50c2 100644
--- a/src/node.rs
+++ b/src/node.rs
@@ -1,8 +1,9 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{which, Check, PathExt};
 use directories::BaseDirs;
-use failure;
+use failure::ResultExt;
 use std::path::PathBuf;
 use std::process::Command;
 
@@ -15,15 +16,20 @@ impl NPM {
         Self { command }
     }
 
-    fn root(&self) -> Result<PathBuf, failure::Error> {
-        let output = Command::new(&self.command).args(&["root", "-g"]).output()?;
+    fn root(&self) -> Result<PathBuf, Error> {
+        let output = Command::new(&self.command)
+            .args(&["root", "-g"])
+            .output()
+            .context(ErrorKind::ProcessExecution)?;
 
         output.status.check()?;
 
-        Ok(PathBuf::from(&String::from_utf8(output.stdout)?))
+        Ok(PathBuf::from(
+            &String::from_utf8(output.stdout).context(ErrorKind::ProcessExecution)?,
+        ))
     }
 
-    fn upgrade(&self, dry_run: bool) -> Result<(), failure::Error> {
+    fn upgrade(&self, dry_run: bool) -> Result<(), Error> {
         Executor::new(&self.command, dry_run)
             .args(&["update", "-g"])
             .spawn()?
@@ -53,7 +59,7 @@ pub fn yarn_global_update(dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(yarn) = which("yarn") {
         print_separator("Yarn");
 
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(&yarn, dry_run)
                 .args(&["global", "upgrade", "-s"])
                 .spawn()?
diff --git a/src/self_update.rs b/src/self_update.rs
index ec9f71f5..fe5a6ade 100644
--- a/src/self_update.rs
+++ b/src/self_update.rs
@@ -1,5 +1,6 @@
+use super::error::{Error, ErrorKind};
 use super::terminal::*;
-use failure::Error;
+use failure::ResultExt;
 use self_update_crate;
 #[cfg(unix)]
 use std::env;
@@ -13,8 +14,9 @@ pub fn self_update() -> Result<(), Error> {
     #[cfg(unix)]
     let current_exe = env::current_exe();
 
-    let target = self_update_crate::get_target()?;
-    let result = self_update_crate::backends::github::Update::configure()?
+    let target = self_update_crate::get_target().context(ErrorKind::SelfUpdate)?;
+    let result = self_update_crate::backends::github::Update::configure()
+        .context(ErrorKind::SelfUpdate)?
         .repo_owner("r-darwish")
         .repo_name("topgrade")
         .target(&target)
@@ -23,8 +25,10 @@ pub fn self_update() -> Result<(), Error> {
         .show_download_progress(true)
         .current_version(self_update_crate::cargo_crate_version!())
         .no_confirm(true)
-        .build()?
-        .update()?;
+        .build()
+        .context(ErrorKind::SelfUpdate)?
+        .update()
+        .context(ErrorKind::SelfUpdate)?;
 
     if let self_update_crate::Status::Updated(version) = &result {
         println!("\nTopgrade upgraded to {}", version);
@@ -36,8 +40,10 @@ pub fn self_update() -> Result<(), Error> {
     {
         if result.updated() {
             print_warning("Respawning...");
-            let err = Command::new(current_exe?).args(env::args().skip(1)).exec();
-            Err(err)?
+            let err = Command::new(current_exe.context(ErrorKind::SelfUpdate)?)
+                .args(env::args().skip(1))
+                .exec();
+            Err(err).context(ErrorKind::SelfUpdate)?
         }
     }
 
diff --git a/src/tmux.rs b/src/tmux.rs
index bf95f3f4..cae45dd7 100644
--- a/src/tmux.rs
+++ b/src/tmux.rs
@@ -1,9 +1,10 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::which;
 use super::utils::{Check, PathExt};
 use directories::BaseDirs;
-use failure::Error;
+use failure::ResultExt;
 use std::env;
 use std::io;
 use std::os::unix::process::CommandExt;
@@ -41,8 +42,10 @@ fn has_session(tmux: &Path, session_name: &str) -> Result<bool, io::Error> {
 fn run_in_session(tmux: &Path, command: &str) -> Result<(), Error> {
     Command::new(tmux)
         .args(&["new-window", "-a", "-t", "topgrade:1", command])
-        .spawn()?
-        .wait()?
+        .spawn()
+        .context(ErrorKind::ProcessExecution)?
+        .wait()
+        .context(ErrorKind::ProcessExecution)?
         .check()?;
 
     Ok(())
diff --git a/src/unix.rs b/src/unix.rs
index 501a15b5..4d05a79c 100644
--- a/src/unix.rs
+++ b/src/unix.rs
@@ -2,7 +2,7 @@ use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{which, Check};
 use directories::BaseDirs;
-use failure::Error;
+use Error;
 
 pub fn run_zplug(base_dirs: &BaseDirs, dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(zsh) = which("zsh") {
diff --git a/src/utils.rs b/src/utils.rs
index d01cc515..37af057f 100644
--- a/src/utils.rs
+++ b/src/utils.rs
@@ -1,5 +1,4 @@
-use failure::Error;
-use failure_derive::Fail;
+use super::error::{Error, ErrorKind};
 use log::{debug, error};
 use std::ffi::OsStr;
 use std::fmt::Debug;
@@ -7,10 +6,6 @@ use std::path::{Path, PathBuf};
 use std::process::{ExitStatus, Output};
 use which as which_mod;
 
