iPhone Email Attachments – Revisited

iPhone Email Attachments – Revisited

My solution for sending messages via email on the iPhone – detailed here – works for every mail client… except Gmail.

Gmail simply will not let you see embedded images.  Period.

Since this kinda crap really grates on my nerves, I started digging a little deeper.  Plus, I really think there should be a 100% universal way to attach stuff to email messages from the iPhone… and I’m not the only one.  My embedded images solution is workable, but is not wholly satisfying – because it is not a 100% solution.

So, like I usually do when trying to sniff out how a particular piece of web software works without having access to the source, I see what is being sent “over the wire.”  And since I knew that iPhoto on the iPhone WAS able to send an attachment, I sent myself a picture… and then checked the raw message source to see how Apple was doing it.

I sent myself a picture, with no accompanying text, and this is what the “interesting” pieces looked like:

Content-Type: multipart/mixed;
X-Mailer: iPhone Mail (5H11)
Mime-Version: 1.0 (iPhone Mail 5H11)
Date: Wed, 11 Mar 2009 12:13:43 -0400

Content-Type: text/plain;
Content-Transfer-Encoding: 7bit

Content-Disposition: inline;
Content-Type: image/jpeg;
Content-Transfer-Encoding: base64

Notice the Content-Type of “multipart/mixed.”  No real surprise there… just that when you send a message using the Email client launched by an iPhone application, this is almost always “multipart/alternative”.  First “hmmm.”

Secondly, when I used my methodology of using embeded images (<img src=”data:image/png;base64[my data here in base64]”>), this gets cobbled out as

Content-Type: text/html;
Content-Transfer-Encoding: quoted-printable

by the Apple Email Client.  By contrast, Apple creates it’s image attachments by doing the following:

Content-Disposition: inline;
Content-Type: image/jpeg;
Content-Transfer-Encoding: base64

So – why not just do the same thing?


I don’t know what MIME boundaries (the “Apple-Mail-1-782786827” above) Apple is using to segregate its constituent email pieces (text, html, images, attachments) ahead of time – and they are generated dynamically by the email client when putting together it’s messages.


If I knew what the boundary tag was, I could fake out the client, create my own inline image, and boogey on down.

Now, even though this does seem like a serious roadblock, it may not be a total loss, because it presents both

  • (a) a possible direction to look (fake out a boundary, unlikely though it may be) and
  • (b) it presents another solution path (go down to the socket level and code my own SMTP alternative, so that I can create the MIME code directly to send out my attachments).

(a) looks to be a total non-starter, as it looks like the boundary is made – in part – of a timer component, and there is no way to guess how long someone will keep the message open before sending to reliably fake this out each and every time.  (b) will absolutely work – provided you are motivated to write this dude.  Looks like a commercial opportunity for a Cocoa Touch class, and I may yet do this.

A final and as yet unspoken work around would be to know how Apple preps an image in their email client before sending, so that it’s Mail.app knows to wrap the image up as an inline attachment.  Unfortunately, I don’t know of anywhere I can look to see how they compose their messages (no view source – dang!).

All in all, this has stimulated me to investigate some additional paths for a problem that I thought I had a reasonable solution for – and for many, I do and did.

Onward and upward.

Embedding Images in Outbound Email Using Cocoa Touch

Embedding Images in Outbound Email Using Cocoa Touch

One of the more commonly asked questions about iPhone SDK development is “how do you send attachments in Email using the iPhone SDK?”

The answer is: you can’t.  At least, not yet.

Well, then how are developers seemingly able to do this?  Many of you have seen apps where this looks like this is being done.  The Apple Photos app, for example, seems to be able to do this.

What’s the secret?

Come closer.  You Ready?

Embedded Images.

Embedded images are most commonly seen in your junk email and are a favorite trick used by spammers to circumvent your email filters to slip content in that can’t be scanned textually.

Here, we will use them for good and not evil.  Promise.

Let’s look at some screen grabs and code from my upcoming iPhone App Interpolate.  Interpolate is a numerical analysis app that finds missing range points given a table of data points representing some function, like y=x squared.  In addition to calculating interpolants, it also produces cartesian graphs of each function set, and allows you to send the chart to your friends using email.


The code below is from a function call to create my email message.  In my app, I am taking a UIView (or at least, a class derived from UIView) and converting it into a PNG image.  Once I convert the view to PNG, I then convert the image data to a Base64 string, and use that Base64 string as the source for my embedded image in the email.

ChartView *cv = (ChartView *)cvc.view;

[cv.layer renderInContext:UIGraphicsGetCurrentContext()];
UIImage *viewImage = UIGraphicsGetImageFromCurrentImageContext();

NSData *imageData = UIImagePNGRepresentation(viewImage);
char encodeArray[64 * 1024];
memset(encodeArray,'', sizeof(encodeArray));

// Exercise for the reader - encode takes the image data buffer and encodes it to base64.

// I can't do everything for you - that spoils the fun.
encode([imageData length], (char *)[imageData bytes], sizeof(encodeArray), encodeArray);

NSString *dataStr = [NSString stringWithCString:encodeArray length:strlen(encodeArray)];

// Save to photo library... maybe another time!
// UIImageWriteToSavedPhotosAlbum(viewImage, self, nil, nil);

NSString *body       = [@"" stringByAppendingFormat:@"<b><img src='data:image/png;base64,%@' alt='Interpolate Chart'></b>", dataStr];
NSString *encoded    = [body stringByAddingPercentEscapesUsingEncoding:NSUTF8StringEncoding];
NSString *title      = [[@"" stringByAppendingFormat:@"Interpolate: Function %@", cvc.title] stringByAddingPercentEscapesUsingEncoding:NSUTF8StringEncoding];
NSString * urlString = [@"" stringByAppendingFormat:@"mailto:me@you.com?subject=%@&body=%@", title, encoded];
[[UIApplication sharedApplication] openURL:[NSURL URLWithString:urlString]];

The really interesting bits are:

  • Converting the UIView to a UIImage using UIImage *viewImage = UIGraphicsGetImageFromCurrentImageContext();
  • Converting the UIImage to NSData using NSData *imageData = UIImagePNGRepresentation(viewImage);
  • Convert the NSData to Base64
  • Converting the Base64 encoded image data into an NSString using NSString *dataStr = [NSString stringWithCString:encodeArray length:strlen(encodeArray)];
  • Embedding the image into email using NSString *body       = [@"" stringByAppendingFormat:@"<b><img src='data:image/png;base64,%@' alt='Interpolate Chart'></b>", dataStr];

IMPORTANT: the <b> and </b> in the embedded image code above must be present, or mail will strip your image.  Don’t ask me why – it just does.

Wait a minute… where is the Base64 encoding mumbo-jumbo done?

Hey – like my old math teacher used to say – the rest is left as an exercise for the reader.

But if you’ve followed along this far, finding a Base64 C routine to use in your own code is the easy part.

Happy Coding.