Set up a Free SSL Certificate on a Windows Server Using Let’s Encrypt

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In Episode 44 of the Tech Smart Boss Podcast, I talked about 3 ways to set your website up with SSL encryption and the reasons you needed to do it as soon as possible (listen here – )

One of the ways discussed was Let’s Encrypt, which provides you a free and easy way to set up SSL on your site.

Since Let’s Encrypt is an API based service, the biggest use case is for software developers to integrate with Let’s Encrypt so that the custom domains you set up in their SaaS app are encrypted.

But what about small businesses that run their own web servers, specifically, Microsoft Windows Servers (I’m raising my hand, that’s me).

Well in this video, I go through how to get a free SSL certificate from Let’s Encrypt, on your self-hosted Windows Server and to do it I use Win Simple which takes that Let’s Encrypt API and puts it in a nice command line GUI (you can download Win Simple here – )

I’m super excited for this as it’s going to save me a lot of money in those SSL renewals from GoDaddy (sorry GoDaddy) and I hope it can save all my Tech Smart Bosses some money too.

Hope you enjoy and if you like this, press the LIKE button on the video and subscribe to our YouTube Channel —

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Rodrigo Vaz · June 29, 2018 at 6:47 pm

Works fine, windows 2008 server with IIS 7. tks!!

Mohamed Elmahal · June 29, 2018 at 6:47 pm

Hello thanks alot for tutorial very very nice and cool
I have very important question please answering me :
is this certificate
Will get renewed automatically
and my site will staying secure
or I have to do some process after three month or something like that pleeeeeeeeease answer me
it's very important to me .
I don't want to renew this certificate manually
is it gonna happened
and get my website inside iis secure
I have to go my server and do this operation again to get
New certificate or renew the old one

Ammar Ameen · June 29, 2018 at 6:47 pm


Minute 5:50 you did some magic what was that? the reason I ask is becuase My ISP blocks port 80 so I only have port 443 working can I still do this process through port 443. thank you for this video.

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