SMTP error 454, wont send outbound but will recieve ok

Greg Merideth · Joined: 06 Aug 2007 Posts: 4

Just installed Exchange 2k over our 5.5 installation (didn't do an
upgrade, did a fresh install and routed users into the new machine). I
setup the default's pretty much on everything but now, when I attempt to
send email out of the office using either outlook, outlook express or
mozilla on standard smtp (for the consultants that are accessing
pop3/smtp remotely) I keep getting back:

"Mail Server returned: . Plese verify your email address is correct in
Mail Prefernces and try again".

The win2k event log shows that "user at (ip address) did not attempt to
authenticate before sending" - yet I've configured all outlooks, oe's
and mozillas to authenticate. The SMTP service is set to use "plain
text" passwords and TLS is turned off. Anon and integrated
authentication is turned off and a fresh reboot was done just to be safe.

If I telnet to the mail server and do a helo and mail to: command the
win2k machine returns "454" as its response with nothing else after it.
A search on google claims that "454" has something to do with Kerberos
authentication but I have integrated authentication turned off.

This is what the log file shows when I attempt to send mail. I changed
the IP's and domain names of the server but you can see the "454" after
the username on the mail from line. But the EHLO was 250'ed as ok.

2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
MAIL - +FROM: 454 0 41 43 15 SMTP - - - -

Exchange is on sp3 and windows itself is fully patched up. Any ideas?

Archived from group: microsoft>public>exchange2000>connectivity

Denis McDowell, MCSE [MSF · Joined: 05 Aug 2007 Posts: 2

Are you using Outlook in MAPI (Corporate\Workgroup Mode)?

First, in the properties of your SMTP Virtual Server, click the Access tab
and the Relay... button. Make sure you've selected "Allow all computers
which successfully authenticate...". This will allow authenticated computers
to send mail.

Second, where did you disable Anonymous access and Windows Integrated
(Access tab > Authentication or Delivery Tab > Outbound Security ?). You be
careful when disabling authentication methods (especially Anonymous), since
external servers connect anonymously.

Denis McDowell [MSFT]

This posting is provided "AS IS" with no warranties, and confers no rights.

"Greg Merideth" wrote in message@comcast.com...
> Just installed Exchange 2k over our 5.5 installation (didn't do an
> upgrade, did a fresh install and routed users into the new machine). I
> setup the default's pretty much on everything but now, when I attempt to
> send email out of the office using either outlook, outlook express or
> mozilla on standard smtp (for the consultants that are accessing
> pop3/smtp remotely) I keep getting back:
>
> "Mail Server returned: . Plese verify your email address is correct in
> Mail Prefernces and try again".
>
> The win2k event log shows that "user at (ip address) did not attempt to
> authenticate before sending" - yet I've configured all outlooks, oe's
> and mozillas to authenticate. The SMTP service is set to use "plain
> text" passwords and TLS is turned off. Anon and integrated
> authentication is turned off and a fresh reboot was done just to be safe.
>
> If I telnet to the mail server and do a helo and mail to: command the
> win2k machine returns "454" as its response with nothing else after it.
> A search on google claims that "454" has something to do with Kerberos
> authentication but I have integrated authentication turned off.
>
> This is what the log file shows when I attempt to send mail. I changed
> the IP's and domain names of the server but you can see the "454" after
> the username on the mail from line. But the EHLO was 250'ed as ok.
>
> 2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
> EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
> 2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
> MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
>
> Exchange is on sp3 and windows itself is fully patched up. Any ideas?
>

Greg Merideth · Joined: 06 Aug 2007 Posts: 4

The Exchange box is at the corporate office behind the firewall and I'm
connecting from a remote location using mozilla to route smtp mail only.
I've even fired up outlook and used the authentication from within
outlook thinking it was a mozilla problem but, neither work.

I disabled anon and integrated access from within
servers->(server)->protocols->smtp+properties. Under the relay tab I
have clicked "allow relaying if authenticated" on.

As a hoot I turned on allow anon and now when we attempt to relay mail
through the server I am getting "mailbox unavailable" on every email I
attempt to send.

When I attempt to send mail to people in the address book it works but
when i try to relay mail outside of our domain I get the "mailbox
unavailable" message.

