GWSMO and Outlook Version 2303: Can't select "From" Addresses When Composing New Message

I found a bug/incompatibility with GWSMO (Google Workspace Sync for Microsoft Outlook, the Google Workspace sync integration for Outlook).  Here's what I found:

Steps to reproduce:

• Install Outlook 365 Version 2010 (I'm using click-to-run build Build 15726.20202)
• Test with a Google user that has multiple Send Mail As addresses configured properly under "Accounts and Import" tab in Gmail settings.
• Install GWSMO from .EXE using recommended settings. Follow the steps to authorize with your Google account via OAuth/browser
• Allow at least 5 minutes after everything is installed for GWSMO synchronization to progress far enough for Google account settings to propagate to Outlook
• Click on "New Message" in Outlook
• Click the From: dropdown to select one of the alternative send addresses
• Observe that the list of available addresses matches the list of Send Mail As addresses in Gmail settings

• Close Outlook, go into Windows Control Panel->Mail and remove the profile.
• Remove Outlook from the system
• Install Outlook Version 2303 (build 16227.20004)
• Repeat above steps to install GWSMO and configure Outlook, allow to sync, start a new Email, and click the From: dropdown
• Observe that now the list of available addresses does not appear when you click From:

Google believes this to be a UI issue with Microsoft Outlook, and thus would not look into it.  They told me to let Microsoft know about it, but I have a pretty good idea what they are going to say. Either way I didn't see anything about this issue anywhere on the web, so I decided to post about it.

So Much To Know...

I once spent an inordinate amount of time with a friend of mine, who I consider to be a master of recording & sound engineering.  He has been at it for decades, paid his dues, and worked with some greats.  He executes his craft with the utmost care and caring... (something I have come to realize is what separates the true pros from the learned hacks). Anyway, I remember watching him in do his thing in the studio as I assumed the role of a quiet observer.  Despite his obvious adeptness and ingenuity, he would always play the part of the  Absent-Minded Professor, as opposed to the James Bond smooth-operator type.  I think it was partly a schtick to make people feel more at ease, but there was a genuineness and willingness to be vulnerable, as though allowing himself to be human probably made the job less fatiguing.   I distinctly remember my favorite phrase of his.  On a couple of occasions, while turning knobs and fixing some problem, in a wonderous voice he would declare, "so much to know..." 

It's stuck with me because it's true about so many things, no matter how much of a master of your craft you are - there is always more to know.  So much more.  I've worked in IT and done various software development for about 30 years now, and yet that's been the theme for me lately - as I try to wrap my head around newer (to me) concepts such as containerization, full stack application development, and more.  I should have started learning these things about 10 years ago, so I have to play catch up.  But it's enough to make me feel old. 

Anyway, follow along as I may post some perspectives on (but not limited to) the following concepts, as I learn them:

• React/Mongoose/MongoDB
• Python/Flask/PyMongo
• Docker
• Kubernetes Clusters, K3S for high availability scalability, management thereof
• Tying all this together: MicroSaaS development and deployment

RANT TIME: Why do replies to a message I sent go to my spam folder?

Despite what one would think/hope, sending a message to a given address does not inherently give Google a high confidence that a reply from this address is expected (and, for example, that it should bypass spam checks). I have confirmed with Google's tech support that there is no way to automatically have this happen. The user can do the following:

1. Add the address to your contacts list in Gmail.

2. Check spam folder for replies, and mark it as "not spam" if something ends up there, which should influence the fate of future replies received. I can also approve an address at the domain level, i.e. if it is a big vendor or similar. I've had to do this with several of our Chinese vendors. I regularly ask engineering and purchasing to give me a list of the supplies we deal with, so I can approve them as a preventative measure.

For what it's worth, all of the false positive instances of reply -> spam we have experienced have involved the sender's email server having a problem. In the most recent case, it appears that the sender IP address appears on at least two internet blacklists. Since that is beyond my control, but we are trying to do business with these people, I can only add the domain to the approved senders list so that future replies from them should bypass the checks. However, if another company with a problematic email server replies to one of us, their message could very well still end up being marked spam.

Since Google can't help us, I am trying to figure out some kind of human process to defend against this, but to getting to a 0% false positive rate looks kind of ugly.  One idea I had is to make a script that is invoked when a user sends a message, and somehow adds the recipient address  to their contacts and/or some sort of approved sender list. 

Has anyone done this?