Outgoing e-mail works intermittently, don't always get a bounceback.

Discussion in 'Help Desk' started by cidzor, Nov 21, 2014.

  1. cidzor

    cidzor New Email

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    Hi,

    I have some troubles with outgoing e-mail that are really making me pull my hair out, and I'm hoping someone can help point me in the right direction. First, a brief explanation of how things are set up:

    This is a business, a small office with 5 users that uses GoDaddy hosting for their website and e-mail. The users are all running various versions of Outlook (a couple still using 2003, a couple using 2007, and one using 2013) on various operating systems (a couple still on XP, a couple of Windows 7, and one on Windows 8) with POP accounts set to use GoDaddy's servers. For the most part, life is good.

    Couple of weeks ago, they noticed that they're suddenly unable to send to certain recipients. We've been fine for years up until that point. It's not entire domains (for example, some verizon.net recipients or aol.com recipients receive our e-mails, while others don't). There's not any one specific domain that seems to be worse, but the problem seems to be scattered across various domains. Incoming e-mail works great, and we're having no problems there.

    We don't get bounce messages at all. We send the e-mail message from Outlook, it appears to have gone out, and we think life is good. No indication that there's a problem until we get a "Hey, why didn't you respond to my e-mail?" call from the recipient a day later.

    Things we've already tried:

    1. Switched hosting providers. We switched from our last provider to GoDaddy. The transition was pretty smooth (it needed to be done anyway because we were having a lot of other, unrelated issues with that provider), but the problem with outgoing e-mail still exists.

    2. Temporarily turning off signatures in Outlook. They have a pretty big signature that's one of those "confidentiality notice" things, so I thought it might be causing some problems. The messages aren't going through, even with the signatures turned off.

    3. Sending from GoDaddy's webmail and from their mobile phones instead of Outlook. No difference.

    4. Contacted GoDaddy's tech support about it. They've checked everything they know to check and can't find anything wrong. They also confirmed that all our DNS records are set up properly and that we've configured our Outlook clients properly. Our previous hosting company's tech support went through the same thing. They previous company wanted us to try and get them the full message headers from the failed messages that were in our sent items folder, which you can't even do to the best of my knowledge (everything I've found about that indicates that you can only get those from received messages). GoDaddy support also checked to make sure we weren't on any sort of blacklist that they could see.

    5. Checked the domain on mxtoolbox.com. It's not on any blacklists, and it passes every check that MXToolbox can throw at it.

    6. Asked a couple of the recipients to add us to their "allowed sender" lists. Still doesn't help. I'm really thinking something else has to be going on anyway, because we're having this problem with so many recipients. I'd hope we're not going to have to call every single one of them and treat it as a bunch of separate issues, considering a) these problems all happened at once and b) the problem recipients are on a lot of different domains.

    7. Contacted the ISP that most of the problem recipients are using (it's a pretty major ISP in this area). They insist that they're not blocking us in any form. We actually use them as an ISP, just that we have our e-mail hosted on GoDaddy. A lot of the problem recipients have e-mail addresses from this ISP though. Some of the recipients are home users while others are businesses.

    8. Switched SMTP ports on the Outlook clients from 25 to 587. Didn't make any difference. Also played around with using encryption in the server settings, which also made no difference.

    Again, we don't even get bounce messages. At this point, I'm at a complete loss for troubleshooting this and have tried everything I know to try. If anyone has any ideas, I'd love to hear them. I'd rather not post any details about their domain or specific e-mail addresses here for the world to see, but I might be willing to do that through PMs if someone has an idea. My gut tells me that we have to be on some kind of blacklist or have a sender reputation problem or something, but I have no idea where to look for that beyond checking MXToolbox. Was first thinking it had to be the huge signature, but considering the fact that turning off the signature in Outlook AND sending from GoDaddy's webmail (where we don't have a signature set up at all) didn't help, I feel that we can eliminate that as a potential problem.
     


    Last edited: Nov 21, 2014
  2. popowich

    popowich EQ Forum Admin Staff Member

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    What's the domain name for the small business?

    Can you post the full headers from a successful send?

    The first things that come to mind are checking the SPF record for the domain and the reputation of the sending IP address(es).

    Also, check your spam folders for error messages from mailer-daemon.
     

  3. cidzor

    cidzor New Email

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    The SPF records are set up. GoDaddy tech support actually set that up for us and helped us get all our other DNS records straight while they were helping us with the transfer from our old provider.

    Nothing in our spam folders (in either Outlook or GoDaddy webmail).

    I'll send you a PM with the domain name and other details you requested, as I'd rather not post them for everyone to see. Thanks for checking it out.
     
  4. popowich

    popowich EQ Forum Admin Staff Member

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    I received the private message.

    Can you get the headers from an email sent out to a 3rd party hosting such as Yahoo or Gmail?

    It doesn't surprise email leaving the Godaddy shared relays is intermittently blocked.

    The existence of the current SPF record specifying Godaddy means the senders should not be sending through other services such as ISP smtp relays (Verizon, Comcast, Time Warner etc)

    Delete the SPF record if you want to send though alternate email services while investigating the Godaddy issues.
     
  5. cidzor

    cidzor New Email

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    Sorry for the delay. I'll try to get those to you this evening.

    Just to be sure, you want me to send from the affected domain to my Gmail account? Or did you mean change the SMTP server in Outlook on one of the affected machines to use the Gmail one, then send you a header from that?

    Also...I think I shouldn't have used the word "intermittently" when I posted this. The recipients we can and can't send to are consistent. In a lot of cases, we can send to some users on a certain domain but not to a lot of other users on the same domain. But those users we can and can't send to have been consistent the whole time.
     
