8 Replies Latest reply: Dec 20, 2007 3:39 PM by Blinky Bill
Blinky Bill Level 1 Level 1 (0 points)
I have had a problem for some time with attaching Word documents to e-mails (I use Mail 2.1.1). If I attach from within Word (File/Send To) it usually works OK but if I just attach it it appears that it never leaves the computer. My assistant who works on an e-mac has the same issue. We use Office:Mac 2004.

I do not have the problem with any other files (including Excel) and while it is somewhat sporadic, it does appear to usually be the case.

We have moved ISPs and it makes no difference. I suspect the problem is in Mail but I cannot isolate it.

Any thoughts?

MacBook 2.16Ghz, Mac OS X (10.4.11), 2 GB SDRAM
  • Thomas O'Carroll Level 2 Level 2 (300 points)
    What do you mean by "it never leaves the computer?"

    Any file you attach to an email is essentially copied from the original file. Say you have a word doc on the desktop and drag it to an email, the file on the desktop will not go anywhere. What goes with the email is a copy of that file on the desktop.

    The only time an ISP has any effect on attachments is when the attachment is too big. Many ISP's have a maximum file size limit that they will transfer via email. My ISP has a very large limit of around 10MB (I think) but I can still have issues with large email attachments due to the recipient's ISP might not like a large attachment. (don't forget the email could go through a few stages in its journey where attachment size limits could be applied).

    Usually if there is a problem the ISP will reject (ie "bounce back") the email altogether and you will receive in return an email pointing this out.
  • Blinky Bill Level 1 Level 1 (0 points)
    Hi Thomas - thanks for your response. This is not quite the issue. (I am a very experienced user and e-mailer if not particularly literate about the mechanics of hard and software).

    What I was intending to convey is this: If I attach a Word document to the e-mail, it never arrives at the addressee. Anything else I attach, does arrive. If I go into the Word program and use the File/Send To method, it usually does arrive OK.

    While this is a workaround, it is not very satisfactory if I wish to attach 2 or more Word documents to an e-mail.

    What is curious is that I never get a 'bounce-back' e-mail indicating that it was not delivered. This is what I mean when I say that it appears to 'never leave the computer'. ie, if it did go to the ISP and was rejected, it would ordinarily let me know.

    It doesn't matter who I send it to, it seems to be the case. I send between 20-50 e-mails a day so it goes to a wide variety of ISP and users.

    Thanks.
  • Thomas O'Carroll Level 2 Level 2 (300 points)
    As far as I understand things, attachments in emails are wholly part of the email, not separate entities, when the email is being delivered. The email and attachment make up just one file, when in transit, so its not like the attachment can just get "lost" or un-attached along the way. The email "file" would have to be analyzed and intentionally changed somewhere along the line for the attachment to be lost.

    Emails are often "analyzed", of course, for viruses - but if a virus is found the whole email, with all attachments is quarantined, so again, I can't see this being the explanation to your missing Word docs.

    Have you tried sending word attachments to yourself? If you can replicate the problem this way then it rules out any problems the recipient may have. When there is an email issue like this its easy to assume its the senders fault when sometimes its the fault of the recipient. For eg its not your fault if the recipient has some over enthusiastic spam/virus filters that remove your attachments.

    Also, have you looked in your "Sent" email folder? Do your emails and attached word docs appear in there once they are sent?

    I assume you are not sending mail through some sort of corporate email system or running your own email server etc. (?)
  • Blinky Bill Level 1 Level 1 (0 points)
    Thanks for following this through with me.
    To clarify, it is the whole e-mail that does not arrive, not just the Word document.
    If I send them to myself, the e-mail does not arrive.
    The e-mail with attachment is still in the Sent folder.
    It doesn't matter where I am sending them from, the problem is still the same. I travel a lot and so use a large variety of ISPs in various parts of the world and around Australia.
    I think it must be a Microsoft issue of some sort but I cannot get my head around it.
  • Thomas O'Carroll Level 2 Level 2 (300 points)
    It sounds to me like the problem is not mail but the ISP you use to send mail. It is quite common to have numerous email accounts with different suppliers, but to use just the one server to send emails. I am guessing you are using smtp? This can found in Mail -> preferences -> accounts and click through your various accounts in the left hand pane to see what "outgoing mail server" is being used. I'm just suspecting a problem with the outgoing mail server.

    Its still freaking weird though! I am struggling to see why the sort of file you attach could make any difference. The size of the file might though. All any mail server sees is an email - it shouldn't notice what sort of attachment is in place. I can only think that some sort of virus checker might be finding some issue! Does your email provider have these in place and switched on?

    Just to be totally clear: you save your word doc on the desktop, then drag it to an open new mail message window. You type the address, subject etc and click send ... and the result is no mail for the recipient - including yourself!

    Can ask how big your typical word docs are? (control -click the wrd file and select "get info"), and the ISP/email supplier you use to send the problem emails?

    I have to admit I am kind of brainstorming here - I'm surprised no one else has chipped in yet!
  • Blinky Bill Level 1 Level 1 (0 points)
    As you eloquently say, it is freaking weird. The smtp changes depending on where I am. My home base is in Sydney and the provider is IINET. My e-mail and domain name is with Smartyhost.

    But when I am travelling, I change the smtp to suit to hotel/airport lounge/friends house system that I am using. I was using as smtp attached to my domain name (with Melbourne IT) but I have recently moved to Smartyhost. It does it with both providers.

    Yes, I save my file to the desktop or other folder on the hard drive then drag it (or press the Attach button) to include it. File size varies from tiny to big but it makes no difference. From a one page letter to a 100 page contract, it is still the same.

    I'm weirded out by this and I'm glad, in a way, that it isn't just me being an idiot. I know so much less about computers since I moved to Macs about 4 years ago... So little goes wrong.
  • Thomas O'Carroll Level 2 Level 2 (300 points)
    To be honest I'm a bit stumped by this one Blinky.

    You could try "zipping" the word file before you attach it (control click the word doc and select "make archive". This would not only make the file smaller but it would change the file type to a .zip from a .doc.

    The other thing to do is to make the Word file into a PDF. For what its worth, I always use PDF when I send Word type documents to people. Although in practise Word docs are a pretty universal format, the format was never really designed to be a used for file sharing. PDF was specifically designed for this job. Indeed I always recommend folk to use PDF when sending text based documents.

    If you find out what's going on with the word docs do post back here.

    Hopefully, someone else will post with a fix.
  • Blinky Bill Level 1 Level 1 (0 points)
    Thanks for your help to this point. I send pdfs when I can but my work means that often things have to be in alterable format.

    Will certainly let you know if i find out anything.

    have a good New Year.