diff --git a/pkg/plugins/manager/signature/manifest.go b/pkg/plugins/manager/signature/manifest.go
index f2c64917f31..4bb035f011e 100644
--- a/pkg/plugins/manager/signature/manifest.go
+++ b/pkg/plugins/manager/signature/manifest.go
@@ -169,6 +169,7 @@ func (s *Signature) Calculate(ctx context.Context, src plugins.PluginSource, plu
 
 	// Make sure the versions all match
 	if manifest.Plugin != plugin.JSONData.ID || manifest.Version != plugin.JSONData.Info.Version {
+		s.log.Debug("Plugin signature invalid because ID or Version mismatch", "pluginId", plugin.JSONData.ID, "manifestPluginId", manifest.Plugin, "pluginVersion", plugin.JSONData.Info.Version, "manifestPluginVersion", manifest.Version)
 		return plugins.Signature{
 			Status: plugins.SignatureStatusModified,
 		}, nil
@@ -194,6 +195,7 @@ func (s *Signature) Calculate(ctx context.Context, src plugins.PluginSource, plu
 	for p, hash := range manifest.Files {
 		err = verifyHash(s.log, plugin, p, hash)
 		if err != nil {
+			s.log.Debug("Plugin signature invalid", "pluginId", plugin.JSONData.ID, "error", err)
 			return plugins.Signature{
 				Status: plugins.SignatureStatusModified,
 			}, nil
@@ -259,7 +261,7 @@ func verifyHash(mlog log.Logger, plugin plugins.FoundPlugin, path, hash string)
 
 	h := sha256.New()
 	if _, err := io.Copy(h, f); err != nil {
-		return errors.New("could not calculate plugin file checksum")
+		return fmt.Errorf("could not calculate plugin file checksum. Path: %s. Error: %w", path, err)
 	}
 	sum := hex.EncodeToString(h.Sum(nil))
 	if sum != hash {