Can't send large attachments

Question

Level 1

20 points

Can't send large attachments

I recently upgraded to Mac OS 10.5.1 (Leopard) and a couple of weeks ago to Entourage (Office for Mac 2008).

I can connect, surf the web, and receive emails with large attachments as usual.

I've been very happy with Entourage for years. But now using Entourage (or even Mail, or Thunderbird), I can't send emails with attached files over 200k or so. My connection times out and I get either of the following error messages:

"The connection was terminated by the remote site. Please try again."

OR

"Operation on the server timed out. The server may be down, overloaded, or there may be too much net traffic."

My ISP checks everything out as okay on their end. I uninstalled my Firewall and AntiVirus programs. I changed the smtp port to 587 - check "SMTP requires authenication..." - deleted and created a new account to manually and carefully input my settings. Tried all the tips from the Entourage Help Page, MacFixIt, Mac Owners Support Group, MacTopia, Microsoft Office Support, etc. etc. I'm at my wits end!

I'm a graphic designer who regularly sends small and large pdf (500k - 2 MB) files to clients. At this point I'm sending clients large files via Gmail - which is slow sending and slow getting to clients compared to what I'm used to with my previous Entourage. This is getting in the way of my work.

I'd really appreciate any help anyone can give me.

Thanks,
pjfiona

G5, Mac OS X (10.5.1), G5 PPC, 2.5 MB memory, Cinema HD display,

Posted on Feb 9, 2008 9:55 AM

Reply

Answer 1

Best reply

Ernie Stamper

Level 8

37,591 points

Feb 9, 2008 5:39 PM in response to PJ Fiona

Hi,

There are two possible issues that are prime candidates for the cause of this. One is MTU (maximum transmission unit) -- this might get resolved by powering down modem, router, and computer and restarting them all too allow your network to balance to the MTU that best works with your ISP and connection. If cabled, a bad cable can act much like this. For more about MTU, see:

http://docs.info.apple.com/article.html?artnum=303192

However, if things were working in Tiger, another issue that is discussed in the topic at the link below may be at the cause of this. See:

http://discussions.apple.com/message.jspa?messageID=6557086#6557086

Ernie

Reply

Answer 2

PJ Fiona Author

Level 1

20 points

Feb 11, 2008 5:59 AM in response to Ernie Stamper

Thanks Ernie,

I tried to power down as you suggested - even unplugged the modem, waited a couple of minutes and plugged the modem back in to reset it. But I'm still having the same problem. I checked out the links you gave me. I do have DNS addresses for my modem that my ISP had given me previously. I'll now call my ISP to see if they will adjust my MTU.

pjfiona

Reply

Answer 3

Feb 11, 2008 6:30 AM in response to PJ Fiona

Hi,

Typically it is your network that must adjust to the MTU that will match the ISP best. MTU can be adjusted in certain routers, or if not, on the computer. This is not thought of as related to the other issue that using the DNS addresses might solve.

Also, since I think there are connectivity issues in Leopard, I am hopeful the next update will fix, but this is not related to MTU, if that is what needs to be addressed.

Ernie

Reply

Answer 4

PJ Fiona Author

Level 1

20 points

Feb 11, 2008 8:45 AM in response to Ernie Stamper

Hi Ernie,

I don't have a router. My modem is connected straight to my Mac via the ethernet cable. So is adjusting the MTU something I could do myself? Is it something I should do myself - or is there a chance of making matters worse?

Thanks for your help so far.

pjfiona

Reply

Answer 5

Feb 11, 2008 9:08 AM in response to PJ Fiona

PJ Fiona wrote:
"Operation on the server timed out. The server may be down, overloaded, or there may be too much net traffic."

I have a similar problem in that I have recently switched Internet service providers here in the U.K. from Demon to TalkTalk. Since doing so I can't send mail from the TalkTalk account but I can receive mail into it.

The annoying thing is that everything worked fine on my wife's Windows PC when I set her new account up.

TalkTalk have suggested that I need to change the MTU on my Mac from 1500 (which they say is the Mac's default setting) to 1432. On searching Mac Help it explains how to do this in Tiger using an Ethernet connection but for Leopard using Airport it states to go into Mail Help and follow the instructions - not very helpful because there aren't any.

Does anyone know how I can adjust the MTU to 1432? TalkTalk did mention something about using a SUDO Command but didn't know the actual command to use and suggested that I contact Apple support.

Thought I would try you knowledgeable people first in the hope that someone can help.

