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550 5.7.1 Unable to relay


550 5.7.1 Unable to relay TerryB
7/4/2007 11:08:01 AM
iis smtp nntp: All of a sudden I can no longer send mail that goes to an address outside my
domain. The mail server in question has been running for about 2 years now
with no problems but a few days ago I started getting this error when sending
or replying to email "550 5.7.1 Unable to relay for"

I can receive mail just fine

As long as I am sending mail within the same domain it goes thru. I have mde
no changes to the mail server and have only added a subdomain in the website

Any ides on where to look for the problem.

BTW I use Outlook 2007 for sending and recieving mail. I have anonymous
access ticked, allow only the list below ticked and allow anyone who
Re: 550 5.7.1 Unable to relay Sanford Whiteman
7/4/2007 2:37:52 PM
[quoted text, click to view]

[1] Ensure that relay-by-IP works, just for testing.

[2] Turn on connection logging in OL and make sure it's sending the right
credentials and whether it is failing at the AUTH step.

[3] Test with another mail client (OE is probably also installed, right?).

[4] I presume you don't _only_ have Anonymous checked in IIS SMTP. You
have to have one of the AUTH methods checked in order for the server to
receive SMTP AUTH from the client.

--Sandy
Re: 550 5.7.1 Unable to relay TerryB
7/5/2007 11:38:06 AM
For reference I have figured out the problem.

I had recently re-installed Office 2007 and rememberd that in Outlook there
are additional settings required than in Outlook 2003.

I needed to tick the "Require logon using Secure Password Authentication
(SPA) and then in "More Settings" tick "Log On using" as well as "Require
Secure Password Authentication (SPA)

I didn't have to do this in Outlook 2003, but for some reason did in Outlook
2007

At any rate all is well now. Thanks much for your assistance

[quoted text, click to view]
Re: 550 5.7.1 Unable to relay Sanford Whiteman
7/6/2007 12:11:19 AM
[quoted text, click to view]

Geez, that's not "making no changes" when you're dealing with a
client-side problem. :)

[quoted text, click to view]

FTR, the first 'Require SPA' (on the main account setup dialog) would
only be applied if you are using the same creds for POP3 and SMTP.
Once you enter separate creds for SMTP, the 'Require SPA' on the SMTP
Advanced tab becomes the active SPA-related setting for SMTP.

That constant aside, 2003 and 2007 differ subtly -- but in some cases
fatally -- in when and if they support SPA/Integrated Windows Auth,
whether or not it is checked as required. If anything, I have seen
2007 be *more* forgiving than 2003 of inaccurate setups... for
example, in failing "up" to SPA if basic isn't supported by the
server, even if 'Require SPA' is not checked. However, YMMV based on
the NTLM trust between your desktop and the SMTP server, possibly
making (as you've observed) 2007 more demanding of attention.

I haven't come to a conclusion yet as to whether 2007's SPA behaviors
are more buggy or more fix-y vs. 2003: too many use cases, and too
much vagueness as to what SPA is "supposed" to be.

[FWIW, I'm not a big fan of SPA. It's not about its proprietary
nature. It's that if you're worried about your credentials being
snooped on the wire, you should be equally worried about your _message
content_ being snooped on the wire, and standards already exist
(SMTPS, STARTTLS) to protect that other important stage of the SMTP
conversation as well as the authentication stage. Why mess around with
spotty support when you can have the whole convo encrypted? Anyway,
just a li'l rant there. And yes, I understand that if every message
you send is PGP-encrypted, that offers guaranteed end-to-end
protection against snooping, but even single-ended SSL has to be a
better step in that direction than SPA, and is easy for users to
adopt.]

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