Outlook (not OE) stripping attachments I send

[RogerDodger]

A business colleague uses full-blown Outlook (not Outlook Express) on
his XP computer, newly purchased in late 2003 (I mention this in hopes
someone might discern the version of Outlook).

Whenever I send him a message containing attachments, he receives the
message, but not the attachments. And there's no notice provided to him
that the attachments have been stripped. I am using Eudora 5.2 for my
primary email program, and I've checked the filters and there's nothing
funny going on in terms of my stripping attachments as I send.

This has happened with Word documents (.doc) and text (.txt) files, but
I'm sure it happens with every other type of file. And it happens EVERY
time I send to him.

Every other email my colleague receives from any other person has the
attachments intact. But if I send a message with attachments to him,
they're gone.

Every other person I know of to whom I've sent messages with attachments
has received the attachments. But again, he can't get them from me.

I have even taken a message and attachments that failed to get to him,
sent the same message and same attachments to another person (who
received the attachments fine), and then that person successfully
forwarded the message and attachments to the guy.

This of course sounds like he has some kind of a filter in place that is
stripping attachments from messages from me. But (1) this guy is the
first to admit that he's not sophisticated enough to use filters, and
(2) no matter which email account I use to send to this guy, the
attachments don't get through.

Any ideas what to look into?

 

[RogerDodger]

A business colleague uses full-blown Outlook (not Outlook Express) on
his XP computer, newly purchased in late 2003 (I mention this in hopes
someone might discern the version of Outlook).

Whenever I send him a message containing attachments, he receives the
message, but not the attachments. And there's no notice provided to him
that the attachments have been stripped. I am using Eudora 5.2 for my
primary email program, and I've checked the filters and there's nothing
funny going on in terms of my stripping attachments as I send.

This has happened with Word documents (.doc) and text (.txt) files, but
I'm sure it happens with every other type of file. And it happens EVERY
time I send to him.

Every other email my colleague receives from any other person has the
attachments intact. But if I send a message with attachments to him,
they're gone.

Every other person I know of to whom I've sent messages with attachments
has received the attachments. But again, he can't get them from me.

I have even taken a message and attachments that failed to get to him,
sent the same message and same attachments to another person (who
received the attachments fine), and then that person successfully
forwarded the message and attachments to the guy.

This of course sounds like he has some kind of a filter in place that is
stripping attachments from messages from me. But (1) this guy is the
first to admit that he's not sophisticated enough to use filters, and
(2) no matter which email account I use to send to this guy, the
attachments don't get through.

Any ideas what to look into?

I guess it would have helped if I mentioned that my Eudora 5.2 is for
the Macintosh.

A lot more digging helped me learn that there is a known bug between Mac
Eudora and many versions of Outlook (but I guess not Outlook Express).

http://home.cwru.edu/~wrv/eudoraoutlookfix.html has the best fix I've
seen. It allows any Outlook user to see and open attachments from me.
I also played around and if I retain the default setting (not the
alternative described in the link above) and send attachments using the
"Double Apple" (MIME) or UUencode, instead of BinHex, that works too.
But that's something that I have to remember every time instead of the
"set and forget" fix documented above.

This still is an odd one to me, and I'd love to hear if there are other
fixes better than what I've listed above.

 

[Peter Ceresole]

I also played around and if I retain the default setting (not the
alternative described in the link above) and send attachments using the
"Double Apple" (MIME) or UUencode, instead of BinHex, that works too.
But that's something that I have to remember every time instead of the
"set and forget" fix documented above.

In practice, AppleDouble is preferable to Bin-Hex anyway, as everybody can
handle it, Mac and PeeCee alike, and all the info is conveyed.

You can set it as the default encoding in Special:Settings:Attachments. Set
the encoding method to Appledouble, and you're done.

 

[RogerDodger]

In practice, AppleDouble is preferable to Bin-Hex anyway, as everybody can
handle it, Mac and PeeCee alike, and all the info is conveyed.

You can set it as the default encoding in Special:Settings:Attachments. Set
the encoding method to Appledouble, and you're done.

I am testing this by emailing from my Mac/Eudora to a yahoo mail account.

If I send a Word document using the modified content-id header, but
Bin-Hex encoding, when I do "View Attachment" in yahoo mail, the
attachment is pure gibberish. I can't even get it to save on a Windows
PC.

If I send a Word document using the normal content-id header with MIME
(Double Apple) encoding, the attachment is viewable in Yahoo Mail view
attachment, but has some garbage characters in it. If I try saving the
attachment from yahoo mail onto my Mac, my browser doesn't recognize it
as a Word document and saves it as something else. I can force Word to
open the document up, but it's not recognizable as the format I sent it.

Granted, this is off topic from my original post, but I think it falls
into the same set of issues - somehow Eudora on the Mac is having a
miscommunication with the majority in the non-Mac world.

Is there a "better" solution for me on my end? Does Eudora 6 address
this issue better? Are there simple solutions to suggest to Outlook
users (since I think the real issue is on the Outlook side, not the
Eudora side)?

 

[Peter Ceresole]

Granted, this is off topic from my original post, but I think it falls
into the same set of issues - somehow Eudora on the Mac is having a
miscommunication with the majority in the non-Mac world.

All I can say from a practical point of view is that I'm using Eudora 3.1.3
Light in Classic/10.2.6, I always use AppleDouble encoding, and nobody, Mac
or PeeCee, has any trouble with the attachments, which are usually Word
files or JPEGs.

Is there a "better" solution for me on my end? Does Eudora 6 address
this issue better? Are there simple solutions to suggest to Outlook
users (since I think the real issue is on the Outlook side, not the
Eudora side)?

There have been issues with Eudora 5.1 and various flavours of OS10,
generally solved by upgrading to 6.0.2, but I'd not heard of that
particular problem.

I've certainly heard of Outlook, and also Outlook Express of some flavour
or other, having problems with Eudora's correctly formed attachments. The
best recommendation is that the recipients should update their software.
Recent versions of OE, and Entourage, certainly don't seem to have those
particular problems.

 

[RogerDodger]

All I can say from a practical point of view is that I'm using Eudora 3.1.3
Light in Classic/10.2.6, I always use AppleDouble encoding, and nobody, Mac
or PeeCee, has any trouble with the attachments, which are usually Word
files or JPEGs.


There have been issues with Eudora 5.1 and various flavours of OS10,
generally solved by upgrading to 6.0.2, but I'd not heard of that
particular problem.

I've certainly heard of Outlook, and also Outlook Express of some flavour
or other, having problems with Eudora's correctly formed attachments. The
best recommendation is that the recipients should update their software.
Recent versions of OE, and Entourage, certainly don't seem to have those
particular problems.

Thanks a lot. I played around more with the yahoo account and it seemed
to like it "best" when I used Eudora with the content-id header set to %
and UUencoding. In fact, nothing else seemed to work.

Anyway, I hope the above permanently solves my problem.