Entourage Attachment Weirdness!
 

I have a satellite office in Massachusetts. They operate on the same domain as we do. They use Macs, we use PCs. For some reason as of last Friday, they have been having trouble sending e-mails with attachments. They can receive e-mail with attachments just fine. They can also forward messages with attachments just fine. But, if they go to create a new message and try and send it with an attachment, it shows up in their sent folder but does not reach its destination. This only happens within our domain though. Example..

jsmith@abccorp.com to jdoe@gmail.com works just fine, however

jsmith@abccorp.com to bsmith@abccorp.com does NOT reach bsmith.

Nothing has been changed since it stopped working that would seem to effect it in anyway. They did have an internet outage but I don't see how that could effect e-mail attachment sending. The funny thing is, in our office in the midwest, we can send and receive e-mail attachments inter-office just fine. Anyone have a clue as to what could be causing this? They are using Entourage 11.4 with every machine but two running tiger and the two are running leopard. Upgrading to leopard is not really feasible at this point. I greatly appreciate any feedback, as this has me pretty much stumped! Thanks in advance,

-Dom

Anyone have ideas on this?

I assume they can send emails without attachments, yah? taking the internet outage as a probable cause, I'm wondering if something on your company's mail server got corrupted. is the server Mac or something else?

Is your mail server running Microsoft Exchange?

Trevor

No we are not running exchange. I did a bit of testing this morning and found something weird. I can send a .pdf file just fine. I can send a .tif file just fine. I cannot however, send an empty excel file. But, if I attach both the .pdf and the excel file, the message comes through WITHOUT the excel file. It is like it withholding certain file extensions. This is getting weirder by the second.

Another addendum, I have found, if I attach a Word document along with the Excel document, they both come through. It just seems that Excel attachments, by themselves, are not working.

so, the case is this: sending an entourage email from your MA office to wherever you are works fine in all ways except that excel attachments don't come through (other attachments work fine, and any attachment works fine unless the recipient is part of your domain). is that correct?

so, are the email attachments getting flagged and removed by spam-checker or virus-checkers on your domain? did your MA office pick up an excel Macro virus that's getting flagged and removed by entourage itself?

Any attachment works to outside e-mail addresses, i.e. GMail, etc...

Any attachment aside from excel seems to be working fine within our domain. If you attach another office document, i.e. Word file along with the Excel file, then they magically go through. It doesn't make a damn bit of sense. The message themselves appear in the sent folder as usual and are not found in my spam inbox on either my local machine or through my web interface.

Actually, I think tw has a good theory regarding an Excel macro virus, or possibly a bad virus-check rule regarding Excel macro viruses catching false positives.

Some virus checkers on the server are configured to check incoming mail but not outgoing, so a mail from one person to another on your mail server would catch an Excel macro virus and remove it (since that's incoming mail), but a mail from a person on your mail server to the outside world would not do anything (since that's considered outgoing mail).

Run a virus checker that knows about Microsoft Office macro viruses against your Excel attachments from this MA office to see if they have caught anything. Then, if that doesn't find anything, triple check the virus rules on your mail server virus checker for any bad rules regarding Excel macros.

Trevor

I'll add that while your local spam-checker (whatever you have running with or through Entourage on your personal machine) will generally put spam mail into a spam folder, mail servers are sometimes configured to dispose of questionable things silently. you won't see those in your spam folder. there might be a line added to your email (sometimes only as a hidden header) saying such-and-such an attachment was removed, or the removal may just get written to a server log with no way to tell the attachment was there from the client end.

I see what you are saying but would said virus affect even blank excel workbooks?

sure. blank workbooks are not really 'blank' - they can contain formulas and macros and all sorts of other hidden stuff.

If the computer in question is infected with a macro virus, a "blank" spreadsheet would actually contain that macro virus.

Trevor

I will attempt to run a Virex scan when I get back to the office. Will I need to scan every machine in the office? Just weird that the attachments go through if there is another office document attached.

To test the theory, find a machine that you know has had the problem, and scan it. Actually, you could save time by just scanning an Excel spreadsheet that you know has been filtered when sent to somebody else in your domain--if the problem is a macro virus, then scanning that single file should show the virus.

If you find a macro virus, THEN you would have to remove macro viruses from all the machines in that office. But until you've confirmed the macro virus theory, no, it's not necessary to scan all of them.

