Mail is corrupting PDF attachments

about 25% of the PDF files I receive as attachments show as an icon in the top part of the msg, but also show as unreadable hex "text" in the bottom part of the msg.
If I click on the PDF ICON in Mail.app, it opens fine in PREVIEW.APP
IF I forward any mail with this sort of PDF Attachment (showing as "text" at the bottom) to a windows user, they can NOT open the file... Adobe Acrobat Reader says the file is corrupt.
A corollary is - a LOT of the PDF files I receive from an e-fax service as PDF files show as CORRUPT on the Mac, but open FINE on Windows (Adobe Acrobat Reader).. saying the file is not "correctly encoded"
This is a SERIOUS PROBLEM... If I can't get mail to reliably open and forward PDF files to Windows users, I have no choice but to give up on Mail.app and use Windows...
I have to deal with way too many PDF files as attachments to worry that every one I send may be corrupt to some windows user.
IF apple would give us a way to submit one of these files, I would gladly do so... but apparently from MAIL.APP they do not!
Any ideas?

Keith,
I saw your other post.
With problem Forwarding, try this again, but before sending, click on Format in the Menubar, and choose Make Plain Text. Then let me know what happens.
I do not you have a transmission problem. The problem in the other topic, with Walter, is still under review, but has been traced to only be with that one IMAP server, and regardless of which network you are connected to.
The text at the bottom may be a clue that that Rich Text is being converted to HTML at some point, and the HTML has compromised the content of the PDF.
Feel free to send me an example, by email. My address can be found by clicking on my name.
Ernie

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Mail corrupts PDF attachments

I've had this problem for a while now, usually on older emails i've kept in my inbox, but it's started happening on more recent emails now and is becoming a real nuisance. Basically, sometimes, when i go to view or download a PDF attachment, preview tells me "Couldn’t open the file. It may be corrupt or a file format that Preview doesn’t recognize." I'm using gmail through imap on Mail. The attachement itself is fine though. I can download the attachment through gmail itself and preview displays it fine. Also, mail displays the inline preview as a small black box.
Any ideas why mail is corrupting my attachements? i've already tried rebuilding all my mailboxes multiple times, and deleting and redownloading all my messages, but the problem hasn't gone away.
Thanks for any help.
Message was edited by: zig_k

zig_k,
How did you re-download the messages? Did you remove the account then re-add it? What I would do is Move the files and folders I list below to the desktop. Then re-setup mail.
com.apple.mail.plist from the Macintosh HD -> User -> YOUR USER -> Library -> Preferences
com.apple.mail.downloads.plist from the same folder as above
& the Mail folder in Macintosh HD -> User -> YOUR USER -> Library
If all works you may delete the files. The plist files hold settings like were you store your notes and todos. And the mail folder is a copy of all you mail. You can go through it if you like.
Hope that helps,
Weston

Mail 4.5 corrupts PDF attachments from gmail (while outlook 2011 doesnt)

I have a gmail account with scanned documents.
I add this account to in Mail and then some of the PDFs are damaged and can not be corrected. The interesting matter is that via web-access and Outlook 2011 there is not a problem.
I have tried many different solutions I could find on the web incl. here. From deleting the mailboxes to deleting the cache-files. Ultimately I deleted the whole mail app (incl. lib files with CleanMyMac), reinstalling and reinstalling the combo.
After adding the account the last time, I minimized the window, till all activity was finished and everything cashed etc.
I opened mail and again the same problem.
Additional remarks: There are many attachments with the same name, because they were send by a HP Office machine. Some have a problem most don't I would estimate the problem is in 10% of the mails.
Again via Web-access and Outlook 2011 all attachments are correct.
I could use Outlook, their calendar doesn't sync with gmail and I also don't like how outlook is handling (and messing-up) my v.cards .
Any help would be highly appreciated.

