Emails stuck in my draft folder

I finally gave up and moved everything to Gmail. Google is our domain host for our biz name and emails anyway. We were just forwarding emails to Outlook because we preferred that platform for email. But I got tired of trying to make it work and emails from drafts still have never sent and it's been 17 days. Our CEO is using both Outlook and Gmail to keep up with his emails for our business. He can read them all in Outlook and maintain the folder organization that we both really love in Outlook. But he has to use Gmail to send emails because nothing will send from Outlook. We are beyond irritated with Outlook right now. But as I stated before, I've always hated Microsoft anyway.

I'm having this same issue and so are two other people on my team. We send an email, it looks like it sends. And then it's back in our Drafts folders. And it's an inconsistent issue. So it's not like we can recreate it to diagnose the problem.

This fault is driving me insane. I have lost business from this and makes me look like an idiot. Please do let us know if you find a solution Tina :)

Is anyone at Microsoft even looking at this forum? We are on their board. I am sick of this issue. This is not complicated. It can send the emails just fine.

Yes, i have the same issues! Its not on every reply, but just random ones - which makes it even more concerning as to which emails actually got sent out. On top of that, random settings seem to keep reverting back to default, no matter how many times I got back and set them the way I want. Microsoft - Please fix these bugs for your paying (for now) customers!