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Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

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RMcD
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Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Since Monday 17th October my outgoing emails (username@msn.com) using a desktop version of outlook (Windows vista) on plusnet broadband wifi or my iphone outlook (on wifi on same router) have not been received by the recipient although they appear in the Sent emails box.

If I use my mobile without wifi and go via O2 then any emails I send are received by the recipient..

My broadband with Plusnet is somehow not sending the emails.

Any ideas?

Thanks in hope.

 

37 REPLIES
Superuser
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

When sending the messages using your Plusnet connection are you using the Plusnet SMTP server relay.plus.net? If the recipient is using SPF verification this will fail because the IP of the Plusnet server will not be authorised to send emails for msn.com addresses.

msn.com publishes an SPF record

v=spf1 include:Spf-a.hotmail.com include:Spf-b.hotmail.com include:Spf-c.hotmail.com include:Spf-d.hotmail.com include:_spf-ssg-a.microsoft.com include:Spf.protection.outlook.com ~all

which uses lots of "includes" but none of those will specify IPs not under Microsoft control.

When sending via O2 are you using outlook.com webmail which is authorised?

David
RMcD
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Thanks for the prompt reply David.

Sorry but I don't know which SMTP server outlook is using on either my phone or desktop (I can't find it in the settings). I do not have an issue with Plusnet's webmail which is working fine and can send to msn.com addresses o.k..

I have changed nothing at my end (windows desktop, iphone or ipad)and the problems started on Monday 17th October 2016.

I probably wasn't clear my issue so I've tried to describe it below in basic levels.

 

PROBLEM:

(I use microsoft outlook on my desktop and my iphone. My email address is "Huh??@msn.com".)
I have Plusnet Broadband with a Plusnet HubOne. I have turned it off then on again.

Just concentrating on the iPhone.
If I have WiFi enabled:
1. Emails that I send to hotmail/msn addresses are sent and received by the recipient.
2. Emails that I send to other addresses (e.g google mail) are NOT received but do show in
my sent mailbox.
If I then switch off the wifi on the iphone and just use 3G (provider O2) then ALL the
emails are received by recipients.

Using my Desktop Windows outlook (or indeed "outlook.live.com") on the Plusnet broadband
1. Emails that I send to hotmail/msn addresses are sent and received by the recipient.
2. Emails that I send to other addresses (e.g google mail) are NOT received but do show in
my sent mailbox.

I can not make changes to the iPhone email settings other than SSL.
I cannot make changes to the outlook.live.com webmail server settings.
The emails are not going into the recipients junk/spam folder.

THANKS

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Having exactly the same problem.  Email is getting moved to sent items folder, but not actually being sent.  Everything works fine if I don't use the wifi (plusnet) connection and use my mobile internet connection instead.

The account is using the default settings (so no pop/smtp account settings visible).  This only started happening as of Monday 17th October.

 

It seems to be affecting both Hotmail (Live Mail) and Gmail accounts.  Interestingly Office 365 accounts not affected.

 

I'm going to try setting up the account as a legacy pop/smtp account and see if that works any better...  Will report back on whether that has any success...

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Makes no difference Sad Gmail was already set up to send mail through the gmail smtp server and not the relay.plus.net one.

It's also affecting email sent using the mail.live.com web interface too - emails 'appear' to get sent, and get moved into sent items, but email never gets received by the recipient.

It's not affecting all hotmail accounts though, so wondering if some of the Microsoft email servers (and seemingly some Google mail servers) have been blacklisted by Plusnet? If you're unlucky enough to have your Hotmail/Gmail account on one that is, mail isn't getting sent, maybe?
RMcD
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Thanks Jamesc.

I contacted microsoft support outlook on line chat (Microsoft Answer Desk) and spent an hour with first line on Sunday. He/she was very thorough (used a remote connection) and cane to the conclusion it could be a problem at their server so has escalated it to level 2 engineering support. I have a call booked for Tuesday with them so will provide an update. My wife has the same problem with her hotmail address so I hope they apply a generic fix (for everyone) and not just me.

What I don't understand is why it works if I use my neighbour's BT wifi or use my mobile data connection. Mind you, if it starts working I'll no longer worry about that one!!

