diff --git a/src/Api/Vault/Controllers/CiphersController.cs b/src/Api/Vault/Controllers/CiphersController.cs
index 32591c6a2..4a416c6df 100644
--- a/src/Api/Vault/Controllers/CiphersController.cs
+++ b/src/Api/Vault/Controllers/CiphersController.cs
@@ -696,7 +696,7 @@ public class CiphersController : Controller
 
         await Request.GetFileAsync(async (stream, fileName, key) =>
         {
-            await _cipherService.CreateAttachmentShareAsync(cipher, stream,
+            await _cipherService.CreateAttachmentShareAsync(cipher, stream, fileName, key,
                 Request.ContentLength.GetValueOrDefault(0), attachmentId, organizationId);
         });
     }
diff --git a/src/Core/Vault/Entities/Cipher.cs b/src/Core/Vault/Entities/Cipher.cs
index 4ef4a1edb..15cbba411 100644
--- a/src/Core/Vault/Entities/Cipher.cs
+++ b/src/Core/Vault/Entities/Cipher.cs
@@ -45,6 +45,10 @@ public class Cipher : ITableObject<Guid>, ICloneable
             foreach (var kvp in _attachmentData)
             {
                 kvp.Value.AttachmentId = kvp.Key;
+                if (kvp.Value.TempMetadata != null)
+                {
+                    kvp.Value.TempMetadata.AttachmentId = kvp.Key;
+                }
             }
             return _attachmentData;
         }
diff --git a/src/Core/Vault/Models/Data/CipherAttachment.cs b/src/Core/Vault/Models/Data/CipherAttachment.cs
index 78817aeb7..6450efe63 100644
--- a/src/Core/Vault/Models/Data/CipherAttachment.cs
+++ b/src/Core/Vault/Models/Data/CipherAttachment.cs
@@ -31,5 +31,10 @@ public class CipherAttachment
         // This is stored alongside metadata as an identifier. It does not need repeating in serialization
         [JsonIgnore]
         public string AttachmentId { get; set; }
+
+        /// <summary>
+        /// Temporary metadata used to store original metadata on migrations from a user-owned attachment to an organization-owned one
+        /// </summary>
+        public MetaData TempMetadata { get; set; }
     }
 }
diff --git a/src/Core/Vault/Services/ICipherService.cs b/src/Core/Vault/Services/ICipherService.cs
index 165be9a59..3168e50ea 100644
--- a/src/Core/Vault/Services/ICipherService.cs
+++ b/src/Core/Vault/Services/ICipherService.cs
@@ -14,8 +14,8 @@ public interface ICipherService
         string key, string fileName, long fileSize, bool adminRequest, Guid savingUserId);
     Task CreateAttachmentAsync(Cipher cipher, Stream stream, string fileName, string key,
         long requestLength, Guid savingUserId, bool orgAdmin = false);
-    Task CreateAttachmentShareAsync(Cipher cipher, Stream stream, long requestLength, string attachmentId,
-        Guid organizationShareId);
+    Task CreateAttachmentShareAsync(Cipher cipher, Stream stream, string fileName, string key, long requestLength,
+        string attachmentId, Guid organizationShareId);
     Task DeleteAsync(Cipher cipher, Guid deletingUserId, bool orgAdmin = false);
     Task DeleteManyAsync(IEnumerable<Guid> cipherIds, Guid deletingUserId, Guid? organizationId = null, bool orgAdmin = false);
     Task DeleteAttachmentAsync(Cipher cipher, string attachmentId, Guid deletingUserId, bool orgAdmin = false);
diff --git a/src/Core/Vault/Services/Implementations/CipherService.cs b/src/Core/Vault/Services/Implementations/CipherService.cs
index f0e84eb63..5686497c6 100644
--- a/src/Core/Vault/Services/Implementations/CipherService.cs
+++ b/src/Core/Vault/Services/Implementations/CipherService.cs
@@ -258,8 +258,8 @@ public class CipherService : ICipherService
         await _pushService.PushSyncCipherUpdateAsync(cipher, null);
     }
 
