Windows Server 2003


Hello, everyone,

I have an annoying problem and I just don’t know how to proceed.

We still have an old Windows 2003 R2 server, which we are not allowed to replace for stupid reasons.
On this one I would need an SSL certificate. However, all tools known to me require Windows Server 2008 or newer (.NET Framework 4.5+).

Is there a possibility to provide this 2003 server with a certificate?

Many thanks and cheers!



It’s possible, however i’m not sure if you could install it manually to the server… (since i’m not familiar with win 2003)

You could always use an online tool to request & issue the certificate… (However this will need to renew manually, without automatic renewals it would be painful…)

Try / ( also provide you the option to use dns validations)

Thank you


Thanks a lot for your answer stevenzhu :slight_smile:

I already saw zerossl but I do not understand the function of HTTP verification. Where exactly do I have to store the required file in a Windows system?


It’s stored underyour website root/.well-known/acme-challenge folder…

Thank you


I’m sorry to ask like a complete idiot, but I don’t have that directory… Do I have to go there via IIS?
Thank you so much for taking the time for me


The website root is just where you store the website files on the server…

For example, it might look like D:/somefiles/mynewsite/site1/

Thank you


Ha-ha-ha, now I really had to laugh.

First of all, I got it right. The path is C:\Inetpub\wwwroot.well-known

Then I had problems on Zero-SSL. Attempt to verify the file came an error with “DNS problem: NXDOMAIN looking up A…”.
Then I noticed the following constellation:

The server is called with FQDN:
But is a completely different company and of course we have nothing to do with their DNS. Our domain is

I was so shocked that I need a cold beer for now. Does anyone have any further suggestions during this time?


Hi @Kathaki

before you try the next step: Create the directory C:\Inetpub\wwwroot.well-known\acme-challenge and put there a file named 123456789 without file-extension.

Then try to fetch this file with your browser:


There may be a problem with such files without extension. Perhaps you have to add a mime type. Later versions can use a configuration file, but I don’t know how to do that with Win2003.


Already finished the verification JuergenAuer :slight_smile:

And you are absolutly right. You need to add a MIME to the new virtual Directory with “. and text/plain” or something like that.

I have now issues with some DNS error cause the FQDN is but our domain ist


You’re not allowed to get a certificate from a publicly-trusted CA like Let’s Encrypt for names that you don’t control. If belongs to a different company in the public DNS and is pointed at your server only from the point of view of your internal LAN, Let’s Encrypt and other publicly-trusted CAs won’t be able to issue you a certificate for


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