diff --git a/src/error.rs b/src/error.rs
index 93afbe0..69dc3f0 100644
--- a/src/error.rs
+++ b/src/error.rs
@@ -1,6 +1,6 @@
 use crate::emoji;
 
-#[derive(Debug, PartialEq, Eq, miette::Diagnostic, thiserror::Error)]
+#[derive(Debug, miette::Diagnostic, thiserror::Error)]
 pub enum Error {
     // Host Triple
     #[diagnostic(code(espup::host_triple::unsupported_host_triple))]
@@ -26,4 +26,15 @@ pub enum Error {
     #[diagnostic(code(espup::config::failed_to_write))]
     #[error("{} Failed to write config to '{0}'", emoji::ERROR)]
     FailedToWrite(String),
+    //  Toolchain
+    #[error(transparent)]
+    IoError(#[from] std::io::Error),
+    #[error(transparent)]
+    RewquestError(#[from] reqwest::Error),
+    #[diagnostic(code(espup::toolchain::failed_to_create_directory))]
+    #[error("{} Creating directory '{0}' failed", emoji::ERROR)]
+    FailedToCreateDirectory(String),
+    #[diagnostic(code(espup::toolchain::unsupported_file_extension))]
+    #[error("{} Unsuported file extension: '{0}'", emoji::ERROR)]
+    UnsuportedFileExtension(String),
 }
diff --git a/src/toolchain/mod.rs b/src/toolchain/mod.rs
index fc1e004..e90d2cb 100644
--- a/src/toolchain/mod.rs
+++ b/src/toolchain/mod.rs
@@ -1,5 +1,5 @@
-use crate::emoji;
-use anyhow::{bail, Result};
+use crate::{emoji, error::Error};
+use anyhow::Result;
 use dirs::home_dir;
 use flate2::bufread::GzDecoder;
 use log::info;
@@ -27,7 +27,7 @@ pub fn download_file(
     file_name: &str,
     output_directory: &str,
     uncompress: bool,
-) -> Result<String> {
+) -> Result<String, Error> {
     let file_path = format!("{}/{}", output_directory, file_name);
     if Path::new(&file_path).exists() {
         info!("{} Using cached file: '{}'", emoji::INFO, file_path);
@@ -39,11 +39,7 @@ pub fn download_file(
             output_directory
         );
         if let Err(_e) = create_dir_all(output_directory) {
-            bail!(
-                "{} Creating directory '{}' failed",
-                emoji::ERROR,
-                output_directory
-            );
+            return Err(Error::FailedToCreateDirectory(output_directory.to_string()));
         }
     }
     info!(
@@ -86,11 +82,7 @@ pub fn download_file(
                 archive.unpack(output_directory).unwrap();
             }
             _ => {
-                bail!(
-                    "{} Unsuported file extension: '{}'",
-                    emoji::ERROR,
-                    extension
-                );
+                return Err(Error::UnsuportedFileExtension(extension.to_string()));
             }
         }
     } else {