Problem sending email with attachment in Mail Client

Johns4dogs

My issue seems a little weird:

After completing the message, I've added an image attachment by using the paperclip button that sits up in the top bar next to the send button. The message remains in the outbox, then a "Message Failure" flag pops up in the bottom right corner.
Rather than using the paperclip button to make the attachment, I use the Insert Image button, in the settings bar that sits above the message body of the draft page.
The message sends successfully, with the image included after the signature.
I have a Vivaldi Webmail account operating within the Mail Client. No problem using the paperclip button to send the same message with attachment as in 1., above.
No problem with sending the same message and attachment via OperaMail. That would seem to rule out there being any operating system or ISP issues. OperaMail uses the same SMTP Port 465 as Vivaldi.

Any ideas why the paperclip attachment routine won't work as it should with my ISP supplied mail accounts?

Thanks,
John

Dancer18

Normally it is working with ease.
What is your operating system?
What version of Vivaldi you're using?
What email-provider you're using?

mib2berlin

@Johns4dogs
Hi, test mail with image attachment from paperclip, send from freenet.de to yahoo.com work without issues.

Vivaldi 3.6.2165.32 / Chrome 88.0.4324.99
Opensuse Tumbleweed x86_64
Intel i5 3570K 16 GB RAM
GTX 760 4 GB /Display card
RTX 2060
Driver 460.32.00

Cheers, mib

Johns4dogs

@Dancer18
I’m using Windows 7, Vivaldi 3.6, Telstra is my ISP.

Johns4dogs

@mib2berlin
Thanks for your reply; I realise that for everyone else, it probably works!

Johns4dogs

@Gwen-Dragon
Yes, I use Vipre Internet Security. But as I pointed out, OperaMail sent the message successfully with Vipre running in the background.

Johns4dogs

@Gwen-Dragon
I’m away from Desktop for a few hours, will follow up checking Vipre as soon as I can.
Appreciate your help!

Johns4dogs

I've turned Vipre email screening off and I'm not using any other security applications.
Still the same problem, I'm afraid. Attachment using the paperclip button, then the email send fails.

Dancer18

@Johns4dogs The question is what causes the failure. Here - with Windows and Linux Mint (dual boot) - I can't reproduce it. I tried 3 of my email-accounts.

Could it be that your email provider has some restrictions as google has with Vivaldi and not accept Vivaldi as a trustful mail-client?

Can you check that? You should get a support ticket from Telstra. Hopefully they can give you a solution.

Johns4dogs

@Dancer18
Thanks for your input and testing.
I'll see what response I get from Telstra, which might take a bit of time, plus dig around further on my computer.
Let you know!

Johns4dogs

I've done some further research into sending emails via Telstra's SMTP server, and have found a couple of references to changing the outgoing port from 465 to 587.
I've done that and I can readily send a simple email without attachment. But the problem of sending failure returns once I attach a file.

Apart from the change of port recommendation, there is also reference to "making sure you have set your email client to authenticate your SMTP session", or similar wording. I can't see any reference to such a setting when I open the Vivaldi Settings:Mail page.

Can anyone tell me where I can activate that, or if it's done automatically already?
Thanks.

Dancer18

That is automatically done by using port 587 or 465.

You should do a support request at your provider.
I very often got help from my provider very quickly.

johnkirby

@Dancer18
Thanks for confirming the authentication process, something else ticked off.
You're fortunate to have timely help provided by your ISP.
Unfortunately, Telstra can be difficult at times when it comes to dealing with support requests. I'm trying third party forums to try and get advice as to best handling the issue.
I acknowledge that it's more than likely a Telstra issue. Frustrating to say the least!

Dancer18

@johnkirby And everybody is fortunate who can move to a better provider without having lacks in business or friendships.

Johns4dogs

@Dancer18 Probably will happen, or at least move regular email address to one that works properly!