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.
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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.