I've just visited a friend's company and they have asked to help setup their IT infrastructure. At the moment they have around 20 laptops with 25 local accounts. I pity the guy who setup the local accounts on all the laptops. They don't have an IT person, just someone who knows a little bit about computers.

Current setup

  • 8 laptops within the main office and 12+ laptop working from home.
  • 25 users sharing the 12+ laptops from home
  • There are no servers or centrally managed storage. Everything stored locally on laptops. They share files just via emailing to each other.
  • Windows 8 Professional on all laptop

I've advised them about Office 365 and Google apps but they have no interest in cloud solution because they had a quote and it was too expensive for a yearly subscription.


  • Centrally managed accounts and file shares.
  • Monitoring software on the laptops (mainly to monitor web browsing)
  • VPN Connection
  • Currently 25 users but will be expanding
  • No interest in cloud solution
  • Cheap or free solution
  • 1TB of data storage

What I propose

  • Windows Server 2012 Essential that runs the DC and File share.
  • Pfsense or some other open source software for their router/firewall and vpn.
  • Rent a VPS somewhere for an offsite backup.
  • Web filtering on router/fw box. For home users, I'll route all their traffic through the VPN.

Looking at licensing for Windows Server Essential 2012, they only support 25 accounts. It is low cost and I don't have to worry about CALS. Whereas if I buy Windows Server 2012 Standard, I need to pay around $30 per user CAL. I have a feeling that my friend will just say that they will cap it 25 user accounts and some users will be sharing accounts.

What am I going to do with these laptops that are at home and never inside the office? Getting the users to logon initially and setup their profile. I can't ask all 25 staff to logon to each laptop once to setup their accounts. Is there a way that I can VPN into the office network before the user logs on?

closed as primarily opinion-based by Greg Askew, Ward, womble Oct 9 '15 at 3:34

Many good questions generate some degree of opinion based on expert experience, but answers to this question will tend to be almost entirely based on opinions, rather than facts, references, or specific expertise. If this question can be reworded to fit the rules in the help center, please edit the question.

  • This entire setup is a nightmare as is, and they're simply going to have to spend money to make it right. If they are unable or unwilling to do so, then my advice would be to run away as fast as you can. – Michael Hampton Oct 3 '15 at 14:23
  • Cheap or free solution - Really. If it were me I'd tell them to call me back when they're serious. Your friend sounds like the kind of person who'd rather live with a crappy, hodge-podge solution then spend the money needed to put in a proper solution. – joeqwerty Oct 3 '15 at 15:32
  • @joeqwerty it's more than that, they do charity work and have very little funding. Hence why I'm helping them to do my bit for humanity. They are just asking to see if there's a way of running a low cost system. Which I will try my best to help. – lbanz Oct 3 '15 at 15:41

You need a product other than Windows Server Essentials. Sharing accounts to avoid license requirements actually violates the license requirements. If you can't get that right, you should pursue a product that is free or has licensing requirements that are more understandable to you. See section 3.3.2 of the Windows Server 2012 R2 Licensing Datasheet:

"Each user account permits a named user to access and use the server software on that server. It may reassign a user account from one user to another provided that the reassignment does not occur within 90 days of the last assignment."

You can't buy 25 Windows Server Essentials licenses and have 10,000 users or even 30 users using the product with shared accounts.

Windows Server 2012 R2 Licensing Datasheet

  • Interesting! I didn't know you could reassign, it might work out as they have users who logon a few times a year and that might fit into the 90 days limit. Ideally I would advise them to go for the Standard licensing. – lbanz Oct 3 '15 at 15:31

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