Ernie Stamper wrote:
The IMAP setting to Keep copies of messages and their attachments has little impact unless not connected to the internet and wanting to work Offline. If connected to the internet, and you click on a message, it will be downloaded, even if not already so by virtue of this setting. If not selected to Keep copies . . . and attachments, then you will be subject to the goodness of the internet connection at that moment. I am only partially keeping abreast of your investigations, but it may be that transmission is muddled at certain times?
I didn't actually try reading the messages without an internet connection. When I had the account in the default "message+attachment" option, the attachments tended to stay on the server. When I switched to "message, no attachment", the attachments were always downloaded. That sure sounds like the opposite of what I would have expected. I've never used the "message, no attachment" setting so that is new to me.
But I may be missing a step in the sequence of things you have found out. Do you have any reason to think that in the message cache created by selecting Keep copies . . . something could be altering files?
I know that if the Mailbox index gets corrupted, it can cause attachments to be lost - at least temporarily. When I do testing with a local mail server, sometimes the timing is off (too fast maybe) and the message is almost always corrupted. Rebuilding the mailbox fixes it.
My initial theory was that the HP devices were spitting out bad MIME messages and that gmail was fixing them. Now I think that gmail IMAP just flakes out every so often with these big files. There could be other explanations too. The PDF was just truncated. I don't think a bug in Apple Mail is a likely possibility.

Missing or corrupt PDF Attachments from Outook

My company uses a software package to auto create customer invoices as PDF documents which it then attaches these to a Plain Text email within Outlook 2003 which are then sent out to our customers email addresses.
The server running this program is using Win Server 2003 SP2 and Office 2003 Outlook to create & send the email.
Some customers see the PDF attachment ok, i.e those using Outlook, others using Hotmail, AOL, Outlook Express, Mozilla Thunderbird are all experiencing problems like missing attachments - Outllook Express / Thunderbird, Corrupt Files - Hotmail /AOL.
Is this to do with Internet Settings in Mail Format of Outlook, this is currently set as Plain Text without UUENCODE and HTML in pictures is checked.
Can anyone help?
John.

Hey John,
You may want to look into how your application is building the PDF. I had a very similar issue with almost the exact scenario you are having. Do some searching around PDF and "dot stuffing". The problem I had related to where the binary stream of the PDF began, there were extra dots (.) inserted causing the data to be invalid when the client attempted to read the encoding.
I believe it was a bug in the VB .net object itself (the code was fine) , I cant recall the version, perhaps v2 ??
-Dan

Why does Mail deliver my PDF attachments as jpegs????

When attaching pfd files to send in Mail, recepients tell me the files come thru as jpegs...

As svs1234 provided, do not touch or use the Image Size adjustment available at the bottom right of the message window with a PDF attachment.
This should be used for image/photo attachments only.

Can Mail send interactive PDF attachments with URL links?

I have tried without success to send a PDF that has URL links embedded (made in InDesign CS3). When this mail arrives the links are stripped out from the attached PDF. I do not want to send html mail for this purpose.
Anyone have any answers? Thanks.

Jon,
The strong probability is that a SPAM filter in the path to the recipient has stripped them out -- Mail would not cause this. Have you tried opening the PDF with Acrobat Pro, doing a Save As, and then attaching that version to see if the same behavior continues.
Ernie

Windows mail and blank pdf attachments

I am new to windows 8. I just started using my HP ENVY -Z Notebook PC
I have been receiving and sending out email for the past week.
This morning however I was having problems sending out emails trying all the email accounts I have added to Windows live - when one email got through, the pdf attachment sent came blank to the recipient? Need guidance on what needs to be done to fix this,,

Hi
Check the below link it might help you
http://answers.microsoft.com/en-us/windows/forum/windows_vista-windows_programs/windows-mail-does-no...
****Click the White Kudos star to say thanks**** I am not an HP employee, I am a volunteer****
****Click on the Accept As Solution button on the lower right side if a suggestion resolves the issue you are having****

Mail V6.3 pdf attachments "the file could not be opened because it is empty"

I received an email with a pdf document attached. When I try to open it by saving it or directly from the email, I get the message "The File 'filename' could not be opened because it is empty."
The file extension is correct with .pdf. Adobe is up to date. It will not open in Preview either. No updates needed for Mac OS 10.8.3.

Does this involve iPhoto in some way?

