Quicken repeatedly crashes during investment account reconciliations

Marty Dopps · December 2019

I'm running Premier 2020, Version R23.18, Build 27.1.23.18 on a Windows 10 desktop PC. I've been reconciling some fairly old Investment accounts over the past month between the Quicken registers and my broker statements. Some accounts were unreconciled since 2012, and I'm bringing them to a reconciled status (currently through Q4-2016, will then proceed to 2019). When I reconcile the accounts I don't move from one month to the next until the cash is tied out exactly, as well as the investment holdings, and the reconciliation function completes as expected. The issue is when I'm updating transactions in Quicken I've been getting a LOT of "would you like to save?" error messages (which I always answer yes to) before it validates the current transaction and then shuts down the entire program. As part of the shutdown process I get a system message asking me if I want to provide email address and description of problem, both of which I've provided every single time. The problem is I've gone through this system crash and reporting exercise several HUNDRED times in the past month. Sometimes it happens multiple times within the same monthly statement cycle, some times it'll go several days in a row without crashing, and some times it happens within the span of just a few minutes. I don't think I'm all that "special" in Quicken's eyes, but I'm kind of surprised that submitting the same error report several hundred times in the past month that Quicken hasn't reached out to me to ask WTH? So, does anyone have any suggestions?