Some sent items never arrive

[davidwilce]

Version: 2008
Email Client: Exchange

Hello Everybody,

I'm at my wits end with this little doozy...

We have a customer that has Entourage 2008 set up correctly on her Mac and works most of the time.

The only problem is that ramdom emails are sending (they send correctly and appear in her SENT ITEMS) but they never arrive!

It's a Fasthosts Exchange 2003 account.

Her co-worker has the same set up but uses Outlook on a Windows machine. He has no problems at all.

Accessing her account using webmail works 100%.

She has this problem at home and at work (different ISPs).

Fasthosts are telling me it's an Entourage issue.

ARGH!

 

[Adam Bailey]

We have a customer that has Entourage 2008 set up correctly on her Mac and
works most of the time.

The only problem is that ramdom emails are sending (they send correctly and
appear in her SENT ITEMS) but they never arrive!

It's a Fasthosts Exchange 2003 account.
[snip]
Fasthosts are telling me it's an Entourage issue.

Clearly it's not that simple.

Tell me more about the recipients. To whom is she sending these messages
that do not receive? One recipient? Several recipients? Are they on the
same service? Multiple services? What email clients are they using? Is
there any pattern to the missing messages - HTML vs. plain text,
attachments, etc.?

Entourage is sending the messages, usually these kinds of problems are
on the receiving end - often spam filters. Although a misconfiguration
in Entourage could make it more likely for messages to be dumped by such
filters.

 

[davidwilce]

We have a customer that has Entourage 2008 set up correctly on her Mac and
works most of the time.

The only problem is that ramdom emails are sending (they send correctly and
appear in her SENT ITEMS) but they never arrive!

It's a Fasthosts Exchange 2003 account.
[snip]
Fasthosts are telling me it's an Entourage issue.

Clearly it's not that simple.

Tell me more about the recipients. To whom is she sending these messages
that do not receive? One recipient? Several recipients? Are they on the
same service? Multiple services? What email clients are they using? Is
there any pattern to the missing messages - HTML vs. plain text,
attachments, etc.?

Entourage is sending the messages, usually these kinds of problems are
on the receiving end - often spam filters. Although a misconfiguration
in Entourage could make it more likely for messages to be dumped by such
filters.
[/QUOTE]

We originally thought it was linked to attachments but we proved that to be wrong.

She can send an email to someone and they receive it. Another day she'll send an email to the same person and it doesn't arrive.

It's happened when she emails me. Most of the time they'll arrive, but occasionally they dont.

She's had this problem sending to all kind of domains.

She doesn't get the problem when using webmail.

 

[davidwilce]

Also, once she's written a problem email (eg. one that isn't received) she can keep trying to resend that email and it'll never be received. But if she writes another email to the same person there's a change it'll arrive.

I really can't see a pattern to emails that dont arrive.

 

[davidwilce]

I mean "a chance it'll arrive"

doh!

 

[Diane Ross]

Also, once she's written a problem email (eg. one that isn't received) she can
keep trying to resend that email and it'll never be received. But if she
writes another email to the same person there's a change it'll arrive.

Do the message go out of the Outbox, or do they stay in the Outbox?

 

[davidwilce]

They leave the Outbox. To her it looks as though the message has sent successfully.

 

[Diane Ross]

They leave the Outbox. To her it looks as though the message has sent
successfully.

I'm wondering if this could be some setting on the server. Let's try this
test. When she sends a message have her Cc an email address outside your
server.

 

[davidwilce]

I'm wondering if this could be some setting on the server. Let's try this

test. When she sends a message have her Cc an email address outside your
server.

She's been CCing her Hotmail address as well. When it doesn't arrive with the recipient it doesn't arrive at her Hotmail either.

 

[Diane Ross]

She's been CCing her Hotmail address as well. When it doesn't arrive with the
recipient it doesn't arrive at her Hotmail either.

Did you check to see if the server had some type of filter that's blocking
those messages?