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
    2022-08-06T21:49:20+00:00

    Well, logs they will get now - this is a smoking gun.

    Hopefully something productive will come out of it.

    Still would have been interesting to know if this is specific to '2016 or Outlook in general.. As previously mentioned, '2016 mainstream support ended Oct '2020.

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  2. 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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