Mail will not send attachments

What indicates you cannot send attachments? Any errormessages?

Here is what I discovered:
1) When I send email with an attachment (2 screendumps that I just made) to my Tiger mailserver at home (over the internet) the transmission stops (in this case) at 27%... Looks like the connection was lost... Mail.app tells me that it cannot send email using this smtp-server and offers me to choose another one...

When I look at the log-file on the server at home I see:
Nov 29 08:13:48 Server postfix/smtpd[17690]: timeout after DATA from pbo....




2) I changed SMTP-server to a relay SMTP-server at the office and retransmitted this email...
The SMTP-server accepted the email and tries to send it to the next relay-SMTP-server...
The process aborts with the message that the 2 SMTP-relays lost the connection while sending the body. This means that while the message has gone out of my Mac, it will probably NEVER reach it's destination!!!

I then logged in onto the relay that the Mac sent the email to, the relay that cannot send it to the next relay.... I went to the postfix directory and found the 'deferred' email...

When I looked at that email-file I was surprised to see that it looked like a mess... Not the kind of email-files that I was used to (I have been a postmaster for many, many years, so I know what email-files should look like!)... It seems that Mail.app has created an outgoing-email-file that is far from perfect, and that SMTP-servers are having troubles receiving those...


Sure wish Apple fixes this problem soon!!!

Message was edited by: Adam van Gaalen

Message was edited by: Adam van Gaalen

Adam, Roger and others,

I have had no problems sending attachments in Mail with Leopard. The only issue was a sluggishness in connecting to any SMTP, but this was not dependent upon there being any attachment.

Typical causes, which may or may not impact all applications would include the MTU (maximum transmission unit) and occurs because a particular application or computer sends too large a packet size. Please check my post at the link below for what might apply to your situation.

http://discussions.apple.com/message.jspa?messageID=6557095#6557095

Another cause can be the use of a SMTP that is not the preferred name or preferred method of authentication for the provider, but which is allowed to relay, but in some cases with large messages, times out.

More info, please.

Ernie

Adam - Thank you very much for the reply!

Since my post to you, I set up a new partition on my drive, and installed Tiger and NetZero (my dial-up ISP) software. I sent a test email from Tiger Mail (2.x?) with an attachment, and got the nice "woosh"! I restarted in Leopard, went to Mail, and my test message with the attachment was there! Cumbersome, but a workaround, nevertheless! I think this adds additional proof that this is a Leopard issue.

I sent this message to another forum as well, and will post at Apple also:

http://discussions.apple.com/thread.jspa?threadID=1399764&tstart=0

I'll keep my fingers crossed like you that this is a Mail versus TCP issue! Now to look at WireShark....Thanks again! Bill

Ernie,

I have been able to send attachments too! It's not all attachments that fail, it's "some do, some don't".

Deliver to people in (one of) my domain(s) or relay to others... That's not an issue here... The SMTP-server handles that AFTER the email has come in... And, when problems arise, the email will not come in at all!

In this post: http://discussions.apple.com/thread.jspa?threadID=1389997&tstart=15
people say they have problems sending to DSL-lines (only?)... My problems show up when I send email from the office to my ADSL-Tiger-mail-server at home...

Fixed IP or dynamic IP has nothing to do with this. That is just a way to get your IP-address (ethernet-inferface) configured...

Now how do we go from here?

How do we get Apple to look at this (I feel: 'URGENT') problem?

Jens,

As Adam has said, yours is a different problem. See:

http://support.apple.com/kb/TS1152

and

http://discussions.apple.com/thread.jspa?messageID=5748076&#5748076

You probably only need to change to Port 587.

Regards,

Ernie

Actually, with tests we have done we know it is not an issue of MTU for Adam. However, I feel that when and if we eliminate other poster's issues it will be constructive in confirming the uniqueness of Adam's problem. It is a factor that when Adam declares his problem to be quite common, lot's of people jump in with other types of sending issues.

