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Cannot connect to SMTP eror

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Unread 02-05-2008, 02:16 AM   #11
VanguardLH
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Posts: n/a
Re: Cannot connect to SMTP eror

"Dale" wrote in
<news:FAF599CC-23E4-4156-B315-6A60A712DE22@microsoft.com>:

> "VanguardLH" wrote:
>
>> "Dale" wrote:
>>
>>> "VanguardLH" wrote:
>>>
>>>> "Dale" wrote:
>>>>
>>>>> I have a client running Outlook 2007 with a POP3 account. The
>>>>> client had been working flawlessly until yesterday, now he cannot
>>>>> send email. He can send and receive fine using OL Express and
>>>>> OWA. Any ideas as to what night have happened and how I can fix
>>>>> it? I have uninstalled the profile and re installed it, same
>>>>> error
>>>>>
>>>>> reported error (0x80042109) : 'Outlook cannot connect to your
>>>>> outgoing (SMTP) e-mail server. If you continue to receive this
>>>>> message, contact your server administrator or Internet service
>>>>> provider (ISP).'
>>>>
>>>> Have the user try to telnet into the mail host:
>>>>
>>>> telnet <smtphost> <port>
>>>>
>>>> The point is not to establish a mail session but just to see if
>>>> the user can reach the host and do a connect only.
>>>
>>> I tried that, the client is unable to reach the host on port 25. I
>>> can't figure out what would be causing this as it worked Monday but
>>> not Tuesday. I disabled the Windows firewall and the email scan
>>> from the Symantec AV as well, still same result. The router
>>> firewall has always been up and it forwards ports 110 and 25. Any
>>> ideas?

>>
>> So does the user actually have a usable route to the mail host? Can
>> they run "tracert <smtphost>" and reach that host?

>
> Yes, traceroute and ping to the host, just no SMTP.


Then my next guess is the same at Orland's: make sure the correct port
number is being used. Port 25 is the standard one for SMTP but many
ISPs are moving to 587 or 995, and may now require SSL connects, in
order to thwart the mailer trojans that inject user hosts. I didn't
suggest it before because you said the user can connect okay using
Outlook Express but the presumption was that the user had the OE account
also configured to use the standard port 25 for SMTP.

You mentioned the user is using Outlook Web Access (OWA). Does that
mean this user is trying to connect to the company's mail service? If
so, does this user have to use a VPN to connect to the corporate network
so they can then get access to the company's SMTP mail host? I doubt
the company is going to let any tom, ****, and harry to connect to their
SMTP server and rely only on login credentials to secure their company's
internal e-mails. They may allow any of their employees to yank from
their POP mail host without using VPN but often they want a secure
channel when using their SMTP mail host. If VPN is required then maybe
this user isn't enabling it. The only reason that I've seen OWA used is
to allow employee access to the corporate mail service from the outside,
so presumably this user is also trying to connect to the corporate SMTP
mail host from the outside.
 
Unread 02-05-2008, 06:20 AM   #12
Dale
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

You are correct the user is connecting to the exchange server via POP3, SMTP
from ouside the network. It is not through VPN and it is only log on
credentials to allow this. The OE actually failed today in th esame manner,
cannot connect to the SMTP server even though it is the same server as the
POP3. Odd thing is that any other user is able to connect with no problems,
it is only this one. Possibly firewall issue but couldn't say for sure, if it
is it is not the local firewall.
Your thoughts?




"VanguardLH" wrote:

