Cannot Open PDF Forward From iPhone

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.

We are having this identical issue at my workplace.

The issue is happening intermittently, and every time it happens it is determined that the corrupt PDF attachment was forwarded from an iPhone (seems to be related to iOS 9.3.x)

When a PC user attempts to open the PDF, the receive an error message "Acrobat could not open 'PDFname' because it is either not a supported file type or because the file has been damaged (for example, it was sent as an email attachment and wasn't correctly decoded.)"

The file is only readable from an iPhone, or from the Mac OSX native viewer (will not open from Adobe on Mac either).

Interestingly enough, the corrupt PDF files CAN be repaired by opening the said PDF on a Mac using the native "preview" app, and using "save As" from there. The resulting PDF can then be opened from PC, Mac, Adobe, etc...

I would really like to make sure Apple is aware of this issue and is working to patch. It appears to be an iOS issue, and not an Exchange issue.

I've seen in another Apple discussion forum where others were having this problem (https://discussions.apple.com/thread/7530950?tstart=0). They have offered a workaround where if the user opens the attachments on their iOS device before forwarding the email, the attachments are not grouped together, and are no longer corrupt. However, when trying this out with my user, who had five attachments that she was forwarding from her iPhone, only two of the attachments were sent. They were not corrupt and could be opened, but not all of the attachments were sent. Two out of the five came through. It looks as if the other attachments show up as ".htm" files, which cannot be viewed as the original file type.

Re: Email forwarding issue

related.. this is all on apples end and no one elses. iPhone 9.3.x has caused this from what i'm seeing on this post. Apple of course has not responded. Also, I had a user have this same thing happen.

1. receives email w/6 or so attachments. various sizes under 1MB. file types were .docx and .pdf

2. forwards me a copy of the email. we use exchange 2013 and iPhone activesync and native mail clients.

3. android device w/same exact account setup has ZERO issues

4. in the thread i linked to; someone on there has literally found the line of code causing the issues.

/snark removed but seroiusly.. ITS ALL APPLES FAULT on this one. i'm also mobile os agnostic; **** i even give WP10 a run once in a while so i can at least complain about it (can't complain about something you never use).

Users in another thread have confirmed that Beta 9.3.3 appears to resolve this issue for them.

This hasn't been completed substantiated, but 2 users on Beta so far report issue is gone.

See this thread:

PDF Attachments From iPhone Become Corrupt iOS 9.3

We are also experiencing this issue with a small but growing % of users. One thing that is interesting is that if the file sent is corrupted, I still can open the message on the iphone. I can't open it in windows. I was able to use admiralperry's suggestion and open it up on a Mac. Then I saved it back to the flash drive. I was then able to open it in windows. I wonder if a person gets the email with a pdf and opens it on their iphone, does that then convert the pdf to some format that makes it unreadable when forwarding it to a windows computer? The fact I can still open it on the phone suggests just that. I don't know how to solve the issue or why it would happen on a select amount of emails.

Has anyone made progress on this? one of our users let me know about it this morning and all my research points to iOS 9.3. with 500 users that are "road warriors" on iphones I hope this is resolved ASAP.

I believe that I am having this issue as well. The following was reported to me a few days ago.

User A sent user B an email with 8 small Word attachments. User B sees the email on his iPhone after hours and forwards it to user C, asking if user C could have the documents printed first thing in the morning. User C receives what appears to be a single attachment only, and upon attempting to open it, receives a message about the file being corrupt.

I was later able to reproduce the symptom, by doing the following.