I think there is another topic that may relate to Adam's issue, and bears following -- see:

http://discussions.apple.com/message.jspa?messageID=6763897#6763897

The time necessary to send with attachment may impact the continued acceptance of the SMTP that is not authenticated, but is screening how it is used. But not sure, since Adam's issue seems quite narrow and specific to the network he is setting on when this happens.

Ernie

Hello all,

The cause of the (#2-type) problems that we were trying to pinpoint here, the problem which drives Mail.app crazy, is the problem that was reported in: http://discussions.apple.com/thread.jspa?messageID=6906443

Avoid blank spaces in the filename, and your attachments will probably go out without any problem.

Come on 007, have that fixed!

If you can let us know what SMTP you are using, it would be helpful. Is is the schools? Is it your own. Only idea I have would be if the school were somehow limiting message size through their ports. You might also save a text file in text edit, just some words so is is around 10kb or less and see if that will send at all.

If you are using some school supplied SMTP, try another if it is a possibility.

Wish my HS had a network students were able to use at free will, heck wish my college had.

Yeah, I just suggested the file size, because it is odd that you can send emails, but not ones with attachments. None the less, can you attempt attaching a small file and sending?

If you can do so on webmail, it is definitely something with the SMTP and it's ports. I have just never heard of an issue where only attachment emails are being held up. Rather bizarre. My other suggestions would be find out what port the Windows machines are using and make sure yours matches, and compare setting between the two.

Does your school require authentication on the SMTP, you could try turning that on and seeing if it helps, perhaps someone else in the forums has heard of a similar predicament?

Hi,

I've been looking for a fix for what I think is a bug in Mail under Leopard. I've also been having a similar problem however I can send mail with attachments. I find the problem is getting the attachments into the message in the first place. The only way I've been able to get it to work is to create an email, save it as a draft, then reopen it and attach the files. At this point mail will load the attachments and send the mail. I'm not sure if this will work for you but it's worth a try.

Message was edited by: vastphoto

Has this been solved now? My colleague seems to be having the same problem with his Mac (at home). He can receive emails fine, whether or not they have attachments, and can send emails without attachments. However, he's getting an error message on the Mac (ie not a bounce report via email) when he tries to send a message with an attachment.

He apparently can't send messages with attachments from his ISP's webmail site either, which would lead me to believe that it's an ISP issue rather than a configuration problem on the Mac.

Unfortunately I don't have details of his system ('a standard iMac, bought in October this year') or of the error message he's getting.

He's just trying to test the webmail issue by connecting and sending something from his Windoze machine at work, but can you suggest any other tests he can do or things he can try? He's explored most of the prefs in Mail and Finder/System but he's a new Mac convert so I'm trying not to scare him off!

Thanks,

C.

So far Apple did not fix this Leopard-related problem. It's a real pain!!!
Some attachments go through, others won't...

I installed Eudora on my MacBook Pro just to be able to send attachments, which is crazy!!

Come on Apple help us Leopard-users!

Hello,

I am having problems sending attachments as well. It started a couple of weeks ago (without me making any changes to prefs, upgrades, etc) where certain people will receive the email that I sent, but not the attachment(s). On my end (sending), everything seems to work fine. If I BCC myself, I receive it with the attachment, but they do not. I send about 20 emails per day with attachments while at work, so it was quite a shock when all of a sudden I started receiving ~7 return messages per day saying "you forgot the attachment!". I have three email accounts on Mail, and all three do the same thing (and all started at the same time). Everything seems to work fine if I send the mail from the web. I am NOT yet on Leopard (still on 10.4.11). Yes, "Always send Windows friendly attachments" is selected, and all recipients are on PCs. This has really become a major problem for me and I don't know what to do!!! Please help!

10.5.2 seems to be an extra problem patch (come download 180MB of All New Problems! Plus 200MB Bonus Bugs if you download the Combi!) not a fix. They didnt even manage to fix the 'new mail sound not working' problem - how difficult could that be?