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

In the same position, having raised a case with Microsoft, who are also passing my case onto their Level 2 support team, however since webchatting with them, I've managed to prove the hotmail and gmail accounts are working absolutely perfectly if I use my work VPN rather than go directly to the hotmail/gmail sites over the Plusnet infrastructure.  I'm going to raise a support case with Plusnet referencing this thread as something must have changed in their filtering rules in the last week.  Will let you know if I hear anything back.

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

So also spent 30 mins on the Plusnet Webchat Support this afternoon.  After explaining what was happening, support team member I was speaking to was certainly surprised by what was being experienced, but supportive and said they'd look into possible causes.  There had been a suggestion it was a Windows 10 related incident, but considering it doesn't occur when I use my mobile phone as a wifi hotspot, or route my internet traffic through my work VPN, and only happens when I use my Plusnet internet connection over wifi or fixed ethernet (on my laptop, PC, tablet and phone), the problem seems lie pretty firmly in something that's happening in the Plusnet infrastructure.

 

There had been a suggestion to try a direct connection into my fibre modem (i.e rather than connecting through my router, set up a PPPoE connection from my computer directly into the Openreach modem), which I've done, and have exactly the same problem.  Thankfully that rules out there being a problem with my router!

I now have a support ticket raised with Plusnet, so hopefully there can be some more investigation and the root cause fixed.

Will keep this updated with info as I hear anything...

RMcD
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Jamesc - I too also spent some time on the Plusnet Webchat on Friday 21st Oct with two different agents. Although very helpful, they both, after a while, seemed to want to bat the problem off onto the third party (Microsoft). They seemed to miss the obvious fact that it worked when I used mobile data on my phone and also worked on my neighbour's wifi but failed on my Plusnet Broadband. Maybe I should have pushed for a support ticket.

 

I suspect the Microsoft level 2 support will quite quickly identify it as being an issue at Plusnet. The problem will then be getting Plusnet to acknowledge the issue and implement a fix (or rollback the change made on the 17th Oct). The second Plusnet agent advised that they would need a number of people to contact them regarding the issue before they would look into it.

 

I can't believe that we are the only two people with this problem (my wife has the same issue so that's one more!)

 

I'll update later tomorrow.

RMcD
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Update: Microsoft Level 2 support let me down twice today. They failed to make the original arranged 9:30am call then again failed to make the rearranged call later today. I'm no closer to getting an answer. Rearranged for next Monday (30th) so I'll see what happens then.

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Unsurprisingly, I've had exactly the same experience with Microsoft...  That said, I really don't think it's a problem with their service, and the more tests I do, the more it points to a problem in the Plusnet infrastructure.

I downloaded the Opera web browser last night, and turned on the integrated VPN.  If I use Hotmail with the VPN service turned on, Hotmail email works absolutely perfectly.  Turn it off, emails don't send.

The ticket I've got open with Plusnet has been escalated to 'G' (whoever/whichever team that is!).  It can't be impacting every hotmail/gmail user, but suspect if you're unlucky enough for your email account to reside on one of the servers that Plusnet seems to be treating differently, you're going to have this problem.  Really not a good position to be in! Sad

I've started investigating VPN services (e.g. nordvpn, vyprvpn, etc) that I can run directly within my router - but I'm reluctant to have to pay for an addition monthly subscription to correct something that was working absolutely fine a few weeks ago, and works fine if I use a different ISP!

 

RMcD
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

I finally did get a call yesterday (this morning early) from Microsoft at 01:30. Finished at 03:30 and am now quite tired. The Level 2 support agent took some traffic details using "Fiddler"(don't know what that is) and some screen shots. All the info is being passed on to Level 3 support and I will get a call next Monday (31st Oct). I have not told them it works on mobile data as I want them to identify what's happening when I'm using my broadband provider.

However, like you, I think the problems lies within Plusnet so here's to hoping your "G" support will be able to shed some light on the problem.

Community Gaffer
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct


@jamesc wrote:

I'm going to raise a support case with Plusnet referencing this thread as something must have changed in their filtering rules in the last week...


Whilst there may well be an issue specific to Plusnet, I fail to see how this can be anything to do with 'filtering' at our side. Those reporting issues in this thread are sending from third party email address, via a third party SMTP server/Webmail platform to an external email recipient. At no point in any of that chain are Plusnet involved. We're just providing the initial transport.

