The dreaded 0x800CCC0F sending error

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I'm able to receive, but still not send,

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Did you let Outlook configure the account or did you manually configure it?

The most common reason for being able to receive but not send is that the Outlook server is not set to authenticate with the inbound server but then you shouldn;t have been able to get the test message - so something is off about this?

While the these questions may seem redundant - have to ask just to confirm things

#1 - you created a new Outlook profile and made sure to set the new Outlook profile as the default - correct?

#2 - Just to cover all bases to check the SMTP authentication

a) - Click on CTRL+ALT+S to bring up the Send/Receive dialog

b) - Select the <Group> and click on <Edit>

c) - Select the email account --> click on <Account Properties>

d) - Click on the <Outgoing Server> tab - is it as shown in the screenshot

Lastly, do you have any messages in the <Sync Issues> folder for either account? If yes, what is contained in the messages?

If you don't see the <Sync Issues> folder, press CTRL+6 to set the Outlook Navigation pane to <Full Folder> view. If the Nav Pane items appear vertically, click on the last icon and select <Folders>

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...and I've been bumped to Tier 2, #2 in the queue.

OK, I did that, but still no love. I'm able to receive, but still not send, from either my GWA or my GMail account.

Oddly, when I reconfigure, Outlook sends a test message to the server, which comes back successfully.

Also oddly: I don't have this issue with using the native email client on either my iPhone or my iPad.

Look forward to hearing the results of your chat session

In the meantime, for a quick test to eliminate anything to do with the Outlook profile, can you create a new Outlook profile and configure the accounts using the <App Password> as the email account password

a) - With Outlook closed open the Control Panel <Mail> app

Just in case you need info regarding how to access the Control Panel Mail app, that's described in the following article by Outlook MVP Diane Poremsky

Where is the Control Panel Mail icon?

https://www.slipstick.com/how-to-outlook/where-...

If using Windows 11

How to Open Control Panel in Windows 11

https://www.lifewire.com/open-control-panel-in-...

b) - Select <Show Profile> --> <Add> --> give the new profile a name (no need to remove the existing Outlook profile)

c) - Configure your email account(s)

*** if you want to configure the accounts as IMAP accounts, you should just need to enter the email address and <App Password> as the account password and Outlook will automatically configure the account using IMAP

d) - Set the newly created Outlook profile as the default for the next time Outlook is opened otherwise it'll use the old profile

Required Forum Disclaimer: The above links are non-Microsoft websites. The pages appear to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.

Karl, I had to enable 2SV as the Google Workspace Adminstrator - I enabled it, and it appeared. So I set 2SV for both, and I created an App PW for both (each is different). I added them to my Outlook config per your instructions, and I'm attempting to send from each... Still no love.

I'm in a Chat now with GWA support, will update this thread.