diff --git a/src/routes/api/image.js b/src/routes/api/image.js
index e5c7181d2..ce181ad73 100644
--- a/src/routes/api/image.js
+++ b/src/routes/api/image.js
@@ -38,7 +38,7 @@ function uploadImage(req) {
         return [400, "Unknown image type: " + file.mimetype];
     }
 
-    const {url} = imageService.saveImage(noteId, file.buffer, file.originalname, true);
+    const {url} = imageService.saveImage(noteId, file.buffer, file.originalname, true, true);
 
     return {
         uploaded: true,
diff --git a/src/services/image.js b/src/services/image.js
index 5fc00eb38..c6551f1e7 100644
--- a/src/services/image.js
+++ b/src/services/image.js
@@ -73,11 +73,15 @@ function updateImage(noteId, uploadBuffer, originalName) {
     });
 }
 
-function saveImage(parentNoteId, uploadBuffer, originalName, shrinkImageSwitch) {
+function saveImage(parentNoteId, uploadBuffer, originalName, shrinkImageSwitch, trimFilename = false) {
     log.info(`Saving image ${originalName}`);
 
-    const fileName = sanitizeFilename(originalName);
+    if (trimFilename && originalName.length > 40) {
+        // https://github.com/zadam/trilium/issues/2307
+        originalName = "image";
+    }
 
+    const fileName = sanitizeFilename(originalName);
     const parentNote = becca.getNote(parentNoteId);
 
     const {note} = noteService.createNewNote({
@@ -95,6 +99,14 @@ function saveImage(parentNoteId, uploadBuffer, originalName, shrinkImageSwitch)
     processImage(uploadBuffer, originalName, shrinkImageSwitch).then(({buffer, imageFormat}) => {
         sql.transactional(() => {
             note.mime = getImageMimeFromExtension(imageFormat.ext);
+
+            if (!originalName.includes(".")) {
+                originalName += "." + imageFormat.ext;
+
+                note.setLabel('originalFileName', originalName);
+                note.title = sanitizeFilename(originalName);
+            }
+
             note.save();
 
             note.setContent(buffer);
diff --git a/src/services/notes.js b/src/services/notes.js
index 3200e3bce..d9008e270 100644
--- a/src/services/notes.js
+++ b/src/services/notes.js
@@ -270,7 +270,7 @@ async function downloadImage(noteId, imageUrl) {
         const title = path.basename(parsedUrl.pathname);
 
         const imageService = require('../services/image');
-        const {note} = imageService.saveImage(noteId, imageBuffer, title, true);
+        const {note} = imageService.saveImage(noteId, imageBuffer, title, true, true);
 
         note.addLabel('imageUrl', imageUrl);
 
@@ -305,7 +305,7 @@ function downloadImages(noteId, content) {
             const imageBuffer = Buffer.from(imageBase64, 'base64');
 
             const imageService = require('../services/image');
-            const {note} = imageService.saveImage(noteId, imageBuffer, "inline image", true);
+            const {note} = imageService.saveImage(noteId, imageBuffer, "inline image", true, true);
 
             content = content.substr(0, imageMatch.index)
                 + `<img src="api/images/${note.noteId}/${note.title}"`