Exchange 2010SP IPhone/Cannot Send Mail

Cannot Send Mail. The message was rejected by the server because it is too large. I have few Iphone users that keep getting this error.  I checked the E2K10 DB and user mailbox for any quota limitation and all is good. Please help!
tomfontanillaAsked:
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Alan HardistyCo-OwnerCommented:
Is it your server doing the rejection or a 3rd party server?

Have you modified the default send/receive limits of 10mb globally?

Alan
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tomfontanillaAuthor Commented:
I tried that, no luck!

C:\Windows\System32\inetsrv\appcmd.exe set config "Default Web Site" -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost
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MurfurFull Stack DeveloperCommented:
What is the server quota limitation and how big is the attachment?
What app are the iPhone users using to send the message (I could assume Mail but safer to ask!)
What is the exact error message?
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tomfontanillaAuthor Commented:
"Cannot Send Mail. The message was rejected by the server because it is too large."
Above is the exact error.
iPhone users are using Active Sync.
The email is a thread of conversation, replying with attachment  and without. With attachment, it is less done 3mbs.
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tomfontanillaAuthor Commented:
On hubs 40mb on the mailboxes DB. No limits.
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Alan HardistyCo-OwnerCommented:
Can you please post a copy of the error message.

Thanks

Alan
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MurfurFull Stack DeveloperCommented:
I wear several email hats so have several accounts on my iPhone and I have encountered a similar problem, albeit intermittently and now I think about it, when I've been "roaming". So it has been interesting to dig into this as a couple of the email accounts are Exchange & now I know what to pass on to my IT bods. Hurrah!

Anyway, the digging reveals a possible cause and solution:

Apparently if you use certificate based authentication and you attempt send an attachment you can get stuck in a negative reality inversion! (see The Young Ones, S02E05 "Sick", 1984)

But to paraphrase a few sources (see below) as a summary, the server receives enough data to process the headers but does not receive the entire request. IIS attempts to answer the request with client certificates but fails to renegotiate the connection because the client is still waiting to send the remaining data from the initial POST.

There is a setting in IIS called uploadReadAheadSize that has a default of 48k and if increased could resolve this. Using 10Mb as below effectively sets your limit at 10Mb:

C:\Windows\System32\inetsrv\appcmd.exe set config -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost

C:\Windows\System32\inetsrv\appcmd.exe set config "Default Web Site" -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost

Open in new window

After this restart the IISAdmin service to load the changed setting.

Give it a whirl & all being well, head home for tea and medals!

Let us know how you get on, would be good to know if this works for you & ditto if anything develops with my IT people.

Sources:
https://discussions.apple.com/thread/5337946

http://technet.microsoft.com/en-us/library/cc737382%28WS.10%29.aspx

http://social.technet.microsoft.com/Forums/exchange/en-US/52f58b47-b95e-4f44-bb4e-6bd8b1b4eb94/iphone-sending-attachment-problems
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tomfontanillaAuthor Commented:
Alan,
This the exact error.
"Cannot Send Mail. The message was rejected by the server because it is too large."
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tomfontanillaAuthor Commented:
Murfur,

See my previous comment. I did exactly what you said, prior to posting here in expert exchange. The bottom that didnt help.
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Alan HardistyCo-OwnerCommented:
Is it your server rejecting the message for being too large or the receiving server?

Alan
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MurfurFull Stack DeveloperCommented:
Probably a silly question Tom, but did you apply BOTH update commands?
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tomfontanillaAuthor Commented:
Yes.
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tomfontanillaAuthor Commented:
Alan,
The answer to your question is yes.
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Alan HardistyCo-OwnerCommented:
Could you please re-read my question and then answer again.

Many thanks

Alan
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tomfontanillaAuthor Commented:
Our is server rejecting the message for being too large. Below is the exact error message.

"Cannot Send Mail. The message was rejected by the server because it is too large."
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Alan HardistyCo-OwnerCommented:
Please check your web.config file (as per the link below) and make sure the size limit is set to a more suitable size.

http://msexchange.me/2013/07/26/exchange-active-sync-message-size-limit/

Alan
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tomfontanillaAuthor Commented:
Alan,
That is similar fixed to my earlier post. But i will give a shot anyway.
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Alan HardistyCo-OwnerCommented:
It looks very different to me and optimistically should solve the problem, but only time will tell.

Alan
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tomfontanillaAuthor Commented:
Alan,
I believe you got this on the nose. I haven't heard any issues, and all my testing were successful. Great find. Thank you.
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Alan HardistyCo-OwnerCommented:
Excellent news - long may it stay that way.

Thanks for the points.

Alan
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rafael MCommented:
Did you have to reboot the exchange server after this modification? please advise,

Thank you,
Rafael
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