-    public async Task CreateAttachmentShareAsync(Cipher cipher, Stream stream, long requestLength,
-        string attachmentId, Guid organizationId)
+    public async Task CreateAttachmentShareAsync(Cipher cipher, Stream stream, string fileName, string key,
+        long requestLength, string attachmentId, Guid organizationId)
     {
         try
         {
@@ -296,8 +296,28 @@ public class CipherService : ICipherService
                 throw new BadRequestException($"Cipher does not own specified attachment");
             }
 
+            var originalAttachmentMetadata = attachments[attachmentId];
+
+            if (originalAttachmentMetadata.TempMetadata != null)
+            {
+                throw new BadRequestException("Another process is trying to migrate this attachment");
+            }
+
+            // Clone metadata to be modified and saved into the TempMetadata,
+            // we cannot change the metadata here directly because if the subsequent endpoint fails
+            // to be called, then the metadata would stay corrupted.
+            var attachmentMetadata = CoreHelpers.CloneObject(originalAttachmentMetadata);
+            attachmentMetadata.AttachmentId = originalAttachmentMetadata.AttachmentId;
+            originalAttachmentMetadata.TempMetadata = attachmentMetadata;
+
+            if (key != null)
+            {
+                attachmentMetadata.Key = key;
+                attachmentMetadata.FileName = fileName;
+            }
+
             await _attachmentStorageService.UploadShareAttachmentAsync(stream, cipher.Id, organizationId,
-                attachments[attachmentId]);
+                attachmentMetadata);
 
             // Previous call may alter metadata
             var updatedAttachment = new CipherAttachment
@@ -306,7 +326,7 @@ public class CipherService : ICipherService
                 UserId = cipher.UserId,
                 OrganizationId = cipher.OrganizationId,
                 AttachmentId = attachmentId,
-                AttachmentData = JsonSerializer.Serialize(attachments[attachmentId])
+                AttachmentData = JsonSerializer.Serialize(originalAttachmentMetadata)
             };
 
             await _cipherRepository.UpdateAttachmentAsync(updatedAttachment);
@@ -489,10 +509,10 @@ public class CipherService : ICipherService
         IEnumerable<Guid> collectionIds, Guid sharingUserId, DateTime? lastKnownRevisionDate)
     {
         var attachments = cipher.GetAttachments();
-        var hasOldAttachments = attachments?.Any(a => a.Key == null) ?? false;
+        var hasOldAttachments = attachments?.Values?.Any(a => a.Key == null) ?? false;
         var updatedCipher = false;
         var migratedAttachments = false;
-        var originalAttachments = CoreHelpers.CloneObject(attachments);
+        var originalAttachments = CoreHelpers.CloneObject(originalCipher.GetAttachments());
 
         try
         {
@@ -502,6 +522,21 @@ public class CipherService : ICipherService
             cipher.UserId = sharingUserId;
             cipher.OrganizationId = organizationId;
             cipher.RevisionDate = DateTime.UtcNow;
+
+            if (hasOldAttachments)
+            {
+                var attachmentsWithUpdatedMetadata = originalCipher.GetAttachments();
+                var attachmentsToUpdateMetadata = CoreHelpers.CloneObject(attachments);
+                foreach (var updatedMetadata in attachmentsWithUpdatedMetadata.Where(a => a.Value?.TempMetadata != null))
+                {
+                    if (attachmentsToUpdateMetadata.ContainsKey(updatedMetadata.Key))
+                    {
+                        attachmentsToUpdateMetadata[updatedMetadata.Key] = updatedMetadata.Value.TempMetadata;
+                    }
+                }
+                cipher.SetAttachments(attachmentsToUpdateMetadata);
+            }
+
             if (!await _cipherRepository.ReplaceAsync(cipher, collectionIds))
             {
                 throw new BadRequestException("Unable to save.");
@@ -513,25 +548,36 @@ public class CipherService : ICipherService
             if (hasOldAttachments)
             {
                 // migrate old attachments
-                foreach (var attachment in attachments.Where(a => a.Key == null))
+                foreach (var attachment in attachments.Values.Where(a => a.TempMetadata != null).Select(a => a.TempMetadata))
                 {
                     await _attachmentStorageService.StartShareAttachmentAsync(cipher.Id, organizationId,
-                        attachment.Value);
+                        attachment);
                     migratedAttachments = true;
                 }
 
