Entourage 2008 -> Exchange server 2007 errorssending attachments...

[BLMATX]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: Exchange

Exchange servers are Exchange 2007 rollup 7 on Server 2008 SP1 HT/cas roles installed on server A, Mailbox role installed on server B.

Clients range from 12.1.x to the new Web Services edition.

Sending files up to 100MB works from Outlook 2007, Mail.app, & Outlook Web Access. Only Entourage has an issue. It appears to be webdav related as IIS logs show /##DavMailSubmissionURI##/ with a status of 404.13

In troubleshooting I attacked that angle first and adjusted IIS 7's requestFiltering/maxAllowedContentLength on both servers to 104857600 bytes.
At this point the the -3253 errors became more rare although they still come up intermittently and the -18596 errors started.

I have changed that setting on the OWA virtual directory as well as at the machine level.
Attempting to set it for the Exchange virtual directory fails with a path not found error, even though I have created the Exchange virtual directory using the exchange management shell.

I also found an issue where if set to unlimited, Exchange defaults to 5MB attachment size so those configuration settings have been set to 100MB as well. (set-transportconfig maxmessagesize and maxreceivesize as well as on both send connectors)

Any help in resolving this issue would be greatly appreciated.

 

[Pawan Kapoor]

As you are on Exchange 2007 you have to set the attachment limit in IIS (as
Entourage interact with IIS) and on Transport server (responsible for
routing emails). for Entourage EWS you also have to set this limit in
web.config file.

thanks,
Pawan

 

[BLMATX]

Yes, I have done this. MaxAllowedContentLength has been set as noted in the original post. Also MaxrequestLength has been set to 102400 for owa, ews, and machine level config files. Is there another attribute I have missed in the web.config file?

Also of note, after an IIS reset this morning, I was able to send one message with a 50MB enclosure, but subsequent sends failed. I thought I had it narrowed down at that point, but another IIS reset did not yield the same immediate results.

 

[NNicholaou]

We worked with Microsoft support's lead tech and discovered the problem and fix. I blogged about it at <http://ministry-it.blogspot.com/2009/08/entourage-ews-attachment-limits.html>

 

[BLMATX]

That did the trick. I set the limits in IIS to triple the desired limit and it works beautifully. Thanks.