diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index e583661f7..aa9ccb858 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -1165,7 +1165,7 @@ func latestCommand(logger *log.Logger, all bool, toolName, pattern string) (err
 	}
 
 	if !all {
-		err = latestForPlugin(conf, toolName, pattern, false)
+		err = latestForPlugin(conf, toolName, pattern, false, os.Stderr)
 		if err != nil {
 			cli.OsExiter(1)
 		}
@@ -1182,7 +1182,7 @@ func latestCommand(logger *log.Logger, all bool, toolName, pattern string) (err
 	var maybeErr error
 	// loop over all plugins and show latest for each one.
 	for _, plugin := range plugins {
-		maybeErr = latestForPlugin(conf, plugin.Name, "", true)
+		maybeErr = latestForPlugin(conf, plugin.Name, "", true, os.Stderr)
 		if maybeErr != nil {
 			err = maybeErr
 		}
@@ -1550,10 +1550,10 @@ func reshimToolVersion(conf config.Config, plugin plugins.Plugin, versionStr str
 	return shims.GenerateForVersion(conf, plugin, version, out, errOut)
 }
 
-func latestForPlugin(conf config.Config, toolName, pattern string, showStatus bool) error {
+func latestForPlugin(conf config.Config, toolName, pattern string, showStatus bool, errOut io.Writer) error {
 	// show single plugin
 	plugin := plugins.New(conf, toolName)
-	latest, err := versions.Latest(plugin, pattern)
+	latest, err := versions.Latest(plugin, pattern, errOut)
 	if err != nil && err.Error() != "no latest version found" {
 		fmt.Printf("unable to load latest version: %s\n", err)
 		return err
diff --git a/internal/cli/set/set.go b/internal/cli/set/set.go
index 407872e81..de22b5796 100644
--- a/internal/cli/set/set.go
+++ b/internal/cli/set/set.go
@@ -40,7 +40,7 @@ func Main(_ io.Writer, stderr io.Writer, args []string, home bool, parent bool,
 		parsedVersion := toolversions.ParseFromCliArg(version)
 		if parsedVersion.Type == "latest" {
 			plugin := plugins.New(conf, args[0])
-			resolvedVersion, err := versions.Latest(plugin, parsedVersion.Value)
+			resolvedVersion, err := versions.Latest(plugin, parsedVersion.Value, os.Stderr)
 			if err != nil {
 				return fmt.Errorf("unable to resolve latest version for %s", plugin.Name)
 			}
diff --git a/internal/versions/versions.go b/internal/versions/versions.go
index 2cf669928..5e2f640bc 100644
--- a/internal/versions/versions.go
+++ b/internal/versions/versions.go
@@ -128,7 +128,7 @@ func InstallVersion(conf config.Config, plugin plugins.Plugin, version toolversi
 
 	resolvedVersion := ""
 	if version.Type == latestVersion {
-		resolvedVersion, err = Latest(plugin, version.Value)
+		resolvedVersion, err = Latest(plugin, version.Value, stdErr)
 		if err != nil {
 			return err
 		}
@@ -235,11 +235,10 @@ func InstallOneVersion(conf config.Config, plugin plugins.Plugin, versionStr str
 // the version it returns. If the callback is missing it invokes the list-all
 // callback and returns the last version matching the query, if a query is
 // provided.
-func Latest(plugin plugins.Plugin, query string) (version string, err error) {
+func Latest(plugin plugins.Plugin, query string, stdErr io.Writer) (version string, err error) {
 	var stdOut strings.Builder
-	var stdErr strings.Builder
 
-	err = plugin.RunCallback("latest-stable", []string{query}, map[string]string{}, &stdOut, &stdErr)
+	err = plugin.RunCallback("latest-stable", []string{query}, map[string]string{}, &stdOut, stdErr)
 	if err == nil {
 		versions := parseVersions(stdOut.String())
 		if len(versions) < 1 {
@@ -253,7 +252,7 @@ func Latest(plugin plugins.Plugin, query string) (version string, err error) {
 		return version, err
 	}
 
-	allVersions, err := AllVersions(plugin)
+	allVersions, err := AllVersions(plugin, stdErr)
 	if err != nil {
 		return version, err
 	}
@@ -276,11 +275,10 @@ func Latest(plugin plugins.Plugin, query string) (version string, err error) {
 
