Windows 2008 Standard Server

I need a one time experienced for hire help to install LetsEncrypt on my Windows 2008 Standard Server II7 for one single domain and one single subdomain.


It's not prohibited to recruit paid help or offer yourself as a consultant here. Staff members have confirmed this a couple of times and I don't think that policy has changed.

That said, you'll probably get a lot more eyeballs by asking for help on a freelance site or something.

I’m sorry to risk invoking one of the tropes of a bad support forum: “your specific question is wrong because you should be doing something else instead.” If you’re already aware of the info below, then I apologize in advance. You can definitely install an LE cert on 2008’s IIS and hopefully someone here will be able to help you with that.

That being said, all editions of Windows Server 2008 are out of support and not receiving security updates, unless you are paying for Extended Security Updates or running them exclusively as VMs in Azure:

I strongly recommend that you upgrade immediately, perhaps as part of hiring someone to help you with this. It is unsafe to serve a Web site from an OS that no longer receives security updates. It is especially unsafe if the Web site is available on the public Internet, even if it is behind a firewall or other security service.

I hope this helps, and best of luck!


If you can't migrate from Server 2008 you can consider putting behind a proxy to limit the type of traffic that the server is exposed to, if you put it behind Cloudflare (for example) that also means you get free https via their proxy. As James noted, you need to migrate your workload away from Server 2008 immediately, because unpatched servers shouldn't be connected to the internet.

If you really want to get a cert working on your server, you can use any tool (Certify The Web, win-acme etc) from another computer to get a certificate as a PFX file, then install that manually. To do so, you can import the certificate into the Personal/My certificate store then select it under IIS, Your Site > Bindings...> then add an https binding and select your certificate, but you will need to repeat this frequently before certificate expiration.

Really though, I would take this is an opportunity (and reason) to upgrade your OS, as an unpatched server exposed to the internet could be a business critical failure waiting to happen.


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