Show full error chain on tool upgrade failures

crates/uv/src/commands/tool/upgrade.rs

@@ -1,6 +1,7 @@
 use std::{collections::BTreeSet, fmt::Write};
 
 use anyhow::Result;
+use itertools::Itertools;
 use owo_colors::OwoColorize;
 use tracing::debug;
 
@@ -95,9 +96,7 @@ pub(crate) async fn upgrade(
     // Determine whether we applied any upgrades.
     let mut did_upgrade_environment = vec![];
 
-    // Determine whether any tool upgrade failed.
-    let mut failed_upgrade = false;
-
+    let mut errors = Vec::new();
     for name in &names {
         debug!("Upgrading tool: `{name}`");
         let result = upgrade_tool(
@@ -125,22 +124,31 @@ pub(crate) async fn upgrade(
                 debug!("Upgrading `{name}` was a no-op");
             }
             Err(err) => {
-                // If we have a single tool, return the error directly.
-                if names.len() > 1 {
-                    writeln!(
-                        printer.stderr(),
-                        "Failed to upgrade `{}`: {err}",
-                        name.cyan(),
-                    )?;
-                } else {
-                    writeln!(printer.stderr(), "{err}")?;
-                }
-                failed_upgrade = true;
+                errors.push((name, err));
             }
         }
     }
 
-    if failed_upgrade {
+    if !errors.is_empty() {
+        for (name, err) in errors
+            .into_iter()
+            .sorted_unstable_by(|(name_a, _), (name_b, _)| name_a.cmp(name_b))
+        {
+            writeln!(
+                printer.stderr(),
+                "{}: Failed to upgrade {}",
+                "error".red().bold(),
+                name.green()
+            )?;
+            for err in err.chain() {
+                writeln!(
+                    printer.stderr(),
+                    "  {}: {}",
+                    "Caused by".red().bold(),
+                    err.to_string().trim()
+                )?;
+            }
+        }
         return Ok(ExitStatus::Failure);
     }
 

crates/uv/tests/it/tool_upgrade.rs

@@ -6,7 +6,7 @@ use uv_static::EnvVars;
 use crate::common::{uv_snapshot, TestContext};
 
 #[test]
-fn test_tool_upgrade_name() {
+fn tool_upgrade_name() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -56,7 +56,7 @@ fn test_tool_upgrade_name() {
 }
 
 #[test]
-fn test_tool_upgrade_multiple_names() {
+fn tool_upgrade_multiple_names() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -131,7 +131,7 @@ fn test_tool_upgrade_multiple_names() {
 }
 
 #[test]
-fn test_tool_upgrade_all() {
+fn tool_upgrade_all() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -205,7 +205,7 @@ fn test_tool_upgrade_all() {
 }
 
 #[test]
-fn test_tool_upgrade_non_existing_package() {
+fn tool_upgrade_non_existing_package() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -223,7 +223,8 @@ fn test_tool_upgrade_non_existing_package() {
     ----- stdout -----
 
     ----- stderr -----
-    `black` is not installed; run `uv tool install black` to install
+    error: Failed to upgrade black
+      Caused by: `black` is not installed; run `uv tool install black` to install
     "###);
 
     // Attempt to upgrade all.
@@ -242,7 +243,7 @@ fn test_tool_upgrade_non_existing_package() {
 }
 
 #[test]
-fn test_tool_upgrade_not_stop_if_upgrade_fails() -> anyhow::Result<()> {
+fn tool_upgrade_not_stop_if_upgrade_fails() -> anyhow::Result<()> {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -314,14 +315,15 @@ fn test_tool_upgrade_not_stop_if_upgrade_fails() -> anyhow::Result<()> {
      + babel==2.14.0
      - pytz==2018.5
     Installed 1 executable: pybabel
-    Failed to upgrade `python-dotenv`: `python-dotenv` is missing a valid receipt; run `uv tool install --force python-dotenv` to reinstall
+    error: Failed to upgrade python-dotenv
+      Caused by: `python-dotenv` is missing a valid receipt; run `uv tool install --force python-dotenv` to reinstall
     "###);
 
     Ok(())
 }
 
 #[test]
-fn test_tool_upgrade_settings() {
+fn tool_upgrade_settings() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -386,7 +388,7 @@ fn test_tool_upgrade_settings() {
 }
 
 #[test]
-fn test_tool_upgrade_respect_constraints() {
+fn tool_upgrade_respect_constraints() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -437,7 +439,7 @@ fn test_tool_upgrade_respect_constraints() {
 }
 
 #[test]
-fn test_tool_upgrade_constraint() {
+fn tool_upgrade_constraint() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -530,7 +532,7 @@ fn test_tool_upgrade_constraint() {
 /// Upgrade a tool, but only by upgrading one of it's `--with` dependencies, and not the tool
 /// itself.
 #[test]
-fn test_tool_upgrade_with() {
+fn tool_upgrade_with() {
     let context = TestContext::new("3.12")
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -578,7 +580,7 @@ fn test_tool_upgrade_with() {
 }
 
 #[test]
-fn test_tool_upgrade_python() {
+fn tool_upgrade_python() {
     let context = TestContext::new_with_versions(&["3.11", "3.12"])
         .with_filtered_counts()
         .with_filtered_exe_suffix();
@@ -639,7 +641,7 @@ fn test_tool_upgrade_python() {
 }
 
 #[test]
-fn test_tool_upgrade_python_with_all() {
+fn tool_upgrade_python_with_all() {
     let context = TestContext::new_with_versions(&["3.11", "3.12"])
         .with_filtered_counts()
         .with_filtered_exe_suffix();