Email Troubles - Random and Not Fun

R

rosco

Gawd
Joined
Jun 22, 2000
Messages
722
We have a SBS 2008 server. In the past few weeks, users have been complaining that some receipients of their emails are not receiving them sometimes. It doesn't seem to consistently be one recipient. Sometimes one recipient at a company will receive the email while others at that company will not receive email from someone else here.

Here is what we have for incoming:
We use Google apps. This is where our MX records point
The email is then downloaded from the Google Apps mailboxes via pop3 connector to the SBS 2008 server.

For outgoing:
We relay email through our ISP's mail server.

Our firewall is an Untangle free box doing some basic virus/web filtering.

What do you think the issue could be? How do I troubleshoot this when emails just drop into a black hole? No returned messages etc.
 
ISP mail servers getting on blacklists maybe? I've run into that before.
 
dave99 said:
ISP mail servers getting on blacklists maybe? I've run into that before.
Click to expand...

I've seen this too, very annoying when it's just a single server in a cluster, and your outgoing emails get routed through them randomly. So 99% of the emails sent are fine, but when you get that special case of outgoing server listed on a blacklist and a receiver dropping blacklisted emails without logging, it's almost impossible to track down the cause.

Worst is that there's virtually nothing you can do, since they're dropped silently, so you don't even know about it.
 
I agree that your ISP's originating address for inbound email is not scoring very high sometimes. Doesn't Google-apps give you an SMTP server you can route sent emails through?
 
Using your ISP's email server to send mail is suicidal.

You need SPF and DKIM set, and you need either your own SMTP box, or to use google.
 
clsGrinder said:
I agree that your ISP's originating address for inbound email is not scoring very high sometimes. Doesn't Google-apps give you an SMTP server you can route sent emails through?
Click to expand...

Yes you can, howerver each user needs to be configured this way. If you try to have your server route all the mail, you'll run into problems. The reason being that google requires login for SMTP and the user you use to login becomes the sender - changed from the original sender.

The real fix is to train the users to use the Gmail interface and move out of outlook completely. When we switched we didn't give them the option. Most users get the hang of it quickly (because many of our users use webmail of some kind at home anyway), but a few (honestly the older ones) had a hard time moving over struggling for a few weeks and eventually getting a firm grasp after a few months.

The transition isn't simple or easy, but in the end it was worth it and we ended up winning over the hearts of 'most' of our users.
 
woof.

we use AppRiver and have configured them as our Smart Host.

i love it!

 
Well, I was going to see if I could figure out a way to use Google apps as our outbound smtp relay. But, it sounds like that won't work because the sender info will change.

I wanted to use a smtp relay to have one less thing to worry about. However, it now has become something I have to worry about.

So you guys are thinking that the ISP's mail servers might have one that's flagged while the others aren't? And that is why some messages to a customer go through while others don't? That makes sense I suppose. I'm working with the ISP's support now but they are SLOW.

So, you guys would either recommend I use our SBS server as the SMTP server without a relay or using a service like AppRiver?

How much does something like AppRiver cost?

The users deal heavily with attachments so they wouldn't like the extra time it takes to attach documents to emails/download attachments. They like once it shows in Outlook they are good to go.
 
rosco said:
Well, I was going to see if I could figure out a way to use Google apps as our outbound smtp relay. But, it sounds like that won't work because the sender info will change.

I wanted to use a smtp relay to have one less thing to worry about. However, it now has become something I have to worry about.

So you guys are thinking that the ISP's mail servers might have one that's flagged while the others aren't? And that is why some messages to a customer go through while others don't? That makes sense I suppose. I'm working with the ISP's support now but they are SLOW.

So, you guys would either recommend I use our SBS server as the SMTP server without a relay or using a service like AppRiver?

How much does something like AppRiver cost?

The users deal heavily with attachments so they wouldn't like the extra time it takes to attach documents to emails/download attachments. They like once it shows in Outlook they are good to go.
Click to expand...

https://support.appriver.com/KB/a73/smart-hosting.aspx
http://www.appriver.com/free-trial.aspx

Smart Host is completely transparent. You set it on your Exchange server and the user doesn't know what happens once they hit Send in Outlook.

 
Turns out the issue was the smtp spam filter on my Untangle box. I didn't realize it was scanning outbound smtp traffic. So, when I setup Appriver smarthost and saw it was leaving the SBS server but never made it to Appriver's smarthost, I looked harder at the Untangle box.

So, Appriver's reporting definitely helped me out with seeing where the issue was.

Thanks.
 
Why aren't you sending mail out through a smart host or receiving mail directly in?
 
I was just using the ISP's mail server's for my smarthost and we are using Google Apps in the middle so that in case we ever have internet/SBS trouble, email will still be delivered while we get things back up and running.

It had worked really well so far. I think I'm going to stick with using Appriver for a smarthost though.
 
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