It could be that Microsoft's servers do not like the IP addresses we're assigning you guys (although I see no commonality). If that was the case, then it's Microsoft's responsibility to establish why it's happening and do something about it.

The only other thing I can think of is a fundamental routing issue between Plusnet and Microsoft, although peoples' failed attempts via the Hotmail Webmail interface aren't really synonymous with this theory.


It's suspicious that 'local' email sent from Microsoft-hosted addresses, to Microsoft-hosted addresses, is getting through. Again, this leads me to raise an eyebrow in Microsoft's direction.

All that ^ said, I have a Live/Hotmail email address knocking about somewhere so I'll see if I can replicate the issue...

Bob Pullen
Plusnet Product Team
If I've been helpful then please give thanks ⤵

jamesc
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Hi Bob,

 

Thanks for the note.  I agree, it does look a bit strange, especially that the 'sent' emails appear in sent items, but don't go anywhere.  It's not ALL Hotmail accounts that are effected, seemingly just some, when they are perhaps located on a particular Microsoft host (maybe)?

The reason why I still think it's in the Plusnet space is that if I use a VPN (such as the VPN in Opera browser for example) the hotmail account works absolutely perfectly.  I can send and receive email without a problem.  Similarly, if I use the same hotmail account with my mobile internet connection (with Vodafone or O2), again, the account works fine.  If I use my neighbour's internet connection (not Plusnet), again no problems.  It's not limited to the web interface though, emails aren't sending for the affected account when I use Outlook (the mail client - it's confusing Microsoft now calling Hotmail Outlook too!).  The challenge with Outlook is the account isn't set up as a traditional pop/smtp setup, but using the 'wizard' such that Microsoft don't show the server settings that are being used.  Thinking it through though, I might try a wireshark trace of the Outlook traffic to see if there's anything shown that suggests why the email isn't actually going anywhere.

What's confusing, is the 'not all hotmail accounts affected bit'.  I have another hotmail account that works absolutely fine.

I've tried to have a look what's going on with wireshark traces at the point in which the send button is clicked, one trace for the hotmail account that's got issues, one trace for the one without, but it's seemingly impossible to determine what's going on as it's all https traffc Sad

 

I've got a ticket open with Microsoft too (trying to co-ordinate a call with them is proving quite tricky as I can't actually CALL them, I need to online chat with them, wait in a queue, then hope they can call me, and when they have scheduled to call me, got the timezones completely mixed up to a point where I couldn't take the call).  Other people in this thread have been a little more successful, albeit their tickets being passed to yet another level of support.

 

What I don't have is this experience "It's suspicious that 'local' email sent from Microsoft-hosted addresses, to Microsoft-hosted addresses, is getting through. Again, this leads me to raise an eyebrow in Microsoft's direction." - For me, if I send an email from an impacted hotmail account to a none impacted hotmail account, even the non-impacted hotmail account doesn't come through.

What I am wondering is whether your suggestion of a fundamental routing issue between Plusnet and Microsoft could be the issue, but only to a particular server (or perhaps a limited number of Microsoft's servers)?  It'd be interesting to try and identify whether the impacted accounts that are failing to send mail correctly are on the same Microsoft host...  I'll see if I can determine what host my failing account is on, and then perhaps see if the SMTP protocol is failing towards that address (bit of a long shot I know!!).

 

Appreciate the offer of help Smiley

nicwhit
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Re: Outlook (Hotmail/MSN) not sending emails but receiving ok since 17th Oct

Hi

 

I have just finished on  the telephone with a man from plusnet regarding the exact problem. I can send emails from both my hotmail accounts and gmail accounts and they all go into the sent folder BUT no one actually receives them. If I forget plusnet broadband/wi fi and use a company vpn they all get sent and received. The man from plusnet said there was nothing they could do and they would try and look into the problems that everyone is facing with this but it could be some weeks until they have collated more information and had other complaints. He suggested that i change provider!!!!!!!

My husband has suggested it may have something to do with the fact that plusnet have made some changes somewhere to their filters/systems etc and because my email address does not have a . ( dot) in it the plusnet system does not like that address i,e joebloggs@hotmail.com now would need to be joe.bloggs@hotmail.com he thought that may be worth a go.