Denis McDowell, MCSE [MSFT] wrote:

> Are you using Outlook in MAPI (Corporate\Workgroup Mode)?
>
> First, in the properties of your SMTP Virtual Server, click the Access tab
> and the Relay... button. Make sure you've selected "Allow all computers
> which successfully authenticate...". This will allow authenticated computers
> to send mail.
>
> Second, where did you disable Anonymous access and Windows Integrated
> (Access tab > Authentication or Delivery Tab > Outbound Security ?). You be
> careful when disabling authentication methods (especially Anonymous), since
> external servers connect anonymously.
>
> Denis McDowell [MSFT]
>
> This posting is provided "AS IS" with no warranties, and confers no rights.
>
> "Greg Merideth" wrote in message
> @comcast.com...
>
>>Just installed Exchange 2k over our 5.5 installation (didn't do an
>>upgrade, did a fresh install and routed users into the new machine). I
>>setup the default's pretty much on everything but now, when I attempt to
>>send email out of the office using either outlook, outlook express or
>>mozilla on standard smtp (for the consultants that are accessing
>>pop3/smtp remotely) I keep getting back:
>>
>>"Mail Server returned: . Plese verify your email address is correct in
>>Mail Prefernces and try again".
>>
>>The win2k event log shows that "user at (ip address) did not attempt to
>>authenticate before sending" - yet I've configured all outlooks, oe's
>>and mozillas to authenticate. The SMTP service is set to use "plain
>>text" passwords and TLS is turned off. Anon and integrated
>>authentication is turned off and a fresh reboot was done just to be safe.
>>
>>If I telnet to the mail server and do a helo and mail to: command the
>>win2k machine returns "454" as its response with nothing else after it.
>> A search on google claims that "454" has something to do with Kerberos
>>authentication but I have integrated authentication turned off.
>>
>>This is what the log file shows when I attempt to send mail. I changed
>>the IP's and domain names of the server but you can see the "454" after
>>the username on the mail from line. But the EHLO was 250'ed as ok.
>>
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
>>
>>Exchange is on sp3 and windows itself is fully patched up. Any ideas?
>>
>
>
>

Greg Merideth · Joined: 06 Aug 2007 Posts: 4

The Exchange box is at the corporate office behind the firewall and I'm
connecting from a remote location using mozilla to route smtp mail only.
I've even fired up outlook and used the authentication from within
outlook thinking it was a mozilla problem but, neither work.

I disabled anon and integrated access from within
servers->(server)->protocols->smtp+properties. Under the relay tab I
have clicked "allow relaying if authenticated" on.

As a hoot I turned on allow anon and now when we attempt to relay mail
through the server I am getting "mailbox unavailable" on every email I
attempt to send.

When I attempt to send mail to people in the address book it works but
when i try to relay mail outside of our domain I get the "mailbox
unavailable" message.

Denis McDowell, MCSE [MSFT] wrote:

> Are you using Outlook in MAPI (Corporate\Workgroup Mode)?
>
> First, in the properties of your SMTP Virtual Server, click the Access tab
> and the Relay... button. Make sure you've selected "Allow all computers
> which successfully authenticate...". This will allow authenticated computers
> to send mail.
>
> Second, where did you disable Anonymous access and Windows Integrated
> (Access tab > Authentication or Delivery Tab > Outbound Security ?). You be
> careful when disabling authentication methods (especially Anonymous), since
> external servers connect anonymously.
>
> Denis McDowell [MSFT]
>
> This posting is provided "AS IS" with no warranties, and confers no rights.
>
> "Greg Merideth" wrote in message
> @comcast.com...
>
>>Just installed Exchange 2k over our 5.5 installation (didn't do an
>>upgrade, did a fresh install and routed users into the new machine). I
>>setup the default's pretty much on everything but now, when I attempt to
>>send email out of the office using either outlook, outlook express or
>>mozilla on standard smtp (for the consultants that are accessing
>>pop3/smtp remotely) I keep getting back:
>>
>>"Mail Server returned: . Plese verify your email address is correct in
>>Mail Prefernces and try again".
>>
>>The win2k event log shows that "user at (ip address) did not attempt to
>>authenticate before sending" - yet I've configured all outlooks, oe's
>>and mozillas to authenticate. The SMTP service is set to use "plain
>>text" passwords and TLS is turned off. Anon and integrated
>>authentication is turned off and a fresh reboot was done just to be safe.
>>
>>If I telnet to the mail server and do a helo and mail to: command the
>>win2k machine returns "454" as its response with nothing else after it.
>> A search on google claims that "454" has something to do with Kerberos
>>authentication but I have integrated authentication turned off.
>>
>>This is what the log file shows when I attempt to send mail. I changed
>>the IP's and domain names of the server but you can see the "454" after
>>the username on the mail from line. But the EHLO was 250'ed as ok.
>>
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
>>
>>Exchange is on sp3 and windows itself is fully patched up. Any ideas?
>>
>
>
>

Greg Merideth · Joined: 06 Aug 2007 Posts: 1

The Exchange box is at the corporate office behind the firewall and I'm
connecting from a remote location using mozilla to route smtp mail only.
I've even fired up outlook and used the authentication from within
outlook thinking it was a mozilla problem but, neither work.

