diff --git a/cmd/traefik/plugins.go b/cmd/traefik/plugins.go
index f94535f92..c2b847819 100644
--- a/cmd/traefik/plugins.go
+++ b/cmd/traefik/plugins.go
@@ -35,12 +35,12 @@ func initPlugins(staticCfg *static.Configuration) (*plugins.Client, map[string]p
 		var err error
 		client, err = plugins.NewClient(opts)
 		if err != nil {
-			return nil, nil, nil, err
+			return nil, nil, nil, fmt.Errorf("unable to create plugins client: %w", err)
 		}
 
 		err = plugins.SetupRemotePlugins(client, staticCfg.Experimental.Plugins)
 		if err != nil {
-			return nil, nil, nil, err
+			return nil, nil, nil, fmt.Errorf("unable to set up plugins environment: %w", err)
 		}
 
 		plgs = staticCfg.Experimental.Plugins
diff --git a/pkg/plugins/client.go b/pkg/plugins/client.go
index e891da5c4..4fcdd1ab4 100644
--- a/pkg/plugins/client.go
+++ b/pkg/plugins/client.go
@@ -264,7 +264,7 @@ func (c *Client) unzipArchive(pName, pVersion string) error {
 	for _, f := range archive.File {
 		err = unzipFile(f, dest)
 		if err != nil {
-			return err
+			return fmt.Errorf("unable to unzip %s: %w", f.Name, err)
 		}
 	}
 
@@ -283,12 +283,17 @@ func unzipFile(f *zipa.File, dest string) error {
 	p := filepath.Join(dest, pathParts[1])
 
 	if f.FileInfo().IsDir() {
-		return os.MkdirAll(p, f.Mode())
+		err = os.MkdirAll(p, f.Mode())
+		if err != nil {
+			return fmt.Errorf("unable to create archive directory %s: %w", p, err)
+		}
+
+		return nil
 	}
 
 	err = os.MkdirAll(filepath.Dir(p), 0o750)
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to create archive directory %s for file %s: %w", filepath.Dir(p), p, err)
 	}
 
 	elt, err := os.OpenFile(p, os.O_WRONLY|os.O_CREATE|os.O_TRUNC, f.Mode())
@@ -347,7 +352,7 @@ func (c *Client) WriteState(plugins map[string]Descriptor) error {
 
 	mp, err := json.MarshalIndent(m, "", "  ")
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to marshal plugin state: %w", err)
 	}
 
 	return os.WriteFile(c.stateFile, mp, 0o600)
@@ -361,10 +366,15 @@ func (c *Client) ResetAll() error {
 
 	err := resetDirectory(filepath.Join(c.goPath, ".."))
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to reset plugins GoPath directory %s: %w", c.goPath, err)
 	}
 
-	return resetDirectory(c.archives)
+	err = resetDirectory(c.archives)
+	if err != nil {
+		return fmt.Errorf("unable to reset plugins archives directory: %w", err)
+	}
+
+	return nil
 }
 
 func (c *Client) buildArchivePath(pName, pVersion string) string {
@@ -374,12 +384,12 @@ func (c *Client) buildArchivePath(pName, pVersion string) string {
 func resetDirectory(dir string) error {
 	dirPath, err := filepath.Abs(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to get absolute path of %s: %w", dir, err)
 	}
 
 	currentPath, err := os.Getwd()
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to get the current directory: %w", err)
 	}
 
 	if strings.HasPrefix(currentPath, dirPath) {
@@ -388,10 +398,15 @@ func resetDirectory(dir string) error {
 
 	err = os.RemoveAll(dir)
 	if err != nil {
-		return err
+		return fmt.Errorf("unable to remove directory %s: %w", dirPath, err)
 	}
 
-	return os.MkdirAll(dir, 0o755)
+	err = os.MkdirAll(dir, 0o755)
+	if err != nil {
+		return fmt.Errorf("unable to create directory %s: %w", dirPath, err)
+	}
+
+	return nil
 }
 
 func computeHash(filepath string) (string, error) {
diff --git a/pkg/plugins/plugins.go b/pkg/plugins/plugins.go
index fdfb9fbce..6888ceea4 100644
--- a/pkg/plugins/plugins.go
+++ b/pkg/plugins/plugins.go
@@ -21,7 +21,7 @@ func SetupRemotePlugins(client *Client, plugins map[string]Descriptor) error {
 
 	err = client.CleanArchives(plugins)
 	if err != nil {
-		return fmt.Errorf("failed to clean archives: %w", err)
+		return fmt.Errorf("unable to clean archives: %w", err)
 	}
 
 	ctx := context.Background()
@@ -32,27 +32,27 @@ func SetupRemotePlugins(client *Client, plugins map[string]Descriptor) error {
 		hash, err := client.Download(ctx, desc.ModuleName, desc.Version)
 		if err != nil {
 			_ = client.ResetAll()
-			return fmt.Errorf("failed to download plugin %s: %w", desc.ModuleName, err)
+			return fmt.Errorf("unable to download plugin %s: %w", desc.ModuleName, err)
 		}
 
 		err = client.Check(ctx, desc.ModuleName, desc.Version, hash)
 		if err != nil {
 			_ = client.ResetAll()
-			return fmt.Errorf("failed to check archive integrity of the plugin %s: %w", desc.ModuleName, err)
+			return fmt.Errorf("unable to check archive integrity of the plugin %s: %w", desc.ModuleName, err)
 		}
 	}
 
 	err = client.WriteState(plugins)
 	if err != nil {
 		_ = client.ResetAll()
-		return fmt.Errorf("failed to write plugins state: %w", err)
+		return fmt.Errorf("unable to write plugins state: %w", err)
 	}
 
 	for _, desc := range plugins {
 		err = client.Unzip(desc.ModuleName, desc.Version)
 		if err != nil {
 			_ = client.ResetAll()
-			return fmt.Errorf("failed to unzip archive: %w", err)
+			return fmt.Errorf("unable to unzip archive: %w", err)
 		}
 	}