Microsoft would like us to think of Office 365, its hosted email and collaboration service, as “cloud”. And it is in many ways; you can even get all your email and Onedrive-stored documents direct from a web browser.

The truth though is that Microsoft has been careful not to disrupt its desktop Office software too much. Most users, in my experience, choose Office 365 in part because of its integration with Outlook, Word and Excel. You can install the software from the Office 365 portal, and open and save documents from Onedrive for Business.

Another part of the service is online chat and conferencing, for which you need the Skype for Business (formerly Lync) client on your PC.

There is an issue here though. Part of the attraction of “cloud” is that you do not have to manage software; but in the case of Office 365 you do have to manage the software that is installed on your PC. Microsoft’s investment in click-to-run installation has helped to simplify the setup, but under the covers it is as complex as ever.

Take the case of a small business I know, which was on the Office Midsize Business plan. Microsoft has retired this plan, so when it came to renewal time the customer had to change to a different plan. If they wanted to keep *all* the features of Midsize Business, including the Access database app, they could migrate to the Enterprise E3 plan – at £14.70 per month, nearly double the £7.80 per user/month for Midsized Business. On the other hand, they could migrate to the Business Premium plan for the same cost and, well, *nearly* the same features. The horrible details are here.

They didn’t use Access so Business Premium seemed OK. On the cloud side, the migration was straightforward. However, since Access was no longer included they had to remove and reinstall Office, as well as the Skype for Business client.

In this particular small business, most of the users needed some assistance with this operation. Unfortunately there is no single button to click that will remove the old Office and install the new one. You have to remove Office using Control Panel, then reinstall it from the Office 365 portal. Removing Office removes the old Skype for Business client, but putting it back means choosing a separate installation option in the portal, which most of them missed. One user somehow ended up with two versions of Office 2016 installed, neither of which worked properly. Office would not activate, reported an error, and offered to repair itself. This was not going to work, since it was the wrong version of Office.

Even when it goes smoothly, the business of removing Office and reinstalling both the desktop software and Skype for Business takes a long time, over an hour.

Overall, life in the Office 365 era is easier than it was in the days of 27 Office floppies, one or two of which were bound to be unreadable. Nevertheless, it is friction, and not fulfilling the seamless promise of cloud.