Trevor

I have scanned both the entire machine and two files that I have been testing with that have not been going through. Neither show a virus using Virex. Any other suggestions? This is driving me (and my boss) crazy!

ok, next thing to try is to take a test email (one you sent with an excel attachment that didn't come through), open both the 'sent' and 'received' versions in Mail, select from the menus View->Message->Raw Source, save the mess of text that results as text files, and attach them to your next post so we can look at them. be very, very careful to vet them first, removing anything that looks like an IP address, URI, Host Name, or email address - there's a lot of information contained in email headers that's not for public consumption.

you should also trim the inline attachments - they look like:
going on extensively, but we only need to see the the first and last lines of all those random-looking letters.

Okay hopefully I did this correctly, I have two rtf files. Mods I apologize in advance if I did this incorrectly...

This is the e-mail that did not go through:

And here is the one that did with the help of the Word document:

couple of problems here: first, you didn't specify whether these were the raw emails from the 'sent' folder or from the inbox on the receiving end. as I understand what you've said, if you send an email with an excel attachment, the email goes through, but without the attachment. we need to see both sent and received so we can compare.

second, it looks like you cut out too much. for instance, you say that the second email delivered both the word and excel documents, but I only see Content-disposition: attachment; for the word document. only cut out personal information and big blocks of unreadable text; make sure all the readable, header-oriented material is still there.

If I send an e-mail with just an excel attachment, I get absolutely nothing. No message at all. If the message contains other attachments besides office files, i.e. pdfs, .tifs, etc... I will receive the message and all attachments minus the excel file. It is only when I send an e-mail with both an excel attachment and word attachment did I get it to come through.

They are both from the sent box the first one didn't go through, the second one did with the help of the word attachment. I went back through and compared the original "source" of both e-mails to what I posted, the only thing I deleted was e-mail addresses and the message ID. In the original "source" for the message that went through with help from the word attachment, it reads like this:
I just checked again and the only thing that is different then what I had before is the sequence of numbers that follow the "--B..." Otherwise everything is exactly the same as I posted before. I can run two more test e-mails and post them up for comparison.

I just ran two more test e-mails, they both are from the sent folder. For some reason it is not showing the excel file in the attachment list along with the word file, however they both go through and can be opened. This is crazy...

Just Excel Attached:

Excel and Word Attached:
The only thing I deleted from the source were e-mail addresses from the "to" and "from" line and the "message ID" line. Other than that, this is exactly what I see.

I'd like to see the raw source on the 'received' emails that you got (not the ones you sent, but the ones your received), both for the ones where excel gets chopped and for the one where excel goes through with a word doc.

incidentally, in the preferences under "Compose" what are the setting you have for attachments?

I am using Outlook 2007 on my end, I looked around online for raw source and it directed me to "internet headers" which has nothing about attachments inside of it. And I am a little unsure of what you mean about "Compose" preferences.

I figured out the "Compose" preferences, here is what they are set to on her machine, hope hot-linking is okay...

http://img107.imagevenue.com/loc252/..._122_252lo.JPG

Another addendum, when I was running tests the last couple days I was sending them from our Cambridge office to myself in Indiana. Well I just tried to test my Word attachment theory with another machine in Cambridge and what do you know, it did not go through. Disappeared like the rest. But I sent an e-mail yesterday from the machine I have been testing to two people here, myself included and one other person in Cambridge and that was received by all parties. This thing has me stumped!

Still have yet to make any head way on this at all. This is one of the most frustrating things I have ever seen! Help...

Okay I was able to get the raw source form the e-mail that went through inner office. What I did was send an e-mail with both attachments (word/excel) to another person in the same office and also to a person here at my office in the midwest. This e-mail was received by all parties with both attachments. Here is the source...

Hopefully there is something here that can help. Thanks in advance as always.

here's what you said in an earlier post (underline for emphasis):
the source of emails that go through correctly tell us very little. the source of emails that don't go through at all tell us nothing at all (since there isn't any email to get the source of). we need to see a "message (which) contains other attachments besides office files, i.e. pdfs, .tifs, etc... (where you) receive the message and all attachments minus the excel file."

I just tried to have her send a .tif and an excel attachment and got nothing. Then I tried having her send a .pdf and an excel attachment and also got nothing. The .tif file by itself went through fine. I think I am losing my will to live.