I itemize my transactions to track sales tax and purchase categories. I itemize the transaction and save. I also make a daily copy of my file. Inevitably, the next day the transactions are not itemized. Normally it's not a big deal, as my daily purchases are small, but after returning from vacation, I itemized about 10 transactions yesterday, and now I find that all those transactions were not saved!
I use Quicken Classic for Windows.
[Edited - Readability]