The dreaded 0x800CCC0F sending error

Anonymous
2022-07-21T19:36:33+00:00

I am now running Microsoft® Outlook® 2016 MSO (Version 2206 Build 16.0.15330.20260) 64-bit, on Windows 8.1; I had been running the 32-bit version, but I upgraded to 64-bit in an attempt to resolve this error on sending: "Task '[email account] - Sending' reported error (0x800CCC0F): 'The connection to the server was interrupted....' "

My Outlook is configured for two IMAP accounts, both with Google - one is a GMail account, the other is Google Workspace account that services email for my domain (59plymouth.net). Outlook is also configured for a work Exchange account.

A few weeks ago - not sure, but I think after a reboot, and when Windows updates were applied - both IMAP accounts stopped sending. The Exchange account continues to work without issue.

The updates were July updates - 5015874, 50156268, and 50154633. Suspecting these, I backed them out and disabled updates. No luck. I then did the Outlook 64-bit upgrade. NADA.

I'd suspect Google, but my iPhone continues to work without issue for both accounts; so does my iPad (which also talks to my Exchange account).

I'm not sure where to go from here. And ideas about how to further diagnose?

adTHANKSvance,

Dan

Outlook | Windows | Classic Outlook for Windows | For business

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  1. Karl Timmermans 3,685 Reputation points Volunteer Moderator
    2022-08-05T17:54:54+00:00

    I'd be happy to try out any other suggestions that may occur to you in the meantime.

    I'd offer other suggestions if I had any. This is the first time I've seen a report about an attachment of 14K or larger running into an issue. That is by no means what would considered a "large" attachment.

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  2. Anonymous
    2022-08-05T17:43:17+00:00

    Well, things are looking up (I think); I had said

    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".

    And it turns out there are several; but I found this one to my liking. And, I learned a lot about smtp connections in the process.

    Despite Microsoft's disclaimer that the retail version of Outlook 2016 did not require 2SV and an App PW, SMTP Console reported back exactly what GMail was saying: An App PW was required, just as you had recommended at the start of this thread. So I put it back, created a new profile, configured the gmail account to use the App PW, and... voila! I can send email.

    ...provided the size of any attachment is somewhere south of 14,083 bytes. I created a "lorem ipsum" text file, and the largest I was able to send was 13,363 bytes. And the thing is - the transmission was near instantaneous for any file 13K or less; but at 14K, the "sending message 1 of 1" message hangs around for about 20 seconds, before the dreaded 0x800ccc0f error message. (I had bumped the timeout from 3 to 4 minutes, to no avail; trouble happens in under a minute.)

    So the problem has been narrowed down considerably. Time to get on Google's radar again; thanks for all your help, I'd be happy to try out any other suggestions that may occur to you in the meantime.

    Dan

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  3. Karl Timmermans 3,685 Reputation points Volunteer Moderator
    2022-08-04T22:24:04+00:00

    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

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  4. Anonymous
    2022-08-04T22:02:51+00:00

    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...

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  5. Karl Timmermans 3,685 Reputation points Volunteer Moderator
    2022-08-04T21:32:54+00:00

    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

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