                 // commit attachment migration
                 await _attachmentStorageService.CleanupAsync(cipher.Id);
             }
-
-            // push
-            await _pushService.PushSyncCipherUpdateAsync(cipher, collectionIds);
         }
         catch
         {
             // roll everything back
             if (updatedCipher)
             {
+                if (hasOldAttachments)
+                {
+                    foreach (var item in originalAttachments)
+                    {
+                        item.Value.TempMetadata = null;
+                    }
+                    originalCipher.SetAttachments(originalAttachments);
+                }
+
+                var currentCollectionsForCipher = await _collectionCipherRepository.GetManyByUserIdCipherIdAsync(sharingUserId, originalCipher.Id);
+                var currentCollectionIdsForCipher = currentCollectionsForCipher.Select(c => c.CollectionId).ToList();
+                currentCollectionIdsForCipher.RemoveAll(id => collectionIds.Contains(id));
+
+                await _collectionCipherRepository.UpdateCollectionsAsync(originalCipher.Id, sharingUserId, currentCollectionIdsForCipher);
                 await _cipherRepository.ReplaceAsync(originalCipher);
             }
 
@@ -546,7 +592,7 @@ public class CipherService : ICipherService
                 await _organizationRepository.UpdateStorageAsync(organizationId);
             }
 
-            foreach (var attachment in attachments.Where(a => a.Key == null))
+            foreach (var attachment in attachments.Where(a => a.Value.Key == null))
             {
                 await _attachmentStorageService.RollbackShareAttachmentAsync(cipher.Id, organizationId,
                     attachment.Value, originalAttachments[attachment.Key].ContainerName);
@@ -555,6 +601,9 @@ public class CipherService : ICipherService
             await _attachmentStorageService.CleanupAsync(cipher.Id);
             throw;
         }
+
+        // push
+        await _pushService.PushSyncCipherUpdateAsync(cipher, collectionIds);
     }
 
     public async Task ShareManyAsync(IEnumerable<(Cipher cipher, DateTime? lastKnownRevisionDate)> cipherInfos,
diff --git a/test/Core.Test/Vault/AutoFixture/CipherAttachmentMetaDataFixtures.cs b/test/Core.Test/Vault/AutoFixture/CipherAttachmentMetaDataFixtures.cs
index 2aa1e0076..58ed9f0a1 100644
--- a/test/Core.Test/Vault/AutoFixture/CipherAttachmentMetaDataFixtures.cs
+++ b/test/Core.Test/Vault/AutoFixture/CipherAttachmentMetaDataFixtures.cs
@@ -14,6 +14,10 @@ public class MetaData : ICustomization
     public void Customize(IFixture fixture)
     {
         fixture.Customize<CipherAttachment.MetaData>(composer => ComposerAction(fixture, composer));
+        fixture.Behaviors.OfType<ThrowingRecursionBehavior>()
+            .ToList()
+            .ForEach(b => fixture.Behaviors.Remove(b));
+        fixture.Behaviors.Add(new OmitOnRecursionBehavior(1));
     }
 }
 
diff --git a/test/Core.Test/Vault/Services/CipherServiceTests.cs b/test/Core.Test/Vault/Services/CipherServiceTests.cs
index 8ab34a130..c866fa282 100644
--- a/test/Core.Test/Vault/Services/CipherServiceTests.cs
+++ b/test/Core.Test/Vault/Services/CipherServiceTests.cs
@@ -1,7 +1,9 @@
 using Bit.Core.Entities;
 using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
+using Bit.Core.Services;
 using Bit.Core.Test.AutoFixture.CipherFixtures;
+using Bit.Core.Utilities;
 using Bit.Core.Vault.Entities;
 using Bit.Core.Vault.Models.Data;
 using Bit.Core.Vault.Repositories;
@@ -44,7 +46,12 @@ public class CipherServiceTests
         Organization organization, List<Guid> collectionIds)
     {
         sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
+
         var lastKnownRevisionDate = cipher.RevisionDate.AddDays(-1);
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [Guid.NewGuid().ToString()] = new CipherAttachment.MetaData { }
+        });
 
         var exception = await Assert.ThrowsAsync<BadRequestException>(
             () => sutProvider.Sut.ShareAsync(cipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
@@ -105,11 +112,438 @@ public class CipherServiceTests
         cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(true);
         sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
 
