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Happy Thanksgiving, Fellow Sysadmins. I’m The New (and First) In-house It Administrator For A ~70-endpoint Company. No Servers, No Domain, And Until Two Weeks Ago Everything Went Through An Msp. Now All Requests Come To Me First, And I Escalate Only When Necessary. Here’s What I Walked Into:

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Almost every workstation is running Windows 11 Home

A handful are Windows 11 Pro

All users log in with local accounts

About half the company is on M365 Business Premium, the other half on Business Standard

No Intune, no Entra ID join, no AD (on-prem or cloud), no real identity management

The MSP provides ThreatLocker and Huntress, and the long-term goal is to reduce the monthly spend and move IT responsibilities more in-house while maintaining a co-managed relationship with the MSP.

My first major project, already approved by leadership, is to:

  1. Upgrade all appropriate users to Business Premium

  2. Upgrade all endpoints to Windows 11 Pro

  3. Entra-join every workstation

  4. Enroll everything into Intune

  5. Begin modernizing the environment and decreasing MSP dependency

My background is seven years as a server engineer, so this is a big shift for me. I’m learning a lot as I go, and I’d appreciate any advice, lessons learned, or “watch out for this” insights from anyone who has gone through a similar small-business modernization or MSP off-ramp process.

What pitfalls should I expect? What would you tackle first?

Thanks in advance and enjoy the holiday.

Edit: Leadership mentioned that in about 6-9 months we will reevaluate and if needed we can either bring in another IT person or continue co-managed with the MSP. ALSO, the long term (3-5 years) plan for my role is to transition into a Director of IT.

submitted by /u/thatflacoman
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