I disabled anon and integrated access from within
servers->(server)->protocols->smtp+properties. Under the relay tab I
have clicked "allow relaying if authenticated" on.

As a hoot I turned on allow anon and now when we attempt to relay mail
through the server I am getting "mailbox unavailable" on every email I
attempt to send.

When I attempt to send mail to people in the address book it works but
when i try to relay mail outside of our domain I get the "mailbox
unavailable" message.

Denis McDowell, MCSE [MSFT] wrote:

> Are you using Outlook in MAPI (Corporate\Workgroup Mode)?
>
> First, in the properties of your SMTP Virtual Server, click the Access tab
> and the Relay... button. Make sure you've selected "Allow all computers
> which successfully authenticate...". This will allow authenticated computers
> to send mail.
>
> Second, where did you disable Anonymous access and Windows Integrated
> (Access tab > Authentication or Delivery Tab > Outbound Security ?). You be
> careful when disabling authentication methods (especially Anonymous), since
> external servers connect anonymously.
>
> Denis McDowell [MSFT]
>
> This posting is provided "AS IS" with no warranties, and confers no rights.
>
> "Greg Merideth" wrote in message
> @comcast.com...
>
>>Just installed Exchange 2k over our 5.5 installation (didn't do an
>>upgrade, did a fresh install and routed users into the new machine). I
>>setup the default's pretty much on everything but now, when I attempt to
>>send email out of the office using either outlook, outlook express or
>>mozilla on standard smtp (for the consultants that are accessing
>>pop3/smtp remotely) I keep getting back:
>>
>>"Mail Server returned: . Plese verify your email address is correct in
>>Mail Prefernces and try again".
>>
>>The win2k event log shows that "user at (ip address) did not attempt to
>>authenticate before sending" - yet I've configured all outlooks, oe's
>>and mozillas to authenticate. The SMTP service is set to use "plain
>>text" passwords and TLS is turned off. Anon and integrated
>>authentication is turned off and a fresh reboot was done just to be safe.
>>
>>If I telnet to the mail server and do a helo and mail to: command the
>>win2k machine returns "454" as its response with nothing else after it.
>> A search on google claims that "454" has something to do with Kerberos
>>authentication but I have integrated authentication turned off.
>>
>>This is what the log file shows when I attempt to send mail. I changed
>>the IP's and domain names of the server but you can see the "454" after
>>the username on the mail from line. But the EHLO was 250'ed as ok.
>>
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
>>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
>>MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
>>
>>Exchange is on sp3 and windows itself is fully patched up. Any ideas?
>>
>
>
>

--

Denis McDowell, MCSE [MSF · Joined: 05 Aug 2007 Posts: 2

Disabling Anonymous Access will break inbound mail, as remote servers need
to connect anonymously to send mail to you. These settings have nothing to
do with relay.

--
--
Denis McDowell [MSFT]

This posting is provided "AS IS" with no warranties, and confers no rights.

"Greg Merideth" wrote in message@uclabs.com...
> The Exchange box is at the corporate office behind the firewall and I'm
> connecting from a remote location using mozilla to route smtp mail only.
> I've even fired up outlook and used the authentication from within
> outlook thinking it was a mozilla problem but, neither work.
>
> I disabled anon and integrated access from within
> servers->(server)->protocols->smtp+properties. Under the relay tab I
> have clicked "allow relaying if authenticated" on.
>
> As a hoot I turned on allow anon and now when we attempt to relay mail
> through the server I am getting "mailbox unavailable" on every email I
> attempt to send.
>
> When I attempt to send mail to people in the address book it works but
> when i try to relay mail outside of our domain I get the "mailbox
> unavailable" message.
>
>
> Denis McDowell, MCSE [MSFT] wrote:
>
> > Are you using Outlook in MAPI (Corporate\Workgroup Mode)?
> >
> > First, in the properties of your SMTP Virtual Server, click the Access
tab
> > and the Relay... button. Make sure you've selected "Allow all computers
> > which successfully authenticate...". This will allow authenticated
computers
> > to send mail.
> >
> > Second, where did you disable Anonymous access and Windows Integrated
> > (Access tab > Authentication or Delivery Tab > Outbound Security ?). You
be
> > careful when disabling authentication methods (especially Anonymous),
since
> > external servers connect anonymously.
> >
> > Denis McDowell [MSFT]
> >
> > This posting is provided "AS IS" with no warranties, and confers no
rights.
> >
> > "Greg Merideth" wrote in message
> > @comcast.com...
> >
> >>Just installed Exchange 2k over our 5.5 installation (didn't do an
> >>upgrade, did a fresh install and routed users into the new machine). I
> >>setup the default's pretty much on everything but now, when I attempt to
> >>send email out of the office using either outlook, outlook express or
> >>mozilla on standard smtp (for the consultants that are accessing
> >>pop3/smtp remotely) I keep getting back:
> >>
> >>"Mail Server returned: . Plese verify your email address is correct in
> >>Mail Prefernces and try again".
> >>
> >>The win2k event log shows that "user at (ip address) did not attempt to
> >>authenticate before sending" - yet I've configured all outlooks, oe's
> >>and mozillas to authenticate. The SMTP service is set to use "plain
> >>text" passwords and TLS is turned off. Anon and integrated
> >>authentication is turned off and a fresh reboot was done just to be
safe.
> >>
> >>If I telnet to the mail server and do a helo and mail to: command the
> >>win2k machine returns "454" as its response with nothing else after it.
> >> A search on google claims that "454" has something to do with Kerberos
> >>authentication but I have integrated authentication turned off.
> >>
> >>This is what the log file shows when I attempt to send mail. I changed
> >>the IP's and domain names of the server but you can see the "454" after
> >>the username on the mail from line. But the EHLO was 250'ed as ok.
> >>
> >>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
> >>EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
> >>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1 DCROOT 1.2.3.4 0
> >>MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
> >>
> >>Exchange is on sp3 and windows itself is fully patched up. Any ideas?
> >>
> >
> >
> >
>
> --
>

