iPad Email Attachments showing up as empty/missing icon question mark

So this is a very odd bug that is happening on both the iPad and iPhone os, albeit it occurs more on the iPad.

When I sent PDF attachments that shows up on my normal apple mail (as a preview PDF inside the email content), it is showing up as a empty icon in the ipad mail even though iPad mail does note it has an attachment with the paperclip mark.

Keep in mind my email acct is synced over imap on the iPad, iPhone, and apple mail. The pdf attachment opens in apple mail without problems.

This problem also occurs on my iPhone but it is less often.

I hope a described the problem well. If anyone like to see the email for themselves contact me at uunders@gmail.com and i I'll forward you the email with the PDF attachment.

Message was edited by: Apple Issac

Macbook Pro Late 2009 unibody 15", Mac OS X (10.5.7), IPad 32gb wifi only

Posted on May 11, 2010 6:58 PM

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90 replies

Oct 31, 2010 5:28 PM in response to BigUpRadio

Hello all. The majority of this post relates to PDF docs. In my scenario it is images, power point presentations, almost any type of attachments. Issue is that it does not do it all the time. Email account has been set up as pop and currently as imap. Provider is yahoo and the account has been set up using the easy set up provided by apple. The majority of emails being sent are jokes and do include embedded images or attachments. All are viewed prior to sending so they would therefore have been downloaded. Have turned on load remote images. I cannot determine what it is. Sometimes it does function properly, other times it does not. Tested with receiver being pc user, Mac user. Has even failed sending it back to myself on the same iPad.

Nov 4, 2010 10:41 AM in response to Robert McGoff

As of this morning, my problem seems resolved. My iPad is now happily displaying .jpg images. Yet, I have not sync'ed this device since reporting my problem. Could Apple have changed its .me mail server? Or, was I missing something obvious in the way attachments are downloaded? Anyway, if you've experienced this problem, I encourage you to revisit the issue.

A Happy Bob

Nov 23, 2010 1:03 PM in response to Apple Issac

What I have noticed is that for example you receive an email with more than 10MB in attachments, let's say .jpg files, the first 10MB of attachments will load and display, regardless the order you tap on them.
After the 10MB limit, only text showing what seems to be a system shortcut to the file shows up.

This problem existed in iOS 3.2.x and still continues in 4.2.1.

It clearly seems to be an iOS bug.

Jul 11, 2011 2:21 AM in response to ColinWirt

I'm having the same problem using the iPad app "pages" an apple developed app, and I can't seem to send a PDF without getting the blue ? appearing half the time. It seems to be random and most definitely a major bug.


Quite embarrassing for apple really. They tout this new fan dangled, most powerful word processing software developed for a tablet, oh except when you click on the share via email button, it will only work half the time, which obviously looks great for you when your clients keep receiving emails with no attachment.


I'm running 4.3.3 iPad 2


If anyone finds a work around I'd love to hear it. Currently I just send a bunch to my own address, then when one works I forward the attachment via my MacBook. Utterly ******** I know, but I like the PDF layout Pages makes...

Jul 18, 2011 9:53 AM in response to Apple Issac

I found the answer to the pdf ? icon issue!!


I had the same problem, could not view pdfs and larger attachments on the IPAD 1 in email and getting a ? icon (but could see the attachment of the same email on my iphone 3gs).


I discovered if you press and hold the ? icon a pop up says 'quick view', then select 'quick view' up pops the pdf/large file in all its glory!


This was driving me nuts for ages, trawling the internet for answers, I was thinking the ipad was no good as a business tool, hope this helps you folks!

Jan 27, 2012 6:51 PM in response to Apple Issac

Had the same problem on ipad and iphone and out of the blue I thought it might have something to do with how the file is saved as a pdf. When I originally created the pdf file it saved it without the .pdf in the file name, but it was a pdf file. When I created a new pdf file, adding .pdf to the file name, and sent it as attachments, mail recognised and opend it in both ipad and iphone.

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iPad Email Attachments showing up as empty/missing icon question mark

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