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Old Aug 6, 2010, 09:00 AM   #1
fred55
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Join Date: Jun 2010
Problem sending attachments via Hotmail

Hi all,
My wife uses Hotmail and we are finding that any images she sends from her iPhone 4 mail app via Hotmail end up not recognised on the other end at all.

Sending via gmail instead seems to work with no problems, but she prefers Hotmail.

Does anyone else see the same problem, have any suggestions, or even better a solution? I couldn't find anything obvious via Google/forum search.

Looking at the raw text of the emails the difference seems to be;
Good mail, note the empty line between Content-Transfer-Encoding and the first encoded line:
Code:
--Apple-Mail-2--7788859
Content-Disposition: inline;
	filename=photo.JPG
Content-Type: image/jpeg;
	name=photo.JPG
Content-Transfer-Encoding: base64

/9j/4AAQSkZJRgABAQEASABIAAD/4QJERXhpZgAATU0AKgAAAAgACwEOAAIAAAAMAAAAkgEPAAIA
AAAGAAAAngEQAAIAAAAHAAAApAESAAMAAAABAAYAAAEaAAUAAAABAAAArAEbAAUAAAABAAAAtAEo
Bad mail, note the line has disappeared:
Code:
--Apple-Mail-1--8609433
Content-Disposition: inline;
	filename=photo.JPG
Content-Type: image/jpeg;
	name=photo.JPG
Content-Transfer-Encoding: base64
/9j/4AAQSkZJRgABAQEASABIAAD/4QJERXhpZgAATU0AKgAAAAgACwEOAAIAAAAMAAAAkgEPAAIA
AAAGAAAAngEQAAIAAAAHAAAApAESAAMAAAABAAYAAAEaAAUAAAABAAAArAEbAAUAAAABAAAAtAEo
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Old Aug 11, 2010, 08:59 AM   #2
tylersimon
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Problem sending attachments via Hotmail

Hi,

Did you ever get a resolution to this? I have exactly the same problem. Sometimes the emails can be read and sometimes they are not read. Where did you try to read them?

I eventually gave up and raised a bug with Apple but no joy so far.
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Old Aug 11, 2010, 05:43 PM   #3
fred55
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Hi,
I am glad to get a response - I thought we seemed to be the only people anywhere who have this issue as there are no comments about this online anywhere as far as I can see.

I haven't had any other responses from hotmail or here and am currently resigned to calling AppleCare/filing a bug with Apple in the hope it will be sorted out behind the scenes.

The emails are corrupted in every other mail client that reads the mail as far as I can see - the iPhone, Apple mail app, gmail and other web mail services. As best I can tell the message as sent from Hotmail is bad, and my guess is that it is an issue between the iPhone mail client and Microsoft's email sending (SMTP) software. I also suspect that sending an email from the Mac Mail application through Hotmail will show the same problem.

Hopefully this will eventually be addressed at Hotmail/Apple as required but I'm not holding my breath given how low profile this issue seems to be.
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Old Aug 12, 2010, 01:32 AM   #4
tylersimon
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I have raised a bug with Apple and through an internal Apple contact I know they are looking at it but no progress so far. So far I have no news as to whether it is an Apple issue, a Hotmail issue or a combined issue.

If you could give me precise details of your setup then I will add it to the report in the hope that it will raise the priority with Apple to identify the root of the cause.

Would you be able to send me precise details of your setup? i.e. iPhone OS version etc, carrier and any email gateways you might be using? The full source of the message should provide most of this.
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Old Aug 12, 2010, 08:40 AM   #5
fred55
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Join Date: Jun 2010
Thanks for the followup and hopeful feedback. That prompted me to try some more combinations to see what was happening and it is a little different to what I thought.

System details:
iPhone OS version iOS 4.0.2
Carrier: Telstra (Australia), problem also happens via WiFi and my home ISP (iiNet)
Email gateway: smtp.live.com as configured by the add account "wizard" in the mail app directly on the phone, iOS Mail Default Account set to Hotmail (other account is set to gmail no issues there).

Test plan:
1. Open Photos app
2. Select photo from Camera Roll
3. Mail from app in medium size to test receiving account, only enter to address and subject

Test Receiving Account + result
gmail.com, send via ISP: Mail received correctly on both webmail and phone
gmail.com, send via carrier: Mail received correctly on both webmail and phone
spamcop.net, send via carrier: Mail corrupted on webmail and phone [1]
spamcop.net, send via ISP: Mail corrupted on webmail and phone [1]
hotmail.com, send via ISP: Mail received correctly on both webmail and phone
spamcop.net, send via hotmail.com webmail: Mail received correctly on both webmail and phone

So for me the issue is localised to mails sent from the iPhone to the Hotmail SMTP servers and then to a spamcop.net account and changing any of those variables results in the successful sending of the photo attachment.

