I usually use GMail in conversation mode.

Suppose I send an email and label it with PersonalStuff
When a reply comes in I see it with labels Inbox and PersonalStuff
If I remove it from Inbox it displays as in PersonalStuff, but when I 
switch off Conversation View it turns out that it is not labelled 
PersonalStuff but is unlabelled.

How do I keep an entire conversation labelled?

And is there a way to organise old emails in this way without going through 
hundreds of emails one by one?

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