 // AllVersions returns a slice of all available versions for the tool managed by
 // the given plugin by invoking the plugin's list-all callback
-func AllVersions(plugin plugins.Plugin) (versions []string, err error) {
+func AllVersions(plugin plugins.Plugin, stdErr io.Writer) (versions []string, err error) {
 	var stdout strings.Builder
-	var stderr strings.Builder
 
-	err = plugin.RunCallback("list-all", []string{}, map[string]string{}, &stdout, &stderr)
+	err = plugin.RunCallback("list-all", []string{}, map[string]string{}, &stdout, stdErr)
 	if err != nil {
 		return versions, err
 	}
diff --git a/internal/versions/versions_test.go b/internal/versions/versions_test.go
index bb5a93874..1affad3fb 100644
--- a/internal/versions/versions_test.go
+++ b/internal/versions/versions_test.go
@@ -2,6 +2,7 @@ package versions
 
 import (
 	"fmt"
+	"io"
 	"os"
 	"path/filepath"
 	"strings"
@@ -334,7 +335,7 @@ func TestLatest(t *testing.T) {
 		assert.Nil(t, err)
 		plugin := plugins.New(conf, pluginName)
 
-		version, err := Latest(plugin, "")
+		version, err := Latest(plugin, "", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, "2.0.0", version)
 	})
@@ -350,25 +351,25 @@ func TestLatest(t *testing.T) {
 		err = os.WriteFile(latestScript, []byte("#!/usr/bin/env bash\necho 1.2.3-dev"), 0o777)
 		assert.Nil(t, err)
 
-		version, err := Latest(plugin, "")
+		version, err := Latest(plugin, "", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, "1.2.3-dev", version)
 	})
 
 	t.Run("when given query matching no versions return empty slice of versions", func(t *testing.T) {
-		version, err := Latest(plugin, "impossible-to-satisfy-query")
+		version, err := Latest(plugin, "impossible-to-satisfy-query", io.Discard)
 		assert.Error(t, err, "no latest version found")
 		assert.Equal(t, version, "")
 	})
 
 	t.Run("when given no query returns latest version of plugin", func(t *testing.T) {
-		version, err := Latest(plugin, "")
+		version, err := Latest(plugin, "", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, "5.1.0", version)
 	})
 
 	t.Run("when given no query returns latest version of plugin", func(t *testing.T) {
-		version, err := Latest(plugin, "4")
+		version, err := Latest(plugin, "4", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, "4.0.0", version)
 	})
@@ -387,7 +388,7 @@ func TestLatest(t *testing.T) {
 		err = os.Remove(latestScript)
 		assert.Nil(t, err)
 
-		version, err := Latest(plugin, "")
+		version, err := Latest(plugin, "", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, "3.4.5", version)
 	})
@@ -424,7 +425,7 @@ func TestLatestWithSamples(t *testing.T) {
 		assert.Nil(t, err)
 
 		plugin := plugins.New(conf, pluginName)
-		version, err := Latest(plugin, "")
+		version, err := Latest(plugin, "", io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, tt.expectedOutput, version)
 	}
@@ -438,7 +439,7 @@ func TestAllVersions(t *testing.T) {
 	plugin := plugins.New(conf, pluginName)
 
 	t.Run("returns slice of available versions from plugin", func(t *testing.T) {
-		versions, err := AllVersions(plugin)
+		versions, err := AllVersions(plugin, io.Discard)
 		assert.Nil(t, err)
 		assert.Equal(t, versions, []string{"1.0.0", "1.1.0", "2.0.0"})
 	})
@@ -449,10 +450,24 @@ func TestAllVersions(t *testing.T) {
 		assert.Nil(t, err)
 		plugin := plugins.New(conf, pluginName)
 
-		versions, err := AllVersions(plugin)
+		versions, err := AllVersions(plugin, io.Discard)
 		assert.Equal(t, err.(plugins.NoCallbackError).Error(), "Plugin named list-all-fail does not have a callback named list-all")
 		assert.Empty(t, versions)
 	})
+
+	t.Run("returns error when callback fails", func(t *testing.T) {
+		pluginName = "list-all-stderr"
+		_, err := repotest.InstallPlugin("dummy_broken_plugin", conf.DataDir, pluginName)
+		assert.Nil(t, err)
+		plugin := plugins.New(conf, pluginName)
+
+		var stdErr strings.Builder
+
+		versions, err := AllVersions(plugin, &stdErr)
+		assert.Equal(t, "exit status 1", err.Error())
+		assert.Empty(t, versions)
+		assert.Equal(t, "List-all failed!\n", stdErr.String())
+	})
 }
 
 func TestUninstall(t *testing.T) {