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Windows Server Forum / Small Business Server / SBS 2000 / January 2008SBS/Exchange 2000 and Yahoo.com email problems
Suddenly about a month ago, we started having problems sending emails to Yahoo.com addresses. These are typically followups to telephone inquiries that we get. The intended recipients complained about never getting the emails. We have had a few problems with Pacific Bell, AT&T, and SBC emails. We are not having this problem with outbound emails to other domains. I set up a test Yahoo email address and found out that test emails were getting placed into the spam/bulk folder. I tracked a few lost emails (through Exchange System Manager) and found that they were all delivered to a Yahoo.com server, sometimes after a few hours of retries. My guess is that Yahoo is falsely labelling our emails as suspected spam for some reason. My further guess is that the Yahoo.com recipients do not know enough to look in their spam folders and do not know enough to figure out if they told Yahoo Mail to discard suspected spam rather than place it in their spam folder. Our SBS 2000 server sends the emails directly under our domain name. We have a fixed IP. I checked the IP against the spam blacklists and we were clean. We have an SPF record and Google Mail says we pass the SPF test. We do not have anything set up for DomainKeys -- I am not sure that we could with SBS/Exchange 2000. Has anyone else experienced this problem? Any solutions? Any ideas for further diagnosis? Thanks, Joe M Hi Joe: How about a ptr record, basically a reverse lookup. -- Larry > Suddenly about a month ago, we started having problems sending emails to > Yahoo.com addresses. These are typically followups to telephone inquiries [quoted text clipped - 25 lines] > > Joe M Forgot to mention that. There is a PTR record for the mail server public IP that points to the SBS/Exchange 2000 mail server host (DNS name mail.<domain>.com.). The A records for <domain>.com point to a hosting service and the MX record for <domain>.com points to mail.<domain>.com which is used for in/out bound email. Thanks for the reply. > Hi Joe: > > How about a ptr record, basically a reverse lookup. > > -- > Larry Have you considered using Smarthost such as your ISP as opposed to sending directly using DNS? I recommend a Smarthost these days since most large ISP's are blocking IP's that are part of a smaller blocks or subnet. Typically its DSL or Cable IP's, even business class.  SignatureJohn Oliver, Jr MCSE, MCT, CCNA Exchange MVP 2008 Microsoft Certified Partner > Suddenly about a month ago, we started having problems sending emails to > Yahoo.com addresses. These are typically followups to telephone inquiries [quoted text clipped - 25 lines] > > Joe M A slightly alternate suggestion si to use both DNS and SmartHost. I generally setup the default SMTP Connector in Exchange on an SBS server to "use DNS", and then set up a secondary SMTP connector using SmartHost. For the SmartHost connector, click on the Address Space tab and enter the specific mail domains (for example yahoo.com) that are being blocked with the default connector. SignatureKevin Weilbacher [SBS MVP] "The days pass by so quickly now, the nights are seldom long" * > Have you considered using Smarthost such as your ISP as opposed to sending > directly using DNS? I recommend a Smarthost these days since most large [quoted text clipped - 30 lines] >> >> Joe M Thanks John & Kevin for the suggestions. I will pursue. Joe M >A slightly alternate suggestion si to use both DNS and SmartHost. I >generally setup the default SMTP Connector in Exchange on an SBS server to [quoted text clipped - 38 lines] >>> >>> Joe M Let us know how it goes. SignatureKevin Weilbacher [SBS MVP] "The days pass by so quickly now, the nights are seldom long" * > Thanks John & Kevin for the suggestions. I will pursue. > [quoted text clipped - 42 lines] >>>> >>>> Joe M Still a problem. The ISP (XO Communications) does not offer a Smart Host type of service. Tough to drop them because they also provide web hosting and phones. Are third-party services viable for this? Any suggestions? Joe M > Let us know how it goes. > [quoted text clipped - 44 lines] >>>>> >>>>> Joe M from google, the 'outgoing mail server' for XO Communications mail.njd.xo.com or smtp.concentric.net Try them as smarthost > Still a problem. The ISP (XO Communications) does not offer a Smart Host > type of service. Tough to drop them because they also provide web hosting [quoted text clipped - 53 lines] >>>>>> >>>>>> Joe M