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [Guid.NewGuid().ToString()] = new CipherAttachment.MetaData { }
+        });
         await sutProvider.Sut.ShareAsync(cipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
             lastKnownRevisionDate);
         await cipherRepository.Received(1).ReplaceAsync(cipher, collectionIds);
     }
 
+    [Theory]
+    [BitAutoData("Correct Time")]
+    public async Task ShareAsync_FailReplace_Throws(string revisionDateString,
+        SutProvider<CipherService> sutProvider, Cipher cipher, Organization organization, List<Guid> collectionIds)
+    {
+        var lastKnownRevisionDate = string.IsNullOrEmpty(revisionDateString) ? (DateTime?)null : cipher.RevisionDate;
+        var cipherRepository = sutProvider.GetDependency<ICipherRepository>();
+        cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(false);
+        sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
+
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [Guid.NewGuid().ToString()] = new CipherAttachment.MetaData { }
+        });
+
+        var exception = await Assert.ThrowsAsync<BadRequestException>(
+            () => sutProvider.Sut.ShareAsync(cipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
+            lastKnownRevisionDate));
+        Assert.Contains("Unable to save", exception.Message);
+    }
+
+    [Theory]
+    [BitAutoData("Correct Time")]
+    public async Task ShareAsync_HasV0Attachments_ReplaceAttachmentMetadataWithNewOneBeforeSavingCipher(string revisionDateString,
+        SutProvider<CipherService> sutProvider, Cipher cipher, Organization organization, List<Guid> collectionIds)
+    {
+        var lastKnownRevisionDate = string.IsNullOrEmpty(revisionDateString) ? (DateTime?)null : cipher.RevisionDate;
+        var originalCipher = CoreHelpers.CloneObject(cipher);
+        var cipherRepository = sutProvider.GetDependency<ICipherRepository>();
+        cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(true);
+        sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
+        var pushNotificationService = sutProvider.GetDependency<IPushNotificationService>();
+
+        var v0AttachmentId = Guid.NewGuid().ToString();
+        var anotherAttachmentId = Guid.NewGuid().ToString();
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted"
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        originalCipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        await sutProvider.Sut.ShareAsync(originalCipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
+            lastKnownRevisionDate);
+
+        await cipherRepository.Received().ReplaceAsync(Arg.Is<Cipher>(c =>
+                c.GetAttachments()[v0AttachmentId].Key == "NewAttachmentKey"
+                &&
+                c.GetAttachments()[v0AttachmentId].FileName == "AFileNameRe-EncryptedWithOrgKey")
+            , collectionIds);
+
+        await pushNotificationService.Received(1).PushSyncCipherUpdateAsync(cipher, collectionIds);
+    }
+
+    [Theory]
+    [BitAutoData("Correct Time")]
+    public async Task ShareAsync_HasV0Attachments_StartSharingThoseAttachments(string revisionDateString,
+        SutProvider<CipherService> sutProvider, Cipher cipher, Organization organization, List<Guid> collectionIds)
+    {
+        var lastKnownRevisionDate = string.IsNullOrEmpty(revisionDateString) ? (DateTime?)null : cipher.RevisionDate;
+        var originalCipher = CoreHelpers.CloneObject(cipher);
+        var cipherRepository = sutProvider.GetDependency<ICipherRepository>();
+        cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(true);
+        sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
+        var attachmentStorageService = sutProvider.GetDependency<IAttachmentStorageService>();
+
+        var v0AttachmentId = Guid.NewGuid().ToString();
+        var anotherAttachmentId = Guid.NewGuid().ToString();
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        originalCipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        await sutProvider.Sut.ShareAsync(originalCipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
+            lastKnownRevisionDate);
+
+        await attachmentStorageService.Received().StartShareAttachmentAsync(cipher.Id,
+            organization.Id,
+            Arg.Is<CipherAttachment.MetaData>(m => m.Key == "NewAttachmentKey" && m.FileName == "AFileNameRe-EncryptedWithOrgKey"));
+