> "Dale" wrote in
> <news:FAF599CC-23E4-4156-B315-6A60A712DE22@microsoft.com>:
>
> > "VanguardLH" wrote:
> >
> >> "Dale" wrote:
> >>
> >>> "VanguardLH" wrote:
> >>>
> >>>> "Dale" wrote:
> >>>>
> >>>>> I have a client running Outlook 2007 with a POP3 account. The
> >>>>> client had been working flawlessly until yesterday, now he cannot
> >>>>> send email. He can send and receive fine using OL Express and
> >>>>> OWA. Any ideas as to what night have happened and how I can fix
> >>>>> it? I have uninstalled the profile and re installed it, same
> >>>>> error
> >>>>>
> >>>>> reported error (0x80042109) : 'Outlook cannot connect to your
> >>>>> outgoing (SMTP) e-mail server. If you continue to receive this
> >>>>> message, contact your server administrator or Internet service
> >>>>> provider (ISP).'
> >>>>
> >>>> Have the user try to telnet into the mail host:
> >>>>
> >>>> telnet <smtphost> <port>
> >>>>
> >>>> The point is not to establish a mail session but just to see if
> >>>> the user can reach the host and do a connect only.
> >>>
> >>> I tried that, the client is unable to reach the host on port 25. I
> >>> can't figure out what would be causing this as it worked Monday but
> >>> not Tuesday. I disabled the Windows firewall and the email scan
> >>> from the Symantec AV as well, still same result. The router
> >>> firewall has always been up and it forwards ports 110 and 25. Any
> >>> ideas?
> >>
> >> So does the user actually have a usable route to the mail host? Can
> >> they run "tracert <smtphost>" and reach that host?

> >
> > Yes, traceroute and ping to the host, just no SMTP.

>
> Then my next guess is the same at Orland's: make sure the correct port
> number is being used. Port 25 is the standard one for SMTP but many
> ISPs are moving to 587 or 995, and may now require SSL connects, in
> order to thwart the mailer trojans that inject user hosts. I didn't
> suggest it before because you said the user can connect okay using
> Outlook Express but the presumption was that the user had the OE account
> also configured to use the standard port 25 for SMTP.
>
> You mentioned the user is using Outlook Web Access (OWA). Does that
> mean this user is trying to connect to the company's mail service? If
> so, does this user have to use a VPN to connect to the corporate network
> so they can then get access to the company's SMTP mail host? I doubt
> the company is going to let any tom, ****, and harry to connect to their
> SMTP server and rely only on login credentials to secure their company's
> internal e-mails. They may allow any of their employees to yank from
> their POP mail host without using VPN but often they want a secure
> channel when using their SMTP mail host. If VPN is required then maybe
> this user isn't enabling it. The only reason that I've seen OWA used is
> to allow employee access to the corporate mail service from the outside,
> so presumably this user is also trying to connect to the corporate SMTP
> mail host from the outside.
>

 
Unread 04-05-2008, 06:16 AM   #13
VanguardLH
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

"Dale" wrote in
<news:1CB4287F-E16C-4D59-87E2-3AC9B5BFA0D0@microsoft.com>:

> You are correct the user is connecting to the exchange server via POP3, SMTP
> from ouside the network. It is not through VPN and it is only log on
> credentials to allow this. The OE actually failed today in th esame manner,
> cannot connect to the SMTP server even though it is the same server as the
> POP3. Odd thing is that any other user is able to connect with no problems,
> it is only this one. Possibly firewall issue but couldn't say for sure, if it
> is it is not the local firewall.
> Your thoughts?


Nope, I've ran out of ideas. Sorry.
 
Unread 04-05-2008, 10:16 AM   #14
N. Miller
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

On Thu, 1 May 2008 20:29:55 -0500, VanguardLH wrote:

> ...many ISPs are moving to 587 or 995...


For SMTP that would be port 465; port 995 is POP3 w/SSL.

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum
 
Unread 04-05-2008, 10:16 AM   #15
N. Miller
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

On Thu, 1 May 2008 22:29:00 -0700, Dale wrote:

> You are correct the user is connecting to the exchange server via POP3, SMTP
> from ouside the network. It is not through VPN and it is only log on
> credentials to allow this. The OE actually failed today in th esame manner,
> cannot connect to the SMTP server even though it is the same server as the
> POP3.


I would still think that K. Orland is on the right track. If the user is
trying to connect into the network from Cox, or an AT&T FastAccess (former
Bellsouth) account, those services definitely block outbound port 25. One
way to fix that is to have the administrator of the Exchange server allow
authenticated access to port 587 (per RFC 2476).

> Odd thing is that any other user is able to connect with no problems,
> it is only this one. Possibly firewall issue but couldn't say for sure, if it
> is it is not the local firewall.
> Your thoughts?


Other users may be coming in from networks (such as Verizon), which don't
block outbound port 25. If the administrator is going to allow authenticated
access from outside of the corporate network, they are going to have to
compensate for the fact that some of their users will be trying to access
the Exchange server from networks which block outbound port 25 access to
servers outside of their own IP networks.

