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iPhone PDF Attachments

Posted on 2014-02-18
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Last Modified: 2016-02-11
Hi,
We have a customer that is having trouble with PDF attachments on his iPhone. What happens is a report is generated and printed by an LOB app. The document is then scanned to e-mail (PDF) and sent via an external SMTP to a company mail account. The company is using Exchange 2003 currently (we will be upgrading them to Exchange 2010 soon). The message has no Subject when sent but we created a whitelist entry for the sending printer. The iPhone is set to pick up the customers e-mail from the Exchange server. The customer states that he receives the message and the attachment is there but when he tries to open the attachment approximately half the time the attachment is blank. If we open the attachment in Outlook or OWA though, the content is there. The other point to this is that this only happens on internal company mail. When he receives PDF's from external companies/people there is no problem with the content.

Anybody have any ideas?

Cheers

Harry
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Question by:jimcrint
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Expert Comment

by:Simon Butler (Sembee)
ID: 39869991
Almost certainly it is down to the way the PDF is generated. Not all PDF files are equal, and the files you are getting from elsewhere are probably generated using a different tool.
Not a huge amount you can do about it, because the PSF tool on the phone you probably have no choice over, likewise for whatever generates the PDFs. I would doubt if the version of Exchange will help.

Simon.
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Assisted Solution

by:Eoin OSullivan
Eoin OSullivan earned 500 total points
ID: 39870024
Try sending one of these defective PDFs to an external email ... and then send it back into the users mailbox from the external mail server.

If the PDF opens properly after the email with PDF attachement has been through this process then the issue lies with Exchange.

If the PDF is still unreadable then the system that generates the PDF isn't properly generating a standards-compliant PDF.
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Expert Comment

by:Iain MacMillan
ID: 39870051
had some experience similar with iphone and ipads, and as Sembee said, it will likely be the PDF format/creation.  

see if they can 'print' the report to PDF using Nitro PDF Printer or CutePDF (both free) and check if the iphone can read those PDFs.  I still have an EX03 server and our Xerox scan to email and other SMTP tasks display fine on mobile devices (though we mainly have Androids)

getting a better PDF reader like Acrobat Reader on the phone might also help.
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Author Comment

by:jimcrint
ID: 39871178
Thanks All,
We can send the e-mail to the client's iPhone through GMail and there is no problem opening the PDF attachment. The only time we have an issue is when we synch directly from Exchange.  Any further ideas?
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Expert Comment

by:Iain MacMillan
ID: 39880906
by sending to Gmail may convert the message to HTML or different format that could affect the pdf, whats the default message format of your exchange server??  also what security/AV software monitors your Ex03 server & user systems (it maybe set to scan attachments/emails)?

have you looked at the pdf file format side, as this may have an effect for pdfs attached on your local server.
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Accepted Solution

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Eoin OSullivan earned 500 total points
ID: 39881782
I've seen this issue in the past with Exchange but unfortunately I don't have a simple answer as I'm not an MS Exchange expert.
The problem is that the format of the email header that exchange puts on internal emails is not the same as emails sent to external servers. Certain email clients such as Apple osx and iOS cannot properly parse the headers and as a result if there are attachments the email programs have problems recognising them.  MS Outlook is designed to deal with the MS formatted emails but apple and other mail programs have issues.
In the past the only solution I've seen is to put a rule in place to forward these emails to an external email server and email account ... and on that external mail account have a rule to forward the email back to the users Inbox on exchange.  This usually standardises the email header and attachments load ok.
I'm sure there are other ways but this has been my fix in the past due to limited access to Exchange on my part as I've usually addressed this issue for minority mac users on large windows networks where changing exchange settings were limited.
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Author Comment

by:jimcrint
ID: 39899417
The issues seems to relate to exchange 2003 and Iphones.  We are upgrading to exchange 2010 at the moment and will see if this resolves it
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Expert Comment

by:Iain MacMillan
ID: 39900103
thanks for the update & good luck (i have this upgrade to look forward to next month!)
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Expert Comment

by:Eoin OSullivan
ID: 39901841
Jim. Why did you accept that answer ?  What was the solution?
If possible you should allocate points to the answer or split points between all answers that helped you get your issue resolved. This may help others who find your issue here on EE and be seeking a similar solution
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Author Comment

by:jimcrint
ID: 39901891
Sorry I made a mistake and it had already happened before I realised
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by:Iain MacMillan
ID: 39902634
i was away to say that was a quick upgrade, Jim, I have asked for a Mod assist, and they should be able to reverse the process for you.
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Author Closing Comment

by:jimcrint
ID: 39905234
We have read of some other issues with Iphone and Exchange 2003.  We did put in place sending the emails with the PDF to Gmail which worked.  We have now changed to exchange 2010 and not had a problem so far.
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Expert Comment

by:3CRetail
ID: 41461222
The problem has returned in IOS 9.2.1.  Linked the file to an in house web server and it opens just fine via Safari.  It worked also when the file was delivered from Exchange 2010.  So it appears to be a combination og the Mail App in 9.2.1 and Exchange 2003.
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