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Level 1

24 points

Mail 4.0 (Snow Leopard) not sending "bigger" attachments Exchange 2007

We are using Apple Mail 4.0 (Snow Leopard release) with Exchange 2007. Almost everything works like a charm except when we try to send attachments which are bigger than (estimated) 4 MB.

We can exclude an issue with our Exchange setup as even attachments larger than 100 MB work if sent via Entourage.

Mail's Activity Viewer indicates

Sending message
Adding messages

with the blue progress bar animated but not finishing for hours.

If anybody has any hints how to resolve – or further troubleshoot – the situation, that would be greatly appreciated.

Best,
-Ralf

MacBook Pro (Unibody), iMac, Mac OS X (10.5.7), iPhone 3GS 32GB, iPhone 3G 16GB, iPhone 16GB (all on OS 3.0)

Posted on Sep 8, 2009 6:11 AM

53 replies

Bytec

Level 1

0 points

Dec 23, 2009 1:28 PM in response to doctormidnight

The same here with two german exchange hosting providers. I´m not be able to sent attachments >4MB
With entourage it´s no problem but I won´t change to that.

I hope Apple will fix it soon.

Greets from Germany

Feb 7, 2010 9:30 AM in response to Bytec

Does anyone have any news on this issue - it's very, very frustrating to have to login to my Exchange Server in a browser with Outlook Web Access in order to send an email with a so-called 'large' attachment - 2mb in my case.

Colin

Feb 17, 2010 7:41 AM in response to colinharbour

I did it with

http://www.fixya.com/support/t2879052-cannotsend_large_email_attachmentsnow

Solution #2

Christoph

Feb 17, 2010 8:17 AM in response to csternberg

Thanks for the link; however, my Exchange is a hosted service from Sherweb which has set an attachment size limit of 50mb. That file size sends fine via Outlook on PC, Outlook Web Access (i.e. in a web browser) and MS Entourage on Mac.

The problem definitely lies within the Apple Mail support for Exchange.

Has anyone any other ideas?

Colin

Feb 17, 2010 10:19 AM in response to colinharbour

In my case it also was possible to send via Entourage, OWA and Outlook, but not with Apple Mail. It was definitly the change of the limit in maxRequestLength of web.config in the ews webpage (default was 13280 KB) that did it for me. But I admit, that there must be an error in Mail, that this parameter has to be increased to make it work.

Christoph

Feb 18, 2010 1:05 AM in response to csternberg

Now that's very interesting. I'm going to try to get Sherweb to change that setting, I've always had great service from them so hopefully they'll agree.

I'll re-post here soon.

Thanks very much Christoph!

Colin

Feb 19, 2010 2:06 PM in response to colinharbour

@colinharbour

I am on Sherweb too. Please let me know if you get them to change the setting. It's a pain to have to switch back to my Outlook on Windows to send large attachments. And one day 20 emails got stuck in my outgoing queue and I didn't know it.

Frank

Feb 21, 2010 2:56 AM in response to boecherer

A very prompt reply from Sherweb support but it doesn't look hopeful:

"I'll pass the request to my admin, but I doubt any change will be made on the server since those changes were not tested and are for a software we do not support"

It looks like we'll have to wait for Apple to fix it.

Colin

Feb 21, 2010 2:56 PM in response to colinharbour

Thanks for checking and posting back Colin. This is just crazy that Apple cannot write a recent mail client that can send > 4MB. Now I have to remember one MORE thing for my clients. "Dear client, Yes, Apples are good, but if you want to send large attachments (>4MB which isn't THAT large) we'll have to use another mail client." And what else do we use? Entourage? I guess we'll have to give MS some more money since Apple can't do it right. I'm sure Apple is blaming MS (Exchange) for the problem, but at the same time it puts more money into MS's coffers.

TimTimTJ

Level 1

0 points

Feb 25, 2010 8:44 AM in response to BeSharp

Try using your Exchange host's SMTP server as the outgoing mail server. This cleared up the large attachment issue. Sure, it's a pain as there is an extra setup step but you can now at least see the progress of the outgoing mail (shown in percentage complete in the Mail activity window).

Give it a try...

Tim

Mac Pros
MacProsConsulting.com
877-622-3491

Feb 25, 2010 9:06 AM in response to TimTimTJ

Thanks for the tip Tim. I'll check into it. It was my understanding that Sherweb blocked SMTP for security/spam reasons, but it looks like they might offer it based on their support pages.

Question: If I use SMTP for sending, do I need to use POP for receiving? And in either case, how will my email get synched with the Exchange server? Do I leave the Exchange mode intact and set up a POP/SMTP connection just for sending and the sent mail will go into the Sent items folder and get synched with the Exchange server?

Frank

Feb 25, 2010 10:47 AM in response to boecherer

You know what? Using SMTP to send mail is the workaround! Well it is for me anyway. I don't know if Sherweb allows SMTP mail on its hosted Exchange Server accounts, but I've got another SMTP server I can use.

I set up the SMTP configuration in Mail preferences, ticked the box so that Mail ONLY uses that server for sending mail and off it goes. The sent mail still goes into 'Sent' in Apple Mail so it syncs with the Exchange Server and appears in my iPhone 'Sent' too.

BINGO!!!!

Thanks so much Tim, you're a star!

Feb 25, 2010 10:58 AM in response to colinharbour

Thanks guys. I'll give this a try. I guess I won't wait for Apple to fix this one since it's been a problem since 10.6 day #1. 😉

Frank

Mar 5, 2010 12:38 PM in response to boecherer

Tim and Colin:

Thanks for the SMTP tip. It seems to work. I'll test it some more for a few days.

I did get a 7MB attachment to send out and possibly another one got stuck. BUT at least SOMETHING is going out whereas with Exchange mode, nothing would go out if it was too large.

I'll test a little more and update you once more.

Frank

SteffMu

Level 1

0 points

Mar 9, 2010 1:52 PM in response to colinharbour

Hi there,

I also setup a separate smtp-server, but Mail doesn't save the large sent mail (> 7MB) to "sent folder" for my configuration.

I can send out large mail now (I tested up to 50MB), but those mails never appear in Apple Mails "sent folder".

Is there anything to adjust? Or does it just take a long time for the mails to arrive in the sent folder?

Regards,
Steff

Mail 4.0 (Snow Leopard) not sending "bigger" attachments Exchange 2007