diff --git a/src/App/Abstractions/Repositories/IAttachmentRepository.cs b/src/App/Abstractions/Repositories/IAttachmentRepository.cs
index 6c615b3b6..f1cde2e89 100644
--- a/src/App/Abstractions/Repositories/IAttachmentRepository.cs
+++ b/src/App/Abstractions/Repositories/IAttachmentRepository.cs
@@ -8,5 +8,6 @@ namespace Bit.App.Abstractions
     public interface IAttachmentRepository : IRepository<AttachmentData, string>
     {
         Task<IEnumerable<AttachmentData>> GetAllByLoginIdAsync(string loginId);
+        Task<IEnumerable<AttachmentData>> GetAllByUserIdAsync(string userId);
     }
 }
diff --git a/src/App/Repositories/AttachmentRepository.cs b/src/App/Repositories/AttachmentRepository.cs
index 86f909bf5..41166640d 100644
--- a/src/App/Repositories/AttachmentRepository.cs
+++ b/src/App/Repositories/AttachmentRepository.cs
@@ -18,5 +18,19 @@ namespace Bit.App.Repositories
             var attachments = Connection.Table<AttachmentData>().Where(a => a.LoginId == loginId).Cast<AttachmentData>();
             return Task.FromResult(attachments);
         }
+
+        public Task<IEnumerable<AttachmentData>> GetAllByUserIdAsync(string userId)
+        {
+            var attachments = Connection.Query<AttachmentData>(@"
+                SELECT
+                    A.*
+                FROM
+                    Attachment AS A
+                INNER JOIN
+                    Site AS S ON S.Id = A.LoginId
+                WHERE
+                    S.UserId = ?", userId);
+            return Task.FromResult<IEnumerable<AttachmentData>>(attachments);
+        }
     }
 }
diff --git a/src/App/Services/SyncService.cs b/src/App/Services/SyncService.cs
index 26cd4d219..016c77d28 100644
--- a/src/App/Services/SyncService.cs
+++ b/src/App/Services/SyncService.cs
@@ -82,6 +82,10 @@ namespace Bit.App.Services
                     case Enums.CipherType.Login:
                         var loginData = new LoginData(cipher.Result, _authService.UserId);
                         await _loginRepository.UpsertAsync(loginData).ConfigureAwait(false);
+
+                        var localAttachments = (await _attachmentRepository.GetAllByLoginIdAsync(loginData.Id)
+                            .ConfigureAwait(false));
+
                         if(cipher.Result.Attachments != null)
                         {
                             foreach(var attachment in cipher.Result.Attachments)
@@ -90,6 +94,19 @@ namespace Bit.App.Services
                                 await _attachmentRepository.UpsertAsync(attachmentData).ConfigureAwait(false);
                             }
                         }
+
+                        if(localAttachments != null)
+                        {
+                            foreach(var attachment in localAttachments
+                                .Where(a => !cipher.Result.Attachments.Any(sa => sa.Id == a.Id)))
+                            {
+                                try
+                                {
+                                    await _attachmentRepository.DeleteAsync(attachment.Id).ConfigureAwait(false);
+                                }
+                                catch(SQLite.SQLiteException) { }
+                            }
+                        }
                         break;
                     default:
                         SyncCompleted(false);
@@ -363,6 +380,11 @@ namespace Bit.App.Services
                 .Select(s => s.First())
                 .ToDictionary(s => s.Id);
 
+            var localAttachments = (await _attachmentRepository.GetAllByUserIdAsync(_authService.UserId)
+                .ConfigureAwait(false))
+                .GroupBy(a => a.LoginId)
+                .ToDictionary(g => g.Key);
+
             foreach(var serverLogin in serverLogins)
             {
                 if(!_authService.IsAuthenticated)
@@ -372,6 +394,8 @@ namespace Bit.App.Services
 
                 try
                 {
+                    var localLogin = localLogins.ContainsKey(serverLogin.Value.Id) ? localLogins[serverLogin.Value.Id] : null;
+
                     var data = new LoginData(serverLogin.Value, _authService.UserId);
                     await _loginRepository.UpsertAsync(data).ConfigureAwait(false);
 
@@ -383,6 +407,19 @@ namespace Bit.App.Services
                             await _attachmentRepository.UpsertAsync(attachmentData).ConfigureAwait(false);
                         }
                     }
+
+                    if(localLogin != null && localAttachments != null && localAttachments.ContainsKey(localLogin.Id))
+                    {
+                        foreach(var attachment in localAttachments[localLogin.Id]
+                            .Where(a => !serverLogin.Value.Attachments.Any(sa => sa.Id == a.Id)))
+                        {
+                            try
+                            {
+                                await _attachmentRepository.DeleteAsync(attachment.Id).ConfigureAwait(false);
+                            }
+                            catch(SQLite.SQLiteException) { }
+                        }
+                    }
                 }
                 catch(SQLite.SQLiteException) { }
             }