diff --git a/pkg/client/client.go b/pkg/client/client.go
index c3eb247..e08dbb6 100644
--- a/pkg/client/client.go
+++ b/pkg/client/client.go
@@ -194,3 +194,15 @@ func (c *Client) addToCache(longURL, shortID string) {
 		})
 	}()
 }
+
+func (c *Client) remFromCache(longURL string) {
+	c.cacheMap.Remove(longURL)
+
+	// Async write to BoltDB
+	go func() {
+		_ = c.db.Update(func(tx *bolt.Tx) error {
+			b := tx.Bucket([]byte("url_cache"))
+			return b.Delete([]byte(longURL))
+		})
+	}()
+}
diff --git a/pkg/client/store.go b/pkg/client/store.go
index 1971e6e..8402897 100644
--- a/pkg/client/store.go
+++ b/pkg/client/store.go
@@ -96,7 +96,8 @@ func (c *Client) enqueueJob(job shortenJob) {
 	select {
 	case c.retryQueue <- job:
 	default:
-		log.Println("Retry queue full, dropping job:", job.ID)
+		log.Println("Retry queue full, dropping job and removing from caches:", job.ID, job.URL)
+		go c.remFromCache(job.URL)
 	}
 }