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Cannot Open PDF Forward From iPhone

Our clients are sending in emails which a few of our users are viewing them on their iPhone. When they forward the message to other users the pdf files won't open. It gives an error message, "There was an error opening this document. The file is damaged and could not be repaired". I've tried saving the pdf to the desktop then try to open it with no success and the same error message.I've also checked to make sure the Add-in is enabled.

We are on Acrobat X 32 bit Standard 10.1.10 and Windows 7 x64 Pro/Ult. Outlook is 32 bit version. Any ideas what the problem is?

Posted on Apr 27, 2016 12:53 PM

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Posted on Jun 2, 2017 11:07 AM

I found out that in our case it had to do with PDF's containing a space character. If opened on the iPhone it would have the name truncated to the position of the first space therefore leaving out the ".PDF" which is at the end of the file. Because of the missing extension, the phone was unable to identify the document type and wasn't able to open it. A work-around was to us Microsoft's Outlook mail app instead.

44 replies

Jun 13, 2016 1:17 AM in response to baldwinjd

We are also experiencing the exact same issue since iOS 9.3.x. It's a random thing and doesn't happen with all PDF attachments. The attachments which on Windows are called corrupted (tried several PDF readers) could be opened easily on an iPhone without any problem.


Someone suggest not to forward the attachments without opening them first on the iPhone (download the attachment on the iPhone first and then send them), but this workaround also doesn't seem to work all the time.


This is for sure an issue with the latest update of iOS which 'does' something with those attachments. I've this problem with around 10 users now and I've asked the rest not to update to the latest version of iOS.


I hope Apple would patch this problem with an update very soon as it'd eventually be a big problem.

Jun 16, 2016 2:40 AM in response to baldwinjd

We have the same issue with one of the 14 iPhone users we have. We are running Exchange 2013 onsite.


Only seems to happen occasionally and not related to emails from a particular sender, the format they are in or the file type as it is corrupting Word and Excel documents as well as PDF's. The other issues we have had is it dropping attachments off as well. Therefore, the original email has 5 attachments 3 are ok 1 is corrupt, and the other is missing.


For compliance all our emails are archived. The attachments are fine on the archived version and the version in the users inbox. The forward version in the sent items is corrupt so definitely the phone that is causing the issue.


I think it is related to where they are when they send it. If they are at home or in the office so on Wi-Fi we don't have an issue. When they are out and about using mobile data we seem to have a problem. Therefore, is it corrupting the attachments when it is downloading and/or sending them on?


They particular user is not the most IT literate so don't really want to go down the Outlook for IOS route. Has anyone tried backup, resetting and restoring the phone?

Jun 16, 2016 3:05 PM in response to dpgator33

I'm having this issue as well. For my scenario, this only occurs when a user receives an email with attachments from outside of our domain. She then forwards the email to her secretary. At the point when she asked to "include" the attachments, only one attachment shows. It looks as if multiple attachments are grouped into one. The attachment displayed is named the same as the first attachment from the original email. This occurs on both an iPhone 6S and an iPad, both running iOS 9.3. This hasn't always been the case, and didn't occur until about a month or two ago. This has been one of the only threads that I have been able to find that is anything similar to what my user is experiencing, and I have a feeling that it is related. This issue only occurs when forwarding an email received from an external domain, with attachments, from an iOS device, using the default Mail application. This user can forward an email sent to her from inside the domain with multiple attachments and not have a problem. Internally, we run an Exchange 2010 environment, and I might as well include that we are also running MobileIron for mobile device management.

Jun 17, 2016 3:27 PM in response to jimmys-iphone

thankfully i have only seen this issue on one of my 400+ iPhone/iPad devices we have in our company but once you see something like this happen for a user.... you get a bit worried that it will affect ALL of your users. I have high level users like one of the posts here mentioned that are what you call 'mobile warriors' and rely HEAVILY on their mobile phones and relaying of data between external clients and internal.