I granted an admin account full rights to user B's email account (Exchange 2010, but I don't think that is relevant). I logged into the user B account, found the original email from user A, and forwarded it to my user D email account (a personal Gmail account). I logged into that account on my iPhone and saw that I had received the email, with 8 attachments. I then attempted to forward the email to user E, and when prompted to "include or not include" the original content, I chose to "include". Before hitting send, I scrolled down and saw that there was only one attachment. I proceeded to send the email to a user E account, where only the single attachment was received, and could not open the one that appeared to be there, but could not because of the "corruption" of the file. I've tried unsuccessfully to isolate the factor that is causing this by changing the characteristics of emails with attachments; number of attachments, special characters in the file name, size of attachments, etc., and nothing is consistent. BUT, I have had it happen with probably half a dozen or more emails so far. Would really like to get this figured out, because my users aren't too happy about it. They're somewhat less happy that I found this thread and can blame it on Apple and not something I can fix, but it doesn't fix the problem.

I see a few missing elements in your issue here...

Plus, the OP was discussing PDFs, not Word docs. Like making PDFs, Word has a number of flavours for output.

When they forward the message to other users the pdf files won't open. It gives an error message

For your scenario...

What is user A's OS and device?

Did user B validate they could see and open the 8 attachments?

What is user C's OS and device?

I am confused about user D and the iPhone Gmail account. You said the 8 attachments were there and then later they weren't, after asking Gmail to include the original content. Correct? That's a Gmail issue IMO. If you successfully had the content on your phone and used Gmail to send it to someone who now can't see it, how is that an Apple thing? Do you use the iOS Mail app or the Gmail app, or a browser?

Do all of the devices involved have a copy of Word at the same version?

They're somewhat less happy that I found this thread and can blame it on Apple and not something I can fix,

Again, this thread was about PDFs, not Word docs. Please tell your users that.

What is user A's OS and device?

User A is an external user, so I do not know what their devices and versions are. The symptom occurs from multiple external sources, though. These are different organizations, possibly similar platforms, but not likely. Besides that, it's not likely to be relevant in this case, because it's not until the email and its attachments are forwarded that the problem arises. If user B (our internal user, the original recipient) goes into his Outlook client, he has no problem opening all 8 attachments in the original email. I only include "user A" as part of the sequence of events, I do not consider anything about user A's activity to be part of the problem for reasons that I mention here.

Did user B validate they could see and open the 8 attachments?

I don't know if user B checked to see if he could open the attachments before he forwarded them, but it's not likely. The next day, after I was showed the symptom, I personally logged into the account in an Outlook profile and had no problem opening all 8 of them. I also forwarded them from that Outlook profile to a number of email addresses, both internal and external, and no issues.

What is user C's OS and device?

In this case, user C was an Outlook 2016 client. I proved later, however, that user C's client/device didn't matter, by showing the when forwarding the email from the iPhone, and BEFORE SENDING, I scrolled down to the bottom of the email, and where it should have shown 8 attachments, there was only one.

I am confused about user D and the iPhone Gmail account

This part really is irrelevant, I admit that, because again, the issue is at the sending device. I have proven (at least with this one particular email) that when it is opened on at least two different iphones, using different accounts (different sending servers, organizations, etc.) that when I attempted to forward the email, it didn't contain the original content.

They're somewhat less happy that I found this thread and can blame it on Apple and not something I can fix

Given that this symptom started for me right about the time that this thread started, and I can't find anything else about this symptom anywhere, I think there is enough evidence here to think there may be more to this than just document type. If someone here can prove that it ONLY happens with PDFs, then by all means, I'm happy to concede. My own efforts in troubleshooting in the matter have shown that it can happen with both Word and PDF documents.

With so little known about the end to end string here, I would not conclude anything whatsoever.

And, if you read above, the PDFs arrive, but are somehow corrupted and in some cases repairable. Not the same as your issue at all. PDFs can be created in dozens of different ways and are subject to embedded font issues that Word docs are not.

When I read this, I can't help but think this is a Gmail issue, not Apple. (fwiw, I do not work for Apple, nor am I a fanboy. I am technologically agnostic, but I despise the constant Apple bashing when something happens on an Apple Device) You didn't answer me about what "Gmail" thing you used to forward the email on from your phone. It seems when you received the email it had 8 attachment, when you sent it it had one. This happened within the Gmail client. That each person along the string may be using a different email client is absolutely a variable.