Their preferred server is secure.xo.com, but that is not the problem. They say they do not have a smart host service (some of them say Wah?). They require an authentication before allowing a relay. That authentication has to be a user (mailbox) listed in the account at XO and password. Once authenticated, they will allow outbound emails from that user only. There is a mechanism to allow "Alteranate From Addresses" which I am now trying. Each alternate address has to be listed and go through an opt-in process. I believe that addresses in the same domain must also be registered with them. I will try this tonight. I do not know how the email comes out of the relay or how many From addresses I will be allowed. Discovering this information has been like pulling hen's teeth. I tried to set up an alternate SMTP connector and ran into problems. I will ask about this on a separate thread. Thanks, Joe M > from google, the 'outgoing mail server' for > XO Communications mail.njd.xo.com or smtp.concentric.net [quoted text clipped - 58 lines] >>>>>>> >>>>>>> Joe M I suspect it is more about 'Wah?' than anything else. ISPs normally provide _at least one server_ for clients attached to that ISP to relay through. Picture Joe Bloggs, ordinary internet user, he wishes to send from joe@isp.com, joeb@company.com, joe54@hotmail etc... his wife wishes to send from joanna@company2.com, his son from joejr@homedns.org. Though I appreciate that it is possible for XO to implement this 'opt in' style restriction I expect you are asking them about something they simply don't understand. _try_ the suggested server(s). Do they work as 'smarthost' (HINT: the term 'smarthost' is purely an MS thing, ask anyone unfamiliar with Exchange/MS terminology and the expected response is 'Wah?') > Their preferred server is secure.xo.com, but that is not the problem. They > say they do not have a smart host service (some of them say Wah?). They [quoted text clipped - 79 lines] >>>>>>>> >>>>>>>> Joe M Your comment makes sense. However, if XO does provide such a server they have hidden it from me, at least 5 of their tech support reps, 2 second level (guess from "please hold while I check") support reps, and Google. I tried setting SmartHost to the 2 servers you suggested, secure.xo.com (XO suggested server for individual mailboxes), and smtp.<domain>.com.xohost.com as suggested by one support rep. All were attempted without any authentication or TLS. None worked. The secure.xo.com attempt returned an NDR saying the client host rejected. The others returned NDRs saying "There was a SMTP communication problem with the recipient's email server." I also tried smtp.<domain>.com.xohost.com and smtp.concentric.net without authentication, but with TLS. I did not get quick NDRs, but I see the test emails in the "Messages with an unreachable destination" queue. I also tried using a connector with the smart host and an authentication via an XO user that was set to allow alternate from addresses. It did not work with alternate from addresses, but did work with the authentication from address. Any suggestions about a 3rd party relay service? Joe M >I suspect it is more about 'Wah?' than anything else. ISPs normally provide >_at least one server_ for clients attached to that ISP to relay through. [quoted text clipped - 93 lines] >>>>>>>>> >>>>>>>>> Joe M OK, so the net result as I read that is that you have tried a lot of things I have no reason to believe will work but _at least_ one thing I expected to work (based on google search) smtp.concentric.net. I did not at any time suggest either secure.xo.com nor smtp.<domain>.com.xohost.com. I suggested the _absolute_, _literal_ names mail.njd.xo.com or smtp.concentric.net. I don't know. Maybe XO are anal retards. 'Technical Support' _can_ be expected to say 'hang on, I'll go ask' if you ask them 'what server can I use as smarthost?' but if you ask them 'What outgoing mail server should I use in outlook?' it would be very unusual for them to give you other than the name of the server you can use as 'smarthost'. NOTE: Ask this question of the ISP, do not ask the 'web/mail hosting' branch of the ISP, do not ask your 'account rep'(who may have preconceptions about your requirements). Pretend to be a single user connected to their service, 'I want to send email'. If XO do not have a server that can do such they are the first ISP on the planet to do so. Recently someone on another ISP was questioning similar restriction (sending identity must equal 'from address'), I also advised them similarly (ie. do not send through the server associated with your 'hosted domain' but through your ISP's 'general server'), AFAIK they haven't confirmed nor denied success. > Your comment makes sense. However, if XO does provide such a server they > have hidden it from me, at least 5 of their tech support reps, 2 second [quoted text clipped - 120 lines] >>>>>>>>>> >>>>>>>>>> Joe M Thanks for your help. Please see my responses inline. > OK, so the net result as I read that is that you have tried a lot of > things I have no reason to believe will work but _at least_ one thing I [quoted text clipped - 3 lines] > smtp.