Abstract
The first session Richard and I did in May was 30 minutes and aimed at the broad picture: why Windows environments end up with certificate sprawl, and what a different approach looks like. A lot of people registered, and most of the questions we got were about specifics.
How does delegated DNS validation actually work if I can’t hand over my DNS provider credentials? What does the agent deployment look like on an IIS box versus a vendor appliance? If I’m already using Certbot and renewal scripts, what does the migration path look like?
Those are good questions, and they deserve more than a quick answer at the end of a 30-minute call.
What we’re covering June 16
Certificate Automation in Practice: A Technical Deep Dive for Windows IT June 16, 2026 | 11:00 AM Central | 60 minutes | Free
Richard will cover the Windows-specific scenarios he sees most often in consulting engagements: Always On VPN, Remote Access, the endpoints where certificate expiration tends to cause the most damage. He knows what certificate mismanagement looks like when it reaches scale because he spends his days cleaning it up.
I’ll do a full deployment walkthrough, live, not a polished demo. Discovery through renewal. The kind of setup where something small goes wrong and we figure it out on the call. If you want to see whether CertKit can handle your environment, this is the closest thing to watching someone actually use it.
We’re leaving significant time for questions. When you register, you can submit a specific scenario you want us to address. If you’ve got a weird appliance, a mixed environment, or a question you couldn’t get a straight answer on from documentation, put it in.
Register here — free, 60 minutes.
CertKit automates certificate lifecycle management across Windows servers, IIS, and vendor appliances, so certificate expiration isn’t something you find out about at 2am.
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