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum
 
Unread 08-05-2008, 06:25 PM   #16
Sue Moore
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

I found this post as I was having exactly the same problem. Fine in OWA but Outlook client same error messages.

My resolution turned out to be far less technical - there was a rogue email on the server - once I cleared down the email on the server, Outlook kicked into action. It's been running fine for about 3-4 days now.

Hope this helps
 
Unread 30-05-2008, 09:22 PM   #17
Penny
Guest
 
Posts: n/a
Re: Cannot connect to SMTP eror

Dale, by any chance is the ISP AT&T or Yahoo or SBC?

"Dale" wrote:

> You are correct the user is connecting to the exchange server via POP3, SMTP
> from ouside the network. It is not through VPN and it is only log on
> credentials to allow this. The OE actually failed today in th esame manner,
> cannot connect to the SMTP server even though it is the same server as the
> POP3. Odd thing is that any other user is able to connect with no problems,
> it is only this one. Possibly firewall issue but couldn't say for sure, if it
> is it is not the local firewall.
> Your thoughts?
>
>
>
>
> "VanguardLH" wrote:
>
> > "Dale" wrote in
> > <news:FAF599CC-23E4-4156-B315-6A60A712DE22@microsoft.com>:
> >
> > > "VanguardLH" wrote:
> > >
> > >> "Dale" wrote:
> > >>
> > >>> "VanguardLH" wrote:
> > >>>
> > >>>> "Dale" wrote:
> > >>>>
> > >>>>> I have a client running Outlook 2007 with a POP3 account. The
> > >>>>> client had been working flawlessly until yesterday, now he cannot
> > >>>>> send email. He can send and receive fine using OL Express and
> > >>>>> OWA. Any ideas as to what night have happened and how I can fix
> > >>>>> it? I have uninstalled the profile and re installed it, same
> > >>>>> error
> > >>>>>
> > >>>>> reported error (0x80042109) : 'Outlook cannot connect to your
> > >>>>> outgoing (SMTP) e-mail server. If you continue to receive this
> > >>>>> message, contact your server administrator or Internet service
> > >>>>> provider (ISP).'
> > >>>>
> > >>>> Have the user try to telnet into the mail host:
> > >>>>
> > >>>> telnet <smtphost> <port>
> > >>>>
> > >>>> The point is not to establish a mail session but just to see if
> > >>>> the user can reach the host and do a connect only.
> > >>>
> > >>> I tried that, the client is unable to reach the host on port 25. I
> > >>> can't figure out what would be causing this as it worked Monday but
> > >>> not Tuesday. I disabled the Windows firewall and the email scan
> > >>> from the Symantec AV as well, still same result. The router
> > >>> firewall has always been up and it forwards ports 110 and 25. Any
> > >>> ideas?
> > >>
> > >> So does the user actually have a usable route to the mail host? Can
> > >> they run "tracert <smtphost>" and reach that host?
> > >
> > > Yes, traceroute and ping to the host, just no SMTP.

> >
> > Then my next guess is the same at Orland's: make sure the correct port
> > number is being used. Port 25 is the standard one for SMTP but many
> > ISPs are moving to 587 or 995, and may now require SSL connects, in
> > order to thwart the mailer trojans that inject user hosts. I didn't
> > suggest it before because you said the user can connect okay using
> > Outlook Express but the presumption was that the user had the OE account
> > also configured to use the standard port 25 for SMTP.
> >
> > You mentioned the user is using Outlook Web Access (OWA). Does that
> > mean this user is trying to connect to the company's mail service? If
> > so, does this user have to use a VPN to connect to the corporate network
> > so they can then get access to the company's SMTP mail host? I doubt
> > the company is going to let any tom, ****, and harry to connect to their
> > SMTP server and rely only on login credentials to secure their company's
> > internal e-mails. They may allow any of their employees to yank from
> > their POP mail host without using VPN but often they want a secure
> > channel when using their SMTP mail host. If VPN is required then maybe
> > this user isn't enabling it. The only reason that I've seen OWA used is
> > to allow employee access to the corporate mail service from the outside,
> > so presumably this user is also trying to connect to the corporate SMTP
> > mail host from the outside.
> >

 
 

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