diff --git a/internal/api/import.go b/internal/api/import.go
index cbe5e5749..ff4e3d85e 100644
--- a/internal/api/import.go
+++ b/internal/api/import.go
@@ -78,7 +78,7 @@ func StartImport(router *gin.RouterGroup) {
 
 		if subPath != "" && path != conf.ImportPath() && fs.IsEmpty(path) {
 			if err := os.Remove(path); err != nil {
-				log.Errorf("import: could not delete empty folder %s: %s", txt.Quote(path), err)
+				log.Errorf("import: failed deleting empty folder %s: %s", txt.Quote(path), err)
 			} else {
 				log.Infof("import: deleted empty folder %s", txt.Quote(path))
 			}
diff --git a/internal/api/zip.go b/internal/api/zip.go
index c08965810..03255cf81 100644
--- a/internal/api/zip.go
+++ b/internal/api/zip.go
@@ -134,7 +134,7 @@ func DownloadZip(router *gin.RouterGroup) {
 		c.File(zipFileName)
 
 		if err := os.Remove(zipFileName); err != nil {
-			log.Errorf("zip: could not remove %s (%s)", txt.Quote(zipFileName), err.Error())
+			log.Errorf("zip: failed removing %s (%s)", txt.Quote(zipFileName), err.Error())
 		}
 	})
 }
diff --git a/internal/photoprism/import.go b/internal/photoprism/import.go
index e1107e16f..30e3a0d07 100644
--- a/internal/photoprism/import.go
+++ b/internal/photoprism/import.go
@@ -183,7 +183,7 @@ func (imp *Import) Start(opt ImportOptions) map[string]bool {
 		for _, directory := range directories {
 			if fs.IsEmpty(directory) {
 				if err := os.Remove(directory); err != nil {
-					log.Errorf("import: could not delete empty folder %s (%s)", txt.Quote(fs.RelName(directory, importPath)), err)
+					log.Errorf("import: failed deleting empty folder %s (%s)", txt.Quote(fs.RelName(directory, importPath)), err)
 				} else {
 					log.Infof("import: deleted empty folder %s", txt.Quote(fs.RelName(directory, importPath)))
 				}
@@ -199,7 +199,7 @@ func (imp *Import) Start(opt ImportOptions) map[string]bool {
 			}
 
 			if err := os.Remove(file); err != nil {
-				log.Errorf("import: could not remove %s (%s)", txt.Quote(fs.RelName(file, importPath)), err.Error())
+				log.Errorf("import: failed removing %s (%s)", txt.Quote(fs.RelName(file, importPath)), err.Error())
 			}
 		}
 	}
diff --git a/internal/photoprism/import_worker.go b/internal/photoprism/import_worker.go
index 8bb3752c4..a6adcae77 100644
--- a/internal/photoprism/import_worker.go
+++ b/internal/photoprism/import_worker.go
@@ -45,7 +45,7 @@ func ImportWorker(jobs <-chan ImportJob) {
 
 			if destinationFilename, err := imp.DestinationFilename(related.Main, f); err == nil {
 				if err := os.MkdirAll(path.Dir(destinationFilename), os.ModePerm); err != nil {
-					log.Errorf("import: could not create folders (%s)", err.Error())
+					log.Errorf("import: failed creating folders for %s (%s)", txt.Quote(f.BaseName()), err.Error())
 				}
 
 				if related.Main.HasSameName(f) {
@@ -57,11 +57,11 @@ func ImportWorker(jobs <-chan ImportJob) {
 
 				if opt.Move {
 					if err := f.Move(destinationFilename); err != nil {
-						log.Errorf("import: could not move file to %s (%s)", txt.Quote(fs.RelName(destinationMainFilename, imp.originalsPath())), err.Error())
+						log.Errorf("import: failed moving file to %s (%s)", txt.Quote(fs.RelName(destinationMainFilename, imp.originalsPath())), err.Error())
 					}
 				} else {
 					if err := f.Copy(destinationFilename); err != nil {
-						log.Errorf("import: could not copy file to %s (%s)", txt.Quote(fs.RelName(destinationMainFilename, imp.originalsPath())), err.Error())
+						log.Errorf("import: failed copying file to %s (%s)", txt.Quote(fs.RelName(destinationMainFilename, imp.originalsPath())), err.Error())
 					}
 				}
 			} else {
@@ -69,7 +69,7 @@ func ImportWorker(jobs <-chan ImportJob) {
 
