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

Hi Steff. I didn't have to change any settings. After sending by SMTP the item moves into the 'Sent' folder and that then syncs with the 'Sent' folder on the Exchange Server. I've not had a problem with that but it does take a short while to get fully synced up.

Colin

Hi Colin,

thanks for your reply. I just tried to send 25MB, sending is no problem, but exchange-sync (into sent items folder on the exchange server) doesn't work.

Did you try with those mail sizes?

Thanks once again

Steff

Hi Steff. First the good news: yes, I just sent a 22mb file and after sending was complete it synced with the Exchange Server account and appears in 'Sent items' on it.

The bad news is that the email took almost an hour to send. It was stuck for the majority of that time right at the end of the sending progress bar with an upload speed of 0kb/s. It was only because I forgot about it that I let it go on that long, normally I would have aborted it and would have assumed it wasn't going to finish.

So there's still something wrong I'm afraid.

Colin

I noticed this sent items thing as well.

My problem is, I'm blocked from using SMTP to relay inbound (Exchange locked by corporate policies).

To add to the noted symptoms, my limitation/issue seems to kick in around 8MB-10MB± when not on the corporate VPN (have 20Mb pipe). If I'm on my company VPN, everything is fine.

My one other issue in Mail.app seems to be spurred by this size limitation issue above but not always. I have multiple accounts config'ed (Exchange 2007 account, IMAP to Exchange 2003, and GMail). Each account is set to ONLY send email through it's own SMTP connection (and Exchange 2007 through it's weird pseudo SMTP server). The issue is, when attempting to send email while outside my corporate network (no VPN), Mail.app sometimes sends through other SMTP servers - even though the check boxes are all set to ONLY allow email out through respective accounts.

I would like to NOT use EntouRAGE but these issues are ridiculous!

I was able to resolve my large file sending problem using the following commands

These instructions are tailored to Windows Small Business Server 2008 (SBS 2008) but they should work just fine with a standard exchange implementation


C:\Windows\System32\inetsrv>appcmd set config "SBS Web Applications/EWS" -section:requestFiltering -requestLimits.maxAllowedContentLength:<size inBYTES>

For Full Blown Exchange 2007 you might want to use or whatever your sitename is where EWS lives in your environment
C:\Windows\System32\inetsrv>appcmd set config "Default Site/EWS" -section:requestFiltering -requestLimits.maxAllowedContentLength:<size inBYTES>

Say you want to allow 50MB attachment the command should read as follows:
C:\Windows\System32\inetsrv>appcmd set config "Default Site/EWS" -section:requestFiltering -requestLimits.maxAllowedContentLength:52428800

this number will need to correspond to the maxRequestLength value in (this value will be in KB)
C:\Program Files\Microsoft\Exchange Server\ClientAccess\exchweb\EWS\web.config

<requestLimits maxAllowedContentLength="51200" />


I was put on to the right track by the following websites
http://www.fixya.com/support/t2879052-cannotsend_large_email_attachmentsnow
http://msexchangeteam.com/archive/2006/11/14/431477.aspx
http://www.exchange-genie.com/2007/11/how-to-set-message-size-limits-in-exchange -2007/

This is a server side issue.

Have your Exchange admin fix the IIS/EWA portion of the server to allow large posts.

this is for Entourage, but it uses the same mechanism. http://support.microsoft.com/kb/935848

here is another method. http://www.technotes.co.uk/snow-leopard-mail-with-exchange-2007-attachment-size

Hi,

i have also had those issues and also solved them by using SMTP to Exchange 2007 instead of using the built in EWS connection of Mail.app.
I still had issues with sending large eMails using SMTP as i am on a low bandwidth connection (1 mbit/s). This because the default 'ConnectionTimeout' setting on an Hub Transport servers SMTP send connector is 10 minutes. I increased this to 30 minutes and could send large emails without issues.

Hope this helps 🙂

Hi,

thx for the SMTP idea. How do you increase the default connection timeout?

Thx for your help.