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Outlook 10 won't send email

FIXED
slowtime
Grafter
Posts: 38
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Registered: ‎06-05-2009

Outlook 10 won't send email

In the last day or so my Microsoft Outlook 10 account has stopped sending email.  It's a bit tardy on receiving them as well but if I re-start it, they pop up.  I have spoken to Plusnet but ended up being more bemused.  I have had connection continuity problems and was told by the agent that they had been reset and I had to turn my router off and then on again but the problem persists.The account settings are as Plusnet say they should be.  

 

The emails that I am trying to send are not very big.

 

I have Windows 10 Home version 1703 64 bit as my operating system.

29 REPLIES
Superuser
Superuser
Posts: 9,925
Thanks: 1,265
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Registered: ‎06-04-2007

Re: Outlook 10 won't send email

By "Outlook 10" do you mean the Windows 10 desktop mail app?

Sending from that using relay.force9.net fails for me but I'm using customised settings which might be causing the problem. Huh

However sending using a non-Plusnet relay works.

I'll set up a test using relay.plus.net with standard settings.

David
Plusnet Help Team
Plusnet Help Team
Posts: 13,737
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Registered: ‎27-04-2007

Re: Outlook 10 won't send email

Hi there,

 

From looking at your account I think there's been some confusion over what you're using to check your email.

 

The page we linked you to is for Windows Live mail, the settings are still the same, just the menus and where you enter them will be different.

 

I'd definitely check that you've got the outgoing mail server set correctly.

If this post resolved your issue please click the 'This fixed my problem' button
 Adam Walker
 Plusnet Help Team
slowtime
Grafter
Posts: 38
Thanks: 12
Registered: ‎06-05-2009

Re: Outlook 10 won't send email

Hello, David and thanks for your reply.  Yes, it's the Microsoft desktop app, the one with the square yellow icon.  The settings that I have are:

 

IMAP Server (I'm assuming that's incoming?):  imap.plus.net and

SMPT (outgoing) Server: relay.plus.net.

 

 

If I open the app and do file>account settings>account settings>change, it brings up a little test thing.  This appears to complete and congratulates me, which is all the more confusing as I can't send an email and haven't been able for a day or two now.

 

Can you explain what you mean by non-Plusnet relay and how I would set it up?  Beware, I am no techie!

slowtime
Grafter
Posts: 38
Thanks: 12
Registered: ‎06-05-2009

Re: Outlook 10 won't send email

Adam,

 

Thanks for your message.  I've just checked through the account settings route again and yes, they are as I've put in my reply to David.

Superuser
Superuser
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Registered: ‎06-04-2007

Re: Outlook 10 won't send email

I've done a test using the Windows 10 mail app and sending through relay.plus.net with non-customised settings worked OK.


@slowtime wrote:

If I open the app and do file>account settings>account settings>change, it brings up a little test thing;This appears to complete and congratulates me, which is all the more confusing as I can't send an email and haven't been able for a day or two now.

That settings path suggests to me that you are using Outlook 2016 rather than the Windows 10 mail app. However sending via relay.plus.net using Outlook 2016 also works fine for me.

The settings you described seem correct. Presumably SSL/TLS isn't selected?

Can you explain what you mean by non-Plusnet relay and how I would set it up? Beware, I am no techie!


By that term I meant using a third-party email provider's relay where I have an account. Unless you have such an account that route isn't open to you. Sad

David
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slowtime
Grafter
Posts: 38
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Registered: ‎06-05-2009

Re: Outlook 10 won't send email

David,

 

Thanks for your message.  Sure, I  may be identifying my mail app wrongly!  I found the following 14.0.7148.5000, 32 bit as some sort of identification of the version so I don't know if this confirms your suggestion that this is a 2016 dated app?  I don't recall installing or buying anything new though.

 

As you say, it doesn't make any difference on your test and thanks for doing that.   To go forward from here, it looks like my setting of relay.plus.net is correct so unfortunately, I'm not going to be able to change anything there that would solve this problem,  You go on to say "with non-customised settings".  I wouldn't have the technical ability to customise anything so can you guide me as to what sort of thing to look for?

You also say "Presumably SSL/TLS isn't selected?"  The only other setting that I can see in the account settings is a tick box for secure password authentication (SPA) and this is not ticked.  Is this what you were referring to?  If not can you guide me towards where I can find the SSL/TLS setting so that I can check it?

If all this doesn't result in a resolution of my problems sending email from my Microsoft email account (whichever version it is) what are the options available to me as I need to send some mail urgently.

Many thanks again

Superuser
Superuser
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Registered: ‎06-04-2007

Re: Outlook 10 won't send email


@slowtime wrote:

Thanks for your message.  Sure, I  may be identifying my mail app wrongly!  I found the following 14.0.7148.5000, 32 bit as some sort of identification of the version so I don't know if this confirms your suggestion that this is a 2016 dated app?  I don't recall installing or buying anything new though.

The "14" in that version string means it is Outlook 2010, but essentially that's functionally the same as Outlook 2016. So not an issue.

As you say, it doesn't make any difference on your test and thanks for doing that.   To go forward from here, it looks like my setting of relay.plus.net is correct so unfortunately, I'm not going to be able to change anything there that would solve this problem,  You go on to say "with non-customised settings".  I wouldn't have the technical ability to customise anything so can you guide me as to what sort of thing to look for?

I wouldn't bother about the customisation I did, you wouldn't have done anything like this inadvertently and would know about it if you had.

