A Headache of an Email Problem

If I could get some advice on this matter I'm working on, I'd GREATLY appreciate it.

I keep running into dead ends on this one, it's pretty odd, mainly because there's nothing apperently consistent about it, so I have no real leads to follow. This client of ours is on a laptop that goes back and forth between office, home, trips, etc. (he's also a VIP client -- ya know, potentially impatient big shot -- so I'm trying to figure this out as fast as possible). Basically, sometimes he can send email, sometimes he can't, and he can always receive email without any problems. Here's the breakdown:

1) He's using Outlook (I forget exactly which -- 2000 or 2003).
2) POP account. POP3 and SMTP connections are properly configured to the right servers. User/pass info is correct.
3) He can always receive email. The problem only occurs with sending email.
4) Sometimes he can send with no problems, others he is prompted for user authentication, but then the authentication window just appears over and over again instead of allowing him to send the message.
5) He also gets "No transport provider was available for delivery to this recipient." bounce back messages.
6) The problem shows no pattern -- Sometimes he can send mail, sometimes he can't -- happens at various different locations, on both ethernet and wireless. So we can't narrow it down to happening at location A or B, or on wireless or off, as it works sometimes in all scenarios, then doesn't others.
7) His mail provider responded that there is no problem on their end, so it has to be on the user's end.
8) Both POP3 and SMTP go through the same server with the same authentication.

So I'm in a bit of a quandry here. Why does it only authenticate part of the time (I have yet to reproduce the problem when I've been on his machine)? And why will it let him receive mail even though he can't send? This has evidently been going on for a while now, so it's definitely not a problem that's going to resolve itself anytime soon.

Any thoughts?

OK...some mail servers do not allow you to send mail....unless you are already authenticated on thier network...

So if the guy is using a different ISP to get on the internet...then try to send mail through the mail servers...that reside at another ISP....it will probably fail....as the mail server will think he is trying to relay???

Another thing....I recently had a site that was having trouble sending mail from an app....where they had someone import the email addresses into the app.....well during the import a ' was added to all the addresses .......hence...all send attempts failed

confirm the address.....

MLF

edit> what is the exact error he recieves when it fails???

Connection type?

In some cases with xDSL and Leased line, you have to use the SMTP server of the ISP server not your mail service's provider .... not sure if this applies to your case ... usually you get a "Relaying Denied 550" message .... try to create a new account ....

Here ya go:

Quote:

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The following recipient(s) could not be reached:

'User Name' on 6/7/2006 9:19 AM
No transport provider was available for delivery to this recipient.

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Evidently the user authentication doesn't produce an error, it just pops up repeatedly...he eventually then gets the above bounce back message.

Quote:

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So if the guy is using a different ISP to get on the internet...then try to send mail through the mail servers...that reside at another ISP....it will probably fail....as the mail server will think he is trying to relay???

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Quote:

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In some cases with xDSL and Leased line, you have to use the SMTP server of the ISP server not your mail service's provider .... not sure if this applies to your case ... usually you get a "Relaying Denied 550" message .... try to create a new account ....

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I suspected that too, but if that were the case, wouldn't the problem then be consistent? The thing is it does allow email through at other times...

You might try blowing away his outlook profile and rebuilding it from scratch.

I'm with Morgan though, I would lean towards a bad address, or even just user error.

does he have multiple profiles set up....???

confirm the address...make sure you can send to it....it probably just one address hes whinning about ...mainly cause he typed it in wrong. :rolleyes: Trust me...I deal with whinners ALL the time ;)

I always send test messages from my exchange account, my hotmail account..and my sympatico account just to try and see where the failure may be....cause if it fail on a web based account...there is something wrong with the addy

MLF

The no transport provider error generally has to do with a malformed address, or an address that is destined for a local email server but its not configured correctly, like notes or something.

I would check the message he tried to send and look in the to: and cc:/bc: and see whats in there

Thanks guys, I'll try those possiblities and scope it out.

And yeah, Layer 8 errors are mostly the main cause of problems, unlike the rest of the 7 layers .. :D

Too funny...I was thinking the same thing :p

Quote:

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The 7 layer model has often been extended in a humorous manner, to refer to non-technical issues or problems. A common joke is the 10 layer model, with layers 8, 9, and 10 being the "user," "financial," and "political" layers.

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under the humor section...

http://en.wikipedia.org/wiki/OSI_model

MLF

Could also depend on the AV he is using and what the settings are for scanning POP and SMTP..


http://support.microsoft.com/?scid=k...d=2557&sid=139

Is this only to certain addresses? They may be dropping your smtp connection and it's not a local mail server issue at all.

to confirm .........

he can ALWAYS access from the office ?
if the problem is when he's away
then I'd check the SMTP settings real close

also, have you 'sat in' as he has logged in ?
have you observed his routine ?

I'm assuming that no on else has these issues ?

would they notice if you SHOT him :D

Quote:

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would they notice if you SHOT him

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ohhhh...how I have soooooo wanted to do that. :eek:

Its is so funny...I have one site....as soon as ANY thing starts messing up...its always something wrong with the server\network....could never possibly be the end user or the application they just upgraded

and mostly ends up being... a top level OSI layer problem ;)

MLF

AngelicKnight,
We're having a similar problem with Outlook 2003 on our network. Every now and again, we get SMTP server timeout error messages when people are attempting to send emails. Outbound emails get stuck in the Outbox and won't send.
We checked every setting possible and couldn't find the cause. In any event, I have used two methods to date that seem to work:
1) I close and restart Outlook, then send/receive
2) I go into the outbox and re-open then send each email, one at a time

I read the microsoft article and I think I might attempt adjusting the timeout setting as proposed in the article. Let me know how it goes. Good Luck.