  6. cidzor

    cidzor New Email

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    Small update: we actually got a bounce message for the first time today.

    [Return Code 554] sid: LHdk1p00B0xVt0q01 :: 5.7.1 [P4] Message blocked due to spam content in the message.Sent to this recipient from Outlook, and we got that bounce almost immediately.

    Oddly enough, I was able to log in to the user's GoDaddy webmail, copy/paste the entire message (including his signature and everything), and send it to the same recipient. No bounce message yet, although I'm still waiting for verification that the recipient actually received it.
     
  7. cidzor

    cidzor New Email

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    So...another update. I think I'm on the right track now. The domain is not on any kind of blacklist, and everything is set up properly on the client ends, from what both I and GoDaddy support can tell. This post is going to be a bit of an unorganized novel, but here goes:

    Interesting development. I have a laptop, with Outlook installed. Take it on site to this office and try to send emails as one of the users on their domain, nothing. Take it to my house and try to send (no changes made, exact same configuration in Outlook and everything), and the emails to recipients that weren't working consistently go through. Send another to the same recipient back in the office from the same laptop, doesn't go through and no bounce message. The laptop's configuration isn't changing at any point throughout this, except for the fact that it's at a different location and utilizing a different Internet connection. In fact, it seems to work just about anywhere except on site at the office. That development makes me think the domain/hosting stuff and Outlook configurations are fine, and there's something going on specifically at this office. As far as I can tell, that leaves either a) the router or b) something to do with the ISP/Internet connection.

    I have tried swapping the router at their office with a different model just to make sure that one's not being flaky (even in one case swapped it out with a cheapo Wal Mart special home-grade router that's wide open and should allow any outgoing traffic with no form of spam filtering capabilities whatsoever, much less any ability to potentially filter outgoing email), and that made no differences. So I think the router can be eliminated as the problem.

    I really doubt the switch is doing anything funny, because it's just a plain/dumb unmanaged switch. In fact, I tried plugging said laptop directly in one of the router's LAN ports (bypassing that switch), and nothing changed for better or worse. So I think blaming the switch for anything is a long shot at this point.

    It's a very small office. Maybe 6 workstations (only 5 of them even using Outlook), with various different versions of Outlook (some 2003, couple 2007, and one 2013) and various different versions of Windows (still a couple of old XP machines, but mostly running Windows 7, and one running Windows 8). The network is run by an old 24-port unmanaged switch and a Cisco RV042 router, and they have a fiber connection with their ISP. The 6 workstations are just on a workgroup together, not a domain. Nothing really fancy or complicated here.

    At the office, they have a deal with the ISP where their WAN IP is set to dynamic, but it's one of those dynamic IPs that never changes (they just receive the same one again any time it releases/renews, and have had that same IP address for years). From what I've read, some spam filters actually look at that line in the OriginatingIP part of the header, see it as "spam" content, and block it (regardless of the fact that all the MX/reverse DNS records are set up properly and point to GoDaddy as they should).

    I'm trying to work with the ISP now and see if there's some way to have that IP changed. I checked the IP itself on mxtoolbox and just get a "no matches found" for it, as I should (since there should be no need for any records to point to that because it's not like they're hosting their own email onsite with an Exchange server or something).

    I first thought that sending from webmail/mobile phones didn't work, but I believe the users who reported that to me were mistaken (my fault for just taking their word on it instead of double checking myself, I suppose). Combine that with the fact that we rarely get any bouncebacks on these, and it made things a bit tricky to pin down.

    I'm guessing some enterprise-level spam filter (at an ISP or something) has decided it didn't like seeing that originating IP in the message headers for some reason and filters based on that (without sending any kind of NDR), but I have no real way to track down where that might be. Anyway...I'm trying to see what I get going that route. Maybe I can just see about getting them on a static IP (that's different from this one) and get this stupid problem off my back.

    Another interesting development: there's another local business, just a little ways up the road, having the EXACT same problem all of a sudden, and they're set up almost the same way (with the same ISP and e-mail through their web hosting provider). I did a little digging, and while they didn't really realize it at first, their problem appears to have happened at around the same time as the other office. The only difference is that they're using a company other than GoDaddy for web hosting, but it's the exact same problem and almost the exact same setup otherwise. More reason for me to think something with the Internet connection or the "dynamic IP that never changes" thing is at the root of this.
     
  8. cidzor

    cidzor New Email

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    So...another update. As mentioned above, I contacted our ISP and convinced them to change that WAN IP address for us. Seems like we're good now.

    Our e-mail is hosted through GoDaddy, and we have all our DNS records/Outlook clients set up properly, so I would think the WAN IP address at the actual office shouldn't matter. But apparently, some spam filters actually check that originating IP line, and one of them out there somewhere decided that it didn't like ours. Contacted ISP, convinced them to change it, and outgoing email works like a champ now. Recipients who haven't been receiving our e-mails for the last two weeks are getting them today, and I made the change late yesterday afternoon.

    I have no idea where the spam filter that's potentially blocking that IP could even be (since none of the recipients had any form of spam filtering enabled and even added us to "allowed sender" lists in programs like Outlook to be sure). I guess it's at some major level, like an ISP somewhere. I can't imagine why anyone would set up a spam filter that way. But yeah...getting that IP address changed apparently solved the problem.

    Thought I'd throw this out there in case someone else runs across the same issue. It's one of the last things I ever would've thought to check, considering that in normal circumstances, that shouldn't matter when using web-hosted email through a POP account with something like Outlook.
     

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