diff --git a/http/resource.go b/http/resource.go
index f03f17fb..f657856e 100644
--- a/http/resource.go
+++ b/http/resource.go
@@ -5,6 +5,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"log"
 	"net/http"
 	"net/url"
 	"os"
@@ -73,6 +74,11 @@ func resourceDeleteHandler(fileCache FileCache) handleFunc {
 			return errToStatus(err), err
 		}
 
+		err = d.store.Share.DeleteWithPathPrefix(file.Path)
+		if err != nil {
+			log.Printf("WARNING: Error(s) occurred while deleting associated shares with file: %s", err)
+		}
+
 		// delete thumbnails
 		err = delThumbs(r.Context(), fileCache, file)
 		if err != nil {
diff --git a/share/storage.go b/share/storage.go
index 4cd263de..398c192d 100644
--- a/share/storage.go
+++ b/share/storage.go
@@ -15,6 +15,7 @@ type StorageBackend interface {
 	Gets(path string, id uint) ([]*Link, error)
 	Save(s *Link) error
 	Delete(hash string) error
+	DeleteWithPathPrefix(path string) error
 }
 
 // Storage is a storage.
@@ -118,3 +119,7 @@ func (s *Storage) Save(l *Link) error {
 func (s *Storage) Delete(hash string) error {
 	return s.back.Delete(hash)
 }
+
+func (s *Storage) DeleteWithPathPrefix(path string) error {
+	return s.back.DeleteWithPathPrefix(path)
+}
diff --git a/storage/bolt/share.go b/storage/bolt/share.go
index 6df94f12..373533f1 100644
--- a/storage/bolt/share.go
+++ b/storage/bolt/share.go
@@ -75,3 +75,16 @@ func (s shareBackend) Delete(hash string) error {
 	}
 	return err
 }
+
+func (s shareBackend) DeleteWithPathPrefix(pathPrefix string) error {
+	var links []share.Link
+	if err := s.db.Prefix("Path", pathPrefix, &links); err != nil {
+		return err
+	}
+
+	var err error
+	for _, link := range links {
+		err = errors.Join(err, s.db.DeleteStruct(&share.Link{Hash: link.Hash}))
+	}
+	return err
+}