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Can send emails, but can't send with an attachment picture - even if only 350kb in size

  • 11 replies
  • 1 has this problem
  • 233 views
  • Last reply by Stans

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As I said above I have suddenly got a problem sending emails with pictures attached. Am using plus.net. Am running Windows 10 via Bootcamp on an iMac. All my SMTP settings must surely be right because I can send ordinary emails no problem. I have tried switching off the Firewall in Windows Defender and then trying to send - still does not work. By default I also have Outlook on this machine. I tried sending myself an email with a 1.7mb attachment from there from there - and it worked.... But I would prefer to use Tb as I have all my contacts etc in there. I'm stumped!

As I said above I have suddenly got a problem sending emails with pictures attached. Am using plus.net. Am running Windows 10 via Bootcamp on an iMac. All my SMTP settings must surely be right because I can send ordinary emails no problem. I have tried switching off the Firewall in Windows Defender and then trying to send - still does not work. By default I also have Outlook on this machine. I tried sending myself an email with a 1.7mb attachment from there from there - and it worked.... But I would prefer to use Tb as I have all my contacts etc in there. I'm stumped!

Chosen solution

Have done as you said. It works!!!!!!!!!!!!!!!!!!!!!!!!!!! My hero... Thanks very much.

Out of curiosity I would like to know why....but it doesn't really matter!

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What is the exact error message that you get when this happens, if any?

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Just get 'timed out to SMTP'

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Sounds like a program could be interfering prior to sending and one possible cause is the Windows Defender Anti-Virus. It could be that Windows defender is scanning the email and it took too long. So, it is not the firewall, but could be the Anti-Virus.

There could be two places to check, one switches on/off email scanning, but there is 'real time protection' which could be the culprit.

Try disabling the real time protection and then send email.

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Thanks. Tried that but it didn't work. Used a tiny picture of 350kb. It started to send , got to 99% then stopped. That is what it does with Real Time protection turned on as well... Same message - 'timed out'

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Now this is curious... I had sent the mail to myself. Although the 'send' message just got yo 99% and said 'timed out' several minutes later it has appeared in my inbox... And, of course, this was only a tiny attachment...

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Regarding your outgoing smtp server - are you using these settings:

  • Server: relay.plus.net
  • Port: 587
  • Connection security: STARTTLS
  • Authentication: Normal password
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Connection security is set as 'none'

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Chosen Solution

Have done as you said. It works!!!!!!!!!!!!!!!!!!!!!!!!!!! My hero... Thanks very much.

Out of curiosity I would like to know why....but it doesn't really matter!

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I discovered that there had been some improvements to the plus.net smtp in the last year, but it is not exactly well publicised by plus.net. Even their help pages are still out of date and not all agree on the settings. So I thought that perhaps you were not aware of the changes and were still using the info as set out in plus.net help pages.

For example:

Under 'what other settings do I need', they mention using port 587 saying you cannot use SSL/TLS, but fail to mention you can use 'STARTTLS'.

Under Thunderbird section, they are still telling people to use port 25 with no security of any type!


Then discovered a conversation in their help forum dated October 2019 which mentioned the new ability to use port 587 with STARTTLS.

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That's really cool... I spoke to Plusnet yesterday 3 times and twice today - no further forward with them! One of the(very nice) chaps said he wouldn't use Plusnet email! So thanks VERY much.

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I too almost recommended not using plus.net email when I did a bit of searching and saw the insecure outdated email settings on their FAQ. Changing providers may not be such a bad idea; something to consider going forward.