Can't send emails with attachments - error know-smtprelay-8-imp cmsmtp ESMTP server ready

[buckhouse]

Unable to send emails with attachments.  Checked settings and all correct.  Have tried sending small attachments but still get this error.  I have to go to my Hotmail email (which I don't use) to send my emails with attachments.  Why is this happening in Virgin?

[ravenstar68]

The one problem I can see is that although the error message clearly says:

know-smtprelay-8-imp cmsmtp ESMTP server ready

That's not in fact an error.  That's the standard greeting seen by all email clients immediately upon connecting to the server.

Here's a conversation between curl and Virgin Media's smtp server to demonstrate (sensitive information has been redacted):

curl -v smtps://smtp.blueyonder.co.uk -u redacted:redacted 2>&1 | grep "<\|>"
< 220 know-smtprelay-9-imp cmsmtp ESMTP server ready
> EHLO box
< 250-know-smtprelay-9-imp hello [51.195.xxx.xxx], pleased to meet you
< 250-HELP
< 250-AUTH LOGIN PLAIN
< 250-SIZE 52000000
< 250-ENHANCEDSTATUSCODES
< 250-PIPELINING
< 250-8BITMIME
< 250 OK
> AUTH LOGIN
< 334 VXNlcm5hbWU6
> redacted
< 334 UGFzc3dvcmQ6
> redacted
< 235 2.7.0 ... authentication succeeded
> HELP
< 214-2.0.0 This is cmsmtp ESMTP service help
< 214-2.0.0 To contact postmaster send email to postmaster@virginmedia.com.
< 214-2.0.0 For local information send email to Postmaster at your site.
< 214 2.0.0 end of HELP info

Likewise, If you can send emails without an attachment, then you should be able to send emails with an attachment from the same server.  I've setup a Hackintosh and installed Office365 for Mac on it.  I've been able to send emails with and without attachments.  So my gut feeling - based on what I'm seeing is that something on your Mac is interfering here.

Are you running any any virus software?

Tim

[thechief]

I am having the exact same issue.

iMac running MacOS BigSur  

Norton Security / Norton Lifelock

Outlook 365 client

I cannot send any mails with attachments from Outlook.Incoming mail is fine. All IMAP / SMTP settings as per the recommendations. Emails without attachments are going fine it seems.

TC

[buckhouse]

Thank you for your response. I have Norton 360 /Norton lifelock. I did think of trying to disable Norton and then try to sent email with attachments, but I was not able to find that feature - which used to be available. You could disable for, say, 10 minutes and then enable. It's probably all down to Norton - I am also having problems with that program at the moment. In the past, when OS has been updated, Norton is lagging a bit behind - think this may have happened. Meantime, I have given up on Microsoft Office 365 and am just using Apple mail, in the hope that this mess will be corrected. I thank you for all your help in this matter.

Joan

[ravenstar68]

Hi guys.

It might be worth chasing this up on the Norton Forums or even starting a support ticket with them.

Looking at this thread on the Microsoft Fora

https://answers.microsoft.com/en-us/msoffice/forum/all/problem-sending-attachments-with-outlook-2016...

Uninstalling Norton seems to fix the issue, but ideally Norton should be looking into this for you.

Tim