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Enterprise Software Thread, Troubleshooting Email Delays in Technical; hi all; was wondering whether someone could provide me with pointers; We have had some intermittent delays in sending emails ...
  1. #1

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    Troubleshooting Email Delays

    hi all;

    was wondering whether someone could provide me with pointers;

    We have had some intermittent delays in sending emails out to reciepents and also receiving. This is fairly random (ie sometime I get an email I sent from school > my yahoo account instant and sometimes it takes 30 minutes to get there. We also had feedback from parents that email sent to school takes 24 hours to arrive.

    My setup is thus:

    Our Exchange > managed Firewall > hosted Spamfilter > Outside world

    Email domain name (hosted by 123.reg) > MX record for our hosted spamfilter/smart host > managed firewall > Our Exchange

    I have enclosed message header for an email that took 20+ minutes to get to my gmail account (some details changed), looks like my exchange delivered the mail instantly but my smarthost sat on it for a while before sending it to gmail? :


    Delivered-To: mrwu@gmail.com
    Received: by 10.194.20.6 with SMTP id j6csp111855wje;
    Fri, 15 Feb 2013 04:53:27 -0800 (PST)
    X-Received: by 10.194.235.196 with SMTP id uo4mr3993891wjc.30.1360932806861;
    Fri, 15 Feb 2013 04:53:26 -0800 (PST)
    Return-Path: <mrwu@mrwuschool.co.uk>
    Received: from mail02.dby2.managedapps.co.uk (lb01-dmz.dby2.managedapps.co.uk. [109.204.xxx.xxx])
    by mx.google.com with ESMTP id n9si19393544wje.93.2013.02.15.04.53.26;
    Fri, 15 Feb 2013 04:53:26 -0800 (PST)
    Received-SPF: neutral (google.com: 109.204.xxx.xxx is neither permitted nor denied by best guess record for domain of mrwu@mrwuoodschool.co.uk) client-ip=109.204.xxx.xxx;
    Authentication-Results: mx.google.com;
    spf=neutral (google.com: 109.204.xxx.xxx is neither permitted nor denied by best guess record for domain of mrwu@mrwuoodschool.co.uk) smtp.mail=mrwu@mrwuschool.co.uk
    Received: from SRV-Exchange.mrwu.sch (unknown [109.204.xxx.xxx])
    by mail02.dby2.managedapps.co.uk (Postfix) with ESMTPS id 96299A31CE
    for <mrwu@gmail.com>; Fri, 15 Feb 2013 12:27:29 +0000 (GMT)
    Received: from SRV-EXCHANGE.mrwu.sch ([fe80::b140:c788:c4c5:b3a1]) by
    SRV-Exchange.mrwu.sch ([fe80::b140:c788:c4c5:b3a1%12]) with mapi id
    14.01.0218.012; Fri, 15 Feb 2013 12:26:44 +0000
    From: mr wu <mrwu@mrwuschool.co.uk>
    To: 'mr wu' <mrwu@gmail.com>
    Subject: test
    Thread-Topic: test
    Thread-Index: Ac4Ld7d0RauCATApTBy8ZdqMSi+Pag==
    Date: Fri, 15 Feb 2013 12:26:44 +0000
    Message-ID: <0342517C4074C242B874D5CFEC8952E61F0D8272@SRV-Exchange.mrwu.sch>
    Accept-Language: en-GB, en-US
    Content-Language: en-US
    X-MS-Has-Attach:
    X-MS-TNEF-Correlator:
    x-originating-ip: [10.18.97.226]
    Content-Type: multipart/alternative;
    boundary="_000_0342517C4074C242B874D5CFEC8952E61F0 D8272SRVExchangehinc_"
    MIME-Version: 1.0

    --_000_0342517C4074C242B874D5CFEC8952E61F0D8272SRVEx changehinc_
    Content-Type: text/plain; charset="us-ascii"
    Content-Transfer-Encoding: quoted-printable



    : a company limited by guarantee Registered in Englan=
    d: Company No: 1234567
    Registered Office: xxxxxxx

    Disclaimer added by CodeTwo Exchange Rules 2010
    www.codetwo.com<http://www.codetwo.com>


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    Content-Type: text/html; charset="us-ascii"
    Content-Transfer-Encoding: quoted-printable

    <html xmlns:v=3D"urn:schemas-microsoft-com:vml" xmlns=3D"urn:schemas-micr=
    osoft-comfficeffice" xmlns:w=3D"urn:schemas-microsoft-comffice:word" =
    xmlns:m=3D"http://schemas.microsoft.com/office/2004/12/omml" xmlns=3D"http:=
    //www.w3.org/TR/REC-html40">
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    colorurple;
    text-decoration:underline;}
    span.EmailStyle17
    {mso-style-typeersonal-compose;
    font-family:"Calibri","sans-serif";
    color:windowtext;}
    .MsoChpDefault
    {mso-style-type:export-only;}
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    <p style=3D"MARGIN: 0cm 0cm 0pt" class=3D"MsoNormal"><font size=3D"2" face=
    =3D"@Malgun Gothic">Hinchley Wood School: a company limited by guarantee&nb=
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    And also a parent that had a 24 hour delay to get her email to school (I suspect the German server / my smarthost is holding up the email?)