Lion Mail PDF attachments occasionally corrupting

Since upgrading to Lion I've noticed that some PDF attachments won't open in Preview - I get the following:
=====
The file “1234.pdf” could not be opened.
It may be damaged or use a file format that Preview doesn’t recognize
=====
This continues to happen even after I drag the attachment to the desktop or rebuild the IMAP inbox.
If I go to the webmail for the email provider, open the mail and download the attchment it is fine - so something in Lion (never had this before in Snow Leopard) seems to be corrupting it.
Anyone able to shed some light on that's going on here?
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So far I'm seeing this with PDFs. In one email, I had two versions of the same PDF: one was the original, and the other had been highlighted and anotated (probably in Preview). The original opens, and the other gives me problems.
I've used the highlighting feature heavily in Preview, but I've found that it occasionally corrupts the PDF, such that if you copy and paste text (not necessarily the highlighted text), it come out all garbled. I'm wondering if Lion does a better job identifying damaged PDF files (damaged by previous OS versions, perhaps). Haven't been able to look into this very much, but I'm eager to find out what the problem is.

Outlook 2010 corrupting incoming pdf attachments for one user

I have one user here that is having incoming pdf attachments get corrupted in Outlook 2010. When she tries to open the file, it gives
the error "Adobe Reader could not open filename.pdf 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)." I can open the pdf files in her
webmail, and I also installed another mail client which can open the same email attachment fine. It is obviously something about Outlook 2010 that is corrupting the pdf. I have a comparison of email headers from a good email and a corrupt email, as well
as a comparison of the content of a good pdf file vs a corrupt one. The corrupt pdf is all zero's. Any input on this would be greatly appreciated. Thanks for looking!

Hi,
Please try to save the PDF file to local and then double-click to open it if you haven't tried this.
Also make sure the user has installed the latest version of Adobe Reader.
In addition, did the user get the PDF attached email from an online mail interface? If so, please try to send the user an PDF attachment email using Outlook to check the result. Some email providors (especially web email) encode the PDF's for a faster
transfer but when they are received at the other end, they aren't recognized as a PDF so they get corrupted. See:
http://forums.adobe.com/message/1943262
Regards,
Steve Fan
TechNet Community Support

Mail is corrupting attachments

Hi
Mail has started corrupting attachments in both sent and recieved emails. This affects jpegs, pdfs, zip files, etc although so far not word or text documents.
Its been a pain usually with me requesting that stuff be resent only to find it corrupted in a different way. My webmail checks out fine and I have even started entourage running to double check. Entourage works fine, for what it is.
So far as I am aware I haven't changed any settings, nor installed anything untoward.
Can I fix this, I'm not keen on switching email software.

APPLE TAKE NOTE OF THIS BUG, PLEASE.
This is a user to user help forum only and although certainly there are some Apple employees who peruse these Discussions, you are not providing anything to Apple directly here.
The Mail.app displays all image/photo and single page PDF attachments inline or viewed in place within the body of the message by default which cannot be turned off.
You can control-click on an inline or viewed in place attachment and select View as Icon but this has no effect on the attachment.
Depending on the recipient's email client and available preference settings, such attachments may appear inline or viewed in place within the body of the message when the message is opened (as with the Mail.app when receiving such attachments) or as attached files only which must be opened separately to be viewed which the sender has no control over.
The same in reverse. Windows Outlook and Outlook Express sends image/photo and single page PDF attachments as attached files only (not displayed inline or viewed in place) but when received and opened by a Mail.app user, such attachments appear inline or viewed in place within the body of the message along with the attached files available below the message header which can be saved outside of the message.
The Image Size adjustment included with Tiger Mail should be used with image/photo attachments only and not with single page PDF attachments that appear inline or viewed in place. When used with single page PDF attachments, the file type is converted to jpg since this is what the Image Size adjustment is for - for images only.
What needs to be changed is not providing the Image Size adjustment when attaching a single page PDF file.

