Windows 10: Unable to send email

I am not able to send email from one particular computer. The computer in question is brand new, fresh out of the box. It had McAffee installed, but I removed this.


My problem is that I am not able to send messages from neither Windows Mail or Outlook 2019. Both stumble at the same point. During the sending of the email after sending the DATA block the following error is reported on the server side.


warning: TLS library problem: error:1408F119:SSL routines:SSL3_GET_RECORD:decryption failed or bad record mac:s3_pkt.c:535:


I have another computer running windows 10 (same version) from which I am able to send messages successfully. So I suspect this might be a problem on the new computer. I have un-installed McAffee as well as reset the firewall, however neither option resolved this problem.


After enabling logging in outlook, the following messages were logged:


2019.04.24 12:03:31 SMTP (smtp.****): Authorizing to server
2019.04.24 12:03:31 SMTP (smtp.****): [tx] AUTH DIGEST-MD5
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 334 bm9uY2U9IkFhTE1RTEs1Y1lTMkhSVjBSdDN4R1duM3M5Q2IyUk9GQzhZdzlLbjhNRlk9IixyZWFsbT0iZ29sZGJlcnJ5LnNwb3R0ZWRtb3VzZS5jb20iLHFvcD0iYXV0aCIsY2hhcnNldD11dGYtOCxhbGdvcml0aG09bWQ1LXNlc3M=
2019.04.24 12:03:31 SMTP (smtp.****): [tx] dXNlcm5hbWU9ImFsZXgiLHJlYWxtPSIiLG5vbmNlPSJBYUxNUUxLNWNZUzJIUlYwUnQzeEdXbjNzOUNiMlJPRkM4WXc5S244TUZZPSIsZGlnZXN0LXVyaT0ic210cC9zbXRwLnNwb3R0ZWRtb3VzZS5jb20iLGNub25jZT0iOWUxNmU2MGJkNjBkZDI1NDJkYzIyNmQ2ZTA2OTcyMWUiLG5jPTAwMDAwMDAxLHJlc3BvbnNlPTUxZGQ0NmUzMDY4YjExZTBhODc5OTZlN2QwM2FmZDJkLHFvcD1hdXRoLGNoYXJzZXQ9dXRmLTg=
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 535 5.7.8 Error: authentication failed: authentication failure
2019.04.24 12:03:31 SMTP (smtp.****): [tx] AUTH LOGIN
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 334 VXNlcm5hbWU6
2019.04.24 12:03:31 SMTP (smtp.****): [tx] YWxleA==
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 334 UGFzc3dvcmQ6
2019.04.24 12:03:31 SMTP (smtp.****): [tx] *****
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 235 2.7.0 Authentication successful
2019.04.24 12:03:31 SMTP (smtp.****): Authorized to host
2019.04.24 12:03:31 SMTP (smtp.****): Connected to host
2019.04.24 12:03:31 SMTP (smtp.****): [tx] MAIL FROM: <*****>
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 250 2.1.0 Ok
2019.04.24 12:03:31 SMTP (smtp.****): [tx] RCPT TO: <*****>
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 250 2.1.5 Ok
2019.04.24 12:03:31 SMTP (smtp.****): [tx] DATA
2019.04.24 12:03:31 SMTP (smtp.****): <rx> 354 End data with <CR><LF>.<CR><LF>
2019.04.24 12:03:31 SMTP (smtp.****): [tx]
.
2019.04.24 12:03:31 SMTP (smtp.****): Connected to host
2019.04.24 12:03:31 SMTP (smtp.****): Disconnected from host
2019.04.24 12:03:31 SMTP (smtp.****): End execution
2019.04.24 12:03:31 Home: ReportStatus: RSF_COMPLETED, hr = 0xffffffff800ccc0f
2019.04.24 12:03:31 Home: Synch operation completed


Computer A: Windows Mail is able to send successfully

Computer B: Windows Mail and Outlook 2019 are not able to send messages


Receiving emails works on both. They are both Windows 10 latest build.


Any suggestions on where to look and how to diagnose this problem further. The problem seems to be only with the DATA portion of the message. Also the test message generated by Outlook during the account configuration is sent and delivered successfully.

:)

 

Unable to send emails to my friends email address

Hi Thomas,

Thank you for responding.

As per your suggestions I understand that your IP address might have blocked.

Do let us know the type of the email address you are using (live.com/ outlook.com/ Hotmail.com)?

Also, is this issue specific to the particular recipient?

I suggest you to try the below and check if it helps.

Step 1: I suggest you to log-in to the online account, try to send an email to the recipient and check.

Step 2: Try to log-in to the web browser, perform step 1 and check.

If the issue still persists, I suggest you to contact the ESP/ ISP service provide and check if that helps.

Hope it helps. Reply to the post with an updated status of this issue and required information for further assistance.

 

Task Scheduler Email Issue

Not at all. I suggested in my previous note that you could schedule this AutoIt script:

1. Take a screenshot
2. Save it to a temporary file
3. Generate an E-Mail
4. Attach the screenshot
5. Send it to its recipient

Do you think that AutoIt is unable to execute each of these steps?

 

Windows Live Mail 2012 refuses to send emails, claims they're spam


My wife uses Windows Live Mail 2012 and says it refuses to send emails, claiming they're spam. This is even replying to someone who is in her contacts list. I have run several different virus checks and nothing comes up. Any ideas or suggestions would be appreciated. TIA