    Received: from mail3.aflex.net (212.21.xxx.xxx) by SRV-Exchange.mrwu.sch
    (10.18.xxx.xxx) with Microsoft SMTP Server id 14.1.xxx.xx; Wed, 13 Feb 2013
    23:37:23 +0000
    Received: from mail3.aflex.net (127.0.0.1) id h3gnbq0171sv for
    <jbloggs@mrwuoodschool.co.uk>; Thu, 14 Feb 2013 00:24:29 +0000
    (envelope-from <parent@email.eu>)
    Received: from moutng.kundenserver.de ([212.227.xx.xx]) by mail3.aflex.net
    (AFLEX) with ESMTP; Thu, 14 Feb 2013 00:24:28 +0000
    Received: from parentPC (cpc3-hxxx-2-0-custxxx.6-x.cable.virginmedia.com
    [86.9.xxx.xxx]) by mrelayeu.kundenserver.de (node=mrbap0) with ESMTP (Nemesis)
    id 0MSHd5-1UUscy02cl-00TePy; Wed, 13 Feb 2013 23:49:23 +0100
    From: sarah smith <parent@email.eu>
    To: 'Jane Bloggs' <jbloggs@mrwuschool.co.uk>
    References: <047501cdfe56$aacaea80$0060bf80$@parent.eu> <67E5612C38239C468F0D0DB306EBA6AB7CCB33@SRV-Exchange.mrwu.sch> <017501ce0326$5f04e540$1d0eafc0$@themorleys.eu> <67E5612C38239C468F0D0DB306EBA6AB7CD62D@SRV-Exchange.mrwu.sch>
    In-Reply-To: <67E5612C38239C468F0D0DB306EBA6AB7CD62D@SRV-Exchange.mrwu.sch>
    Subject: RE: parent enquiry
    Date: Wed, 13 Feb 2013 22:49:27 +0000
    Message-ID: <b4c501ce0a3c$61212240$236366c0$@parent.eu>
    MIME-Version: 1.0
    Content-Type: multipart/alternative;
    boundary="----=_NextPart_000_B4C6_01CE0A3C.61284E30"
    X-Mailer: Microsoft Outlook 14.0
    Thread-Index: AQH3x+xR3CllCizSoPbRqHU/pLEyOwJDU7rTAhTwQxoCG/aWlZfxRR2w
    Content-Language: en-gb
    X-Provags-ID: V02:K0:nT0tPQL4oC4oP9U78ZR+4VIgdRxwFNkWKK8oq8VUaaS
    qVVNHHSeC8Lc3LI1WTvzYPYYN24mLWmCKAVzO73CH05vtUyQPo
    tvVtOZrg6/lNK8VE/9ZcoGkXGhua3Yq5Ep3aNrhmWUaFKkTDCP
    FXP7jQWvdEYeSKoNEcYwbS6Q/+FclqfW/KEbKpmx+j3p6djmOD
    MVmSWPDfkb4aYtHgdq+GRVTa4PMQ6+lIi3OJ/gPCIswhwYcFWI
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    vNnwI4a8bIb/OK0cY4To+8f4xDrboC0FyKo+4p/haZE0XVMcft
    kg0CHqhnnt/OY1MOaUJHQkkYbMHhgVQDxo9v6wsTx
    X-Mlf-KeyWords: music,composition,pop,drum,autumn,often,emails,gcs e,attached,4pm,discuss,meeting
    X-Mlf-Language-Detected: NoLanguageFilter_english
    X-Mlf-Connecting-IP: 212.227.xxx.xxx
    X-Mlf-Country-Code: DE
    X-Mlf-Threat: nothreat
    X-Mlf-Threat-Detailed: nothreat;none;none;none
    X-Mlf-UniqueId: i201302140024280050885
    Return-Path: parent@email.eu
    X-MS-Exchange-Organization-AuthSource: SRV-Exchange.mrwu.sch
    X-MS-Exchange-Organization-AuthAs: Anonymous

  2. #2

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    I'd suspect you smart host provider should be able to she'd more light on it.

    Do you have valid SPF entries for your domain in DNS? Perhaps you are getting tar-pitted?

    Also have you tried seeing what the ms connectivity tools have to say? https://www.testexchangeconnectivity.com/

  3. Thanks to psydii from:

    MrWu (19th February 2013)

  4. #3

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    Quote Originally Posted by psydii View Post
    I'd suspect you smart host provider should be able to she'd more light on it.

    Do you have valid SPF entries for your domain in DNS? Perhaps you are getting tar-pitted?

