diff --git a/cli/src/cmd_auth.rs b/cli/src/cmd_auth.rs
index 57a2f91f..fb04df48 100644
--- a/cli/src/cmd_auth.rs
+++ b/cli/src/cmd_auth.rs
@@ -486,6 +486,27 @@ impl CmdAuthStatus {
 
 #[cfg(test)]
 mod tests {
+    #[test]
+    fn test_cmd_auth_login() {
+        use assert_cmd::Command;
+        use predicates::str;
+
+        let bad_url = "sys.oxide.invalid";
+
+        // Validate connection error details are printed
+        Command::cargo_bin("oxide")
+            .unwrap()
+            .arg("auth")
+            .arg("login")
+            .arg("--host")
+            .arg(bad_url)
+            .assert()
+            .failure()
+            .stderr(str::starts_with(format!(
+                "Request failed: error sending request for url (https://{bad_url}/device/auth):"
+            )));
+    }
+
     #[test]
     fn test_parse_host() {
         use super::parse_host;
diff --git a/cli/src/main.rs b/cli/src/main.rs
index 9e70b5b8..91093ef0 100644
--- a/cli/src/main.rs
+++ b/cli/src/main.rs
@@ -101,7 +101,8 @@ async fn main() {
         .await
         .unwrap();
     if let Err(e) = result {
-        eprintln!("{e}");
+        let src = e.source().map(|s| format!(": {s}")).unwrap_or_default();
+        eprintln!("{e}{src}");
         std::process::exit(1)
     }
 }