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I have a small business client who has a few windows servers and many workstations but as far as I can tell only has a few valid oem licences (some mismatched like xp home when xp pro is installed) for the workstations and almost no valid licences for the servers (It came with 2000 and now has 2003). They're partially interested in going legit and becoming properly licensed but fear its going to be a large cost. Interestingly enough they also fear that they'll get hammered on not being licensed so far and would rather keep under the radar.

I can't say this is the first time I've come across this, someone gets a hold of a slipstreamed xp pro cd or an office install that includes the key and are happy when it just works.

I'm not interested in giving them a hard time or turning them in. As I said I see this in my small business clients all the time and it wouldn't behoove me to mess with their businesses. I'm just looking for a good path to get them back into legitimacy.

Anyone have experience with this?

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  • I'm liking a lot of your answers, their applicability varies from small shops (<10 people) to bigger businesses (30-60 people) which happens to match my clientele =) – reconbot Jun 16 '09 at 14:43

Consult your local license provider. They wont get slammed at running illegal software - especially if you're looking at legitimising them. I'd look at how many clients you have, and how many servers. The Action Pack is really meant for IT Professionals (ie. You and I).

Consider their position too; If they're in Education or Non-Profit, they can get heavy discounts and get VLK (Volume Licensing). Alternatively look at "Microsoft Open License" ( https://partner.microsoft.com/UK/licensing/licensingprograms/ltvolumelicensing/vlopenlicense ) This allows for Pay-as-you-Go, and only requires a minimum of 5 PC's.

Good luck! :)

  • Do "local license providers" get better rates? Are they just MS partners? – reconbot Jun 16 '09 at 14:40
  • +1 for the fact that MS are far more interested in getting the client licensened than slamming them for being un-licensed – Mark Henderson Jun 16 '09 at 22:34
  • @ Wizard: I'm not 100% sure on that; My experience has only been in the education / Non-Profit Sector. It is possible, however, that different licensee's would run the MS Products at different costs: After all, they're just another reseller trying to cash in on a product :) – oldSkool-Soldier Jun 17 '09 at 9:58

Start by inventorying their software.

Compare the inventory with their licenses, take note of how the software is used, some licenses only allow certain types of use (MSDN licenses, for example).

Prepare a report for them, listing their software and identifying any items for which you could not find licenses. Suggest that they locate or purchase licenses for this software, since not having them available is a legal liability.

  • I like this one but I can't see many of my clients listening to me on this approach. – reconbot Jun 18 '09 at 19:46
  • Well, you said "properly", not "realistically" ;) – sangretu Jul 9 '09 at 20:26

I would start with Microsoft's Volume Licensing page. It can be cheaper to get them on a volume licensing plan than to purchase the licenses at full retail price.


This will be controversial I am sure. You mention them having various Windows XP installs and a server that originally came with Win2k. With such old systems, would you as a business owner and not an IT pro, see any value in paying potentially thousands of dollars for licences when you have successfully skirted along so far?

These systems are likely ready to be replaced soon given their relative age. You may have better luck by standardizing their procurement process for systems by sticking with 1 vendor and level (i.e. Dell Small Business instead of just Dell) and replace the machines running illegal OSes with legally licensed new machines. Then get them onto an MSDN Volume Licensing program for their applications (which are also likely several versions behind).

By phasing them in you can get them all legal, build the processes to keep them legal and spread what can potentially be a devastating cost with little relative upside over time.

  • 1
    Just remember that MSDN is for developer licenses only and does not offer any licenses except for that user. – Aaron Weiker Jun 16 '09 at 16:27
  • @Aaroon - you are correct - that was a poor choice of words on my part. I meant to say Volume Licensing. – Rob Allen Jun 16 '09 at 16:30
  • I like this one too - I honestly think this is going to be the most effective approach in most places, but even then everyone wants things on the cheap. Which makes it hard to keep it legal, I just do my best not to be an enabler. – reconbot Jun 18 '09 at 19:48

If you're not too hard pressed on financial side, you could restart by volume licensing everything and discarding OEM legacy. You could also get Software Assurance, the same key for everything, home usage program, easy upgrades in number of licences etc.


Microsoft has some licensing options specific to small business with as few as 5 computers, that allow them to spread payments over three years, finance the cost, etc. The information is here: http://www.microsoft.com/smallbusiness/buy/software/buy-software.aspx#VolumeLicensing


I'd start first with assessing their business needs and determining what software is required for their business functions. Then determine what would be the hardware+software costs for new servers. Then take a look at the hardware available and see if it's worth keeping. In a similar situation I was able to get the client to dump 6 older machines and buy 1 copy of windows server datacenter edition. This version allows for unlimited virtualization so seperating servers was still possible without the overhead. Direct savings over licensing wass about $3K Same goes for the laptops/desktops. It might be cheaper to lease new OSes with the hardware than setting up a seperate openlicense. If they want or need SA rights you can still enroll OEMd licenses.


If the servers originally came with Windows 2000, its about time they were replaced anyway, and most servers come with quite cheap Windows software bundled in. If they went for a hardware refresh at the same time it could be quite cost-effective.

If not, I won't reiterate the answers given (except to say that, yes, it can be very expensive!) have they thought about migrating to Linux based desktops or servers? Evaluate what software they need and if, like the French police, they don't need games then it might well be a valid solution.

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