Looking For Culprit Inhibiting Outgoing Mail

[RGTheProf]

Hell-o Outlook Forum -

Outlook 2019 is putting all outgoing messages in Outbox, and leaving them there. When I shut down Outlook and restart, the messages are then sent. Sometimes twice, sometimes to myself. If I start Outlook in Safe Mode, all is normal. Messages are sent when they are supposed to be. If it's due to add-ins, as some have suggested, there's a list of 4 in a box, but none are checked. 

My Email uses an att.net address, and used to be MyAtt, but is now Yahoo Mail. I have a "Key" between the Yahoo Mail and Outlook. All I need to fix is the dumping of my sent mail going straight to Outbox, and not sending. My service is bad here, but in safe mode, at least it's making it all the way to the Sent folder without restarting the Program. 

Thanks for any suggestions you might be able to offer - RGTheProf

[#2]

Do they send if you hit send and recieve?
Any send and receive error messages?

[#3]

@Diane Poremsky Hi - In order to respond, I'll need to get very detailed, sorry. My problems started when Outlook would not perform it's duties until using Task Manager to "End Task" on Outlook entry.

When re-started, everything would be normal. Recently, problems got worse, because now emails that are sent, go straight to the Outbox. Now I need to shut down, and on restart, the mail gets sent.

My Email is an "att.net" address, which recently became Yahoo Mail. My browser mail works fine. I have succeeded in syncing my "Security Key" between Yahoo Mail and Outlook, using that key for password in my Email Account in Outlook. After entering the remaining mail credentials, and running "Test Account Settings" procedure, I happily saw the two green checkmarks. Ok.

Meanwhile, the Sent mail is still going to Outbox and hanging there. Upon Googling the issue, it was suggested that I run Outlook in Safe mode, to discover what "Add-in" is the issue or the culprit.

In Safe mode, everything works as it should. In examining Add-ins, only one was, no longer is, active: "Microsoft.VbaAddinForOutlook.1". Three are inactive and one is disabled. In "Manage" the drop down is "COM Add-ins", and when I hit "Go", the COM Addins page has four entries with checkboxes, and none are checked.

This is what I've learned, and if I can grasp how to get the add-ins setup where they allow me to send emails, I'll be so happy! Thanks, Diane - TheProf

[#4]

@RGTheProf   I have an update: The only remaining problem is the outgoing mail goes to Outbox, after hitting send on the message itself. The message will sit there until I hit the send/receive button, then it goes out as it should. I have received no Forum suggestions for any repairs. All repairs I have made have been with the assistance of the gentlemen at Outlook. They've been very generous with their time, and we've accomplished a lot. I could still use a tip to repair this final glitch, but will most likely find it elsewhere, sorry. TheProf

[#5]

Is send immediately enabled? Are your send and receive s groups set to send every 5 minutes or so (no lower).