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Mail changes attachment extension

This is so weird... I'm sending an email with two attachments (Word 2004 documents). The file names are

Compréhension de l'écrit B, 2.doc
Expression écrite A, 1 et 2.doc

For some reason, Mail insists on appending a "0" (zero) to the file extension of the first file name, making it ".doc0"' (the second one is left intact). First, I thought it had something to do with using accented characters and commas in file names, but again, the second file name is perfectly fine and its extension does not get changed.

Several recipients use Macs, and there it's not an issue, but WIndows users have a problem because their system refuses to open the file unless they get rid of the "0" and thus restore the proper extension first.

Does anyone have a clue why Mail adds this character to the extension?

Daniel

Dual 1GHz G4 PM and 15" MacBook Pro, Mac OS X (10.5.1)

Posted on Feb 22, 2008 2:39 PM

68 replies

rabiraz

Level 1

0 points

May 27, 2008 2:27 AM in response to Daniel Kiechle

Hi all,

i had the same problem, all my attached pdf files got their extension changed into .pdfpdf, so i did remove all accented characters from my files names and then everything was ok.

😉

DRJGH

Level 1

10 points

May 27, 2008 10:28 PM in response to Daniel Kiechle

I have encountered a related but slightly different problem in sending .jpg files to my editor - While my emails appear with the appropriate extensions .jpg on my MacBook, the files can only be saved as .bmp files on his pc. This just started with the last update of the operating system and mail. I tried it myself by emailing my photos to another account I have and opening them on my pc. Sure enough I could only save the .jpg files as .bmp files which is totally unacceptable.

Does anyone have any solutions to this?

May 28, 2008 1:40 PM in response to DRJGH

I am unable to duplicate this problem. I have sent JPEG files to one of my email accounts accessible from my work PC (running Windows XP SP3) and have successfully opened and saved these files to JPEG and other formats. What software are you using to a) create the files on the Mac and b) open the files on the PC? Finally, what email app is used to receive the files on the PC? This does not look at all like the same problem.

Daniel

Jun 6, 2008 2:00 PM in response to rabiraz

Hello!

I have the same problem, and I was wondering if the upgrade 10.5.3 fixes the problem...

Any ideas?

Thanks,

Daniel P.

Jun 6, 2008 3:06 PM in response to Daniel Pigeon

I just tried sending attachments with the exact fame file names shown in the original post, and now that I'm running 10.5.3 I can't seem to be able to duplicate the problem. It would be good if others could try as well; maybe Apple fixed the bug at long last.

Daniel
(keeping my fingers crossed...)

Mediakip

Level 1

19 points

Jun 6, 2008 3:37 PM in response to Daniel Kiechle

Here is the list of issues fixed in mail, in 10.5.3. Nothing about the extensions, that I can see anyway. But maybe they fixed it anyway, who knows...

About the update:

Mail

* Resolves an issue in which Mail may prevent idle sleep when set to automatically check for new messages every minute.
* Addresses stability issues that may be encountered when dragging large attachments into an email message.
* Fixes an issue that could occur if two compose windows are open when dragging a file to the Mail icon in the Dock.
* Addresses reliability issues when changes are made to a mailbox while offline.
* Resolves wrapping issues that may be found with consecutive spaces in plain text.
* Fixes issues with certain web pages appearing garbled when emailed from Safari.
* Fixes an issue in which the Sent, Drafts, and Outbox mailboxes incorrectly list the "cc" recipients in the "To" column.
* Addresses reliability issues with attachments added to plain text notes.
* Fixes reliability issues with authenticated RSS feeds.
* Resolves an issue in which attaching an alias to an email message may not send the actual file.

Jun 7, 2008 5:12 AM in response to Daniel Kiechle

Merci Daniel.

I may run the upgrade today to see if it resolves the problem.

I am afraid to run it though, because the combo upgrade crashed my iBook G4... I had to format the HD and reinstall 10.5.2... Grrr!

I'll see depending on other users reports about 10.5.3, concerning Mail's attachment problem.

À plus!

Daniel P.

Jun 7, 2008 5:28 AM in response to Daniel Pigeon

Daniel Pigeon wrote:
I am afraid to run it though, because the combo upgrade crashed my iBook G4... I had to format the HD and reinstall 10.5.2... Grrr!

