What might prevent organizations from moving to Microsoft Exchange Online if they’re currently using on-prem Microsoft Exchange Server?

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Chief Technology Officer in Software, 11 - 50 employees
I’ve seen this a few times. In my experience this tends to be the upper CSuite not valuing the project sufficiently. Sometime too old. Sometimes too set in their ways “if I can see it i can control it”.

I don’t think I have come across a CTO or CIO who were objecting to it.
Director in Manufacturing, 1,001 - 5,000 employees
The cost calculations may be a deterrent

We had a tendency to stay on exchange until the version was to end of life and all security patches were ended. This was less money but didn’t have the new features etc. We did switch to Exchange Online and it’s great. But on a pure cost basis it is more expensive than how we used to run Exchange. We did squeeze every nickel and penny out of our systems before upgrades which perhaps wasn’t always the best security strategy
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Director in Manufacturing, 1,001 - 5,000 employees

In some cases this meant skipping an entire full version. When that was possible it was significantly less cost than Online

MSP & IT Director in Services (non-Government), 2 - 10 employees
I’ve got clients that prefer to buy a server and licensing once every 5+ years and not deal with monthly or annual pricing, despite how everything is moving to a subscription model. Agree or disagree it’s a common reason I see.
IT Director in Education, 51 - 200 employees
Lack of executive buy-in for something new.

Worries about security with using a more public offering.

Recent Azure AD authentication outages affecting ability to access email.

Lack of skill on the IT team to handle the migration combined with limited budget to hire consultants to help.

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Poor communication46%

Too many customizations47%

Misalignment with business priorities34%

Skills gaps31%

Lack of resources26%

Other (please list in the comments)1%


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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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Discretionary budgeting8%

Strategic budgeting72%

A combination of discretionary & strategic budgeting17%

Other (please explain in the comments)1%


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