Let’s Encrypt is an initiative to give https support to as many sites as possible by providing free ssl certificates and making implementation easier. However, most tools for this are only available from the commandline. Certify Ssl Manager provides a graphical interface for requesting and managing these certificates on Windows Servers with IIS. The developers released version 4.0.10 earlier this month and made the following improvements:

Version 4.0.10:
Important: Fix issue with binding not being updated to the latest certificate (bug from v4.0.9)
Version 4.0.9:
Fix wildcard domain binding matches
Improve Azure DNS API provider
Implement retries for IIS simultaneous binding updates
Certify SSL Manager 4.0.4

Version number 4.0.10
Release status Final
Operating systems Windows Server 2008, Windows Server 2012, Windows Server 2016
Website
Certify the web
Download
https://certifytheweb.com/home/download
License type Conditions (GNU / BSD / etc.)