-#[derive(Fail, Debug)]
-#[fail(display = "Process failed")]
-pub struct ProcessFailed;
-
 pub trait Check {
     fn check(self) -> Result<(), Error>;
 }
@@ -20,7 +15,7 @@ impl Check for ExitStatus {
         if self.success() {
             Ok(())
         } else {
-            Err(Error::from(ProcessFailed {}))
+            Err(ErrorKind::ProcessFailed(self))?
         }
     }
 }
diff --git a/src/vim.rs b/src/vim.rs
index da0d4e6b..73701caa 100644
--- a/src/vim.rs
+++ b/src/vim.rs
@@ -1,8 +1,8 @@
+use super::error::Error;
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{which, Check, PathExt};
 use directories::BaseDirs;
-use failure;
 use std::fs;
 use std::path::PathBuf;
 
@@ -54,12 +54,7 @@ fn nvimrc(base_dirs: &BaseDirs) -> Option<PathBuf> {
 }
 
 #[must_use]
-fn upgrade(
-    vim: &PathBuf,
-    vimrc: &PathBuf,
-    plugin_framework: PluginFramework,
-    dry_run: bool,
-) -> Result<(), failure::Error> {
+fn upgrade(vim: &PathBuf, vimrc: &PathBuf, plugin_framework: PluginFramework, dry_run: bool) -> Result<(), Error> {
     Executor::new(&vim, dry_run)
         .args(&[
             "-N",
diff --git a/src/windows.rs b/src/windows.rs
index 946dba33..4efbda20 100644
--- a/src/windows.rs
+++ b/src/windows.rs
@@ -1,7 +1,8 @@
+use super::error::{Error, ErrorKind};
 use super::executor::Executor;
 use super::terminal::print_separator;
 use super::utils::{self, which, Check};
-use failure;
+use failure::ResultExt;
 use log::error;
 use std::path::PathBuf;
 use std::process::Command;
@@ -11,7 +12,7 @@ pub fn run_chocolatey(dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(choco) = utils::which("choco") {
         print_separator("Chocolatey");
 
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(&choco, dry_run)
                 .args(&["upgrade", "all"])
                 .spawn()?
@@ -32,7 +33,7 @@ pub fn run_scoop(dry_run: bool) -> Option<(&'static str, bool)> {
     if let Some(scoop) = utils::which("scoop") {
         print_separator("Scoop");
 
-        let success = || -> Result<(), failure::Error> {
+        let success = || -> Result<(), Error> {
             Executor::new(&scoop, dry_run)
                 .args(&["update"])
                 .spawn()?
@@ -65,10 +66,11 @@ impl Powershell {
     }
 
     pub fn has_command(powershell: &PathBuf, command: &str) -> bool {
-        || -> Result<(), failure::Error> {
+        || -> Result<(), Error> {
             Command::new(&powershell)
                 .args(&["-Command", &format!("Get-Command {}", command)])
-                .output()?
+                .output()
+                .context(ErrorKind::ProcessExecution)?
                 .check()?;
             Ok(())
         }()
@@ -77,8 +79,11 @@ impl Powershell {
 
     pub fn profile(&self) -> Option<PathBuf> {
         if let Some(powershell) = &self.path {
-            let result = || -> Result<PathBuf, failure::Error> {
-                let output = Command::new(powershell).args(&["-Command", "echo $profile"]).output()?;
+            let result = || -> Result<PathBuf, Error> {
+                let output = Command::new(powershell)
+                    .args(&["-Command", "echo $profile"])
+                    .output()
+                    .context(ErrorKind::ProcessExecution)?;
                 output.status.check()?;
                 Ok(PathBuf::from(
                     String::from_utf8_lossy(&output.stdout).trim().to_string(),
@@ -98,7 +103,7 @@ impl Powershell {
         if let Some(powershell) = &self.path {
             print_separator("Powershell Modules Update");
 
-            let success = || -> Result<(), failure::Error> {
+            let success = || -> Result<(), Error> {
                 Executor::new(&powershell, dry_run)
                     .arg("Update-Module")
                     .spawn()?
@@ -120,7 +125,7 @@ impl Powershell {
             if Self::has_command(&powershell, "Install-WindowsUpdate") {
                 print_separator("Windows Update");
 
-                let success = || -> Result<(), failure::Error> {
+                let success = || -> Result<(), Error> {
                     Executor::new(&powershell, dry_run)
                         .args(&["-Command", "Install-WindowsUpdate -MicrosoftUpdate -AcceptAll -Verbose"])
                         .spawn()?