I've also been running Quicken since the days of DOS. Usually not many problems. Everything was running fine in Win 7 Pro except I was not able to run the updates. They would fail. That didn't seem to matter as everything I needed was working fine. Then my Win 7 machine crashed and I had to get this new Win 10 computer. Installed Quicken and it appeared to run the updates successfully. Reloaded latest backup file and started using it again. Everything was fine until I started using that one account. That's when it started happening (just that one account crashing). Tried reloading it, same problem. Tried uninstalling and re-installing Quicken and went back to a backup prior to the problem. That appeared to fix it and everything worked just long enough for me to manually add all the data that I got after that older backup date. Just when I had everything caught up it happened again. I contacted Quicken for support and the nice lady started having me try all kinds of things. We couldn't find a problem. Then she had me create a new account and told me how to copy all the transactions from the old (problem) account into the new account. While doing that, after over an hour on chat with her, the whole Quicken program and the chat window crashed, possibly because she had me copy too much data at once. That's what it looked like anyway but why the chat window crashed at the same time baffles me. So I lost that chat but I had the case # so contacted them again. This time the guy wouldn't help because he said they were not supporting Q 2014. The lady before him didn't seem to care about that but he did. So I knew what she was trying to have me accomplish so I started at it again only I just copied a few years worth of data at a time and I got everything copied over to the new account. This was a VISA account and it is linked to my checking account for the payments so when I went to look at the checking account is was something like 90k in the red. What was happening was that all the entries copied into that new account included the linked payments and they were deducted a second time due to the linking. I'm ready to give up, go buy Quicken 2017, go back and get that old backup and manually re-enter all the new (since that backup) data again. It took me two days to do it last time so I'm not looking forward to it. I hate new computers.