diff --git a/leo/errors/mod.rs b/leo/errors/mod.rs
index bc7859ca5d..9fa3bd3d12 100644
--- a/leo/errors/mod.rs
+++ b/leo/errors/mod.rs
@@ -19,3 +19,6 @@ pub use self::cli::*;
 
 pub mod commands;
 pub use self::commands::*;
+
+pub mod updater;
+pub use self::updater::*;
diff --git a/leo/errors/updater.rs b/leo/errors/updater.rs
new file mode 100644
index 0000000000..8bfa4bdec9
--- /dev/null
+++ b/leo/errors/updater.rs
@@ -0,0 +1,31 @@
+// Copyright (C) 2019-2020 Aleo Systems Inc.
+// This file is part of the Leo library.
+
+// The Leo library is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+
+// The Leo library is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+// GNU General Public License for more details.
+
+// You should have received a copy of the GNU General Public License
+// along with the Leo library. If not, see <https://www.gnu.org/licenses/>.
+
+#[derive(Debug, Error)]
+pub enum UpdaterError {
+    #[error("{}: {}", _0, _1)]
+    Crate(&'static str, String),
+
+    #[error("The current version {} is more recent than the release version {}", _0, _1)]
+    OldReleaseVersion(String, String),
+}
+
+impl From<self_update::errors::Error> for UpdaterError {
+    fn from(error: self_update::errors::Error) -> Self {
+        tracing::error!("{}\n", error);
+        UpdaterError::Crate("self_update", error.to_string())
+    }
+}
diff --git a/leo/updater.rs b/leo/updater.rs
index 84f088f68f..a37ee7d184 100644
--- a/leo/updater.rs
+++ b/leo/updater.rs
@@ -13,7 +13,7 @@
 
 // You should have received a copy of the GNU General Public License
 // along with the Leo library. If not, see <https://www.gnu.org/licenses/>.
-use crate::config::Config;
+use crate::{config::Config, errors::UpdaterError};
 
 use colored::Colorize;
 use self_update::{backends::github, version::bump_is_greater, Status};
@@ -27,7 +27,7 @@ impl Updater {
     const LEO_REPO_OWNER: &'static str = "AleoHQ";
 
     /// Show all available releases for `leo`.
-    pub fn show_available_releases() -> Result<(), self_update::errors::Error> {
+    pub fn show_available_releases() -> Result<(), UpdaterError> {
         let releases = github::ReleaseList::configure()
             .repo_owner(Self::LEO_REPO_OWNER)
             .repo_name(Self::LEO_REPO_NAME)
@@ -42,7 +42,7 @@ impl Updater {
     }
 
     /// Update `leo` to the latest release.
-    pub fn update_to_latest_release(show_output: bool) -> Result<Status, self_update::errors::Error> {
+    pub fn update_to_latest_release(show_output: bool) -> Result<Status, UpdaterError> {
         let status = github::Update::configure()
             .repo_owner(Self::LEO_REPO_OWNER)
             .repo_name(Self::LEO_REPO_NAME)
@@ -58,7 +58,7 @@ impl Updater {
     }
 
     /// Check if there is an available update for `leo` and return the newest release.
-    pub fn update_available() -> Result<Option<String>, self_update::errors::Error> {
+    pub fn update_available() -> Result<String, UpdaterError> {
         let updater = github::Update::configure()
             .repo_owner(Self::LEO_REPO_OWNER)
             .repo_name(Self::LEO_REPO_NAME)
@@ -70,9 +70,9 @@ impl Updater {
         let latest_release = updater.get_latest_release()?;
 
         if bump_is_greater(&current_version, &latest_release.version)? {
-            Ok(Some(latest_release.version))
+            Ok(latest_release.version)
         } else {
-            Ok(None)
+            Err(UpdaterError::OldReleaseVersion(current_version, latest_release.version))
         }
     }
 
@@ -89,7 +89,7 @@ impl Updater {
             }
         } else {
             // If the auto update configuration is off, notify the user to update leo.
-            if let Some(latest_version) = Self::update_available().unwrap() {
+            if let Ok(latest_version) = Self::update_available() {
                 let mut message = "🟢 A new version is available! Run".bold().green().to_string();
                 message += &" `leo update` ".bold().white();
                 message += &format!("to update to v{}.", latest_version).bold().green();