You also say "Presumably SSL/TLS isn't selected?"  The only other setting that I can see in the account settings is a tick box for secure password authentication (SPA) and this is not ticked.  Is this what you were referring to?  If not can you guide me towards where I can find the SSL/TLS setting so that I can check it?

The SPA checkbox you mentioned should not be ticked - so your setting is correct. Smiley

The SSL/TLS settings are hidden deeper down in the settings. To get to these you need to click More Settings bottom right of the account page where you found the SPA tick box. Then select the Advanced tab. I expect your page to be like the following:

OL2016advSettings.png

The encryption settings ("none") and port numbers are in the top section.

If all this doesn't result in a resolution of my problems sending email from my Microsoft email account (whichever version it is) what are the options available to me as I need to send some mail urgently.


As a temporary solution you could try using Webmail at https://webmail.plus.net. Make sure the identity setting (sender email) which should be shown top right is correct or you might not get any replies.

For further diagnostic work I have in mind using Telnet to bypass Outlook, but that will require guidance and take time.

David
slowtime
Grafter
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Registered: ‎06-05-2009

Re: Outlook 10 won't send email

David,

 

Thanks for the reply and additional information.  The SSL/TLS settings show "25" in the outgoing and not 587.  Should I change this?

I've sent some messages by web mail so, I'll see what I get back.

 

As for further analysis then, Please, let me know if there is anything that I need to do as I would like to track this issue down.

Superuser
Superuser
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Registered: ‎06-04-2007

Re: Outlook 10 won't send email

Do you connect to your router using a cable (Ethernet) or WiFi? It shouldn't make any difference but WiFi can be connected to a neighbour's router by mistake.

Also is it possible that a setting in your antivirus is blocking email sending?

Using Port 25 for sending should be OK. Some mobile connections restrict Port 25 to their own relays though allow external relays on Port 587 - but that shouldn't apply here.

To use telnet for diagnostic work it needs to be enabled in Windows Features. The steps to do this are:

  • Right-click the start button and select Apps and Features.
  • Scroll to the bottom of the list and click Programs and Features.
  • On the left click Turn Windows features on or off.
  • Scroll down the list and select the Telnet Client check box.
  • Click OK and wait while Windows installs this.

Post back when you have this installed. Thumbs Up

David
Superuser
Superuser
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Re: Outlook 10 won't send email


@spraxyt wrote:

Using Port 25 for sending should be OK. Some mobile connections restrict Port 25 to their own relays though allow external relays on Port 587 - but that shouldn't apply here.

Though that is typically true, being a bit of a pedant, port 25 is intended for MTA to MTA message relay, where as port 587 is intended for email client message submission.  Port 587 is therefore more correct, albeit port 25 is frequently used and does work ... in many circumstances.

https://en.wikipedia.org/wiki/Simple_Mail_Transfer_Protocol

SMTP communication between mail servers uses TCP port 25. Mail clients on the other hand, often submit the outgoing emails to a mail server on port 587. Despite being deprecated, mail providers sometimes still permit the use of nonstandard port 465 for this purpose.


 

slowtime
Grafter
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Registered: ‎06-05-2009

Re: Outlook 10 won't send email

Thanks for the additional information and Telnet instructions, which have been completed.  Please, let me know what to do next.

slowtime
Grafter
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Registered: ‎06-05-2009

Re: Outlook 10 won't send email

Thanks for the reply Townman.  I changed the outgoing port from 25 to 587 and tried sending but unfortunately no luck.  My sent message is stuck in my outbox! 

Superuser
Superuser
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Registered: ‎06-04-2007

Re: Outlook 10 won't send email

The steps to try sending via telnet are below. I've just confirmed they (still) work. Before you start you need to have decided what sender/from and recipient/to  addresses you are going to use. These can be identical if necessary, though I prefer to use different ones. Note that you will be communicating directly with the relay so need to get the structure correct. If you mistype something over-typing won't work, just press Enter and let the mail server issue a message. Then type the line again.

To get started you need to open a Command Prompt window. To do this type Command in the search box and click Command Prompt at the top of the list. In the window that opens type the commands shown in the box below. Note the lines beginning with a number are server responses.

C:\> telnet relay.plus.net 25
The window will clear after this with a reply similar to
that following - though this might be hidden)
220 avasout06 smtp relay.plus.net ehlo telnet 250-avasout06 hello [xxx.xxx.xxx.xxx], pleased to meet you 250-HELP 250-AUTH LOGIN PLAIN 250-SIZE 104857600 250-PIPELINING 250-8BITMIME 250 OK mail from: <david@username.plus.com> 250 <david@username.plus.com> sender ok rcpt to: <david@example.co.uk> 250 <david@example.co.uk> recipient ok data 354 enter mail, end with "." on a line by itself from: David <david@username.plus.com> to: David <david@example.co.uk> subject: From telnet <<<<<< Note this needs to be an empty (blank) line Message created using telnet <<<<<< The message text . <<<<<< Just a full stop on this line 250 709e1w0010a3eHw010Ac4i mail accepted for delivery quit 221 avasout06 smtp closing connection Connection to host lost. C:\>

Fingers crossed this works. Cool

David
slowtime
Grafter
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Registered: ‎06-05-2009

Re: Outlook 10 won't send email

David,

 

I've run the telnet test which I hope that I have done correctly.  I assumed that after I get the message "Connection to host lost" at the end then that is the completion of the test?  There was another line in your script "C:\>" but I assumed that wasn't asking me to input any more commands?

I used a second email address for the recipient but unfortunately, nothing has appeared in the inbox.  I'll check again later but I guess it should appear fairly instantaneously?