diff --git a/db/migrations/0230__vector_embeddings.sql b/db/migrations/0230__vector_embeddings.sql
index 07c425fd2..e275fc8ff 100644
--- a/db/migrations/0230__vector_embeddings.sql
+++ b/db/migrations/0230__vector_embeddings.sql
@@ -28,7 +28,8 @@ CREATE TABLE IF NOT EXISTS "embedding_queue" (
     "priority" INTEGER NOT NULL DEFAULT 0,
     "attempts" INTEGER NOT NULL DEFAULT 0,
     "lastAttempt" TEXT NULL,
-    "error" TEXT NULL
+    "error" TEXT NULL,
+    "failed" INTEGER NOT NULL DEFAULT 0
 );
 
 -- Table to store embedding provider configurations
diff --git a/db/schema.sql b/db/schema.sql
index a4f153042..8451326d9 100644
--- a/db/schema.sql
+++ b/db/schema.sql
@@ -158,7 +158,8 @@ CREATE TABLE IF NOT EXISTS "embedding_queue" (
     "priority" INTEGER NOT NULL DEFAULT 0,
     "attempts" INTEGER NOT NULL DEFAULT 0,
     "lastAttempt" TEXT NULL,
-    "error" TEXT NULL
+    "error" TEXT NULL,
+    "failed" INTEGER NOT NULL DEFAULT 0
 );
 
 CREATE TABLE IF NOT EXISTS "embedding_providers" (
diff --git a/src/services/llm/embeddings/queue.ts b/src/services/llm/embeddings/queue.ts
index 9ea9fc3a7..102b52ff8 100644
--- a/src/services/llm/embeddings/queue.ts
+++ b/src/services/llm/embeddings/queue.ts
@@ -17,26 +17,32 @@ export async function queueNoteForEmbedding(noteId: string, operation = 'UPDATE'
     const now = dateUtils.localNowDateTime();
     const utcNow = dateUtils.utcNowDateTime();
 
-    // Check if note is already in queue
-    const existing = await sql.getValue(
-        "SELECT 1 FROM embedding_queue WHERE noteId = ?",
+    // Check if note is already in queue and whether it's marked as permanently failed
+    const queueInfo = await sql.getRow(
+        "SELECT 1 as exists, failed FROM embedding_queue WHERE noteId = ?",
         [noteId]
-    );
+    ) as {exists: number, failed: number} | null;
 
-    if (existing) {
-        // Update existing queue entry
-        await sql.execute(`
-            UPDATE embedding_queue
-            SET operation = ?, dateQueued = ?, utcDateQueued = ?, attempts = 0, error = NULL
-            WHERE noteId = ?`,
-            [operation, now, utcNow, noteId]
-        );
+    if (queueInfo) {
+        // Only update if not permanently failed
+        if (queueInfo.failed !== 1) {
+            // Update existing queue entry but preserve the failed status
+            await sql.execute(`
+                UPDATE embedding_queue
+                SET operation = ?, dateQueued = ?, utcDateQueued = ?, attempts = 0, error = NULL
+                WHERE noteId = ?`,
+                [operation, now, utcNow, noteId]
+            );
+        } else {
+            // Note is marked as permanently failed, don't update
+            log.info(`Note ${noteId} is marked as permanently failed, skipping automatic re-queue`);
+        }
     } else {
         // Add new queue entry
         await sql.execute(`
             INSERT INTO embedding_queue
-            (noteId, operation, dateQueued, utcDateQueued)
-            VALUES (?, ?, ?, ?)`,
+            (noteId, operation, dateQueued, utcDateQueued, failed)
+            VALUES (?, ?, ?, ?, 0)`,
             [noteId, operation, now, utcNow]
         );
     }
@@ -49,15 +55,15 @@ export async function queueNoteForEmbedding(noteId: string, operation = 'UPDATE'
  * @returns List of failed notes with their error information
  */
 export async function getFailedEmbeddingNotes(limit: number = 100): Promise<any[]> {
-    // Get notes with failed embedding attempts
+    // Get notes with failed embedding attempts or permanently failed flag
     const failedQueueItems = await sql.getRows(`
-        SELECT noteId, operation, attempts, lastAttempt, error
+        SELECT noteId, operation, attempts, lastAttempt, error, failed
         FROM embedding_queue
-        WHERE attempts > 0
-        ORDER BY attempts DESC, lastAttempt DESC
+        WHERE attempts > 0 OR failed = 1
+        ORDER BY failed DESC, attempts DESC, lastAttempt DESC
         LIMIT ?`,
         [limit]
-    ) as {noteId: string, operation: string, attempts: number, lastAttempt: string, error: string}[];
+    ) as {noteId: string, operation: string, attempts: number, lastAttempt: string, error: string, failed: number}[];
 
