Iphone 3GS Email issue

My email works fine, but I don't use Exchange server. It may have something to do with how the Exchange server is setup. If it worked before, I would suggest deleting the email account and recreating it.

We also have the same problem but haven't found a solution as yet. The emails are fine if you don't include the attachment but the same error occurs when you do.

I have the same problem with my 3GS. Cannot confirm whether prior versions of the iPhone are problem free.

Why is it that an email of a few kilobytes sends fine, and an email larger then a few K re-tries...This doesn't appear to be an Exchange exclusive issue, I read the same failures for multiple technologies.

Apple Furthermore: Why is it that you are not prolific in addressing these forum posts, seems like such a waste of my time... I read on one of Apple Web pages the anwser to the large size attachment issue, delete it from your iphone, and send it from your PC. This is not acceptable, if you aren't going to get seious in the Business Market, get out and let someone else in to do a better job. Myself, and many other System Administrators, have caused multitudes of issues, on our own Email Servers, and Systems because there are not simple straight answers that are accurate from you the vendor.
Get a Voice, Respond with corrections that are not a means to shuffle someone off the phone, similar to Microsofts Old Days Problem with your PC, Please Re-install your Operating System, then call us back...
To re-state the question Why is the iPhone 3G, and 3GS having trouble sending simple 10K plus sized attachments.

Clarifications for my first post,
In my current configuration, depending on the size, the email with attachment will eventually send, the larger the file, the longer it takes, and the more repetitive messages stating "Cannot Send Mail...". I have blown away my email configuration, on my iPhone many times, have never not been able to send emails without attachments, I have three iPhones, multiple Blackberry's, and multiple Windows Mobile based phones. I am using a professional Cert, not home grown, and is listed among trusted authorities...
Most importantly of all regarding my previous Jeer to Apple, I don't want you to not be in the Business Market, I want you to Shine in the Business Market You have wonderful Products, We need Your presence...
Thank You
Jim Lawless

I get the same problem. My iPhone 3GS is stuck in a "sending mail" loop, and there doesn't seem to be a way to end it.

My phone is configured with gmail, normally it works wonderfully except for this issue.

This issue is a nightmare. It makes using the iPhone for sending email pretty useless. Apple, I'm tempted to send you the bill for all the data usage when my phone tries and retries (until I figure out that it's stuck).

For anyone else who's stuck in a "sending 1 of 1" loop, I had to restart my iPhone before the "outbox" folder showed up, at which point I was able to delete the culprit email.

Apple, take note: that's 2 glitches with your email software. Please file them separately.

Below is my response to Apple Customer Survey:
This issue is not within his power to resolve. The iPhone email issue sending attachments greater then 10k or 15k is apparent on multiple email systems. It has cost my company many hours, and dollars to determine that it will have to be resolved, by Apple &/or AT&T. I will be glad to give further details, until then I will use the forums to communicate with others regarding this flaw. As Below
"Iphone 3GS Email issue" has been updated one time.
http://discussions.apple.com/thread.jspa?messageID=10268336#10268336

I have this same problem. Actually had it on my 1G iphone and was hoping it would go away when I upgraded to 3GS. no dice. Customer svc is no help. They either blame AT&T or my I/T "department" (me & the I/T guy who I annoy all day with new ideas to get this working)

This is just rediculous.

Anyway, to continue to humor myself & try to troubleshoot this - are you guys running exchange 2003 or 2007? I'm on 2003 right now. We're upgrading soon, holding out hope that will fix this issue.

*Large Email and Attachment Test Results:*

I Sent a Voice Recording 1687 KB
In a little over a minute by bouncing in and out of EMail Folders, also periodically I would Press the Fetch Control the file was Sent at
12:52 AM Received at 12:53:56 AM

Sent from my iPhone 3GS

On Sep 24, 2009, at 12:39 AM,
Sent Multiple pictures (3), email size 484 KB. Process Below Select
photos from Camera Roll, by first pressing the File Action Control
Then select 1, 2, 3 then chose Share, email

Next I went to Mail, in the Outbox, or Inbox, then error message
saying Cannot Send Mai An error occurred while delivering this message

Now Go Back to Top Mail Folder Tree
Scroll Down to Sent Folder Tap, Status should show Connect...then
Sending 0-------------0

Observation:
+Many times at this stage, is where the Email with Attachment+
+Successfully Sends.+

At times for Larger Files over 500 KB, I have, had to go into other
folders, and back out and into Sent, I did receive the error again
repeated steps above and it went.

Patience ultimately pays off here.

Sent from my iPhone 3GS

This iPhone 3GS Email was Sent (Put in the Outbox at 3:53 PM.
To confirm the ability to still send email I sent another email at 4:44 PM, no attachment went through and was confirmed received by the recipient at 4:44 PM. Email continues to send, and receive bypassing the stuck larger email in the Outbox.

This Photo is 2.25 MB, all the while when asked to Fetch you will receive the Error on your iPhone saying Cannot Send Mail An error occurred while delivering this message. Though this documentation event is regarding a 2.25 MB file this happens as low as 81 KB, and I believe even smaller sizes. There have still been times when sending files up to 200 + KB that have gone through with little or no delay.

I tested this during an Apple iCare Support session and naturally the email with attachment happened to go through during the Support Phone call.
Checking the size of the attachments they probably weren't the best examples to test with, 55 KB, and 220 KB.

Going into Sent Box...Seems to be an accelerator for the Checking Mail...It also seems to have a positive impact on the sending of EMails with Attachments...I just discovered this but hope this will be valid.

Hi everyone,

I have the same problem with emailing photos. I use private exchange account. The problem appeared after upgrading to OS 3.0. Recently had my phone exchanged to a new one at apple store bt it seams to be not a hardware problem. It is something to do with how the phone hadles exchange settings.
What I realised is that emailing a photo through my work email account whis has been set up as an IMAP account is no problem at all.
So it might be a temp solution to this problem. I will ask my it guy to open an IMAP access to my personal account and will let you know how it works.

Were you ever able to conclude what was needed to fix the problem, or does it still continue for you?

This issue continues, the methods I outlined above continue to work for me. My environment is Exchange 2003, We have iPhone 3G, and 3GS. The 3G is more problematic than the 3GS are, problematic meanning it takes much longer on average, but going into and out of Sent Folder, and Drafts Folder causing the connectivity to retry over and over, allows the email with attachment to be sent.

Have your IT guy look at this article. This is an IIS setting that affects SSL connections.

http://technet.microsoft.com/en-us/library/cc737382(WS.10).aspx (if your exchange server is running on server 2003)

The key setting here is the UploadReadAheadSize. Set it to 5,000,000.

If you are running server 2008, they can run the following command on the Exchange CAS server,

appcmd.exe set config -section:system.webServer/serverRuntime /uploadReadAheadSize:"5000000" /commit:apphost


Hope that helps.

Hello Just FYI this made no difference, made the changes to the Metabase, restart IIS, and Reset IIS tested shortly after with two different iPhones (both 3GS) same result. Using the quirky method I use did get the file to send still. Problem I do have with making the adjustment to UploadReadAheadSize it does potentially create a DOS Hazard, I probably won't leave this setting active for more then a day or two. But if it does wind up having a positive affect I will report back. Thank You for the HOPEFUL Tip. If I find anything I will let you all know.