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Hotmail problems
I didn't know where else to post this

 5:18 am on Jan 5, 2009 (gmt 0)

I have an application that regularly sends me status updates. whenever certain critical events are triggered in the app, I receive an email full of relevant info so I can go check it out.

Well, this worked fine until a few weeks ago. During my peak season (xmas) I was getting quite a lot of these messages - not *insane* quantities, but at peak times, in the realm of 30-40 per hour. Then suddenly... they stopped.

I tested it out, and it seems Live Hotmail has started filtering those messages. They get sent, but they don't arrive. Microsoft thinks I'm a spammer because I was sending myself lots of email! They don't even make it into my "Junk" folder!

I have added the sender's address (it's like, my_app@my_app_name.com) to my whitelist, but it's made no difference. They still do not arrive.

I changed the "from" address in my app. added that to my "allowed sender" list too. Still no luck.

Does anyone know how I can fix this?



 12:21 pm on Jan 5, 2009 (gmt 0)

Just a thought, but did you check the RBLs for your mail server IP?


 2:17 pm on Jan 5, 2009 (gmt 0)

thanks coop, but how do I do that?


 4:21 pm on Jan 5, 2009 (gmt 0)

spamhaus is one of the more popular, but there are a few you may want to review. Here is an MS doc that explains a little how it is done ...


 4:35 pm on Jan 5, 2009 (gmt 0)

I would just send the notifications to a non-Hotmail address. In fact, I would exclude any free e-mail service (Hotmail, Yahoo, Gmail, etc.)- repeatedly sending numerous messages to the same address sounds like it would trip most SPAM filters.


 7:42 pm on Jan 5, 2009 (gmt 0)

LifeInAsia, I think you're right, I'll eventually have to use a different recipient address. That makes me sad because Live/Hotmail is so portable and it provides instant alerts via MSN Live Messenger when a new one arrives. And setting up webmail on my own server is such a drag (roundcube, squirrel, horde, or something similar)

I checked some of the more popular blacklists, and my IP isn't on any of them. Hotmail must be keeping their own spammerific list with me on it. Sheesh!


 8:05 pm on Jan 5, 2009 (gmt 0)

Blacklists were only the first suggestion, somewhat of a quick peek type suggestion to see if there was anything blatantly obvious. You should log into your server which is sending the messages and initiate a TELNET session.

Check your send mail queue to see if the messages are loading up (not being delivered). If the accepting mail server (hotmail) didn't issue your sending mail server a failure notice they should be in the queue for a period of time, typically about seven days ... or perhaps your mail server is blocked. Hotmail may be initiating a connection closure as soon as the connection is made. This emulated behavior is usually indicative that the mail server is busy and you should retry. So basically, their mail server is blocking your mail server because it doesn't meet it's criteria for connecting. All mail servers should identify themselves with a valid hostname with a forward address. The forward dns address must also match the reverse address. Make sure you have your PTR set up correctly.

Here is what an example failure may look like (substitute localhost IP here with hotmail server IP that you are attempting to connect) ...

# telnet 25 
Connected to Escape character is '^]'.
Connection closed by foreign host


 8:33 pm on Jan 7, 2009 (gmt 0)

FYI -- you don't seem to be alone in this issue. Ever since they started their "LIVE" rollover there have been complaints. Also, currently on the "new" hotmail support site you can read this banner right at the top ...

Outage: Windows Live Hotmail is currently experiencing issues with inbound mail delivery. Customers may see a delay in receiving email into their inbox.


Seems you are not the only one experiencing difficulties with their growing pains.


 2:25 pm on Jan 8, 2009 (gmt 0)

Customers may see a delay

what I'm experiencing isn't a delay, it's an outright ban. It's now been about 4 weeks since the alerts stopped arriving and I haven't seen one since. I can query the database and see records of events that should have triggered them (for example, I should have received 24 of them yesterday)

Besides, these alerts are very time-sensitive. They arrive when something needs to be done immediately -- that's the whole point of setting up email alerts. If they arrive 3 hours late, they're already useless to me.

My forensic investigation shows that around the time the fuse blew I was sending myself on average 210 per day, more or less. So if there's a frequency threshold, it's probably near 200.

Live mail has a very aggressive spam filter, and I like that. I get almost NO spam in my hotmail, and it's an address I use a lot for online correspondence. However I think it's presumptuous of Microsoft to filter mail from addresses I've explicitly whitelisted.


 4:23 pm on Jan 20, 2009 (gmt 0)

That's nothing, they arbitrarily deleted all stored emails from my account as part of the rollover.

The impression that I have is that Hotmail has two levels of filtering and messages only get offered to the recipient's own filters and white list if they pass the first level.


 6:28 pm on Jan 20, 2009 (gmt 0)

@piatkow, I have the same suspicion. And that first filter is tight as a [simile omitted]


 3:51 am on Feb 9, 2009 (gmt 0)

... and suddenly the gates opened and the mail started flowing again. I'm off the blacklist!


 6:10 am on Feb 9, 2009 (gmt 0)

Anything you might have done to cause this change?


 6:57 pm on Feb 9, 2009 (gmt 0)

nothing noteworthy... at least not lately...

the flow of email slowed down substantially since the xmas season ended, and I disabled most of the alerts in early January anyways. I left one hooked up which tells me when someone closes an account. Those started to arrive again on Feb 8

I don't know what kind of spam filter they use so I'm hesitant to guess anything at this point. Perhaps their spam filter "unlearned" my IP, or let it out on parole for good behaviour. Mysterious behaviour of the ghost in the machine.

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