 				if opt.RemoveExistingFiles {
 					if err := f.Remove(); err != nil {
-						log.Errorf("import: could not delete %s (%s)", txt.Quote(fs.RelName(f.FileName(), importPath)), err.Error())
+						log.Errorf("import: failed deleting %s (%s)", txt.Quote(f.BaseName()), err.Error())
 					} else {
 						log.Infof("import: deleted %s (already exists)", txt.Quote(relativeFilename))
 					}
diff --git a/internal/photoprism/index_related.go b/internal/photoprism/index_related.go
index 7948aa53e..a997c5376 100644
--- a/internal/photoprism/index_related.go
+++ b/internal/photoprism/index_related.go
@@ -29,7 +29,7 @@ func IndexMain(related *RelatedFiles, ind *Index, opt IndexOptions) (result Inde
 
 	if opt.Convert && !f.HasJpeg() {
 		if jpegFile, err := ind.convert.ToJpeg(f); err != nil {
-			result.Err = fmt.Errorf("index: creating jpeg failed (%s)", err.Error())
+			result.Err = fmt.Errorf("index: failed converting %s to jpeg (%s)", txt.Quote(f.BaseName()), err.Error())
 			result.Status = IndexFailed
 
 			return result
@@ -37,7 +37,7 @@ func IndexMain(related *RelatedFiles, ind *Index, opt IndexOptions) (result Inde
 			log.Infof("index: %s created", fs.RelName(jpegFile.FileName(), ind.originalsPath()))
 
 			if err := jpegFile.ResampleDefault(ind.thumbPath(), false); err != nil {
-				result.Err = fmt.Errorf("index: could not create default thumbnails (%s)", err.Error())
+				result.Err = fmt.Errorf("index: failed creating thumbnails for %s (%s)", txt.Quote(f.BaseName()), err.Error())
 				result.Status = IndexFailed
 
 				return result
@@ -49,7 +49,7 @@ func IndexMain(related *RelatedFiles, ind *Index, opt IndexOptions) (result Inde
 
 	if ind.conf.SidecarJson() && !f.HasJson() {
 		if jsonFile, err := ind.convert.ToJson(f); err != nil {
-			log.Errorf("index: creating json sidecar file failed (%s)", err.Error())
+			log.Errorf("index: failed creating json sidecar for %s (%s)", txt.Quote(f.BaseName()), err.Error())
 		} else {
 			log.Infof("index: %s created", fs.RelName(jsonFile.FileName(), ind.originalsPath()))
 		}
@@ -59,7 +59,7 @@ func IndexMain(related *RelatedFiles, ind *Index, opt IndexOptions) (result Inde
 
 	if result.Indexed() && f.IsJpeg() {
 		if err := f.ResampleDefault(ind.thumbPath(), false); err != nil {
-			log.Errorf("index: could not create default thumbnails (%s)", err.Error())
+			log.Errorf("index: failed creating thumbnails for %s (%s)", txt.Quote(f.BaseName()), err.Error())
 			query.SetFileError(result.FileUID, err.Error())
 		}
 	}
@@ -107,7 +107,7 @@ func IndexRelated(related RelatedFiles, ind *Index, opt IndexOptions) (result In
 
 		if res.Indexed() && f.IsJpeg() {
 			if err := f.ResampleDefault(ind.thumbPath(), false); err != nil {
-				log.Errorf("index: could not create default thumbnails (%s)", err.Error())
+				log.Errorf("index: failed creating thumbnails for %s (%s)", txt.Quote(f.BaseName()), err.Error())
 				query.SetFileError(res.FileUID, err.Error())
 			}
 		}
diff --git a/internal/photoprism/mediafile.go b/internal/photoprism/mediafile.go
index ed9afca62..301cffc48 100644
--- a/internal/photoprism/mediafile.go
+++ b/internal/photoprism/mediafile.go
@@ -493,7 +493,7 @@ func (m *MediaFile) Move(dest string) error {
 	}
 
 	if err := os.Rename(m.fileName, dest); err != nil {
-		log.Debugf("could not rename file, falling back to copy and delete: %s", err.Error())
+		log.Debugf("failed renaming file, fallback to copy and delete: %s", err.Error())
 	} else {
 		m.fileName = dest
 
