Calendar appointment fails to save to organizer calendar when created by calendar delegate

Does Outlook client or Exchange have the ability to retry a failed Save action to a calendar folder for a meeting event? The scenario specifically is an instance where a calendar delegate creates a meeting on behalf of the organizer. The attendees receive the invite, accept, and their calendars update, but not the organizer. This also occurs when a delegate sends updates to existing meetings and cancellations. 

I am aware of a similar issue with Skype meetings failing to save to the organizer’s calendar. There is a documented workaround advising to lengthen the time delay for AutoSave in the delegate’s Outlook, or to disable the delegate’s AutoSave altogether. Our environment has mixed results.

"The operation cannot be performed because the item has changed" error when a delegate creates a Skype or Teams meeting in Outlook

Currently, our team is deploying Office Update Version 1909 Monthly Channel, which includes an update to the calendar sharing feature using REST instead of MAPI. This update appears to address the very factors in Outlook's design that result in poor performance for delegate-based calendar management.

That having been said, have others experienced this issue where a meeting invite / update sends successfully, but fails to save to the organizer's calendar?

Outlook calendar sharing updates

Shared calendars updates in preview

Release notes for Monthly Channel releases in 2019