+        await attachmentStorageService.Received(0).StartShareAttachmentAsync(cipher.Id,
+            organization.Id,
+            Arg.Is<CipherAttachment.MetaData>(m => m.Key == "AwesomeKey" && m.FileName == "AnotherFilename"));
+
+        await attachmentStorageService.Received().CleanupAsync(cipher.Id);
+    }
+
+    [Theory]
+    [BitAutoData("Correct Time")]
+    public async Task ShareAsync_HasV0Attachments_StartShareThrows_PerformsRollback_Rethrows(string revisionDateString,
+        SutProvider<CipherService> sutProvider, Cipher cipher, Organization organization, List<Guid> collectionIds)
+    {
+        var lastKnownRevisionDate = string.IsNullOrEmpty(revisionDateString) ? (DateTime?)null : cipher.RevisionDate;
+        var originalCipher = CoreHelpers.CloneObject(cipher);
+        var cipherRepository = sutProvider.GetDependency<ICipherRepository>();
+        cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(true);
+        sutProvider.GetDependency<IOrganizationRepository>().GetByIdAsync(organization.Id).Returns(organization);
+        var attachmentStorageService = sutProvider.GetDependency<IAttachmentStorageService>();
+        var collectionCipherRepository = sutProvider.GetDependency<ICollectionCipherRepository>();
+        collectionCipherRepository.GetManyByUserIdCipherIdAsync(cipher.UserId.Value, cipher.Id).Returns(
+            Task.FromResult((ICollection<CollectionCipher>)new List<CollectionCipher>
+            {
+                new CollectionCipher
+                {
+                    CipherId = cipher.Id,
+                    CollectionId = collectionIds[0]
+                },
+                new CollectionCipher
+                {
+                    CipherId = cipher.Id,
+                    CollectionId = Guid.NewGuid()
+                }
+            }));
+
+        var v0AttachmentId = Guid.NewGuid().ToString();
+        var anotherAttachmentId = Guid.NewGuid().ToString();
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        originalCipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        attachmentStorageService.StartShareAttachmentAsync(cipher.Id,
+            organization.Id,
+            Arg.Is<CipherAttachment.MetaData>(m => m.AttachmentId == v0AttachmentId))
+            .Returns(Task.FromException(new InvalidOperationException("ex from StartShareAttachmentAsync")));
+
+        var exception = await Assert.ThrowsAsync<InvalidOperationException>(
+            () => sutProvider.Sut.ShareAsync(cipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
+            lastKnownRevisionDate));
+        Assert.Contains("ex from StartShareAttachmentAsync", exception.Message);
+
+        await collectionCipherRepository.Received().UpdateCollectionsAsync(cipher.Id, cipher.UserId.Value,
+            Arg.Is<List<Guid>>(ids => ids.Count == 1 && ids[0] != collectionIds[0]));
+
+        await cipherRepository.Received().ReplaceAsync(Arg.Is<Cipher>(c =>
+                c.GetAttachments()[v0AttachmentId].Key == null
+                &&
+                c.GetAttachments()[v0AttachmentId].FileName == "AFileNameEncrypted"
+                &&
+                c.GetAttachments()[v0AttachmentId].TempMetadata == null)
+        );
+    }
+
+    [Theory]
+    [BitAutoData("Correct Time")]
+    public async Task ShareAsync_HasSeveralV0Attachments_StartShareThrowsOnSecondOne_PerformsRollback_Rethrows(string revisionDateString,
+        SutProvider<CipherService> sutProvider, Cipher cipher, Organization organization, List<Guid> collectionIds)
+    {
+        var lastKnownRevisionDate = string.IsNullOrEmpty(revisionDateString) ? (DateTime?)null : cipher.RevisionDate;
+        var originalCipher = CoreHelpers.CloneObject(cipher);
+        var cipherRepository = sutProvider.GetDependency<ICipherRepository>();
+        cipherRepository.ReplaceAsync(cipher, collectionIds).Returns(true);
+        var organizationRepository = sutProvider.GetDependency<IOrganizationRepository>();
+        organizationRepository.GetByIdAsync(organization.Id).Returns(organization);
+        var attachmentStorageService = sutProvider.GetDependency<IAttachmentStorageService>();
+        var userRepository = sutProvider.GetDependency<IUserRepository>();
+        var collectionCipherRepository = sutProvider.GetDependency<ICollectionCipherRepository>();
+        collectionCipherRepository.GetManyByUserIdCipherIdAsync(cipher.UserId.Value, cipher.Id).Returns(
+            Task.FromResult((ICollection<CollectionCipher>)new List<CollectionCipher>
