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?

[Corey_C]

Thanks for your post and for reaching out to the Community Forums, buckhouse,

Sorry to hear this is happening with your emails. Is this happening when you send the emails directly from our site here:  https://my.virginmedia.com/my-apps/email/mailbox

Or are you using an email app like Outlook or Thunderbird?

Cheers,

Corey C

[HowardML]

@buckhouse 

It is clear from the bit of the error message you have quoted from that you are using an email program/app to send mail. It doesn't really matter which one. What does matter is that we need to see the whole error message before we can advise about what may be going on. So please post it here and make sure to redact/edit out your full email address and the address of the recipient. Leave the part after the @ symbol in place. We need to see the domain names. 

[buckhouse]

Hi Corey.  Thanks for your response.  I use an iMac.  The mail program I use is 'Microsoft Office 365' - been using it for years.  Sending attachments was no problem until recently.  Emails send perfectly without attachments - to various providers, but as soon as I try to send with an attachment (pdf, doc, etc), I get an error message and the email sits in my Outbox and does not send.  Every so often I get this message:  A secure connection cannot be established with the server smtp virginmedia.com.  When I try to send an email with an attachment, it doesn't send and I get an error message at the bottom left of my screen saying Sync Error - showing the date and time 'know-smtprelay-8-imp cmsmtp ESMTP server ready' Details Email could not be sent.

This only happens with the Microsoft Office 365 application - NOT with the Apple Mail or Hotmail - which I prefer not to use.

Thanks,

Joan

[buckhouse]

Thanks for your response.    I use an iMac.  The mail program I use is 'Microsoft Office 365' (not the New Outlook) - been using it for years.  Sending attachments was no problem until recently.  Emails send perfectly without attachments - to various providers, but as soon as I try to send with an attachment (pdf, doc, etc), I get an error message and the email sits in my Outbox and does not send.  Every so often I get this message:  A secure connection cannot be established with the server smtp virginmedia.com.  When I try to send an email with an attachment, it doesn't send and I get an error message at the bottom left of my screen saying Sync Error - showing the date and time 'know-smtprelay-8-imp cmsmtp ESMTP server ready' Details Email could not be sent.  Attempts at sending email with attachments to @ntlworld.com,@outlook.com, @btconnect.com, @gmail.com, etc.

My Security is Norton 360/Norton Lifelock.

This only happens with the Microsoft Office 365 application - NOT with the Apple Mail or Hotmail - which I prefer not to use.

Thanks,

Joan

[HowardML · Accepted solution]

Are you so careless of your personal privacy that you not only disclose your personal email address on a public forum but the addresses of others? Where do think spammers and scammers get their information from? Public forms are a source. . Edit this stuff out now. Go to Post Options in the post concerned. We don't need it. I didn't ask for it. I asked for the full error messages you are getting. Not a paraphrase. There is more to the message than you are giving us. Useless in solving the issue. You can just copy and paste the full message into this thread. 

[buckhouse]

Apologies.  I misunderstood what you asked me for.   I did wonder about the security of that.  I hope I have removed the relevant details.  Thank you for that.

[Lee_R]

Hi Buckhouse. 

I am really sorry you're having issues sending emails with attachments.  Just for my understanding.  Are you definitely having this issue if you attempt to send attachments via the webmail and not the 3rd party client?

Regards

Lee_R

[HowardML]

@Lee_R

The issue is only with email programs. Look at the error message. It comes from the SMTP servers at Knowsley. The OP hasn't mentioned web mail. She is obviously not using it. I've already had to make this clear to Corey_C today.

[buckhouse]

Hi Lee.

Thank you for your response.  I can send email with attachments using the virginmedia website mail.  The problem only arises when using Microsoft Outlook for Mac version 16.48, (21041102).  I have not switched to the 'New Outlook' in the application as it says some things won't be migrated.

Thanks,Joan