    Also have you tried seeing what the ms connectivity tools have to say? https://www.testexchangeconnectivity.com/
    Thank you.

    I used the test and inbound all ok (I think the parent's email was from a German server and that was delaying mail coming in)

    It did flag that there was no SPF record associated with my domain, so I will investigate this...is there an issue adding SPF record if I go through a Smarthost and the email domain is hosted at 123.reg?

    Cheers

  5. #4

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    Also my ISP said they had no influence over outbound mail

    However On Exchange we use thier Smarthost as a send connector

    Looking at a portion of the header the delay occurs at the smarthost end:

    Received: from mail01.dby2.managedapps.co.uk ([109.204.127.10]) by COL0-MC4-F11.Col0.hotmail.com with Microsoft SMTPSVC(6.0.3790.4900);
    Mon, 18 Feb 2013 09:16:58 -0800
    Received: from SRV-Exchange.mrwu.sch (unknown [109.204.98.19])
    by mail01.dby2.managedapps.co.uk (Postfix) with ESMTPS id 3BF31A48DB
    for <axxx_87@hotmail.com>; Mon, 18 Feb 2013 15:36:36 +0000 (GMT)
    Received: from SRV-EXCHANGE.mrwu.sch ([fe80::b140:c788:c4c5:b3a1]) by
    SRV-Exchange.mrwu.sch ([fe80::b140:c788:c4c5:b3a1%12]) with mapi id
    14.01.0218.012; Mon, 18 Feb 2013 15:35:47 +0000


    • User sends email from Exchange (through Outlook 2010) to his hotmail at 15:35:37pm -0000
    • managedapps.co.uk gets the email from our Exchange server at 15:36:36pm -0000
    • Hotmail does not receive the email from managedapps.co.uk until 09:16:58 -0800 (so translates to 17:16:58 +0000(GMT) – over an hour delay

    Would this definitely point to Smarthost sitting on my emails?

    Thanks

  6. #5

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    Hi

    Turned out, after a bit of pushing with our ISP that it was the smarthost with a SPAM backlog slowing down SMTP

  7. #6

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    I had a few issues using a smarthost for forwarding mail last year - so I decided to go direct to MX records with the exchange server.

    Only had a couple of small issues at the start (need a reverse lookup in your external dns etc...) but now it runs without fault, messages are queued by exchange (and viewable in the queue) when the other end has issues - as opposed to you not knowing till a lot later as the smarthost makes these decisions.

    Edit - users also get a message saying that the email has failed, but exchange will retry for 24 hours before generating a failure message etc... / our smarthost was blocked by hotmail as someone used it to spam = no emails to hotmail for a couple of days whilst they dealt with it.
    Last edited by Psymon; 19th February 2013 at 04:45 PM.

  8. Thanks to Psymon from:

    MrWu (19th February 2013)

  9. #7

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    Thanks for the help, will plan using MXrecords...

    Just an update they promised it should have been resolved last thursday but as of today still having upto 8 hour delays to yahoo and gmail for example, any more aggro i'm going name and shame this ISP....

    Si I have spent a while troubleshooting, I have no relay issues for Exchange(tried MX toolbox) not been blacklisted, as far as the managed Firewall people says no funny SMTP traffic coming out from my LAN..so dont know how much more I can do..

    Although my MX toolbox test flagged 2 warnings:

    SMTP reverse mismatch
    SMTP transaction time warning : 5894 seconds

    Does SMTP transaction times also point to issue with my Smarthost?

  10. #8

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    Personally - I would set up a second send connector (direct to MX) and test with that.

    You can keep your smarthost one set up, just temporarily disable smarthost, enable MX.

    See what results you get from that - will give you a better idea of what exactly the issue is.

    Si

  11. Thanks to Psymon from:

    MrWu (24th February 2013)

  12. #9

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    If you've got a campus/schools/software assurance you might already have access to MS FOPE which is MS's SMTP Hygiene in the cloud service. Worth trying as an alternative if you can? Microsoft Forefront Online Protection for Exchange

  13. Thanks to psydii from:

    MrWu (1st March 2013)

  14. #10

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    Some of the possible reason for this delay could be related connection issue, spam filtering or offline server. I think you are using Outlook 2010. Also try to turn off your anti-virus software and now try again. Also you can perform some troubleshooting steps like :
    - In Exchange server 2010, open toolbox -> mail flow troubleshooter and enter a label for analysis and select 'messages destined to recipients are delayed'.
    - Click next and enter the server name and GC name. Now enter sender and recipient's email address. Click nest twice.
    Export the reports and save it as .xml file. Then compress the file and after it upload it to

    www.skydrive.live.com for testing.

    Regards
    Sarah

  15. Thanks to sarahsmith from:

    MrWu (1st March 2013)

  16. #11

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    Thanks all,

    all back to normal now, it most definitely was the smarthost that was affecting our outgoing mail.

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