Quicken Classic desktop on Win10 - After resolving a previous issue along this same line a while back everything has been working as advertised for a few weeks now. Starting around May 18th, the automatic sync feature didn't start when exiting the application following a checking / savings / credit card register transaction entry or update. If I restart the application, select the Mobile and Web tab, and manually sync the data, everything works fine. The settings are SYNC is ON, and Sync to cloud on closing Quicken is enabled.
Don't know if it is related, but I noticed an occasional error message during two manual syncs on the 21st regarding "server errors" and to try again later. However, to the best of my memory, the auto sync function has been non-working or unreliable since the 18th or 19th.