Sample headers from a bad email here[2].

[1] Missing blank line as mentioned previously, also results in triggering the following SpamAssassin rule as a result:
SpamAssassin Rule: MISSING_MIME_HB_SEP
Standard description: Missing blank line between MIME header and body

Explanation
The format for e-mail requires a blank line between the headers and the body of a message, the lack of one causes this rule to fire.

[2] Sent from iPhone mail application through hotmail account to spamcop account, corrupted:
Code:
Return-Path: <xxxx@hotmail.com>
Delivered-To: spamcop-net-xxxx@spamcop.net
Received: (qmail 1773 invoked from network); 12 Aug 2010 11:35:39 -0000
X-Spam-Checker-Version: SpamAssassin 3.2.4 (2008-01-01) on filter7
X-Spam-Level: *****
X-Spam-Status: hits=5.8 tests=MISSING_MIME_HB_SEP,TVD_SPACE_RATIO,TW_DX,TW_XB,
	TW_XL version=3.2.4
Received: from unknown (192.168.1.86)
  by filter7.cesmail.net with QMQP; 12 Aug 2010 11:35:39 -0000
Received: from blu0-omc4-s8.blu0.hotmail.com (65.55.111.147)
  by mxin2.cesmail.net with SMTP; 12 Aug 2010 11:35:12 -0000
Received: from BLU0-SMTP37 ([65.55.111.135]) by blu0-omc4-s8.blu0.hotmail.com with Microsoft SMTPSVC(6.0.3790.4675);
	 Thu, 12 Aug 2010 04:35:36 -0700
X-Originating-IP: [xxx.xxx.xxx.x]
X-Originating-Email: [xxxx@hotmail.com]
Message-ID: <BLU0-SMTP37BB0F2926022FA68474478A970@phx.gbl>
Return-Path: xxxx@hotmail.com
Received: from [10.218.81.146] ([xxx.xxx.xxx.x]) by BLU0-SMTP37.blu0.hotmail.com over TLS secured channel with Microsoft SMTPSVC(6.0.3790.4675);
	 Thu, 12 Aug 2010 04:35:31 -0700
Subject: Test9
From: xxxx <xxxx@hotmail.com>
Content-Type: multipart/mixed; boundary=Apple-Mail-5-510503636
Date: Thu, 12 Aug 2010 21:34:57 +1000
To: xxxx <xxxx@spamcop.net>
Content-Transfer-Encoding: 7bit
Mime-Version: 1.0 (iPhone Mail 8A400)
X-Mailer: iPhone Mail (8A400)
X-OriginalArrivalTime: 12 Aug 2010 11:35:34.0295 (UTC) FILETIME=[7A204A70:01CB3A12]
X-SpamCop-Checked: 
X-SpamCop-Disposition: Blocked SpamAssassin=5


--Apple-Mail-5-510503636
Content-Transfer-Encoding: 7bit
Content-Type: text/plain;
	charset=us-ascii


--Apple-Mail-5-510503636
Content-Disposition: inline;
	filename=photo.JPG
Content-Type: image/jpeg;
	name=photo.JPG
Content-Transfer-Encoding: base64
/9j/4AAQSkZJRgABAQEASABIAAD/4QMaRXhpZgAATU0AKgAAAAgADAEOAAIAAAAMAAAAngEPAAIA
AAAGAAAAqgEQAAIAAAAHAAAAsAESAAMAAAABAAEAAAEaAAUAAAABAAAAuAEbAAUAAAABAAAAwAEo
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Old Aug 12, 2010, 08:41 AM   #6
fred55
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By the way, what are your details - what is the receiving account at your end?
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Old Aug 13, 2010, 02:57 AM   #7
tylersimon
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Join Date: Aug 2010
Very similar situation this end. I have seen the issue on all iPhone 4 OS I have tried it on. Older OS's are not an issue.

I am using O2 in the UK and I use exactly the same mechanism to reproduce as you do.

Very similar results as well. Depending on where I send the mail it sometimes turns up OK and sometimes not.

Not joy with Apple so far. Just no response.

Simon
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Old Aug 13, 2010, 06:13 AM   #8
fred55
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Well I guess the news that it is a new issue for iOS 4 gives some hope that it will be resolved sooner or later. Hopefully a specific set of services for them to look at plus the how to reproduce info should be enough to get it worked out.
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Old Aug 31, 2010, 07:46 AM   #9
fred55
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A solution from Microsoft!

As of today you can setup access to Hotmail via ActiveSync (see http://windowslivehelp.com/solution....7-ab8b11237ed0), and when I do this attachments are finally mailed without error!

Of course there is also support for push, read and delete synchronisation with the server etc. which is great.

I hope this also works as a solution for you.
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