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. 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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  2. 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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  3. 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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  4. 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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  5. Anonymous
    2022-08-06T21:28:46+00:00

    It's not attachments. And it's not Outlook. It's a problem with Google Workspace.

    I took your advice, and installed emClient; it supports OAUTH, which both GMail and Yahoo support. I configured accounts I have on both, and was successfully able to send emails to both with "test" as the body. I then used "lorem ipsum" text in the attachment as the body of the email; ~32K bytes worth. The email to Yahoo went through; the email to Google Workspace did not. Log snippets below.

    I spent several frustrating hours on the phone with Google yesterday, only for them to conclude it was a problem with Outlook, and they wanted logs from me. Well, logs they will get now - this is a smoking gun.

    Yahoo:

    17:16:54.085|016| eM Client 9.0.1708+2cfb4a5e03 (Windows)

    17:16:54.085|016| Account's UID is 0fb5491b-d1b2-4d97-a58a-babfca36c932

    17:16:54.085|016| AccountBase.ChangeOnlineState : State changed to ONLINE due User

    17:17:24.230|01E| SMTP S: 220 smtp.mail.yahoo.com ESMTP ready

    17:17:24.235|01E| SMTP C: EHLO [192.168.1.170]

    17:17:24.277|01E| SMTP S: 250-hermes--production-ne1-6649c47445-tp7sw Hello [192.168.1.170] [100.34.152.185])

    17:17:24.277|01E| SMTP S: 250-PIPELINING

    17:17:24.277|01E| SMTP S: 250-ENHANCEDSTATUSCODES

    17:17:24.285|01E| SMTP S: 250-8BITMIME

    17:17:24.285|01E| SMTP S: 250-SIZE 41697280

    17:17:24.286|01E| SMTP S: 250 AUTH PLAIN LOGIN XOAUTH2 OAUTHBEARER

    17:17:24.290|01E| SMTP C: AUTH OAUTHBEARER <Parameter removed for privacy reasons.>

    17:17:24.553|01E| SMTP S: 235 2.7.0 Authentication successful

    17:17:24.558|01E| SMTP C: MAIL FROM:<******@yahoo.com> SIZE=28978

    17:17:24.666|01E| SMTP S: 250 2.1.0 Sender <******@yahoo.com> OK

    17:17:24.667|01E| SMTP C: RCPT TO:<******@yahoo.com>

    17:17:24.708|01E| SMTP S: 250 2.1.5 Recipient <******@yahoo.com> OK

    17:17:24.708|01E| SMTP C: DATA

    17:17:24.749|01E| SMTP S: 354 Ok Send data ending with <CRLF>.<CRLF>

    17:17:24.758|01E| SMTP C:

    17:17:24.758|01E| SMTP C: .

    17:17:25.255|01E| SMTP S: 250 OK , completed

    17:17:25.258|01E| SMTP C: QUIT

    17:17:25.300|01E| SMTP S: 221 Service Closing transmission

    Google Workspace:

    17:11:18.726|015| eM Client 9.0.1708+2cfb4a5e03 (Windows)

    17:11:18.726|015| Account's UID is 1e302ec2-6d7d-4777-b876-5b64f0b9407f

    17:11:18.726|015| AccountBase.ChangeOnlineState : State changed to ONLINE due User

    17:13:02.680|024| SMTP S: 220 smtp.gmail.com ESMTP y5-20020a37f605000000b006b5f8f32a8fsm5608350qkj.114 - gsmtp

    17:13:02.681|024| SMTP C: EHLO [IPv6:2600:4040:7664:500:4d45:15a4:d1a8:daf0]

    17:13:02.703|024| SMTP S: 250-smtp.gmail.com at your service, [2600:4040:7664:500:4d45:15a4:d1a8:daf0]

    17:13:02.703|024| SMTP S: 250-SIZE 35882577

    17:13:02.712|024| SMTP S: 250-8BITMIME

    17:13:02.712|024| SMTP S: 250-STARTTLS

    17:13:02.712|024| SMTP S: 250-ENHANCEDSTATUSCODES

    17:13:02.712|024| SMTP S: 250-PIPELINING

    17:13:02.712|024| SMTP S: 250-CHUNKING

    17:13:02.712|024| SMTP S: 250 SMTPUTF8

    17:13:02.713|024| SMTP C: STARTTLS

    17:13:02.732|024| SMTP S: 220 2.0.0 Ready to start TLS

    17:13:02.749|024| SMTP C: EHLO [IPv6:2600:4040:7664:500:4d45:15a4:d1a8:daf0]

    17:13:02.979|024| SMTP S: 250-smtp.gmail.com at your service, [2600:4040:7664:500:4d45:15a4:d1a8:daf0]

    17:13:02.979|024| SMTP S: 250-SIZE 35882577

    17:13:02.979|024| SMTP S: 250-8BITMIME

    17:13:02.979|024| SMTP S: 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH

    17:13:02.980|024| SMTP S: 250-ENHANCEDSTATUSCODES

    17:13:02.980|024| SMTP S: 250-PIPELINING

    17:13:02.980|024| SMTP S: 250-CHUNKING

    17:13:02.980|024| SMTP S: 250 SMTPUTF8

    17:13:02.980|024| SMTP C: AUTH OAUTHBEARER <Parameter removed for privacy reasons.>

    17:13:03.113|024| SMTP S: 235 2.7.0 Accepted

    17:13:03.114|024| SMTP C: MAIL FROM:<******@59plymouth.net> SIZE=28958

    17:13:03.132|024| SMTP S: 250 2.1.0 OK y5-20020a37f605000000b006b5f8f32a8fsm5608350qkj.114 - gsmtp

    17:13:03.132|024| SMTP C: RCPT TO:<******@59plymouth.net>

    17:13:03.150|024| SMTP S: 250 2.1.5 OK y5-20020a37f605000000b006b5f8f32a8fsm5608350qkj.114 - gsmtp

    17:13:03.150|024| SMTP C: DATA

    17:13:03.306|024| SMTP S: 354 Go ahead y5-20020a37f605000000b006b5f8f32a8fsm5608350qkj.114 - gsmtp

    17:13:03.310|024| SMTP C:

    17:13:03.310|024| SMTP C: .

    17:13:22.714|024| Exception: MailClient.Accounts.SocketException: Sending messages failed due to the following reason:

    17:13:22.714|024| "Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.."

    17:13:22.714|024| at MailClient.Protocols.Smtp.SmtpSendCommand.Execute(WorkerStatus status)

    17:13:22.714|024| at MailClient.Commands.Command.Process(WorkerStatus status)

    17:13:22.715|027| AccountBase.ChangeOnlineState : State changed to OFFLINE due BrokenConnection

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