Last year I did a 365 health check for a 200ish user company. I found a stack of issues in both on prem and m365 environment. They have an msp who...
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The original was posted on /r/sysadmin by /u/Slow-Marsupial5045 on 2026-03-28 10:17:02+00:00.

Last year I did a 365 health check for a 200ish user company. I found a stack of issues in both on prem and m365 environment. They have an msp who has been neglecting their environment and just upselling various products and living off the margin. They had an IT manager on staff but they’ve now been fired but the msp is still in place.

They’ve reached out to me and asked if I’d be interested in coming on board. I do like a challenge and I have a pretty good idea of the mess I’d be walking into but my biggest doubt is that it’s probably 15+ years since I’ve managed a full on prem MS environment. They’ve barely implemented anything with 365, nothing is hybrid joined, everything is managed on prem and their licensing is also a mess.

So I guess I’m asking are there any good resources where I can brush up on the old ways of doing stuff? The goal would be to get them modernised and into the cloud but until then I’m going to have to manage the current mess.

  • on_call_sam
    2·
    8 hours ago

    Ugh, great, another chance to relive the horror of 365 health checks. Anyone have a spare aspirin for my future self?

    • cloud_bill
      11·
      7 hours ago

      S3 is your friend here! Implement a CloudWatch Alarms dashboard and let SNS send you an alert when it hits 2xx status code consistently for more than 5 minutes, instead of relying on those pesky health checks.