+            {
+                new CollectionCipher
+                {
+                    CipherId = cipher.Id,
+                    CollectionId = collectionIds[0]
+                },
+                new CollectionCipher
+                {
+                    CipherId = cipher.Id,
+                    CollectionId = Guid.NewGuid()
+                }
+            }));
+
+        var v0AttachmentId1 = Guid.NewGuid().ToString();
+        var v0AttachmentId2 = Guid.NewGuid().ToString();
+        var anotherAttachmentId = Guid.NewGuid().ToString();
+        cipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId1] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId1,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId1,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [v0AttachmentId2] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId2,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted2",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId2,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey2",
+                    Key = "NewAttachmentKey2"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        originalCipher.SetAttachments(new Dictionary<string, CipherAttachment.MetaData>
+        {
+            [v0AttachmentId1] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId1,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId1,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey",
+                    Key = "NewAttachmentKey"
+                }
+            },
+            [v0AttachmentId2] = new CipherAttachment.MetaData
+            {
+                AttachmentId = v0AttachmentId2,
+                ContainerName = "attachments",
+                FileName = "AFileNameEncrypted2",
+                TempMetadata = new CipherAttachment.MetaData
+                {
+                    AttachmentId = v0AttachmentId2,
+                    ContainerName = "attachments",
+                    FileName = "AFileNameRe-EncryptedWithOrgKey2",
+                    Key = "NewAttachmentKey2"
+                }
+            },
+            [anotherAttachmentId] = new CipherAttachment.MetaData
+            {
+                AttachmentId = anotherAttachmentId,
+                Key = "AwesomeKey",
+                FileName = "AnotherFilename",
+                ContainerName = "attachments",
+                Size = 300,
+                Validated = true
+            }
+        });
+
+        attachmentStorageService.StartShareAttachmentAsync(cipher.Id,
+            organization.Id,
+            Arg.Is<CipherAttachment.MetaData>(m => m.AttachmentId == v0AttachmentId2))
+            .Returns(Task.FromException(new InvalidOperationException("ex from StartShareAttachmentAsync")));
+
+        var exception = await Assert.ThrowsAsync<InvalidOperationException>(
+            () => sutProvider.Sut.ShareAsync(cipher, cipher, organization.Id, collectionIds, cipher.UserId.Value,
+            lastKnownRevisionDate));
+        Assert.Contains("ex from StartShareAttachmentAsync", exception.Message);
+
+        await collectionCipherRepository.Received().UpdateCollectionsAsync(cipher.Id, cipher.UserId.Value,
+            Arg.Is<List<Guid>>(ids => ids.Count == 1 && ids[0] != collectionIds[0]));
+
+        await cipherRepository.Received().ReplaceAsync(Arg.Is<Cipher>(c =>
+                c.GetAttachments()[v0AttachmentId1].Key == null
+                &&
+                c.GetAttachments()[v0AttachmentId1].FileName == "AFileNameEncrypted"
+                &&
+                c.GetAttachments()[v0AttachmentId1].TempMetadata == null)
+        );
+
+        await cipherRepository.Received().ReplaceAsync(Arg.Is<Cipher>(c =>
+                c.GetAttachments()[v0AttachmentId2].Key == null
+                &&
+                c.GetAttachments()[v0AttachmentId2].FileName == "AFileNameEncrypted2"
+                &&
+                c.GetAttachments()[v0AttachmentId2].TempMetadata == null)
+        );
+
+        await userRepository.UpdateStorageAsync(cipher.UserId.Value);
+        await organizationRepository.UpdateStorageAsync(organization.Id);
+
+        await attachmentStorageService.Received().RollbackShareAttachmentAsync(cipher.Id, organization.Id,
+            Arg.Is<CipherAttachment.MetaData>(m => m.AttachmentId == v0AttachmentId1), Arg.Any<string>());
+
+        await attachmentStorageService.Received().CleanupAsync(cipher.Id);
+    }
+
     [Theory]
     [BitAutoData("")]
     [BitAutoData("Correct Time")]