I've just read through all of the threads pertaining to email alerts not working to external addresses, but I think I have have a slight twist on that problem. In all of those other threads nothing was getting through, but in my case a little bit is. What we have is two AD trees, one for internal users and one for all external partners. Users on the internal tree are able to set up alerts and they work just fine. Users on the external tree set up an alert, they get the notification that an alert has been set up, and then they never receive another thing. I've tested this again and again. I have a site with a library set up. I add my own internal ID to an alert and get the notification right away. I then add an alert for a dummy ID in the EXT tree that has my Gmail address on it, and immediately get a notification about the new alert. I then go add a document to that library and a few minutes later my internal email address get's the alert, but I never get one at my Gmail account. If I go in and remove my external dummy id and re-add it I get another notification of a new alert, but still no alerts come through. I've tried this on several sites and libraries, but I only have one externally facing web app so that's all I could try it on for those. All emails from any system that are going to another system, (i.e. sharepoint to exchange, unix to exchange, exchange to unix, anything to external, etc), all get routed through a central virus scanner. In addition to virus scanning it takes care of routing emails to the proper destination. Unfortunately the one thing it doesn't do is any logging, which is TREMENDOUSLY annoying in cases like this. I'm 99% sure that it isn't affecting this since the Exchange emails work, and I can send emails from unix apps and exchange out to gmail, so I don't think it's a routing issue. And if it didn't like the content in the gmail email, why would it let it through to exchange? I don't know what happens differently when an alert is actually triggered than when an alert is set up that would cause the external addresses not to work. Any suggestions would be greatly appreciated. Thanks. Ted

Try checking the relay rule in the SMTP server. Probably, your SharePoint Server is only allowed to send messages to the local domain. Cheers.Miguel Ballesteros

I thought that at first as well... but notice in the description of the problem - the user does get the initial email notifying them of the alert being set.I'm lurking on this thread as I am very curious what the answer is!Jeff DeVerter, MCSERackspaceblog:http://www.social-point.comtwitter: http://www.twitter.com/jdeverter

Please take a look at the troubleshooting steps provided by http://blogs.technet.com/steve_chen/archive/2009/11/20/alerts-in-sharepoint-troubleshooting-moss-wss.aspx . I would very appreciate if you share with us the results!

I went through the link to Steve's blog, and verified that all of the IP addresses for every one of my sharepoint boxes (including the SQL box), are listed in the authorized relay section. I then manually connected to each of the 4 WFE's and configured an alert. Once again internally I correctly got all 4 of them, but externally I only got the initial notification, but none of the followup alerts. I will have to assimilate the stuff at the bottom of Steve's blog a bit before I try it. I'm not a big one for SQL queries, so I am a little hesitant to do that. I'll take a look at that some more and try the queries after hours. Other than that I am really leaning towards it's some wierd problem between sharepoint and AD. Everything comes down to the fact that the email routing works fine for every alert to an internal address, but on every external address the only email that goes through is the initial setup email. If it was one of the WFE's not in the relay list, then occasionally, 1/2 or 1/4 of the time, the initial alert would fail, or occasionally the regular alert emails externally would work, assuming that they got generated from the WFE either on or off the relay list. I'm pretty positive it's not an email issue now. I'm not sure how it works between the two AD trees for generating the alerts. Why if a user is in one tree, with an internal email address, it works. But if the user is in the other tree, with an external email address, it doesn't? And why would the external user get just the initial notification of the new alert, but nothing else? This one is frustrating. Ted

I am seeing the exact same symptoms here. Only the initial notice that an alert was created reaches the external email address. The actual alerts never do. Additionally, when I look at the Message tracking logs on the Exchange server, I only see those initial notices... The alerts don't show up on Exchange! Has anyone made any progress in tracking this problem down?