GlassWire does this intentionally with app updates. There was another bug with “ask to connect” and I should have read your post more closely. Sorry about that.
We are going to add a new mode to GlassWire that should solve this issue for you in the future. You will be able to allow certain publishers if you want, like Microsoft for example.
We do not believe it is safe to allow app updates to connect to the internet because it could cause a malware application to just name itself the same as the Outlook file name.
Currently GlassWire checks if you should allow an app to connect to the network if it has completely changed. For example, it may not even be the same app at all, but it may just have the same name.
Please be on the lookout for this future publisher solution that should solve the issue for you.
Thanks for your feedback.