Fortunately, I've never had this happen to me. Your iBook must have had a problem if the combo upgrade crashed it; hopefully it should work now since you reinstalled 10.5.2 cleanly. You may be a bit tight on RAM, though (unless your profile is out of date). My wife has a 12" Powerbook G4 (1 gig RAM) and the combo installer was used to bring it to 10.5.3 without a hitch. I used it for my MacBook Pro as well as my Mac Pro; no problem on any of the machines.

It's good to have a full backup (Time Machine, SuperDuper, or similar) before doing an upgrade, especially if you've had problems before. That way you don't have to manually reinstall everything (though it's sometimes good to do it anyway).

Bonne chance,

Daniel

PS T'es où ?

Jun 7, 2008 5:54 AM in response to Daniel Kiechle

Thanks for the info! It is reassuring, though I will make a Time Machine backup before I upgrade this time.

As soon as I run the upgrade, I'll let you know about Mail's attachment problem.

Ciao!

Daniel P.

P.-S. : I am in Montréal... and upgraded my profile 😉

Leif M.

Level 1

10 points

Jun 8, 2008 10:51 PM in response to Daniel Pigeon

I run 10.5.3 and I just got the problem. This is a catastrophy for me since I help people to convert filmscript made in Final Draft/Screenwriter to PDF.
Some time it has helped to remove blank, scandinavian letters and brackets... but quite the attachemen t changes. Does anyone know if this behavior happens in any other program than mail?

One swedish thread suggested to send PDF.s with attachement "hidden", and so far it has worked.

Leif

Jun 9, 2008 5:20 AM in response to Daniel Kiechle

Hello!

Unfortunately, I upgraded my iBook with 10.5.3, and the same problem with Mail (v. 3.3) occurs.

I tried to save a Word document without the .doc extension, and the same problem occurs. The file named «Mystère médical 104» became «Mystère médical 10404».

This has definitely something to do with «foreign» characters.

Anxiously hoping for 10.5.4!

Good day!

Daniel

Jun 9, 2008 5:40 AM in response to Daniel Pigeon

Daniel Pigeon wrote:
I tried to save a Word document without the .doc extension, and the same problem occurs. The file named «Mystère médical 104» became «Mystère médical 10404».

Daniel,

This is not what I claimed the original problem was because I never attempted to send a document without its extension. Most of the time, the Mac does fine opening a document without extensions, but Windows must have the extension. Therefore, you should always include an extension, no matter what type of document you send. You should also check the "Always send Windows-friendly attachment" menu option.

Now, before 10.5.3, attachments I sent had characters added +to the extension+ when the file name contained foreign characters and/or spaces. In your example, «Mystère médical 104.doc» might have become "«Mystère médical 104.doc4». This is what I cannot duplicate any longer in 10.5.3 (I did try a few times).

Can you try this and see if you still have a problem under those conditions, i.e., menu option checked and extension added?

A+,

Daniel

PS Ah ! Le pays de Lynda... et de ma guitare Seagull !

Jun 9, 2008 8:38 AM in response to Daniel Kiechle

Daniel,

I tried to save a Word document without the extension just to check if the problem were to occur, and it did (10.5.3 and 10.5.2; Mail versions 3.3 and 3.2).

Now, I checked the menu option (window-friendly), and saved the Word document with the extension (.doc), and here we go again! Same problem.

In order to run a test, I reinstalled 10.5.0 on my iBook, and the problem DOES NOT occur with Mail version 3.0.

Is that interesting or what? Now I have to choose which bug annoys me the least, unless I can upgrade to 10.5.3 without upgrading Mail... Is it possible?

Anyway, thanks for all the info you provided, and let's hope Apple comes with a fix soon!

Ciao!

Daniel

Jun 11, 2008 3:00 AM in response to Daniel Pigeon

Unfortunately, I have to confirm that the problem still exists with 10.5.3.
An attached PDF with a german 'Umlaut' ä in its name changes its extension from ".pdf" to ".pdf0".

A workaround may be: Sending Html-Mails. I have not done a lot of testing, but so far it seems to work here. I've changed the setting in Mail's preferences and it seems that there has to be an "html element" in the body of the email (like bold or colored text etc.), which forces Mail to send it as "Content-Type: text/html;" (if you have just plain text, Mail will send it as "Content-Type: text/plain;", no matter what you have set in your preferences).

Yes, I know that html-mails is a no-no, but until Apple fixes this I will do it this way.

Greetings,
Peter

Jun 11, 2008 3:58 AM in response to Peter Heilingbrunner

Thanks, Peter.

I will try that when I get tired to save my documents without accent!

Cheers!

Daniel

Mail changes attachment extension