diff --git a/src/Infrastructure.Dapper/Vault/Repositories/CipherRepository.cs b/src/Infrastructure.Dapper/Vault/Repositories/CipherRepository.cs
index b85f1991f7..3df365330c 100644
--- a/src/Infrastructure.Dapper/Vault/Repositories/CipherRepository.cs
+++ b/src/Infrastructure.Dapper/Vault/Repositories/CipherRepository.cs
@@ -711,7 +711,7 @@ public class CipherRepository : Repository<Cipher, Guid>, ICipherRepository
             row[creationDateColumn] = cipher.CreationDate;
             row[revisionDateColumn] = cipher.RevisionDate;
             row[deletedDateColumn] = cipher.DeletedDate.HasValue ? (object)cipher.DeletedDate : DBNull.Value;
-            row[repromptColumn] = cipher.Reprompt;
+            row[repromptColumn] = cipher.Reprompt.HasValue ? cipher.Reprompt.Value : DBNull.Value;
             row[keyColummn] = cipher.Key;
 
             ciphersTable.Rows.Add(row);
diff --git a/src/Infrastructure.EntityFramework/Vault/Repositories/CipherRepository.cs b/src/Infrastructure.EntityFramework/Vault/Repositories/CipherRepository.cs
index e4930cb795..090c36ff29 100644
--- a/src/Infrastructure.EntityFramework/Vault/Repositories/CipherRepository.cs
+++ b/src/Infrastructure.EntityFramework/Vault/Repositories/CipherRepository.cs
@@ -863,8 +863,30 @@ public class CipherRepository : Repository<Core.Vault.Entities.Cipher, Cipher, G
         using (var scope = ServiceScopeFactory.CreateScope())
         {
             var dbContext = GetDatabaseContext(scope);
-            var entities = Mapper.Map<List<Cipher>>(ciphers);
-            await dbContext.BulkCopyAsync(base.DefaultBulkCopyOptions, entities);
+            var ciphersToUpdate = ciphers.ToDictionary(c => c.Id);
+
+            var existingCiphers = await dbContext.Ciphers
+                .Where(c => c.UserId == userId && ciphersToUpdate.Keys.Contains(c.Id))
+                .ToDictionaryAsync(c => c.Id);
+
+            foreach (var (cipherId, cipher) in ciphersToUpdate)
+            {
+                if (!existingCiphers.TryGetValue(cipherId, out var existingCipher))
+                {
+                    // The Dapper version does not validate that the same amount of items given where updated.
+                    continue;
+                }
+
+                existingCipher.UserId = cipher.UserId;
+                existingCipher.OrganizationId = cipher.OrganizationId;
+                existingCipher.Type = cipher.Type;
+                existingCipher.Data = cipher.Data;
+                existingCipher.Attachments = cipher.Attachments;
+                existingCipher.RevisionDate = cipher.RevisionDate;
+                existingCipher.DeletedDate = cipher.DeletedDate;
+                existingCipher.Key = cipher.Key;
+            }
+
             await dbContext.UserBumpAccountRevisionDateAsync(userId);
             await dbContext.SaveChangesAsync();
         }
diff --git a/test/Infrastructure.IntegrationTest/Vault/Repositories/CipherRepositoryTests.cs b/test/Infrastructure.IntegrationTest/Vault/Repositories/CipherRepositoryTests.cs
index 6f02740cf5..fde625e272 100644
--- a/test/Infrastructure.IntegrationTest/Vault/Repositories/CipherRepositoryTests.cs
+++ b/test/Infrastructure.IntegrationTest/Vault/Repositories/CipherRepositoryTests.cs
@@ -883,4 +883,33 @@ public class CipherRepositoryTests
         Assert.Contains(user2TaskCiphers, t => t.CipherId == manageCipher1.Id && t.TaskId == securityTasks[0].Id);
         Assert.Contains(user2TaskCiphers, t => t.CipherId == manageCipher2.Id && t.TaskId == securityTasks[1].Id);
     }
+
+    [DatabaseTheory, DatabaseData]
+    public async Task UpdateCiphersAsync_Works(ICipherRepository cipherRepository, IUserRepository userRepository)
+    {
+        var user = await userRepository.CreateAsync(new User
+        {
+            Name = "Test User",
+            Email = $"test+{Guid.NewGuid()}@email.com",
+            ApiKey = "TEST",
+            SecurityStamp = "stamp",
+        });
+
+        var cipher1 = await CreatePersonalCipher(user, cipherRepository);
+        var cipher2 = await CreatePersonalCipher(user, cipherRepository);
+
+        cipher1.Type = CipherType.SecureNote;
+        cipher2.Attachments = "new_attachments";
+
+        await cipherRepository.UpdateCiphersAsync(user.Id, [cipher1, cipher2]);
+
+        var updatedCipher1 = await cipherRepository.GetByIdAsync(cipher1.Id);
+        var updatedCipher2 = await cipherRepository.GetByIdAsync(cipher2.Id);
+
+        Assert.NotNull(updatedCipher1);
+        Assert.NotNull(updatedCipher2);
+
+        Assert.Equal(CipherType.SecureNote, updatedCipher1.Type);
+        Assert.Equal("new_attachments", updatedCipher2.Attachments);
+    }
 }