I hate how Apple's responsiveness to any issue is basically a non-response or a "sounds like an Exchange issue, you should contact Microsoft" or sounds like a google / gmail issue, you should contact them. They really make us IT geeks feel like we have nowhere to go when we run into a major issue like this. the post i linked to has a company that has 400+ devices and most are being affected.


Sorry to LACAllen for my childish ranting. My bad, I have scolded myself. 😉

Jun 17, 2016 3:32 PM in response to PH03N1X_115

Sounds like the similar circumstance that i saw today too. outside/external email sender and email had about 4 docx files and 4 pdfs; once i received the fwded version of the message on my Outlook client; i only saw the non-pdf attachments in the email i received. my user has an iPhone 6 w/9.3.2 os and sees the same thing happening on his iPad w/9.3.2 also.

Jun 20, 2016 8:36 AM in response to jimmys-iphone

what a waste of my time. apple care / support is total crap. the chat support person can't even VIEW links to these forums?? Really??? Of course the support person had no idea of the issue or it being listed as an outstanding issue for 9.3.2. I'm having a senior support person call me back. Details as I get them. Not confident anything will be done. Seems issues are fixed in the beta for 9.3.3 as someone previously posted.

Jul 6, 2016 4:08 AM in response to Boon Hong Wong

This did not work. While outlook did open the message after changing the extension, there was no legible content, just some crazy characters, and no attachments. However, if you open a good pdf document using notepad you will see they all begin the same with %PDF and then the version number and some tag-like content. The pdf documents received from an iPhone, opened with notepad do not have the same format. Below are 3 examples of extract from good PDF docs and 3 PDF docs sent from an iPhone. Obviously, something on the iPhone (iOS, apple mail) is changing the format of a PDF document which makes no sense. PDF means Portable Document Format and is supposed to be OS agnostic and portable across devices.


Good PDF docs

%PDF-1.4

2 0 obj
<<


%PDF-1.7
%âãÏÓ
1 0 obj
<</Type /Pages


%PDF-1.6
%âãÏÓ
2801 0 obj <<


Sent by iPhone

Eç Š÷~º&= ƒ1}5¾*Ü¢g(›mzã»ÛO Êf¢–g‡ «mÊ&×½µë^·Ó „Èœ®‹(~ÔŒLôž®÷«L´


Eç Š÷~º&= ƒ1}5¾*Ü¢g(›mzã»ÛO Êf¢–g‡ «mÊ&×½µë^·Ó „Èœ®‹(~ÔŒLôž®÷«L´


Eç Š÷~º&= ƒ1}5¾*Ü¢g(›mzã»ÛO Êf¢–g‡ «mÊ&×½µë^·Ó „Èœ®‹(~ÔŒLôž®÷«L´

Jul 26, 2016 10:12 AM in response to thorod336

I would be very curious if you could let the group know what the "/Producer" tag is that exists in plain text within the PDF file (viewing a pdf with notepad) as it seems that only certain PDF files are effected?

We have not been able to successfully reproduce the issue and we are also hopeful that the 9.3.3 patch has resolved the issue altogether!

Jul 26, 2016 10:19 AM in response to thorod336

Obviously, something on the iPhone (iOS, apple mail) is changing the format of a PDF document which makes no sense. PDF means Portable Document Format and is supposed to be OS agnostic and portable across devices.

That is the theory. In reality, there are so many tools now to "write" PDFs that these issues come up.


It's like sending a "word doc" now. What flavour? What version was it created in? How was it saved?


PDFs have suffered from simple font issues since day 1. If the creator does not embed or convert the fonts before saving, the receiver may not be able to render the file.


Checking the lineage of the sent file is part of the sleuthing you may need to do.

Jul 26, 2016 6:00 PM in response to Bohler-IT

I don't know what the "/Producer" tag is, all I know is that every PDF file that opens correctly begins with %PDF, though that is not enough to guarantee they will open. If you open jpegs and tifs with notepad you will also see a common pattern within the first line. Probably with many file types. If I have a file without an extension I open it with notepad to see if it is one I recognize.

Cannot Open PDF Forward From iPhone

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