Entourage Email Issue - An Unusual Problem

[ryannewman]

In need of desperate help.

We are having problem with people recieving our emails and attchments
when we send emails through Entourage. It is a very unusual situation.
We tested out Mac Mail to see if is Entourage. When we used Mac Mail to
send emails people were able to recieve the emails. However, we need to
be able to use Entourage. If i forward using Entourage to a colleague
and he sends the email out then other people are able to recieve the
email. There does not seem to be a any consistency. It is now effecting
all machines with OS X 10.3.9 with Mac: Office 2004.

We have two machines that are OS 9 and they are not having this
problem. When people send email using Entourage, most of the time
people on the other end are not recieving the emails. However, on some
days the same people are recieving the emails. Also attachments are
coming through on the other end as viruses. The thing is there does not
seem to be any consistency at all. We are thinking about uninstalling
the OS and Office to see if this does it. We have already uninstalled
Office and did an update and this did not solve the problem.

Any help or suggestion will be appreciated.

 

[Barry Wainwright [MVP]]

I think we need a few more details.

From the comment "we need to use Entourage" am I right in thinking that you
are using an Exchange server?

Also, what do you mean by "Also attachments are coming through on the other
end as viruses."? - Entourage & the MacOS cannot become infected by macro
viruses in the way windows machines can, so cannot infect documents they
send. If the document was infected when received, then the infection may be
passed along, but the infection is not 'inserted' by entourage. Do you mean
that the receiving mail server/mail client is marking the mails afs infected
in some way, or are they genuinely virus laden? If the latter, what route do
they take after leaving the senders machine to get to the recipient?

 

[ryannewman]

Hi Barry, thanks for your reply.

I don't think we are using Exchange. I wrote "we need to use entourage"
because nobody on the network likes using Mac Mail. When i got people
to use Mac Mail (just to test) the recipients were able to recieve the
emails all the time. From this i assumed that it must be an Entourage
problem or an OS problem. By the way we are using OS.3.9 iMacs (the
machines affected by this problem).

Our server hardware is a G3 Power Mac. So i am assuming that it's not
running an MS Exchange or MS Server Operating Systems. We have 6
machines on the network. They are all iMacs. Two of the machines are
running OS 9. These two machines are not having any problems. The four
machines running OS X 10.3.9 are having the Entourage email problem.

With regards to the Attachments: when the recipient tries to open an
attachment, their machine is telling them that its a virus. See the
unusual thing is: if i send the same email to a colleague, and he then
sends it to the recipient it is going through most of the time.

I am not too familiar with Mac Server OS's. Can yo tell me if Mac runs
something similar to Exchange. Also is there is anything like an "MCSE"
or similar qualification/education system for Mac's. Somewhere i could
go to learn some of this (that does not cost a fortune).

I hope this information helps. If you need any more info, just let me
know.

 

[Barry Wainwright [MVP]]

Hi Barry, thanks for your reply.

You're welcome...

I don't think we are using Exchange. I wrote "we need to use entourage"
because nobody on the network likes using Mac Mail. When i got people
to use Mac Mail (just to test) the recipients were able to recieve the
emails all the time. From this i assumed that it must be an Entourage
problem or an OS problem. By the way we are using OS.3.9 iMacs (the
machines affected by this problem).

Our server hardware is a G3 Power Mac. So i am assuming that it's not
running an MS Exchange or MS Server Operating Systems.

That is correct! No exchange on a G3

Do you know if you are running a server version of OS X or just the plain
desktop version? If you go to the Apple menu (on the Server) and select
'about this mac', it should say either "OS X" or "OS X Server" followed by a
version number.

We have 6
machines on the network. They are all iMacs. Two of the machines are
running OS 9. These two machines are not having any problems. The four
machines running OS X 10.3.9 are having the Entourage email problem.

And these are Office 2004, yes?

With regards to the Attachments: when the recipient tries to open an
attachment, their machine is telling them that its a virus.

Is this recipients in your office, or recipients in the outside world? Is
the dialog saying it IS a virus, or is it a standard dialog saying words to
the effect of "this type of attachment can carry viruses - do you trust
whoever sent it?"

See the
unusual thing is: if i send the same email to a colleague, and he then
sends it to the recipient it is going through most of the time.

I am not too familiar with Mac Server OS's. Can yo tell me if Mac runs
something similar to Exchange.

Tiger versions of 'server' use Postfix and Cyrus for sending mail & IMAP
connections - I seem to recall that earlier versions used 'sendmail', but I
would need to refresh my memory as to when the switch was. If you're running
a server on a G3, then it won't be Tiger.

I also need to go back in time and see what AV packages were being used on
whatever version you are running, but it sounds like a client configuration
problem rather than a server-side problem.

Also is there is anything like an "MCSE"
or similar qualification/education system for Mac's. Somewhere i could
go to learn some of this (that does not cost a fortune).

Apple do provide 'certification' training:
<http://training.apple.com/certification/macosx.html>

I have no idea what the cost is though.