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Theres no nice way to say it: File sharing to Windows Server on macOS is a half-baked solution at best. I am not sure if its how Apple implemented the protocol, but Ive talked with countless IT professionals over the past year and everyone comes to the same conclusion: Its the worst part of using a Mac at work. Disconnects plague macOS in the middle of transfers while Windows stays readily connected to the same server.

About Apple @ Work:Bradley Chambers managed an enterprise IT network from 2009 to 2021. Through his experience deploying and managing firewalls, switches, a mobile device management system, enterprise grade Wi-Fi, 100s of Macs, and 100s of iPads, Bradley will highlight ways in which Apple IT managers deploy Apple devices, build networks to support them, train users, stories from the trenches of IT management, and ways Apple could improve its products for IT departments.

The only reason this buggy implementation isnt a bigger deal externally for Apple is that so many organizations have moved to OneDrive, Google Drive, etc. Network file shares were already on the way out pre-pandemic, but its much easier to use cloud storage for file sharing when employees are fully remote or even in a hybrid setting. Connected to a local network when youre hundreds of miles away from the office requires a VPN connection which many organizations have stopped using in the age of SaaS products. Its much simpler for employees to access documents in OneDrive or Google Drive than it is to activate a VPN, connect to a file share, etc.

Initially connected to network file shares on Windows is still much easier in my opinion. Some of that is due to the streamlined process of having a file server inside the same server as your local Active Directory. Yes, a local AD server isnt as common today as many companies are turning to cloud-based solutions like JumpCloud instead. JumpCloud tightly integrates with Google Workspace and Microsoft 365, so companies can build their own alternative solution. With that being said, theres a benefit to AD if youre using a local file server setup.

Even once youre connected through a slightly clunky process, good luck staying connected. Ive run a few tests where I connected to an Intel NUC I have in my house acting as a media server. Ill connect to the share and just let it sit with no file transfer. Theres almost no chance I can do two to three days without losing connection to the server. There are only plenty of times that Ill be in the middle of an active transfer and it decides to disconnect. In my situation, its annoying. If youre at work and this happens, its a big problem. In a nutshell, the implementation isnt reliable.

Is this an issue with how Microsoft has implemented the file sharing protocol? Possibly. Even so, its one of those situations where it might not be Apples fault, but its their problem. Ive tried all the hacks. Ive tried the Terminal commands. Ive tried alternative apps to enable different protocols for file sharing. If youre thinking theres a trick Ive not tried and youre gonna offer a solution in the comments feel free to note it, but Ive probably tried it. If you spend time on DuckDuckGo researching the problem, youll find countless support posts and Reddit threads with people in the same situation.

In enterprise settings, Ive consulted with experts of 25+ years on Windows Server, and theyve all come to the same conclusion this is something Apple has to fix. Some versions of macOS are better than others. Some upgrades make it a bit better, but then others take a step back.

Whatever the problem, Apple needs to recognize it and figure out a permanent fix. Yes, its a dying art, but plenty of organizations still need it. Even in the home, its not uncommon to remotely connect to another computer acting as a home server.

For macOS 10.16, the only bug fix I want to see is rewritten implementation of Windows file sharing.

Apple @ Work is brought to you by Kandji, the MDM solution built exclusively for organizations that run on Apple. Kandji is a modern, cloud-based platform for centrally managing and securing your Mac, iPhone, iPad, and Apple TV devices, saving IT teams countless hours of manual work with features like one-click compliance templates and 150+ pre-built automations, apps, and workflows. Request access.

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Apple @ Work: Windows file shares are still buggy on macOS; its time to fix it once and for all - 9to5Mac