MAC size attachments in SBS2008 vs. SBS2011

I have a few SBS2008 servers running fine. However when there are MACs involved using "Mac Mail" for Exchange email, there are issues with attachment size settings. I set the server to 20MB's. Works fine with Windows PC's in the SBS domain but the MACs (not in the domain) obviously don't take advantage of the settings.

I know there are sbs2008 server settings specifically for the MAC's but they don't work. At least I have had no luck

My question: Is this issue resolved in SBS2011 ?
I asked 2 different Microsoft SBS techs this question and they did not know. Bottom line, Microsoft isn't always the first place to go for Microsoft server support. It is what it is! This is why we have this site.

Before I decide to build an SBS2011 server to replace the SBS2008 server, this MAC issue is my primary concern. I know there are other benefits such as "workplace" vs. "Remote Web Access" - not enough for me to go to 2011 at this time
Andreas GieryicComputer Networking, OwnerAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Lee W, MVPTechnology and Business Process AdvisorCommented:
MAC to me is Media Access Control Address.... I don't THINK you're talking about this but I'm not sure.... are you talking about Macintosh OS X based computers or network attachment limitations - the latter doesn't make sense to me but frankly neither does a "special limit" for Macintosh computers.

(It may seem silly but I've had people say one thing and mean something else - proper terminology is important if at all possible)

Assuming for the moment you're talking about e-mail attachments in Exchange, then I'd ask you why you think OS X based applications don't work properly?  As a rule, when I set message size limits, I make sure ALL transport mechanisms are set at the same levels.  For more information I'd suggest reviewing the blog below: and note that some mail applications (such as Entourage) may use the web based (EWS) transport.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
David AtkinTechnical DirectorCommented:

Just out of interest, why are you upgrading the SBS2011?   I'd be surprised if you can get your hands on the software now unless you have an existing disc and licence.

I'd consider moving to Windows Server 2012 Essentials with Office 365.

Lee is correct regarding the message limits in Exchange.
Andreas GieryicComputer Networking, OwnerAuthor Commented:
Sorry for the delay, I replied the same day with a  very large reply and somehow it wiped out my reply. I'm responding now by creating my reply in a document and ten pasting it here.
The 7 Worst Nightmares of a Sysadmin

Fear not! To defend your business’ IT systems we’re going to shine a light on the seven most sinister terrors that haunt sysadmins. That way you can be sure there’s nothing in your stack waiting to go bump in the night.

Andreas GieryicComputer Networking, OwnerAuthor Commented:
“MAC to me is Media Access Control Address”

Folks, I was a little thrown off by this reply and wasn’t planning to respond to this but hoping for more of a response to my posted questions.

Anywhere you read about computers, folks refer to Macintosh computers (Mac Book Pro or iMACS) as MACS. Yes, I was referring to MACS.

There is a difference how a MAC or a PC handles attachment sizes. The link provided, I am familiar with - setting attachment sizes for Windows PC’s (whether they are in the domain or not).

Mac users connect via EWS, which has different limits.
You need to change the EWS limit. This requires a registry change and/or editing the web.config

I apologize that it’s taken this long to reply but I really was hoping to get help from someone who is familiar with MACS in an Exchange environment. Only the MACs are having issues with attachments over 10MB’s the Windows PC’s are fine

If I’m wrong, please correct me
Lee W, MVPTechnology and Business Process AdvisorCommented:
So you're angry with me because I took issue with poor terminology and thus you don't want to read the link I provided which has a potential answer to your question?  

Quoting my previous link:
Exchange Web Services (EWS)

Just like OWA, EWS is bound to the maxRequestLength value in it’s web.config.  The default value for this is 13280 KB (13 MB) and can be changed to the value you require.  Clients such as Entourage for Mac would be affected by this value.  For more information, please read:

How to allow Microsoft Entourage 2008 for Mac, Web Services Edition to send large e-mail message to an Exchange 2007 server running on Small Business Server 2008;EN-US;2500318

Now if you actually looked through it and it didn't work, you need to say so before we waste time hypothesizing what else might be wrong.
Andreas GieryicComputer Networking, OwnerAuthor Commented:
Lee, I did not come here to get into a "pissing" match with anyone. I truly appreciate your feedback and you have been very helpful in the past. I brought up the reference with "MACS  because everyone one on this portal knows what it is and its assumed by my post. My concern was that your expertise may have been with Windows and perhaps not a MAC - that's all. I did not and have not researched your background expertise although I'm sure its exceptional.

The first link you provided is helpful with Windows systems. Macs with Exchange 2007 require additional settings on the server with attachment size issues. I know the recommended settings but have had no luck, thus looking for more assistance with other techs who may have come across the same issue. I did see a link within this article about EWS ";EN-US;2500318" but the link would not open

Your last link (which is the same link;EN-US;2500318 ) did not work again.
Andreas GieryicComputer Networking, OwnerAuthor Commented:
the article
How to allow Microsoft Entourage 2008 for Mac, Web Services Edition to send large e-mail message to an Exchange 2007 server running on Small Business Server 2008;EN-US;2500318 

Although  I cant open it up, I know it relates to Entourage. I am familiar with the settings but I have had no luck making this work for Mac Mail (default email client for Mac)

The user doesn't want to use Entourage or Outlook for Mac.
Andreas GieryicComputer Networking, OwnerAuthor Commented:
I was able to resolve the URL for the EWS to this address:
Lee W, MVPTechnology and Business Process AdvisorCommented:
I cannot control your reactions.

"I did see a link within this article about EWS ";EN-US;2500318" but the link would not open"

If you have trouble opening a link sourced from MS and posted, then respond back.  A simple tip that would have been to google 2500318.  The KB Article number of the link.

In my experience - on this web site and working with others, problems get resolved fastest and best when there is a dialog and people use proper terminology.  When you go off on your own and get upset at the reactions or inability to get a one comment answer you don't help obtain a resolution any faster and usually delay getting a solution.

Best of luck.
Andreas GieryicComputer Networking, OwnerAuthor Commented:
Lee, again I appreciate all your input. Please lets drop the "MAC" thing. It was a total waste of time for both of us. I should never have responded to the "MAC" reference.

I did google the link and located the URL prior to your last post.

The original Link you provided was helpful but still didn't resolve the issue. I found a very similar link. It contained one additional command for OWA and it worked.   

The article "How to allow Microsoft Entourage 2008 for Mac. . . . " was geared to Entourage and no mentioning of MAC Mail - but its was all thats available I found and it helped towards resolution

So here's everything I did to get the attachment size issue from a Mac to work.

Entered the follow
C:\Program Files\Microsoft\Exchange Server\ClientAccess\exchweb\ews

C:\Windows\System32\inetsrv>appcmd set config "SBS Web Applications/ews" –section:requestFiltering –requestLimits.maxAllowedContentLength:50000000

Note for Small Business Server (SBS) 2008 users:

Ran the appcmd lines, but modified as follows:

appcmd set config "SBS Web Applications/ews" -section:requestFiltering -requestLimits.maxAllowedContentLength:50000000

appcmd set config "SBS Web Applications/owa" -section:requestFiltering -requestLimits.maxAllowedContentLength:50000000

Andreas GieryicComputer Networking, OwnerAuthor Commented:
thanks for all your input
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.