I logged into that account on my iPhone and saw that I had received the email, with 8 attachments. I then attempted to forward the email to user E, and when prompted to "include or not include" the original content, I chose to "include". Before hitting send, I scrolled down and saw that there was only one attachment

OK, have you tried not including the original content in your forward, instead detaching and then manually attaching the 8 files? This would isolate the issue to a failure for the Gmail client on your phone to effectively forward attachments. I accept this isn't convenient for your users and they won't necessarily accept the solution, but IMO, it will point you at the right issue to resolve and most importantly, with the correct vendor..

This has nothing to do with Gmail. I never said there was a Gmail mail client involved, only that I thought to include a different variable than just sending to users in my domain. However, as I mentioned, when I scrolled down BEFORE EVEN HITTING SEND, the attachments were already stripped; I could have been sending them anywhere. If you're suggesting the the IOS mail client "sensed" that I was sending to a gmail address and then something bad happened, then you're more than technologically agnostic, I'm afraid.

As far as manually attaching, there are two really big reasons why that is a bad idea. One, it requires a third party app, like MS Outlook for IOS (which I'm actually not a fan of) and also some local storage like a folder or something. You can kinda sorta attach files manually with third party apps, like Google Drive or maybe OneDrive or DropBox, but that takes probably 100 times as long as just hitting "Forward->Include->Send", which takes about 5 seconds.

These end users, I don't like many of them. They're high priced attorneys who, for the most part, feel very highly of themselves and their time. However, when put into the context of their work, and the fact that they are billing at $300-500 or more an hour, they have a right to not expect to have to stop and spend 5-10 minutes to strip and email of 8 attachments (which is typical in the industry) to a storage location that may or may not (most likely not) exist on their mobile devices, then draft a new email and attach them. It's just not happening. Not to mention, these people are not the kind that are going to take kindly to being trained to use something like Google Drive or DropBox, just to get something like this to work, when it used to work just fine a month ago. Not to mention, that's probably in violation of any number of industry security standards.

You said this my friend.

forwarded it to my user D email account (a personal Gmail account). I logged into that account on my iPhone and saw that I had received the email, with 8 attachments. I then attempted to forward the email to user E, and when prompted to "include or not include" the original content, I chose to "include". Before hitting send, I scrolled down and saw that there was only one attachment. I

How is Gmail not part of this?

Best of luck solving this.

I literally just performed this "test" maybe it will simplify things. I have the original email, sent from an external user, in the Inbox of a mailbox that I administer (userB@123domain.com). If I open the email account of the userB@123domain.com in Outlook on a Windows 10 computer (just to be specific, not to distinguish between MS and Apple, I really couldn't care less), and forward this email to xyz@blahblah.com, it sends every attachment just fine. If I view the same email on an iPhone connected to the account for user B and forward it to xyz@blahblah.com, only one attachment shows up, and I can't open it.

There are 8 attachments, 4 .doc and 4 .docx. All of them are under 100Kb, total email with overhead shouldn't be more than 10MB on any system. There are come minimal email signatures, no images or anything, just text and email addresses, things like that. Same with disclosures, nothing fancy, no weird fonts or things of that nature that might raise an eyebrow if looked at closely. It's something about one or more of the attachments. They have sort of long file names, but not a lot individually, maybe 30-40 characters average.

I have had several users experience this problem as well. When forwarding an email that contains an attachment (usually a PDF) in certain cases the PDF file is corrupt when the receiving user tries to open it. It didn't corrupt the entire file as perhaps the first 7 or 8 pages were readable and then it was corrupt after that. I have run a byte by byte compare against the 'corrupt' file and the original file that was forwarded and there are indeed differences in the file.

I also ran into a situation today where a user forwarded an email with 2 attachments (1 was a 60k Excel file and the other was a 2MB PDF). The receiving user received 1 attachment that was a corrupt .xls file. The interesting thing is that when looking at the original files and the received file the size of the .xls that was received was just over 2MB. Slightly larger than a combo of the 2 files.