Thanks for opening the issue @shiftenterprises. We have been watching the Bug
https://tracker.zentyal.org/issues/2747 in the tracker since we have tried out Zentyal, and - like you - are still waiting for the fix.
Same as for you guys, for our customer such a "solution" like pushing the send + receive button would not be acceptable. Somebody has suggested another workaround, like manually setting the interval of checking Outlook mailboxes to 1 minute. This might be feasible for a 5-persons company, but I can hardly imagine any admin who wants to go back to the times where it an admin was necessary in order to setup an email account in Outlook.
There has been an update to the bug, just a few days ago, mentioning that the bug is going to be fixed, but only in the commercial version. This makes me angry, although we would offer nothing but the commercial version to our customers. If this bug is as complicated as Zentyal says (open for 5 months), it might need extensive community tests to give customers confidence.
Advertising on the Zentyal front page says: "Zentyal is the first ever provider of Fully native Microsoft® Exchange protocol compatibility to the worldwide messaging and collaboration market". The other slogan on the front page promotes a conference, sponsored by Microsoft, saying "Where protocols talk openly together". - From these slogans I would assume that Zentyal does everything possible in order to achieve maximum compatibility with Outlook as well as involving the community. The bug updater unfortunately seems to have a different perspective.
However, let's think about how to fix this with a workaround. The community also has to do its part to being open and adapting to issues.
The question first sounds simple to me, but I did not do any research yet. Can we configure Outlook remotely or via script in the right way? - I can imagine that a logon script could set registry settings, or maybe even a group policy could solve the problem. Does anyone know where Outlook stores these settings, and how exactly it does? The "send & receive" itself can obviously be triggered programmatically (
https://www.add-in-express.com/creating-addins-blog/2011/10/05/outlook-send-receive-programmatically/) - so it even might be feasible to code a windows service which is notified by a server-side piece of software whenever new emails arrive (or checks it via IMAP ;-)) - and then triggers a send & receive. Sounds complicated as a process, but is quite few effort to code, and who knows, it might solve it!
If anyone has more suggestions, please let us discuss these here. We are definitely up for doing some hands-on work in terms of coding.
If the task could be automated, and thus would not be a manual admin task anymore, it might be an acceptable bug at least for a while. Do you agree?