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PianoMoverFlag for Canada

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Office 365 and apple products iphone/ipad

I haven't been able to get a straight answer from Microsoft tech support on this and my patience for waiting for an answer is at its end.  They've had 2-3 months with no sign of answer or if they are even still trying to solve problem.

Here is my problem:
I upgraded from Microsoft Small Business Server 2008 to 2011 and did the Office 365 email hosting so I would not have to manage email anymore.  My company uses iphones for all its users.  We are a transport and often need to take pictures of things and send them to other users or customers.  For the most part Office 365 works fine with the exception of one major exception.  If i try to send pictures at there actual size and the total email is over about 7.5MB it bounces back and sits in the outbox trying to send.  I cannot get a straight answer from Microsoft whether the limit is 10 or 25MB, but either way I am not even getting that.  In one case for one of my users the email tried for about 3 weeks to send before we realized it was still trying to send and consumed over 5GB of data on his phone plan (lets talk cell data overages).  Also explained why his phone was running so slow for those 3 weeks.  Our current work around is to send pictures in large format which keeps email in the 3MB range or send the actuals 1-2 at a time which is frustrating when you should be able to send 5 pictures at a time.  Microsoft tech support has been able to simulate on iphone/ipod/ipad for troubleshooting purposes and has recognized the problem which seems to be limited to apple devices.  I have a gmail account on my phone as a backup email service and it works perfectly fine sending same emails around 13MB in size which isolates the problem to office 365 service.  No I don't want to use this account for emailing pictures at the moment, because people reply to it, instead of my main email account then.

Options to date:
1. Ignore problem and keep working around it, hoping Microsoft might get a fix for it some future day over the rainbow.
2. Convert Office 365 to Google apps for domains which doesn't have the email problem on iphones.

I really don't want to do an email conversion if I don't have to and so far have not seen any easy ways to convert from Office 365 to gmail, because I am scared about losing data in the conversion.  Seems like I am the only person asking this question on the internet so far.  But I am seriously considering it.

Two questions here:
1. Does anyone know a solution to my emailing pictures off iphones problem?
2. Does anyone know an easy way to convert from Office 365 to gmail for domains?
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Alan Hardisty
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Having read you message and not having tried this before, I have just tried to email myself 4 pictures and it appear to be struggling on my iPhone 4S, so you are not alone.

I will see if I can find anything out and hopefully find a solution.

The following blog may well be the problem / solution, but getting Microsoft to implement this might be interesting:

In case the link breaks in the future and this is the solution:

On the CAS server under the install directory go to ClientAccess\Sync folder
Open the web.config file
Find the <httpRuntime maxRequestLength=”10240¿/> entry
Up the value to the KB value you want (bear in mind phone data costs!)
Save the file
Restart IIS
have them send the pictures to your gmail account, and then in office 365, sync the gmail account to your o365 account. Use this as a workaround for now.
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Not sure I follow what you are suggesting.  The problem is if I send the pictures out to people with my gmail account, they will reply to them through the gmail account.  I currently have it forwarding to the office 365 account so I get the emails, but then people get confused when they see two email addresses for me in their mail programs.  Already had this problem with one customer, so I am trying to use this sparingly or for emergencies only.
You have a few options:

Upgrade your Office 365 license and upload pics to sharepoint and share them from there.  You may need to pay for accounts for your customers.

Continue to play with work-arounds that hurt productivity

Move to Google Apps for Business
I'm guessing that you are getting the pictures for a reason.. Why don't you save them and then create a new message and add the picture..
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Excellent news - just hope they make the change soon.

Only solution to problem.  Microsoft eventually fixed.