     // Add titles to the failed notes
     const failedNotesWithTitles = [];
@@ -66,16 +72,19 @@ export async function getFailedEmbeddingNotes(limit: number = 100): Promise<any[
         if (note) {
             // Check if this is a chunking error (contains the word "chunks")
             const isChunkFailure = item.error && item.error.toLowerCase().includes('chunk');
+            const isPermanentFailure = item.failed === 1;
 
             failedNotesWithTitles.push({
                 ...item,
                 title: note.title,
-                failureType: isChunkFailure ? 'chunks' : 'full'
+                failureType: isChunkFailure ? 'chunks' : 'full',
+                isPermanent: isPermanentFailure
             });
         } else {
             failedNotesWithTitles.push({
                 ...item,
-                failureType: 'full'
+                failureType: 'full',
+                isPermanent: item.failed === 1
             });
         }
     }
@@ -93,26 +102,23 @@ export async function getFailedEmbeddingNotes(limit: number = 100): Promise<any[
 }
 
 /**
- * Retry embedding generation for a specific failed note
- *
- * @param noteId - ID of the note to retry
- * @returns Success flag
+ * Retry a specific failed note embedding
  */
 export async function retryFailedEmbedding(noteId: string): Promise<boolean> {
-    // Check if the note is in the embedding queue with failed attempts
-    const exists = await sql.getValue(
-        "SELECT 1 FROM embedding_queue WHERE noteId = ? AND attempts > 0",
+    const now = dateUtils.localNowDateTime();
+    const utcNow = dateUtils.utcNowDateTime();
+
+    // Check if the note is in the embedding queue and has failed or has attempts
+    const existsInQueue = await sql.getValue(
+        "SELECT 1 FROM embedding_queue WHERE noteId = ? AND (failed = 1 OR attempts > 0)",
         [noteId]
     );
 
-    if (exists) {
+    if (existsInQueue) {
         // Reset the note in the queue
-        const now = dateUtils.localNowDateTime();
-        const utcNow = dateUtils.utcNowDateTime();
-
         await sql.execute(`
             UPDATE embedding_queue
-            SET attempts = 0, error = NULL, dateQueued = ?, utcDateQueued = ?
+            SET attempts = 0, error = NULL, failed = 0, dateQueued = ?, utcDateQueued = ?, priority = 10
             WHERE noteId = ?`,
             [now, utcNow, noteId]
         );
@@ -128,20 +134,20 @@ export async function retryFailedEmbedding(noteId: string): Promise<boolean> {
  * @returns Number of notes queued for retry
  */
 export async function retryAllFailedEmbeddings(): Promise<number> {
-    // Get count of failed notes in queue
+    const now = dateUtils.localNowDateTime();
+    const utcNow = dateUtils.utcNowDateTime();
+
+    // Get count of all failed notes in queue (either with failed=1 or attempts>0)
     const failedCount = await sql.getValue(
-        "SELECT COUNT(*) FROM embedding_queue WHERE attempts > 0"
+        "SELECT COUNT(*) FROM embedding_queue WHERE failed = 1 OR attempts > 0"
     ) as number;
 
     if (failedCount > 0) {
         // Reset all failed notes in the queue
-        const now = dateUtils.localNowDateTime();
-        const utcNow = dateUtils.utcNowDateTime();
-
         await sql.execute(`
             UPDATE embedding_queue
-            SET attempts = 0, error = NULL, dateQueued = ?, utcDateQueued = ?
-            WHERE attempts > 0`,
+            SET attempts = 0, error = NULL, failed = 0, dateQueued = ?, utcDateQueued = ?, priority = 10
+            WHERE failed = 1 OR attempts > 0`,
             [now, utcNow]
         );
     }
@@ -174,10 +180,11 @@ export async function processEmbeddingQueue() {
         return;
     }
 
-    // Get notes from queue
+    // Get notes from queue (excluding failed ones)
     const notes = await sql.getRows(`
         SELECT noteId, operation, attempts
         FROM embedding_queue
+        WHERE failed = 0
         ORDER BY priority DESC, utcDateQueued ASC
         LIMIT ?`,
         [batchSize]
@@ -275,9 +282,16 @@ export async function processEmbeddingQueue() {
                     [dateUtils.utcNowDateTime(), "All providers failed to generate embeddings", noteData.noteId]
                 );
 
-                // Remove from queue if too many attempts
+                // Mark as permanently failed if too many attempts
                 if (noteData.attempts + 1 >= 3) {
                     log.error(`Marked note ${noteData.noteId} as permanently failed after multiple embedding attempts`);
+
+                    // Set the failed flag and update the attempts
+                    await sql.execute(`
+                        UPDATE embedding_queue
+                        SET attempts = 999, failed = 1
+                        WHERE noteId = ?
+                    `, [noteData.noteId]);
                 }
             }
         } catch (error: any) {
@@ -295,15 +309,14 @@ export async function processEmbeddingQueue() {
 
             log.error(`Error processing embedding for note ${noteData.noteId}: ${error.message || 'Unknown error'}`);
 
-            // Don't remove from queue even after multiple failures, just mark as failed
-            // This allows manual retries later
+            // Mark as permanently failed if too many attempts
             if (noteData.attempts + 1 >= 3) {
                 log.error(`Marked note ${noteData.noteId} as permanently failed after multiple embedding attempts`);
 
-                // Update the attempts to a very high number to indicate permanent failure
+                // Set the failed flag and update the attempts
                 await sql.execute(`
                     UPDATE embedding_queue
-                    SET attempts = 999
+                    SET attempts = 999, failed = 1
                     WHERE noteId = ?
                 `, [noteData.noteId]);
             }