Sometimes Tortoise requires me to do cleanup for no good reason - meaning I didn't abuse / kill it / stop it in the middle ... IMO this is "normal opertaional flow" and shouldn't require a manual cleanup.
Is there a way to not show these cleanup requests to the user but rather just do them silently under the hood and present a consistent experience to the user?
Actually it's not TortoiseSVN, but svn itself which requires this. It means that something did get messed up. What and how is hard to answer with the facts you've given.
The best might be you try to work more consciously so that you remember what you did immediately before this happens and watch for a pattern there. If you found one, maybe someone could answer your question.
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