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I did something similar once.
It was along the lines of making changes, and then deciding to do a server sync without closing the application or going to the realm selection screen -- to backup the amount of data, just in case.
I had several changes to the tab I was on.
I clicked to sync with the server, and it asked if I wanted to save my work. Accidentally clicked no.
Synced without saving, and those changes were gone.
I'm generally in the habit of making a few changes.
And then the hotkey Control S to save stuff.
Make a few more and Control S again.
It wasn't the end of the world, I rarely have more than a snippet or two, without a save.
Hero Lab was, at one point randomly crashing whenever I added hostiles to the portfolio (I have one with the entire party, and add the bad guys who are saved in theirs... so the party can loot and I can transfer gear from the bad guy to the heroes. Then remove the enemies from the portfolio and import the next encounter whatever and whenever that is).
Anytime I do any change in HL, I save.
General habit... it sucks to distribute six pieces of loot across seven characters... sometimes the group gives three things to one guy and one each to three more with three getting nothing... helps the group the most.
Well, move one thing and save. Move the next and save.
It sucked moving six things, and crash next encounter importing (or maybe removing the guy we looted) and then need to re-import, re-distribute etc.
Easier to save with every last little change.
Not often is there a lot of changes (HL or RW, or Word etc) without saving recently.
But I have lost a few things in RW from asking if I wanted to save, and clicking wrong by clicking too quickly, or by having worked on tomorrow's D&D session well past my normal bed time.
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