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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
Question marked as Best reply

Posted on Feb 9, 2008 5:39 PM

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
29 replies

Feb 20, 2008 11:36 AM in response to Ernie Stamper

Ernie - Thanks again for the reply. I checked the diagnostic page you recommended. I don't have wireless or ethernet...I'm in the sticks, and only have dial-up. (It took quit a while getting the 10.5.2 upgrade...but it did!). Is there a similar diagnostic I can us with dial-up? I'm using the Apple external modem. Also, please note that I can send attachments with no problem using Netzero as my SMTP server by restarting on my 10.4.10 partition and running Mail under Tiger. Mail works for me on Tiger...not on Leopard. Thunderbird works for me on Tiger...not on Leopard. Thanks again for taking the time with this.

Regards, Bill

Feb 20, 2008 2:13 PM in response to Ernie Stamper

Ernie - I just have standard Netzero install, which works fine on Tiger...with or without attachments. As a matter of fact, Netzero doesn't offer their "high-speed" service for Mac. I guess that iMac007 is implying, perhaps, at another post that you have participated in, that Apple knows something is wrong, and is working on it. Have you heard anything of this?
http://discussions.apple.com/message.jspa?messageID=6647530#6647530
Thanks again,Bill

Feb 20, 2008 2:24 PM in response to Bill Cruise

Bill,

I didn't really try to guess the meaning that analogy. I think Apple knew there were connection issues, and the update to 10.5.2 addressed those. I have no knowledge of further suspicions that Mail engineering might have in this regard.

The Mac I use Leopard on -- a Mac Pro -- has no internal modems. They are not an option, to my knowledge, from Apple. Were I to need dial-up, I would have to attach one via USB.

Ernie

Feb 20, 2008 8:27 PM in response to Bill Cruise

Thanks for your help, Bill.

A tech at my ISP decided to try and adjust my upload speed, but this apparently is a temporary fix. The tech said he didn't know how long the adjustment would "stick" - maybe for a couple of weeks.

I'm considering upgrading to a dedicated IP address or even T1 service. That can get very pricey considering it's just me on one Mac. But as I said, this problem is affecting my graphic design business - so if I must, I must. But before I switch, I just want to see if I can resolve this problem once and for all - or to at least be sure I won't have the same issue even with a T1 connection.

All I know is, I've been with the same ISP for years and I never had any problems until I upgraded to Leopard and to Office 2008.

And since I'm seeing so many people on this forum (and other Mac forums) having the same type of email problem - (getting the same error message though they're using various ISPs and email programs, including Apple Mail) - I can't help but think it's a Leopard issue.

I'll definitely keep you posted if I find any answers. Thanks again.
pjfiona

Feb 21, 2008 3:09 AM in response to PJ Fiona

Hi again PJ,

I would think what might be temporary about this "fix" is how the MTU was adjusted. If an entire LAN is powered down, and then everything turned back on the sequence the ISP suggests, then discovery of the proper MTU for proper uploading should take place someplace between the modem, router, and computers connected to the router -- if no router, should be easier. Computers (and applications) are now common that will communicate in a network at much faster and robust speeds than what can be achieved when going outside the LAN. This is why the balancing must take place, so that the connection is not overwhelmed during any upload.

Verizon was once famous when using Linksys routers to need MTU of 1492, rather than the 1500 default. Linksys used to have a special support document about how to change the MTU in the routers, so that all computers on the router will work. MTU of 1492 vs 1500 seems like a small difference, but it was (may still be but no confirmation) a critical difference.

The support document that I often link to here is for troubleshooting, and not the permanent fix. The longer term fix should depend on communication between the ISP and the user, and perhaps the manufacturer of devices used in the LAN.

See:

http://www.dslreports.com/faq/695

http://help.expedient.com/broadband/mtu.shtml

http://en.wikipedia.org/wiki/Maximumtransmissionunit

and

http://wiki.wireshark.org/MTU

Unfortunately much of what is written about MTU is oriented towards Windows, rather than OSX and Macs.

The need to "fix" the MTU arises only when the computer pushes the packet size and connection speed beyond what is optimum. This may be triggered by a new application, OS, modem, computer or other hardware.

What devices are in your LAN and connection to the internet?

Ernie

Feb 21, 2008 4:00 AM in response to PJ Fiona

PJ,

In addition, let me review: the only problem I have ever had with sending via any SMTP in Leopard was a sluggishness in connecting before beginning uploading content. In my case, this long delay in connecting never resulted in any timing out or failure to deliver. My issue, as I have posted elsewhere, was solved (unwittingly) when a tech with my ISP, chasing a completely different issue (turned out to be on their end) had me enter primary and secondary DNS addresses in my modem (their modem, actually), rather than have that take place automatically as is the normal default situation.

As long as you are in contact with a tech from your ISP, it might be worth asking him/her to try that in your situation. It could be that would eliminate a cause of timing out, if that is a fair description of your issue.

Ernie

Feb 21, 2008 5:45 AM in response to Ernie Stamper

Hi Ernie,

Again, I appreciate your help with this.

On your earlier advise, I ran a test and found that my MTU was set at 1492 (for my PPPoE DSL modem with no router) - and long before the Leopard upgrade I had configured my settings with primary and secondary DNS addresses given me by my ISP.

It's so very frustrating! I've been dealing with this for better than 3 weeks now.

Apples says it's a problem with my ISP or with Entourage - Microsoft says the problem is with Apple or with my ISP - and my ISP says the problem is with Apple or Entourage. As I've said at the beginning of this discussion, I've tried all kinds of tips and advice from Apple Forum, Entourage Help Page, MacFixIt, Mac Owners Support Group, Mac OS X Hints, Microsoft Office Support, etc. etc. - and even Google searches!!

I'll probably give it a couple more weeks and then upgrade my ISP service to see if that solves the problem. With my current workload, trying to solve this issue is starting to take up way more time than I can afford to spend.

pjfiona

Feb 21, 2008 7:22 AM in response to Ernie Stamper

Hi Ernie,

I don't understand your question. When I turn on my computer in the morning, I go to my modem icon in the finder menu bar, click and scroll to "connect." I can see the couple of second it takes to authenticate and connect. Once connected I don't see any kind of constant status bar or anything like that - just the icon. It stays connected until I disconnect, shut down - or when I try and send a large attachment and it "times out."

pjfiona

Feb 21, 2008 7:32 AM in response to PJ Fiona

The ISP tech should be able to give you an address you can enter into your browser, and the pages that will show what is in the modem. The address may be on the order of 192.168.xxx.xxx. That will then require the entry of an Username and Password, which often are the defaults of admin & admin. This is something you should only do while you have the tech on the phone, probably. If like mine is now set, then Dynamic DNS will be disabled, and the screen in Setup for DHCP Configuration will contain the DNS addresses he has given you.

Ernie

Can't send large attachments

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