Greg Merideth · Joined: 06 Aug 2007 Posts: 4

Found the problem. The firewall was stripping off the AUTH commands so
exchange never got to see our attempts to provide smtp authentication.

Its just annoying that all SMTP returned was "454"

Denis McDowell, MCSE [MSFT] wrote:
> Disabling Anonymous Access will break inbound mail, as remote servers need
> to connect anonymously to send mail to you. These settings have nothing to
> do with relay.
>

d · Joined: 06 Aug 2007 Posts: 1

You probably need to set on the client "my server
requires authentication" on the outgoing mail server tab

>-----Original Message-----
>Just installed Exchange 2k over our 5.5 installation
(didn't do an
>upgrade, did a fresh install and routed users into the
new machine). I
>setup the default's pretty much on everything but now,
when I attempt to
>send email out of the office using either outlook,
outlook express or
>mozilla on standard smtp (for the consultants that are
accessing
>pop3/smtp remotely) I keep getting back:
>
>"Mail Server returned: . Plese verify your email address
is correct in
>Mail Prefernces and try again".
>
>The win2k event log shows that "user at (ip address) did
not attempt to
>authenticate before sending" - yet I've configured all
outlooks, oe's
>and mozillas to authenticate. The SMTP service is set
to use "plain
>text" passwords and TLS is turned off. Anon and
integrated
>authentication is turned off and a fresh reboot was done
just to be safe.
>
>If I telnet to the mail server and do a helo and mail
to: command the
>win2k machine returns "454" as its response with nothing
else after it.
> A search on google claims that "454" has something to
do with Kerberos
>authentication but I have integrated authentication
turned off.
>
>This is what the log file shows when I attempt to send
mail. I changed
>the IP's and domain names of the server but you can see
the "454" after
>the username on the mail from line. But the EHLO was
250'ed as ok.
>
>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1
DCROOT 1.2.3.4 0
>EHLO - +xxxx.xxx 250 0 316 26 0 SMTP - - - -
>2003-10-01 15:51:59 68.36.190.157 xxxx.xxx SMTPSVC1
DCROOT 1.2.3.4 0
>MAIL - +FROM: 454 0 41 43 15 SMTP - - - -
>
>Exchange is on sp3 and windows itself is fully patched
up. Any ideas?
>
>.
>

split route for outbound smtp email I have a requirement to assign diferent routes for outbound email depending on the source smtp domain. Basically we have an internal mail relay smart host which is currently relaying all email to the internet, and I now need to forward all email for one o

Exchange 2000 SMTP outbound question Dear sir, Is that any method for me to set specify destination use "smart host". Another, use direct connect? Because I have a "specify destination" seems not accept my Exchange connection. -david

How to for DisasterR: have two sites recieve mail for same d Here is the situation I am in. At the main locations, I have two sites via T-1. Mail comes in through site A and is sent over the bridgeheads to Site B. I have another MX record in place if Site A is unreachable. It points to Site B ISP. T

Pop Before Send SMTP My ISP requires me to Pop before SMTP to retrieve email. I managed to do this on my old SBS 4.5 server, but can't seem to get the right settings in SBS 2003. Anybody got any ideas? Thanks Neil

unable to send email on other servers via virtual smtp I have several servers on my internal network that run IIS, specifically, SMTP virtual server. For example, on my web server, I will have a form that will be submitted and through an .asp file, the email is routed through the SMTP virtual server on the w