Windows Server, Microsoft 365, migrations
Servers watched at three in the morning.
A server that fails quietly is worse than one that fails loudly. Monitoring, patching, tested backups and a plan for the day the hardware dies — plus honest advice on what belongs in the cloud and what genuinely does not.
What it costs
$349 per server per month managed, including monitoring, patching, backup verification and quarterly test restores. Project work such as replacements and migrations quoted fixed-price.
The failure nobody sees coming
Servers rarely die all at once. A drive in the RAID array fails, the array carries on with no visible symptom, and nobody notices because nobody was watching. Months later a second drive goes and the whole thing is gone — along with, very often, the backups that were quietly failing for the same period.
This is the single most common serious incident we get called into, and it is entirely preventable with monitoring that costs a fraction of the recovery.
What managed server support covers
At $349 per server per month: 24/7 monitoring on hardware health, disk capacity, services and backup status. Patching in a maintenance window you agree. Antivirus. Backup verification with quarterly test restores. Performance review before things get slow enough to complain about.
Plus the thing that matters when it goes wrong: documentation good enough that someone who is not the person who built it can rebuild it.
Cloud, on-premise, and the honest middle
Not everything belongs in the cloud, and the people telling you otherwise usually sell cloud. Line-of-business applications with heavy local file access, systems with hardware dongles, and anything where your internet connection going down means the business stops — those often still make sense on-premise. Downtown you at least have the connectivity to make cloud viable — most Loop and West Loop buildings carry several carriers, so a genuinely diverse second circuit is obtainable, which is not true everywhere.
Email, file sharing and collaboration, on the other hand, have very little business being on a server in your closet in 2026. Microsoft 365 does it better, cheaper and with far less to go wrong.
Most businesses we see should be somewhere in the middle, and the useful conversation is about which workload sits where — not a slogan.
Migrations without the weekend from hell
Server replacements and 365 migrations are planned, staged and done outside working hours, with the old system kept running until the new one is verified. Mailboxes migrate with history intact, shared drives keep their permissions, and staff get a page of what changed rather than a surprise on Monday.
We quote migrations fixed-price. Hourly billing on a migration puts the risk of the unexpected on you, which is exactly backwards — we are the ones who are supposed to have anticipated it.
Microsoft 365 administration
New starters set up before their first day, leavers disabled the hour they leave with their mailbox preserved, licences audited so you stop paying for people who left in 2023, multi-factor authentication actually enforced rather than merely available, and retention configured so a deleted mailbox is not a permanently deleted mailbox.
Worth saying plainly: Microsoft does not back up your 365 data in the way you probably assume. Their retention windows are short and their remit is availability, not your recovery. Separate 365 backup is inexpensive and is on our standard recommendation list — see backup and recovery.
FAQ
Questions we get asked
Should we move our server to the cloud?
Some of it, probably. Email and file sharing belong in Microsoft 365 for almost everyone. Line-of-business applications with heavy local file access, or anything that must keep working when your internet does not, often still make more sense on-premise. The answer is usually a split, and it depends on your applications and your connection.
How old is too old for a server?
Five years is where we start planning a replacement, six is where we start pushing. Not because it stops working, but because out-of-warranty hardware failure turns a four-hour incident into a four-day one while a part is found.
Does Microsoft back up our 365 data?
Not in the way most people assume. Microsoft protects the service's availability; recovering your data after an accidental deletion, a departed employee's mailbox purge or a ransomware event is your responsibility. Retention windows are short. Third-party 365 backup is cheap and we recommend it as standard.
Can you take over a server someone else built?
Yes, and it is common. We document what is there first — which is frequently the first time anyone has — then flag anything urgent before agreeing what ongoing support looks like.
What does a migration cost?
Quoted fixed-price after we have seen the environment. Fixed-price rather than hourly is deliberate: on a migration, the risk of something unexpected should sit with the people who were supposed to anticipate it.
Do you support Linux servers?
Yes for common infrastructure roles — file, web, database and application servers. If you are running something genuinely specialised we will tell you honestly where the edge of our competence is.
Ready when you are.
Ring us and describe the problem in plain English. We will tell you what it costs before anyone drives anywhere.