The dreaded 0x800CCC0F sending error

Even if Office 365 works, I refuse to pay for software by subscription. I can get Office 2021 for about $40 bucks, it seems - that's supported, correct? Any reason I shouldn't go that route?

Even if Office 365 works, I refuse to pay for software by subscription. I can get Office 2021 for about $40 bucks, it seems - that's supported, correct? Any reason I shouldn't go that route?

First, the only purpose for suggesting trying Outlook 365 is that it's a free way to see if Outlook '2016 is the culprit - no more no less

As for the $40 options - all depends on which offer you are referring to so I'm not going to speculated on that. There was a legit version being offered for around that price (not from Microsoft) and don't know of that is still being offered but there are a whole lot of illegitimate online offers. Usually a good thing to go by is that "if it sounds too good to be true it's because it usually is"

BTW - I've noted that each time I delete an email from my inbox and it goes to Trash, I get a synch error. Not surprising, I guess, given I can't smtp. But it's maddening, that I can receive email...

I/m old school and like to deal with one issue at a tune. Would confirm that the server timeout issue doesn't occur when the Trash folder is empty. After that, it becomes a phone related issue.

Another thing you can try is installing <emClient> to see if there are any issues with that email client (it's free if you only have 2 email accounts)

eM Client | The Best Email Client for Windows and Mac

Even if Office 365 works, I refuse to pay for software by subscription. I can get Office 2021 for about $40 bucks, it seems - that's supported, correct? Any reason I shouldn't go that route?

BTW - I've noted that each time I delete an email from my inbox and it goes to Trash, I get a synch error. Not surprising, I guess, given I can't smtp. But it's maddening, that I can receive email...

Given everything to date, unfortunately I don't have any additional suggestions.

Given that has involved two different systems where one is a new relatively virgin install - the only common element in this is the Google account. It certainly is not a generic problem since the forum here would be lit up like a XMas tree given the large number of Google email account users.

Normally I would suggest checking in with Microsoft Support but mainstream support for '2016 ended Oct '2020.

One last thing that you can try in the unlikely chance it would make any difference is to try this using Outlook '365 (via the free 30 day trial version)

Free Trial - Try Microsoft 365 for a month - Microsoft Store

If you do decide to try this -

#1 - Make sure to turn of recurring billing so that it doesn't automatically charge your credit card at the end of the trial period

Turn recurring billing on or off for Microsoft 365 for home https://support.microsoft.com/en-us/office/turn-recurring-billing-on-or-off-for-microsoft-365-for-home-c7c0bc32-9744-4acf-9818-815d5c96cc59

#2 - Before installing '365 - uninstall '2016

*** if things work, you can verify that this is strictly a '2016 issue by uninstall '365 and re-installing '2016 to see if still has the same problems

Well, nothing is going outbound at the moment (I continue to receive emails into the account); no sense in trying more or less attachments. I did extend the connection time to three minutes, but before that time is up, I get the 'The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP)' message. However, last time I was on the horn with Google, they suggested I should contact Microsoft, deeming it a problem with Outlook.

And so it goes. It seems to me: There ought to be some diagnostic tool, that see what is or isn't going out of Outlook, and what is or isn't coming back from Google; and if something does come back, what it is unhappy about besides "the connection was interrupted".

I am at a total loss here. I've been able to manage 20+ years of email, archived to .pst, with Outlook; and now the whole system I've set up is broken. Even after buying a new computer, and moving my Office license to it. And I just don't know why, nor does it appear I will ever know.

Hi Karl, to quickly reply before heading to bed (after midnight ET) - I'll experiment in the a.m. with fewer attachments. But just to point out, this is an out-of-the-box Lenovo Windows 10 computer, followed by the free Windows 11 upgrade. I haven't installed Symantec Endpoint, or tinkered with Defender in any way.

Then the only thing left to play with is the server timeout setting - really don't know what else to suggest given that this is a vanilla system other then trying to connect to Google support to see if they have any words of wisdom to share.