I have three computers with Outlook 2019 installed, two desktops and a laptop. All three are running Win10 PRO version 20H2. I have Outlook set up on all three using my gmail account as an IMAP. I can send emails with attachments from desktop 2 and the laptop with no issues. If I try to send an email with an attachment on desktop1, It hangs in the outbox until deleted, never sent. I can send emails with attachments using the web interface for gmail and an Ipad and an Android phone with no problems. I have disabled all COM addins to no avail.
So far, I have reinstalled Win10 on a freshly formatted drive, uninstalled and reinstalled Office 2019 while deleting the Office and Outlook folders in the AppData directory. I have deleted all .pst and .ost files. I have also removed all profiles using the mail app in Control Panel.
It's driving me frickin' nuts. Cold beer for the solution but don't tell me to send attachments from anywhere but desktop1
Thanks!!!