Mac Mail to Gmail truncates attachments names and removes exstenstions

I have a user that has mac Mail 2.1.1 and is on OS X 10.4.9. Sometimes when he sends mails to his colleagues, the attachments are truncated and the extensions are removed. For Example:

In Mail, he attaches a file called "Heid Survey.doc". Mail sends the file and the Sent mail looks ok. On a windows machine, using firefox and gmail.com, another person checks the email and gets an attachment named "heid". It does not recognize it as a word file. If the attachment is downloaded and the .doc added to it, it will open. If the same recipient checks the mail message in Mac Mail, the email and attachment come through fine.

I have tried this using both "Send Windows Friendly attachments" and with out it.

This does not always happen he reports, but I was able to recreate it with my gmail account and his laptop consistently. My Mac Mail shows the attachments fine as well.

I also tried to zip the file before sending it to gmail, and gmail recognized that it was a zip file, but when I tried to save it to the desktop on windows, it only saved the truncated version after gmail un-zipped it.

I do not know if this is a Mac Mail or a Gmail issue. I am not sure what is happening to these messages. Can any shed some light or give me some troubleshooting tips? Anything that I can try would be great. Thanks!

MBP 17" 2.4Ghz 2Gb, MBP 15" 2.16Ghz 2Gb, Power Mac G4 MDD Dual 1Ghz 1.5Gb, Mac OS X (10.5)

Posted on Dec 18, 2007 11:56 AM

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8 replies

Dec 18, 2007 12:11 PM in response to Russell Myers

Gmail support has this article about truncating names of attachments when the is not ASCI (encoding used to name attachment)

http://mail.google.com/support/bin/answer.py?answer=10290&topic=12850

however, the attachment was named heid let.doc and isn't very likely to be anything weird about it. When I send myself the attachment from Leopard and Mail, it shows fine. However, from my Tiger machine, the attached file gets truncated and the extension removed!

I tried a new document and it sent to gmail fine from my 10.4 machine. I think the issue is in the document that we are trying to send. It is a word doc, anyone have any ideas?

Dec 19, 2007 1:46 PM in response to Russell Myers

Hi,

I have exactly the same problem with filenames, from mail 2.1.2, using OSX10.4.11 - I found out from a recipient, and have duplicated the problem myself with different types of attachment (pdf, doc, xls) with my own online gmail account - but there is only a problem when I check the mail online - when I bring the same email through to AppleMail using POP3 then the attachment comes through fine.

The 'send win friendly attachments' had no effect for me either, and the filenames only included ASCII characters which means the google help did not cover it.

I think I have had the same problem sending to an AOL account too, but am trying to find out from the recipient exactly what is happening. I think it must be something to do with the combination of my mail settings and the online mail Google server - if it was a common Mail or even Google bug, then surely there would be more info on forums about this. Has anyone any ideas? Help!!?

Dec 20, 2007 6:41 AM in response to davidappleyard

That's interesting to hear that your having the same issue, I assumed it was just the document I was sending.

Just like you have stated, mac mail to mac mail is fine. It is only when sending to gmail, and it is only a few of the documents. Can you try recreating the word docs and PDF's and send them again to see if it has something to do with the individual documents or the entire program and process?

Jan 10, 2008 9:45 AM in response to Russell Myers

It has nothing to do with the contains. I believe it's a bug, and if you search translators lists like Systran's, you will discover this issue is spreading virically. Do not know what happens. What is known about this by embattled Mac users who now have to stop using Mail app: the phenomena begins out of the blue, one day works, one do not, it affects every file type (seems to be a problem with the name only, nothing to do with ASCII issues) and also, activating the "windows friendly" part does nothing. My case is really funny because I have one mac account with several mail accounts included, and it began with the main one (the others sent files ok) and now every account is affected. My boss is crazy with this. After a certain amount of time in the gmail account, the names appear fully sometimes, but obviously you can't tell a client, "sorry, you have to wait one day to check your mail, because I'm using Mac and it looks great, but it can't send attchments". Google says it's Apple's error, and Apple do not answer.

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Mac Mail to Gmail truncates attachments names and removes exstenstions

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