Welcome to my Cloudy Thoughts...

Welcome to my musings in all things Cloud. We will travel through the inner workings of my brain to open the doors and explore Cloud Computing, whether it be fully in the cloud, hybrid or hyperconverged.

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One of the biggest things lacking from Azure local was a proper and easy migration path. I have used many tools to accomplish this including SCVMM, Veeam and

Fully Upgrading Azure VMs to Trusted Launch Azure • Security • How-To I had a client call me needing to upgrade all their supported virtual machines from Gen

We had a large customer who fell off their chair when they seen the price on their Broadcom bill and wanted to get off the platform ASAP. They

Microsoft has been on fire this week. Besides releasing a module to Migrate VMWare to Hyper-V, they have released Windows Backup for Organizations! What it actually does (in

On 8/26/2025 Microsoft released a new extension (in preview) for Windows Admin Center. This module is much needed and brings functionality from SCVMM into WAC to migrate VMWare

So I am minding my own business doing worky things and I hear a ding on my phone. I look at the Summary Siri gave me and I

In this article I wrote about how Microsoft is deprecating direct send due to security concerns. I also wrote a report to help identify what’s being sent via

If you are using the Direct Send feature, or if your tenant is old (which means this is enabled by default), your tenant is not secure. WAIT WHAT???

I am trying to deploy a Virtual Machine on Azure today, and I have been met with nothing but troubles and azure local not listening to me…. NO

Rolling out Azure Site Recovery…. So I am rolling out ASR for some posts on designing redundancy and failover for Azure Local, and I have some small intel

New Month… New Azure Local updates! Azure local is always changing and it seems new features are coming out, it’s like your favorite holiday with presents come every

This is part of an on going series on my shenanigans in rolling out an Always On VPN Solution. Part 1: Always On VPN Overview Part 2: AoVPN

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About Me

Hi. I am Jay Calderwood and I am a 25 year IT professional. These days I am rocking out on Cloud Architecture and design focusing on Azure and M365 services including Exchange Online, Intune, Teams and Security. I hold several Azure and M365 certifications, and I aim to assist people using what’s stuck in my head mixed with witty banter. 

Check out my Microsoft Certifications:

Azure Certified: Solutions Architect
Azure Certified: Administrator 
Microsoft Certified: M365 Administrator Expert 
Microsoft Certified: Teams Administrator