> I can't find a way in the new UI to go back more than ~6 months of conversation history. First, you'll want to make sure Skype is set to keep message history

> I can't find a way in the new UI to go back more than ~6 months of conversation history. First, you'll want to make sure Skype is set to keep message history forever: Skype -> Privacy -> Keep history for... -> Forever Then, you can right-click on a contact -> View Old Messages -> 1 Year, etc. This is assuming you're using Skype, and not Skype for Business; they are not the same: https://en.wikipedia.org/wiki/Skype_for_Business https://en.wikipedia.org/wiki/Skype_for_Business