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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

Reply
90 replies

Nov 16, 2012 6:02 AM in response to Apple Issac

I am having the same problem. "Open in" is not showing for 1-page PDF files I have sent from my iPad.


Also, when opening a 1-page PDF in iBooks and sending it via mail, the recipient cannot open the file anymore. Somehow the preview does destroy the file.


I already tried out a full reset and it solved the problem for a short time. Suddenly the same happened again.


What is going wrong?

Nov 27, 2012 12:52 AM in response to Apple Issac

I finally solved the issue ... At least for my special case.


If you have an automated signature added to your emails, which includes bolt letters, then the one-page PDF files are massed up! Also the recipient will not have shown the open in tap in that case.


Try to remove the automated signature if you send your email. It is due to the settings of the sense only, not he recipient of the email.

Dec 24, 2012 9:17 AM in response to SMR2000

I am having the same issue with received Excel spreadsheets on an iPad 3. The act of receving them on an iPad appears to have corrupted them. They don't appear in the forwarded email and if you try and send them via for example Dropbox or an attachment to a new email, the spreadsheets still are totally corrupted. Unfortunately I was in Africa, when I received them on my iPad and had set my mail to clear down from the server after 7 days, so I would not have a great mass of mail re-loading when I got back. I therefore cannot access the original on any of my Macs. Not a great feature for someone trying to use an iPad as a laptop replacement when travelling.


Wilson

Feb 7, 2013 5:19 PM in response to iUSER10011

ISSUE: email attachments FROM iPad TO outlook - attachments show up as red "X"


Yup, this worked for me too. Took some time trawling through the answers, though!


  • one app in particular (but probably others i'm sure) was sending the email with 2 attachments.
  • one attachment is the signature (a .txt file), and the other is the file i needed to send (the PDF)
  • i had a fairly convoluted email signature set up with all of the usual corporate disclaimers and such.
  • I set the signature to something that a .txt file would be more likely to handle i.e:


Regards

John Doe


no colours, bold, italic, or any other peculiar stuff


works ok now. will probably try to format the signature to plain text just to cover my *** in the event of a mass computer virus outbreak.

Jun 24, 2013 8:02 PM in response to Apple Issac

Hi,


I have just recently occurred a problem with receiving pdf's that are sent from goodreader (ipad) to outlook. This is only happening with 2 ipads, the other one I am able to receive pdf's from. When I send the pdf to both my outlook and my macmail, I only receive the pdf via macmail. Does anyone have any idea what caused this and what can be done to fix this?


Thanks!

Oct 7, 2013 4:54 AM in response to ohforgodsake

I have the same issue with my iPad 2 64G wifi; PDF's appear in Microsoft outlook with a question mark. Removing my signature before sending does the trick but is a bit of an awkward step to remember.


However when I send a PDF from my iPod Touch 5G 64 or my iPhone 4S 64G, all works fine and my signature actually appears as an .htm attachment along with the PDF attachment when received in Microsoft Outlook. Whereas with the iPad, the signature remains within the body of the email.


Let's hope an update fixes this.

May 9, 2014 7:28 AM in response to Apple Issac

hi all, just thought id fill anyone in with some info I found - maybe it might help someone save a day of troubleshooting!


anyway we use BES10 for our iPhone management and we had this problem where email attachments were showing as a question mark and we werent able to open them in any other apps either. Turns out in BES10 there are 2 policy settings hidden away called "Limit personal data to personal apps and accounts" and "Limit work data to work apps and accounts." if these are enabled the ? appears on attachments and cant open them in other apps either. hopefully the above may be of use to someone.

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

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