Stop updating one app at a time.
The installer/updater needs to be improved to evaluate installed components and offer to update them all at once.
Today, when I opened SSMS, I received a suggestion to update SQL Prompt. When I was done I reopened SSMS. From within SSMS, I opened a Dependency Diagram and was offered to update that component, which also requested to close SSMS. When that was completed and SSMS was reopened, I needed to open SQL Compare, which, in its turn, offered to perform an update and requested to close SSMS.
All this could have been accomplished with a single SSMS restart if the SQL Prompt updater were to offer to update other SQL Toolbelt Essentials components as well.
Louis Somers commented
Using Chocolatey to install Toolbelt resolves this issue, however it does seem like Chocolatey updates lag behind for a few days. It would be great if the Chocolatey package is ready before the update-pop-ups start appearing.