Many OLSB customers have argued that the transition to Office 365 or to another third-party email/website hosting provider is too complicated technically for them to carry out.

Some have suggested that Microsoft could have closed OLSB to new signups while keeping the service operational for existing customers.

Many have said that Microsoft could have made the transition to Office 365 easier. A specific issue that has drawn many complaints is that the work of migrating an OLSB website to Office 365 is arduous and erratic, because the Web hosting platforms are different. As a result, some functionality and design features have to be manually re-done in Office 365.

Thus, many users are in the transition, especially if the websites have .

Recently, some Microsoft partners developed automated tools to transfer websites from OLSB to Office 365, including . However, Microsoft never developed its own tool to do this.