Thanks, Mike

Reply

Answer 6

PJ Fiona Author

Level 1

20 points

Feb 12, 2008 4:28 AM in response to Michael J Roberts

Mike and Ernie,

I just saw that yesterday Apple posted a Leopard 10.5.2 update on their site that, among other things, "Addresses an issue in which Mail might not send mail on some networks to some SMTP servers." I'll update tonight. Hopefully this will resolve the problem for all email programs - not just Mail. I'll let you know how it works. See the following:

http://docs.info.apple.com/article.html?artnum=307109
http://www.apple.com/support/downloads/macosx1052comboupdate.html

Thanks,
pjfiona

Reply

Answer 7

PJ Fiona Author

Level 1

20 points

Feb 16, 2008 12:56 PM in response to PJ Fiona

Okay - so I upgraded to 10.5.2 and my email problem is STILL not resolved!

This is a real pain since I regularly NEED to send attachments larger than 200-300K for my work. Does anyone have any other suggestions? I'd really appreciate the help!

Thanks,
pjfiona

Reply

Answer 8

Feb 18, 2008 5:52 PM in response to PJ Fiona

I have the same problem after the Leopard upgrade. I had no problems with large attachments with Mail or Thunderbird on Tiger.

I have found two work-arounds...both are cumbersome, and I don't believe either is acceptable, but they do work for me. 1) Send mail from your ISP's webmail facility (or gmail, for example). or, 2) I have made a new partition on my disk on which I (re)installed Tiger. I can drag attachments or other info into this partition from my Leopard disk, then restart in the Tiger disk. From Tiger, I can compose and send email from Tiger's Mail app. Aaaaaargh! Good luck! Bill

(I have posted this in other replies also).

Reply

Answer 9

Feb 18, 2008 6:00 PM in response to PJ Fiona

As a follow up to clarify - I don't want to use the work-arounds in the long-term...they work just fine for now, and I think it better than not being able to send attachments! It didn't take more than an hour to set up the new partition and install a minimum Tiger OS. Bill

Reply

Answer 10

Feb 19, 2008 5:03 AM in response to Bill Cruise

Bill,

I would assume since you have reported using 10.5.2, that your Mail is now v 3.2? Please clarify.

Also, when you attempt send with attachment in Mail 3.x, please open the Activity Monitor and report how much time is being spent connecting to the SMTP before actually beginning to send content?

Ernie

Reply

Answer 11

PJ Fiona Author

Level 1

20 points

Feb 19, 2008 5:41 AM in response to Bill Cruise

Thanks for your help, Bill,

I have begun to send large attachments via my ISP's webmail. But I can't be assured how fast my clients will receive my pdfs, which can be "time sensitive" when I'm under deadline. I'll consider your partition idea - but you're right, that is really cumbersome - especially since I send many large attachments throughout the course of my work day.

pjfiona

Reply

Answer 12

Feb 19, 2008 5:06 PM in response to Ernie Stamper

Ernie - I'm sorry to take so long to get this info to you...I've been out all day. In response, I'm running 3.2 Mail. I've run the following tests showing the elapsed time after hitting "Send":

Attachment size 98KB Pages document 68 KB PDF

Activity Monitor
Delivering message
Connecting to SMTP server 12 sec 9 sec
Sending Recipients 16 sec 10 sec
Sending message - 100% 20 sec 10 sec

"Cannot send the message" error 9 minutes 8 min 51 sec

After the "Sending message - (100% done)" completes, the Mail activity indicator is about 99% complete, and indicates sending at 0 KB/s. This goes on for about 8 or 9 minutes until it fails. The "Sending message" bar continues to display "100% done" during this period of time.

Interestingly, I haven't seen the "Cannot connect to SMTP server" message tonight that I see frequently. Tonight all I've seen is the "Cannot send the message content to the server" error.

I greatly appreciate the time you take to look at this! Regards, Bill

Reply

Answer 13

Feb 20, 2008 2:32 AM in response to Bill Cruise

Bill,

Who provides this SMTP, and how is it authenticated?

Ernie

Reply

Answer 14

Feb 20, 2008 7:41 AM in response to Ernie Stamper

Ernie - I use Netzero...authsmtp.netzero.net. Port 587 with password authentication. Text messages are sent immediately...no problems. Emails are received, with or without attachments, with no problem. I have the same problem with Thunderbird, though, as I do with Mail. I'll be installing Eudora today for a test. The connection to Netzero works fine with Safari. Thanks again! Bill

Reply

Answer 15

Feb 20, 2008 8:00 AM in response to Bill Cruise

Bill,

Did you ever run the diagnostic described at:

http://docs.info.apple.com/article.html?artnum=303192

How are you connected -- wireless or ethernet cable? If the latter, it is very simple to run that diagnostic.

Ernie

Reply