Advice for Windows users; successfully implementing LE

I’m posting this for inspiration to those of you who are having difficulty creating certs, as I first did, and as Windows user here’s the relatively easiest path I discovered:

Obvious prerequisites:

What I did:

What I found particularly useful was being able to cut-and-paste from my VirtualBox/Linux/Terminal window into my Windows PuTTY SSH session with my webhost. You really need to be able to cut/paste those lengthy alphanumeric strings regarding the domain verification steps.

While I do have a programming background, it’s been years since I’ve done command-line Linux commands and I’ve rarely needed to SSH into my webhost account, but even if you’ve never done it before, however unnerving, it’s not so bad. You aren’t going to crash your web server.

Once my certs were generated I had to work with the tech support folks at SiteGround to install them ($30 fee), since users aren’t authorized to do so, but they installed them within 10 minutes. I suspect when LE moves out of beta and adoption grows, we’ll be able to install the certs for free at webhosts that don’t already allow access.

Anyway, just wanted to share my steps to success as I know this can be a brutal process if you’re new to Linux, SSH, etc.

And thank you, LE Community! Can’t wait till free SSL is a right instead of a privilege.


Great guide! CLI (command line interface) can def be a pain at first I agree. I am glad you used my suggestion I made on another post and boot into linux mint via vbox to create the certs, pretty easy to do.

I would like to add some improvements to your instructions for hardcore windows users that dont know how to use cli very well.

Instead of using terminal->putty, just use terminal
ssh -p (port) username@ipaddress
It will then ask for a password and can continue from there.

An even EASIER way would be to just use the package manager in Linux Mint and install filezilla, connect with same info as your ssh but use sftp. Then you have an easy to use gui and can get everything working without the CLI (excluding cert generating).

Also, SiteGround has LE in the works for integration in their cpanel:

Once my current hosting time is up, I will be moving to SiteGround, since they have everything I have ever wanted in a shared hosting company which others haven’t done: free SSL certs and pagespeed module (in their supercache plans).

Until Windows have native SSH/SSL support, it will always be a pain. For those are going with manual installation, probably Git (comes with OpenSSH) is all they need (apart from the Windows implementation of the ACME client). Tunnelier (a nicer alternative to Putty)/WinSCP will be useful for file transfers.

Indeed, I could’ve staying within the Linux environment, but I had the other Windows stuff going and was familiar with it, so that may be true for others. And I am in the process of switching all my sites to SiteGround. They are really responsive and helpful,