My organizers won't print to DMS. I have updated Lacerte and DMS, and checked that "suppress organizer " is not checked, and run PDF Repair utility. I can print other things from Lacerte to DMS (e.g. a single page document). I do not get an error message, but the organizer is not in DMS. I have checked all folders, sorted by date, nothing printed.
Here is my workaround. I have a folder "DMS Temp". Print organizer to pdf and put them in "DMS Temp". You can then drag and drop into DMS.
Honestly, I will be very surprised if they do any more repair work on the Organizer. I worked really well for 2019. What did they have to mess with it to get it to where it is now. It is above my skill level to understand why you break something to make it better.
I use thunderbird and have is use imap with gmail.https://support.mozilla.org/en-US/kb/thunderbird-and-gmail#w_configuring-your-gmail-account
That will then keep your e-mail on your computer and the "cloud" and be able to send things from Lacerte.