<domain>.com.xohost.com. I suggested the _absolute_, _literal_ names > mail.njd.xo.com or smtp.concentric.net. No, you did not. I tried to make it clear that the others were suggested by XO. I apologize if I said anything that implied that I thought that you did. I tried the two names you suggested and also two others that XO support reps mentioned. I expected low odds of success with the others, but I was in there messing around and the extra cost was not much. > I don't know. Maybe XO are anal retards. 'Technical Support' _can_ be > expected to say 'hang on, I'll go ask' if you ask them 'what server can I > use as smarthost?' but if you ask them 'What outgoing mail server should I > use in outlook?' it would be very unusual for them to give you other than > the name of the server you can use as 'smarthost'. I had long since abandoned the term "smart host" when dealing with them. The problem is that the answer to "What outgoing mail server should I use in Outlook?" is very different from "What outgoing/relay mail server should I connect to from Exchange?". They have an answer for the former -- similar to the normal POP3/SMTP type of service. It requires pre-registration of an email address and authentication using that email address and a password. Once the connection is established, it will _only_ accept email with the same From address. Usable from Outlook. Not usable for a relay from Exchange with emails from multiple addresses within the domain. > NOTE: Ask this question of the ISP, do not ask the 'web/mail hosting' > branch of the ISP, do not ask your 'account rep'(who may have [quoted text clipped - 7 lines] > 'hosted domain' but through your ISP's 'general server'), AFAIK they > haven't confirmed nor denied success. I will try the ISP side. I had directed the calls the the mail/hosting side. XO only services business accounts and requires the account number/name before they will talk to you. Pretending to be a single user would be tough. Note from above that they _do_ have an answer for a single user or many single users -- each with a _separate_ connection to a mail server to transfer mail _solely_ for the authenticated user. Thanks, Joe M FYI - for closure. I tried the ISP side of XO tech support who quickly transfered me to the hosting/email side. Still no useful server name or methodology to relay outgoing email through XO. They are "working on it." I set up an account with AuthSMTP.com and set an SMTP connector to route all outgoing email for Yahoo.com through the AuthSMTP server. This seems to have solved the problem of Yahoo's dumping/rejecting the emails. We will direct other problem sites through it as they arise. We may direct all outgoing email through AuthSMTP if it continues to work, we have problems with other sites, and avoiding the administrative hassle is worth the higher cost subscription. I believe that a relay through any large and generally trusted relay would have solved our problem with Yahoo. Joe M Just as an aside, I think this thread highlights an industry-wide problem whereby spamfilter providers are dictating that small business mailsites shall adopt policies which are generally only available to leased-line coprporate users. Since most domain-registrars make no provisions for anything beyond A and MX records, it follows that their demands for PTR records, etc. are unreasonable and impractical. The issue with using a smarthost is firstly that many are of poorer reliability than an onsite server. Also, you have no way of tracing an email once it leaves your premises. (which it will do even if undeliverable) The ridiculously long timeouts (5 days) on most smarthosts are archaic in origin, and unacceptable for most business users. If a message cannot be delivered within say 24hrs, we need to be able to CANCEL that message, unfortunately you cannot do so when at the mercy of a smarthost. Just my thoughts on the matter. > I set up an account with AuthSMTP.com |
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