@@ -802,8 +802,9 @@ func (m *MediaFile) Thumbnail(path string, typeName string) (filename string, er
 	thumbnail, err := thumb.FromFile(m.FileName(), m.Hash(), path, thumbType.Width, thumbType.Height, thumbType.Options...)
 
 	if err != nil {
-		log.Errorf("mediafile: could not create thumbnail (%s)", err)
-		return "", fmt.Errorf("mediafile: could not create thumbnail (%s)", err)
+		err = fmt.Errorf("mediafile: failed creating thumbnail for %s (%s)", txt.Quote(m.BaseName()), err)
+		log.Error(err)
+		return "", err
 	}
 
 	return thumbnail, nil
@@ -850,7 +851,7 @@ func (m *MediaFile) ResampleDefault(thumbPath string, force bool) (err error) {
 		}
 
 		if fileName, err := thumb.Filename(hash, thumbPath, thumbType.Width, thumbType.Height, thumbType.Options...); err != nil {
-			log.Errorf("mediafile: could not create %s (%s)", txt.Quote(name), err)
+			log.Errorf("mediafile: failed creating %s (%s)", txt.Quote(name), err)
 
 			return err
 		} else {
@@ -881,7 +882,7 @@ func (m *MediaFile) ResampleDefault(thumbPath string, force bool) (err error) {
 			}
 
 			if err != nil {
-				log.Errorf("mediafile: could not create %s (%s)", txt.Quote(name), err)
+				log.Errorf("mediafile: failed creating %s (%s)", txt.Quote(name), err)
 				return err
 			}
 
diff --git a/internal/photoprism/mediafile_test.go b/internal/photoprism/mediafile_test.go
index 22afdd1d0..d2a8a33e0 100644
--- a/internal/photoprism/mediafile_test.go
+++ b/internal/photoprism/mediafile_test.go
@@ -1586,7 +1586,7 @@ func TestMediaFile_Thumbnail(t *testing.T) {
 
 		thumbnail, err := image.Thumbnail(thumbsPath, "tile_500")
 
-		assert.EqualError(t, err, "mediafile: could not create thumbnail (image: unknown format)")
+		assert.EqualError(t, err, "mediafile: failed creating thumbnail for canon_eos_6d.xmp (image: unknown format)")
 
 		t.Log(thumbnail)
 	})
diff --git a/internal/workers/share.go b/internal/workers/share.go
index 31dd85b95..f2592bd4d 100644
--- a/internal/workers/share.go
+++ b/internal/workers/share.go
@@ -90,7 +90,7 @@ func (worker *Share) Start() (err error) {
 
 			if _, ok := existingDirs[dir]; !ok {
 				if err := client.CreateDir(dir); err != nil {
-					log.Errorf("share-worker: could not create folder %s", dir)
+					log.Errorf("share-worker: failed creating folder %s", dir)
 					continue
 				}
 			}
diff --git a/internal/workers/sync_upload.go b/internal/workers/sync_upload.go
index 305a00354..5e40d0ea4 100644
--- a/internal/workers/sync_upload.go
+++ b/internal/workers/sync_upload.go
@@ -44,7 +44,7 @@ func (worker *Sync) upload(a entity.Account) (complete bool, err error) {
 
 		if _, ok := existingDirs[remoteDir]; !ok {
 			if err := client.CreateDir(remoteDir); err != nil {
-				log.Errorf("sync-worker: could not create remote folder %s", remoteDir)
+				log.Errorf("sync-worker: failed creating remote folder %s", remoteDir)
 				continue // try again next time
 			}
 		}