OneDrive & SharePoint — A Tale of the Fallen File Gods

Mark Alayev
Apr 10, 2019 · 7 min read

It is rare that I post a tale of product woe as it takes a unique combination for such emotion to arise. There are three things that must align for such an event. First, I must love the product company and I agree with its overall vision. Second, it must be close to succeeding, otherwise what’s the point, and finally, it must affect me closely. Microsoft has managed to do just that with its File Collaboration offering in Office 365. Full disclosure, I work as a Director of Service Delivery and have done dozens of roll outs of this product. Microsoft has made an incredible push into O365 and we love the suite. MS Flow has empowered our business to do business robotics, PowerBI has empowered our own company and our clients to self serve reports. But we simply can not understand the philosophy behind OneDrive. I ran as the internal champion of OneDrive and now I’m standing with a headache trying to figure out what went wrong.

And so let us begin the tale . A tale of a wrong direction, but a story that can end well!

Microsoft has been building up a file collaboration platform since its launch of SkyDrive and in its development of their intranet platform, SharePoint. In 2019, the two have become entangled in a web that is hard to explain to our consumers, and often times even harder to manage. The latest version of this file solution is OneDrive for Business, which is a combination of a private file space as well as team collaboration. Be careful though, don’t look at the URL in your browser. The personal site’s companyname-my.sharepoint.com and then team OneDrive sites are companyname.sharepoint.com/team-name. Wait, but I thought it was OneDrive for Business. In fact OneDrive is powered by Document Libraries from SharePoint. What are document libraries you ask? They are seeming SharePoint lists designed for document management with Folder and File constructs. But why would it go this way?

Let’s take it back for a second. Microsoft dominated the file collaboration market not too long ago with its Windows Server that would run in the closets of companies. In fact, it still has a huge presence, and for a good reason. It was a solid product that was simple and easy to use. People created Folders and were able to share it to groups. It would lock when multiple people accessed the same file, and supported any file type you can imagine. Quickbooks worked like a charm. It even got more advanced with Distributed File System allowing multiple offices to cache the folders and synchronize across organization with local file servers. It seemed like the dominance would continue on forever.

Then along came Dropbox. With it, paved the new file system of the future. Built in the cloud, powered by agents running on the computers, it allowed for computers outside of the local area network to synchronize files. The creative engineers there hijacked the file system of Windows and Mac and made it look so well integrated that you couldn’t tell the difference.


Here’s what’s wrong

Let’s get to the meat & bones here, we have problems with our main character. He is running away from his past but not fast enough and not in the right direction.

Here are the things that we think are flawed in order of importance:

  1. The folder and permission structure. I’m fairly sure that’s the core of any file app. Creating a top level folder requires, now as it’s just changed, a new O365 group which creates a SharePoint site with the name and a document library called Documents. Want to sync it down, it’ll come up as “TeamName — Documents”. What in the world? If you to do a 1–1 Migration from File server you’ll never succeed unless you make one big team site, one document library, and break permission inheritance. This is clunky and a visible crack in the SharePoint backend.
  2. Mapped Network Drives. We love it in IT, it might be the only thing users love about IT. S is shared, H is home. Excel references it, Word uses it and it happens at login. SharePoint has partial support via WebDAV, but no offline access and is not recommended by Microsoft. OneDrive over rides all logic and appears as a magic icon on your file explorer, which is a shortcut to a folder. Google Drive on the other hand creates a G: drive when you use their file sync tool, arg!
  3. Recycle Bin. Honestly the first two items would save the world and this might be related to the SharePoint backend, but once you face this, you will never be able to unsee it. As users tend to accidentally do things, such as delete folders, IT staff tend to have to restore things. But you can’t easily! It flattened out the restructure and shows you a few hundred items at a time. We’ve had 50,000 items lost and no easy way of restoring it. No top level folders you can just restore. In fact Powershell scripts can attempt to automate it, at a PAINFULLY SLOW rate. No worries I’ll call Microsoft, raise a ticket and there is a back door channel that will restore it within 48–72 hours.
  4. OneDrive or Office Upload Center? If things weren’t clear enough before, you can sometimes synchronize items via OneDrive other times via Office Upload Center. Items from office 365 productivity suite are uploaded via that tool, and troubleshooting steps recommend to clear the cache there. That tends to fix it, unfortunately. Another layer of complexity. But performance is also a matter of perception. There is no LAN sync option for a tool designed to replace a LAN server. It also is the 2nd most requested feature on the OneDrive uservoice since 2015, with no response for 4 years from Microsoft.

But our character has something going for itself.


O365 & Azure Is The Future

OneDrive has something going for itself — it’s placed in O365. Office 365 has been an incredible shift for many business to a productivity SAAS and OneDrive comes free (or so it feels when you are buying email and get it on the side). This means people will try it, and try it. The users are there, Microsoft needs to answer and complete the domination.

There is one more complexity we need to talk about before saving OneDrive. Azure Files. Azure Files is another file service offering, not to be confused with Azure Blob Storage. It is built as a File system with SMB access (Mapped Network Drives) and FTP. But it seems to be geared to System Admins in need of cloud storage as you can’t manage permissions on it directly. Microsoft has released a file sync tool to use Azure File as a cloud storage for File Server. With file server you can control permissions like we know and love, but you can’t cache files locally, and it will rely on VPN for connectivity in most environments.

Wait that sounds like a new seed, a seed of hope. We’ve drawn so many diagrams trying to marry the products, it doesn’t work! My background is in product development, and we are building lots of our own products. We could build it, but they wouldn’t come. Microsoft can.

Here is what we believe that Microsoft should do, and we would love to help!

O365 Files Online UI Concept
  1. O365 Files. SharePoint isn’t working as the back end. It feels hacked, it is hacked. It feels like it will require a lot of programming to get to what we’ll need, and it’ll end up with something you already have. File Server. Azure Files shows that the infrastructure for a SaaS File Server is being built. If Microsoft can build O365 File App, a UI built on top of APIs, that are connected to File Server infrastructure (Azure Files) would solve the number 1 problem. This would be a similar relationship as O365 Flow is to Azure Logic Apps. This way we would have real folders with the ability to grant permissions. It would make it easy again, and Microsoft’s competitors copied from you! This would bring back the essence of file server. It would fix problem number 3, recycle bin. We would be able to restore folders normally! The migrations would be tremendously easier and we could even deploy on-prem O365 Filers for performance onsite.
  2. OneDrive Agent Upgrades. You’ve recently released OneDrive Files On Demand, which we love and without it we couldn’t even start considering it as File Server replacement. Although it only works on Windows 10 because it’s a file system change, we’ll get over it. Now it’s time to polish the agent, heavily. Give it the ability to assign a drive letter. This will help migrations! Consolidate office upload center in OneDrive. That is core to the agent. It needs to be 99.9999%. Finally and importantly, get LAN sync working. You own Skype, the crusader of peer to peer technology. The underlying technology should be leveraged for moving files within a network.
Introducing O365 Files

These two things would open the doors to success and harden the hold that Microsoft has on enterprise.


We are a Microsoft shop through and through. We have come up with our own formulas to make the OneDrive migrations work, and we are one of the best from what I’m seeing. We want it to be better, so our clients, us ourselves, and Microsoft can enjoy the future of productivity. We don’t think building another solution is the answer, we want to help Microsoft fix it! If we had access to the OneDrive source code, we could build a Proof of Concept with the existing Agent simply replacing the back end to File SaaS. If you, Microsoft, want a stab at it, please involve us in the conversation.

Let’s fix this!

Mark Alayev

Written by

I am innovation - Professional Thinker - Food Enthusiast - CEO, Appetude

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