Pdf attachments do not come through on iCloud mail but they do on other email accounts on same device

I have several email accounts set up that appear on all my devices: iMac, iPhone and iPad. I use 2 email accounts for work purposes, and good thing I use two. I receive pdf attachments in non-apple email accounts, but the same email sent to my iCloud address comes through minus the attachment and shows only "winmail.dat". I am using the same device to read the email from the different accounts, but the problem is consistent with all my apple devices. This has to be a setting in iCloud mail but I can not figure it out. Please help.

Basic troubleshooting steps clearly outlined in the User Guide are restart, reset, restore from backup, restore as NEW.
If the basic troubleshooting steps don't work, then you'll need to bring your phone into Apple for evaluation and probable replacement.

Some PDF attachments are corrupted when emailed using javamail

I have a java class that takes a file name, 'To' email, and 'From' email as parameters, and then emails the named file to the specified address as a Multipart email.
The problem that I am facing is that sometimes the PDF cannot be opened when it arrives because it is corrupt. I know that prior to sending, the PDF opens without issue, so the problem is in the code somewhere.
There are a couple of oddities here:
1) PDFs that get corrupted and PDFs that do not get corrupted are generated from the same source (Oracle Report), so I believe that rules out a problem with malformed emails?
2) If I compare the PDF before it gets sent to the PDF that arrives in my inbox using a hex editor (XVI32), the files are identical except that an extra character is getting added to the corrupt PDFs at the end of each line - hex '0A', which corresponds to ASCII linefeed. This indicates to me that maybe there is a problem with the way that the file is getting encoded when it is read. If I remove all of the 0A characters, the file opens correctly.
I believe that the code I am using is set up correctly, as I have looked at countless examples of this online to try to find my problem. Hopefully someone can point me in the right direction. Code is included below.
Thanks,
Nick
import java.util.*;
import javax.activation.DataHandler;
import javax.activation.FileDataSource;
import javax.mail.*;
import javax.mail.internet.*;
public class test {
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        System.out.println("Made it to SEND method");
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            MimeBodyPart attachFilePart = new MimeBodyPart();
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                    new FileDataSource(fileName);
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            mp.addBodyPart(messageBodyPart);
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}Edited by: nbacon on Sep 2, 2010 12:12 PM

Normally pdf files are text, with any binary data represented as encoded text. If your pdf files
include raw binary data, JavaMail can be confused. JavaMail will try to guess what encoding
is appropriate for your data. If the data is mostly text, JavaMail will use quoted-printable encoding,
and will canonicalize the text lines to end with CRLF (0x0D, 0x0A). A 0x0D in the binary will look
like an end of line and will turn into 0x0D, 0x0A.
You can force JavaMail to use base64 encoding for your data, which will preserve the binary
data exactly, by using
attachFilePart.setHeader("Content-Transfer-Encoding", "base64");
after setting the content for the part.
Alternatively, you could figure out how to generate pdf files that don't include raw binary data.

I recently purchased an Iphone 6plus and I am receiving pdf attachments that are shown as winmail.dat attachments on the phone. When I check e-mail via my macbook pro the attachment is a pdf and I can open it. Why is this happening?

I recently purchased an Iphone 6plus and I am receiving pdf attachments that are shown as winmail.dat attachments on the iphone. When I check the same e-mail on my macbook pro the attachment is a pdf and I can open it. Why is this happening?

I had this problem too after i upgdatd to OS X Mavericks... only the songs on my iphone 5s that i purchased from itunes would play.
i read something about it being a syncing issue. when you plug your phone into your computer with the usb cable, the person said to switch from automatic syncing of itunes to the "manual" option. mine was already set to manual so i wasn't sure anything would work. BUT, when i plugged my phone into my computer, it started to sync all of my music on my phone again (top of itunes bar where song playing/time is listed said "now syncing 123/534 songs to x's iphone"). once that was completed, i checked the music app on my iphone and everything was back to normal!
so, i would suggest setting your music syncing settings to manual if you haven't tried that yet!
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Some pdf attachments missing in mail 5.2

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I have the same problem, failing to receive pdf attachments intermittently using Mail 5.2 running OS X 10.7.3 (Lion), and not being counted among the attachments
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Mail is corrupting PDF attachments

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