Hi Colin,

On 2/18/2016 7:24 AM, Colin Jack wrote:

> Generating server: EXCHANGE.mainline.local
> Receiving server: solarspeed.net (208.77.221.199)
>
> mstau...@solarspeed.net
> Remote Server at solarspeed.net (208.77.221.199) returned '400 4.4.7 Message 
> delayed'
> 18/02/2016 13:09:44 - Remote Server at solarspeed.net (208.77.221.199) 
> returned '441 4.4.1 Error encountered while communicating with primary target 
> IP address: "Failed to connect. Winsock error code: 10060, Win32 error code: 
> 10060." Attempted failover to alternate host, but that did not succeed. 
> Either there are no alternate hosts, or delivery failed to all alternate 
> hosts. The last endpoint attempted was 208.77.221.199:25'


Well there are many things that it could be, and I might suggest 
starting with some diagnostics on your system.

I see that the Exchange server you're using doesn't report a proper 
hostname.   Although that may be simply cosmetic, it's something that as 
a sysadmin would drive me up a wall.   So... that could be fixed.

There's a DNS oddity in that message in that your Exchange server says 
"Remote Server at solarspeed.net (208.77.221.199)"... but the MX record 
is mail.solarspeed.net.   Both A records point to the same destination 
IP, so that's not the cause of your issue, but again, something odd that 
may warrant a look.

Finally, the 400 error is indicating a DELAY, most likely due to 
greylisting on the solarspeed.net server.  Why your Exchange server 
would treat that as an outright rejection is a cause for investigation 
on the Exchange system.   You may find that your queue timeout is too 
short.  Set for 5-minute retries and at least a 1-hour timeout (though 
I'd recommend longer) to accommodate proper greylisting - not to mention 
other legitimate delivery delays.

Why the 400 4.4.7 turns into 441 4.4.1 is a mystery to me.

Based simply on the information shared here, and understanding that I am 
not by any stretch an Exchange admin (I'm far too handsome for that - 
LOL!) I would recommend taking a good look at that Exchange server. 
There's enough to suggest that something(s) may be a little off.

I hope that helps point in a direction.

-- 
Chris Gebhardt
VIRTBIZ Internet Services
Access, Web Hosting, Colocation, Dedicated
www.virtbiz.com | toll-free (866) 4 VIRTBIZ
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